You don’t have to drive far to feel you’re away from the city! Wisconsin’s countryside is a picturesque tapestry of rolling, glacially-carved hills, lush emerald pastures, and charming rustic barns that perfectly capture the quiet, welcoming heart of the Midwest. Towns like New Glarus, Paoli, and Mount Horeb act as the “Hamptons of Madison,” serving as highly sought-after escapes.
We found 40 towns worth visiting that are within a 45-minute drive of Madison’s heart. All provide affluent, laid-back retreats and offer artisanal shops and boutique dining, acting as luxurious getaways from the city life.
If 2026 is your year of a “staycation” you have no shortcomings of towns to explore around Madison! Let’s dive into our beautiful surrounding towns up to 45minutes outside of Madison:
1. Belleville (35min.):
Best known for its outdoor recreation centered around Lake Belle View and the Sugar River, this town offers a relaxed, rural lifestyle with excellent highly-rated public schools and an easy commute into Madison. Top outdoor recreation choices include the 40-mile Badger State Trail which runs directly through Belleville, making it a hotspot for biking and hiking. The Sugar River and Lake Belle View offer fantastic kayaking, canoeing, and fishing. An interesting fact is that Belleville is famously known as a “UFO Capital of Wisconsin” and hosts a quirky, highly anticipated UFO Day festival and parade every October. For dining, located in a historic 1917 garage, Hop Garden Brewing and Tap Room welcomes you to gather with friends and family for a beer and yummy bites in their tap room or outside in the beer garden.
2. Beloit (45min.):
Experience Beloit by exploring its vibrant downtown riverfront, catching a minor league baseball game, and indulging in the city’s famous supper clubs and farm-to-table eateries. Top things to do in Beloit include their Saturday morning farmers’ market. This sprawling downtown market is one of the largest and best in the state. Check out the ABC Supply Stadium and catch a Beloit Sky Carp (MiLB) game. Walk or bike the scenic trails at Big Hill Park or Riverside Park, both offering great views of the Rock River. Pick up a passport at the visitor’s center to complete the Beloit Beer Trail or Coffee Trail for prizes. Visit Ironworks Golf Lab and play year-round indoor golf and other interactive games. Dining is plenty is Beloit. For classic Wisconsin steaks, prime rib, and Brandy Old Fashioned’s, book a table at The Butterfly Club or The 615 Club. For downtown dining, head to Merrill & Houston’s steak joint for upscale dining, or Truk’t for creative tacos and tequila. For casual bites, check out Lucy’s #7 Burger Bar for creative, local beef burgers and sweet potato fries. For local, farm-to-table organic fare, visit Bushel & Peck’s.
3. Black Earth (30min.):
The first Europeans to permanently settle arrived in rural Black Earth in 1843.Top activities include visiting the interactive Children’s Museum, shopping at the massive Shoe Box store, and exploring local nature at Morton Forest County Park. The village is famous for its trout-fishing creek and serves as a quiet base for exploring the surrounding driftless area. Visit the Old Halfway Prairie Schoolhouse, the oldest rural school in Dane County. For family fun, go to Black Earth Lanes for classic bowling, bar, and casual food. Finally for dining, check out The Shack Bar & Grill, known for casual food in a log cabin setting.
4. Blue Mounds (30min.):
Blue Mounds offers the perfect blend of geological wonders, scenic outdoor adventures, and small-town charm. Top activities include Cave of the Mounds. Explore the “jewel of the cave” with guided, 1-hour walking tours through naturally lit, vibrant limestone formations. Above ground, you can visit their rock gardens, fossil mines, and bird observation areas. Visit Blue Mound State Park which is located at the highest point in southern Wisconsin. This park offers over 20 miles of hiking and off-road biking trails, a swimming pool, and an observation tower providing stunning views of the driftless area. Also, worth going is the Military Ridge State Trail. This 39-mile former railroad trail cuts through Blue Mounds and is perfect for a scenic afternoon bike ride or a walk. Grab a drink or bite right off the Military Ridge Trail at Brix Cider, known for its local ciders and farm-to-table food with outdoor seating, or stop into Harley Blue for a classic, small-town Wisconsin tavern burger and beer. Tip for cyclists: Blue Mounds hosts a yearly bike event called the Horribly Hilly Hundreds, named after beautiful but hilly cycling terrain.
5. Brooklyn (30min.):
The charming village of Brooklyn offers a quiet, scenic escape. The best things to do include hiking the 1,700-acre Brooklyn Wildlife Area spanning parts of Dane and Green counties. It’s a premier spot for hiking, birdwatching, and enjoying quiet, tree-lined marsh trails. Don’t miss to golf at the Legend at Bergamont, featuring an 18-hole championship golf course, designed by Andy North, a two-time U.S. Open Champion. For dining, unwind with a bite and a drink at local favorites like Dot’s Tavern or the Anchor Club.
6. Cambridge (25min.):
Cambridge offers a charming escape, blending outdoor adventure at Lake Ripley and CamRock Park with a vibrant arts and distillery scene. Visit the CamRock County Park. This park is ideal for hiking, kayaking, and fishing along Koshkonong Creek. It features extensive multi-use trails popular with mountain bikers for all skill levels, including a designated bike park area. Explore Lake Ripley, a 420-acre lake featuring a public beach, fishing for bass and northern pike, and a boat launch. Visit Ripley Park! Situated on Lake Ripley, this park offers a sandy swimming beach, volleyball courts, a disc golf course, and picnic areas. Enjoy Dancing Goat Distillery, known for tours, a spirits vault, and a hands-on Gin Academy experience as well as Cambridge Winery featuring wine flights and dining, including outdoor seating.
7. Columbus (35min.):
Columbus offers a peaceful, historic escape from Madison. Top local highlights include browsing the massive Columbus Antique Mall, enjoying farm-fresh treats at Sassy Cow Creamery in nearby Columbus/DeForest, and paddling the Crawfish River at Astico Park, making it a scenic, quiet spot for picnicking, fishing, and paddling. Enjoy a historic downtown stroll! Take a walk down Dickason Boulevard to admire the 19th-century architecture, highlighted by the striking Clocktower City Hall. Stop into cozy spots like the Tea Time Wine Bar & Bakery. Visit the Fireman’s Park & Aquatic Center, a fantastic summer stop for families, featuring a pool, diving boards, water slides, and a splash pad.
8. Cottage Grove (25min.):
Cottage Grove offers a mix of outdoor recreation, agricultural tourism, and local craft drinks. Top activities include biking the Glacial Drumlin State Trail, visiting the local craft distillery Doundrins Distilling for handcrafted cocktails and take advantage of their indoor tasting room and outdoor cocktail garden. Visit the Warm Belly Farm! This agri-tourism destination offers seasonal u-pick hydroponic strawberries, a beautiful garden center, and a lively annual fall harvest festival complete with a corn maze, sunflower fields, and a beer garden. Cottage Grove’s dining scene is heavily rooted in cozy Midwestern comfort and traditional Wisconsin bar & grill fare. For a great local bite, consider these top spots: Kozy Nuk Cafe, Oakstone Recreational, Mr Queso Sports Bar and the Oakleaf restaurant.
9. Cross Plains (20min.):
Explore the Ice Age Trail and its Cross Plains Segment. Traverse some of the most beautiful terminal moraines and rolling prairies in the state. The segment offers great ridge views and connects right into the state park. Explore Cross Plains’ State Park! Just off Old Sauk Pass Road, this park is renowned for its outstanding glacial meltwater gorge and offers excellent hiking and birdwatching. Visit Glacial Valley Park! Known locally as one of the best playgrounds in the Madison area, this park features massive climbing structures, basketball courts, and popular zip line swings. Don’t miss the beautiful Indian Lake Park. This 483-acre park features wooded trails, a dog off-leash area, and a scenic hike up to the historic St. Mary of the Oaks Chapel. Finish off your day at the these eateries: Morgans Bar and Grill: A highly-rated local favorite off the beaten path that features great pub food, live entertainment, and summer fish boils; The Red Mouse: A cozy, longtime local bar offering a friendly, relaxed atmosphere and the Esser’s Cross Plains Brewery: A historic establishment that highlights the region’s brewing roots.
10. DeForest (20min.):
DeForest is a charming village offering a great mix of whimsical roadside stops, interactive sports, and scenic parks. Snap a picture with the famous 1960s Pink Elephant statue and say hello to Sissie the Cow at Ehlenbach’s Cheese Chalet, where you can shop for artisanal Wisconsin cheeses and snacks. Check out Pinseekers and head to this year-round sports and entertainment destination. It features climate-controlled Toptracer driving suites, mini-bowling, and a full restaurant and bar. Visit the Schumacher Farm Park. This 40-acre heritage farm features hiking trails, restored prairies, and historic buildings. If you are traveling with a pet, visit Token Creek Dog Park. This heavily wooded, off-leash park spans over 40 acres and is one of the most popular dog spots in the Madison area. Treat yourself to a slice of scratch-made Norwegian pie or comfort food at the famous Norske Nook Restaurant & Bakery.
11. Delafield (45-50min.):
Delafield offers a perfect blend of scenic outdoor adventures, rich history, and vibrant downtown shopping. Hike the glacial terrain of Lapham Peak (Kettle Moraine State Forest) and hike 17+ miles of trails or climb the 45-foot observation tower. It’s especially famous for vivid fall foliage and cross-country skiing in the winter. Tour the 19th-century Hawks Inn and grab a drink at Revere’s Wells Street Tavern. Enjoy a peaceful 3.5-mile gentle walk directly through downtown Delafield along the Bark River Ice Age National Scenic Trail. Visit the Nagawaukee Park & Lake which is perfect for a boardwalk stroll, lake views, or kayaking and boating on the water. Step back in time at the preserved 19th-century stagecoach stop, offering guided tours of frontier-era history. Ten Chimneys Estate is worth seeing and located nearby. This breathtaking 18th-century estate was the beloved home of Broadway legends Alfred Lunt and Lynn Fontanne. Wander around downtown and Genesee Street and browse boutique shops like the Bliss Main Street Boutique before grabbing a fresh brew at Blue Collar Coffee Co. The Delafield Farmers Market is open Saturday mornings from May to October. This is the perfect place to find certified, locally grown produce and artisan goods. For a great meal, try the contemporary American Kitchen, inside the Delafield Hotel or dine at the Red Circle Inn, Wisconsin’s oldest restaurant and supper club.
12. Edgerton (35min.):
Edgerton is a charming city known for its rich history, vibrant summer festivals, and lakefront recreation. It offers a relaxed alternative to the city, with notable attractions like the boyhood home of “Rascal” author Sterling North, the historic Rock River Thresheree, and easy access to Lake Koshkonong, a top destination for boating, fishing, and kayaking, featuring lakefront restaurants like The Buckhorn for live music and drinks. No matter your preferences or style, there is something tasty waiting for you to eat in Edgerton as well. Downtown pubs like Red Baron and 2 Brothers make for a great night out with friends. The supper club at Coachman’s Resort is a perfect anniversary date-night spot.
13. Evansville (30min.):
Evansville offers a charming, small-town getaway. It is highly walkable and renowned for its 19th-century architecture, outdoor recreation, and local boutiques. Explore Leonard-Leota Park and stroll through this historic 1930s-era park. It features the 28-acre Lake Leota (great for kayaking and fishing), a scenic covered bridge, and a public swimming pool. Wander Historic Downtown! Take a self-guided walking tour of the downtown area to see some of the state’s best-preserved 19th-century Italianate and Gothic Revival architecture.Visit the Hop Garden and enjoy locally brewed craft beer in a relaxed, family-friendly outdoor beer garden setting. Browse Local Boutiques like the Evansville Craft Market and unique downtown shops including Mommies Little Creations. Grab a Bite at Rock’N Rollz Sandwich Company for highly rated deli sandwiches or El Vallarta for excellent Mexican food.
14. Fall River (40min.):
Fall River is a quaint village that serves as a great starting point for exploring the rural charm of Columbia County. Popular activities include shopping for antiques through three massive floors of antiques and collectibles at the expansive Columbus Antique Mall (just 4 miles west in Columbus), enjoying local treats, outdoor adventures at nearby parks, and even thrilling skydiving. Grab fresh Wisconsin dairy, cheese curds, and artisan ice cream at Sassy Cow Creamery in nearby Columbus, or stock up on specialty cheddar at Schultz’ Cheese Haus. Hike, picnic, or fish at the 460-acre Astico Park, located right on the Crawfish River. Go Skydiving and experience an adrenaline rush and jump with Seven Hills Skydivers, a local club offering tandem jumps just minutes from the village center. Finally, visit Local Orchards like the Sadie Bee’s Orchard right in Fall River, or take a short drive to Lapacek’s Orchard in nearby Poynette for apple picking and family fun in the early fall. Fall River offers highly-rated, classic Wisconsin tavern and comfort food. The best local spots include Wingz n Thingz. This local favorite is celebrated for its huge variety of wing flavors, loaded cheese curds, and relaxed sports-bar atmosphere. Also try out CJ’s Bar & Grill. Located on Main St, this spot serves up great, classic American bar food and lunch specials. It’s highly rated by locals and features passing trains that add a fun, rustic vibe.
15. Fitchburg (15min.):
Fitchburg is a vibrant, bike-friendly suburb. It offers a unique mix of urban and rural living, acting as a gateway between the bustling city and the rolling farmland of Dane County. Fitchburg is a recognized bicycle-friendly community. You can easily hop onto the Capital City State trail or the Badger State trail right from town. Rent an electric bike using the Madison BCycle stations spread across the city. The Quarry Ridge Mountain Bike trail is amazing. It is located on Fitchburg’s west side and offers scenic, wooded single-track routes for all skill levels. Visit McKee Farms Park, a massive local park, featuring walking loops, a splash pad, and recreational sports fields. The UW-Madison Arboretum is close by. Only a few minutes north, this massive 1,200-acre preserve offers restored prairies, woodlands, and miles of walking trails. For breweries & bites try out Delta Beer Lab, a highly rated, community-focused craft brewery featuring rotating taps, a sustainable ethos, and trivia nights. Very popular is also The Thirsty Goat, a local gastropub with a great outdoor patio, local beers, and elevated pub food. Not to miss and worth to see is Quivey’s Grove! Dine in a restored 1855 historic estate. It offers classic Wisconsin supper club dining in the Stable Grill or formal dining in the Stone. One of Fitchburg’s hidden gem is Perennial Yoga, one of the most beautiful places you can practice yoga and mindfulness in the Madison-area.
16. Janesville (40min.):
Janesville is famously known by its nickname, “Wisconsin’s Park Place”. This phrase highlights the city’s impressive network of over 60 public green spaces, spanning 2,600 acres, including the nationally acclaimed Rotary Botanical Gardens, a stunning 20-acre award-winning botanical garden featuring 26 different themed areas, including a Japanese garden, sunken garden, and a massive illuminated winter lights festival during the holiday season. The Ice Age Trail is worth checking out! Hike or bike sections of the famous thousand-mile trail, which winds directly through Janesville’s scenic green spaces and the Robert O. Cook Memorial Arboretum. A must do in Janesville is catching a free, high-energy water ski show of Rock Aqua Jays at Traxler Park during the summer months. If you love history, then step back in time with a tour of the Civil War-era Lincoln Tallman House or the nearby Milton House Museum. For local dining, sip craft beer at Rock County Brewing Company, grab a classic Wisconsin Old Fashioned at the Draft House, or stop for a coffee and pastry at Mocha Moment, a trendy place with outdoor wooded seating.
17. Lake Mills (35min.):
Lake Mills is a charming, small-town escape. The area perfectly blends outdoor recreation with a vibrant downtown filled with breweries, wineries, and unique shops. Relax at the Tyranena Brewing Company, known for its spacious outdoor beer garden, food trucks, and live music. Head to Lewis Station Winery, a uniquely repurposed vintage gas station serving craft wines and bistro fare. Explore the Aztalan State Park. This significant archaeological site features ancient Native American earthen mounds and trails along the Crawfish River. Relax at Rock Lake: Enjoy the water at Bartel’s Beach or Sandy Beach, which feature roped-off swimming areas, playgrounds, and picnic spaces. Walk the Glacial Drumlin State Trail. This scenic, 52-mile multi-use trail runs right through the area and is perfect for biking, walking, or running. Stroll downtown Lake Mills and grab a coffee at Simple Kup, explore the heirloom-quality pieces at Ephraim Faience Pottery, and pick up some sweets at James J. Chocolate Shop.
18. Lake Ripley (25min.):
Lake Ripley is a 420-acre, spring-fed lake and recreational haven in the town of Oakland, famously characterized as having “crystal clear waters” and offering a scenic year-round escape for swimming, paddling, and fishing since the late 1800s. The best things to do at Lake Ripley include relaxing at the sandy beach, boating, and enjoying the quiet atmosphere of this unique, beautiful lake. The area offers a mix of classic, historic Wisconsin lakeside charm and active outdoor recreation. Enjoy a relaxing afternoon on the porch swing of a historic 19th-century lodge. For dining at Lake Ripley, try Hering’s Lake Ripley Inn, a classic Wisconsin tavern right on the lake, known for its popular Friday fish fry, fresh hand-battered fish, tender prime rib, and a warm, welcoming atmosphere. Also, visit the Lake Ripley Family Restaurant, a popular, casual spot on the lake known for great comfort food, homemade pies, and a fantastic Friday night fish fry as well. Finally, visit Cash & Olive’s Pub! Located near the southern shore, this spot offers unique made-from-scratch food, a full bar, and a nice outdoor patio with friendly service. Finally, there is also Mink Farm: A cozy, “go-to” tavern for great burgers and Cajun perch.
19. Lodi (40min.):
Lodi offers a perfect blend of scenic bluffs, outdoor recreation, and a charming, walkable downtown. It is an ideal quick day trip for nature lovers and foodies alike.Top things to do include the Gibraltar Rock State Natural Area. Hike to the top of this dramatic geological formation for sweeping, panoramic views of the Wisconsin River valley. Explore downtown Main Street and wander through locally-owned boutiques and shops housed in historic buildings. Be sure to stop by Sunfall on Main for antiques, local art, and garden heirlooms, or visit Three Bats in the Belfry for unique gifts.Take the Merrimac Ferry and drive just a few minutes north to Lake Wisconsin and ride the Merrimac Ferry, one of the last remaining free, continuous-service car ferries in the United States. Check out Slack’s Jams and Jellies. Visit this quaint, family-owned gem for locally made, highly-rated preserves, baked goods, and country gift items. If you are visiting in the fall, Treinen Farm’s Corn Maze & Pumpkin Patch is a must. This award-winning destination features an 18-acre maze, scenic walking trails, and family-friendly activities. Finally, grab a bite or a drink at La Grotta Wine Bar in downtown Lodi, or grab a slice or two at the popular Log Tavern Pizzeria.
20. Marshall (30min.):
The small town of Marshall offers a few unique, family-friendly attractions and beautiful outdoor spots. Have some family fun at Little Amerricka, a classic, family-owned amusement park, featuring vintage rides, an antique wooden roller coaster, and scenic miniature train tours. Explore Steven’s Rocks & Gifts, a sprawling gem, mineral, unique rocks and polished stones, quartz crystals and fossil -store. Head to Marshall Boats & Marshall Park, the western edge of nearby Lake Mendota for boat, canoe, and stand-up paddle board rentals. You can relax on the water, grab a bite at the cafe, or enjoy a picnic. Visit Lions Park & Riley-deppe County Park for a quieter afternoon. These local parks offer scenic walking trails, fishing docks, and great picnic areas. For the thrill-seekers, Seven Hills Skydivers is a must. This volunteer-run club operates just outside of Marshall and offers tandem jumps and student training for those looking to experience the sport. For fish fry and pub-style food, finish your day at The Barrel Inn.
21. Mazomanie (35min.):
Mazomanie offers a charming, artistic small-town experience with strong ties to nature, including its notable Midwest Microcar museum and scenic nearby bluffs. It is a quaint, historic town known for its artistic community and proximity to the Wisconsin River. Visit Carr Valley Cheese, a renowned store for award-winning Wisconsin cheese varieties. Visit also the Mazomanie Historical Society Museum and explore the local history of the village. Browse Iron Horse Gallery and the historic downtown. Relax at the Morton Forest County Park and hike through a scenic, medium-sized park in the driftless area. The Ferry Bluff State natural area is located nearby and offers birdwatching and beautiful views. Check out the Wolf Run Trail, a trail suitable for walking and biking. Near by to reach is the Wollersheim Winery & Distillery, located in Roxbury/Prairie du Sac, offering tastings and scenic river views Visit Dr. Evermore’s Sculpture Park, a unique art park featuring large-scale metal sculptures and the Cave of the Mounds, a popular natural landmark located in nearby Dane County. For dining, try out the Hop Tap House, a self-serve tap house, featuring Wisconsin brews, also stop by Base Camp Cafe, known for soups and sandwiches and the Shack Bar & Grill for casual dining.
22. McFarland (20min):
McFarland offers a charming, nature-filled escape. The top things to do include biking or walking the scenic 2.5-mile Lower Yahara River trail boardwalk across Lake Waubesa. It features stunning water views, an accessible fishing pier, and bird-watching spots. You can access it directly from McDaniel Park, which also offers a BCycle bike-rental station. McDaniel Beach & Park is located on the shores of Lake Waubesa. This park is perfect for swimming, launching small watercraft (like kayaks or paddleboards), and enjoying lakeside picnics. Visit Indian Mound Conservancy and explore a quiet, scenic trail that highlights well-preserved Native American effigy mounds. Best dining options are the Tree Supper Club, a classic Wisconsin supper club experience known for its prime rib, and fish fries. Also try out Angelo’s McFarland, a cozy, local Italian eatery, serving up excellent pasta and pizza and finally the Green Lantern Restaurant which is a warm, longstanding American eatery, great for hearty breakfasts and surf-and-tail dinner menus.
23. Middleton (15min.):
Middleton is known for its tight-knit, welcoming vibe and its official and highly fitting motto: “The Good Neighbor City.” Start out with a hike or bike of the 550-acres Pheasant Branch Conservancy. You will most likely view deer and turkeys. Play a round of golf with scenic views at the Pleasant View golf course, untouched by ancient glaciers, the Driftless is defined by its rugged hills, deep valleys, and striking natural contours and features that shape the Pleasant View landscape and inspired its beloved nickname, “Goat Hill.” Relax and sit outside at Capital Brewery’s beer garden, shop and dine in the open-air boutiques at Greenway Station, or head downtown to walk around and check out the shops and restaurants. Visit the downtown National Mustard Museum, and catch live music or family programming at the community outdoor space. One of our favorite and family owned restaurants is Villa Dolce, serving authentic and classic pasta, pizza and amazing deserts or Longtable, a beer cafe with outdoor seating and mouth-watering burgers, hand-cut fries and sandwiches.
24. Mineral Point (45-55min.):
Mineral Point is Wisconsin’s third-oldest city and offers a charming Driftless area escape. It is famous for its preserved 19th-century limestone architecture, vibrant arts scene, and historic Cornish roots. Explore the Arts & Culture High Street galleries and browse the eclectic mix of handmade art, jewelry, and pottery at local galleries like Wantoot Gallery and Brewery Pottery. Take a workshop or stroll through the historic campus of the popular arts retreat, called Shake Rag Alley Center for the Arts. Experience the legacy of Wisconsin’s 19th-century lead-mining boom through guided tours of these beautifully restored Cornish cabins. Visit the beautiful Mineral Point Railroad Museum and step inside the restored 1856 Milwaukee & Mississippi Railroad depot. Enjoy the Outdoors at Governor Dodge State Park, located just a few minutes north of town. This sprawling park features waterfalls, hiking trails, and two lakes for kayaking. For dining, enjoy some local classics! Grab a famous Cornish pasty at the Red Rooster Café or enjoy a pint and burger at the Commerce Street Brewery. Stop for small-batch chocolates at NightShift Chocolate or enjoy a tasting at the American Wine Project.
25. Monona (15min.):
Monona is a charming, independent waterfront city, nestled along the Southeastern shores of Lake Monona. Completely surrounded by the greater Madison area (and over four miles of shoreline), it offers a laid-back, tight-knit community feel while sitting just minutes away from downtown Madison. Monona offers breathtaking skyline views of the state Capitol across the water, miles of bike trails, and small-town charm. Popular spots like Schluter Beach are perfect for swimming, boating, or catching spectacular sunsets. Visit Winnequah Park! This 45-acre “crown jewel” of the city features a winding pond, pavilions, and the famous Monona Youth Dream Park, an extensive, medieval-style castle playground that is a massive hit with families. A must is a visit at Aldo Leopold Nature Center: A peaceful, enchanting sanctuary offering hands-on environmental education, hiking trails, and interactive programs for all ages. Certified as a bronze-level bike-friendly community, Monona offers extensive, safe cycling routes and convenient, quick connections straight into downtown Madison. Monona is home to local favorites like Buck & Honey’s, Wayward, and the Monona Farmers’ Market. Wisconsin’s first Topgolf is currently under construction in Monona, This 37,000-square-foot facility is scheduled to open in the fall of 2026.
26. Monroe (45min.):
The town of Monroe is known as the “Swiss Cheese Capital of the USA,” offering a blend of historic downtown charm, local breweries, and outdoor adventures. Key highlights include touring the Minhas Craft Brewery, one of the oldest in the US, sampling Limburger cheese at Baumgartner’s, and exploring the historic courthouse square. Explore the historic downtown square and stroll around the National Historic District, featuring the 1891 Green County Courthouse, unique shops, restaurants and cafes. Join a Minhas Craft Brewery tour and visit the Lazy Mutt Lounge for beer tastings and take a tour of one of the nation’s oldest breweries. Rent an ATV/UTV or hike/bike the 47-mile trail that connects Monroe to neighboring counties. Dine on authentic Swiss cuisine at Turner Hall, a historic landmark setting . Relax in Twining Park, which features disc golf, tennis courts, and a swimming pool. More popular dining spots are: Pancho & Lefty’s for ribeye steak sandwiches (cash only), Vince’s Restaurant & Pizzeria, known for Italian baked pasta dishes, the Bullquarian Brewhouse, a casual brewery and bistro in downtown and Amy’s Corner Cafe, a downtown favorite for breakfast and homemade lunch specials.
27. Mount Horeb (35min.):
Mount Horeb is known as the “Troll Capital of the World”. Stroll down Historic Main Street (known as the “Trollway”) to discover over a dozen life-sized, hand-carved wooden troll statues hiding in front of shops and businesses. Explore the glowing, underground crystal formations at Cave of the Mounds, or hike and mountain bike at nearby Blue Mound State Park. For an easy stroll, access the 40-mile Military Ridge State Trail right in town. For farm-to-table dining, experience local heritage at Campo di Bella for estate-grown wine and heritage-breed dinners, or grab European chocolates and treats at Sjölinds Chocolate House. A cultural highlight is a visit of the award-winning Driftless Historic to learn about the region’s unique un-glaciated landscape and Scandinavian roots. Best of (near) Madison’s winter spots to ski, tube or snowboard is the family owned Tyrol Basin. In the summer, you can also hike and enjoy a bite at the Tyrol Tavern or play sand volleyball – a beautiful gem to visit & perfect for recreation in every season.
28. New Glarus (40min.):
New Glarus is famously known as “America’s Little Switzerland”, an affectionate nickname that highlights the village’s deep-rooted Swiss heritage, alpine-style architecture, and rich cultural traditions. The town is filled with outdoor Swiss art and decor and local small shops and just walking around town is fun here! The Sugar River State trail and Badger State trail offer miles of scenic, wooded paths for biking and walking right near the village. Step Back in Time and explore local heritage at the 14-building Swiss Historical Village Museum or the unique Chalet of the Golden Fleece Museum. New Glarus is famous for craft beers you can only find in Wisconsin. Their original Riverside brewery features a rock garden, retail store, and outdoor patio. This beautiful little town has authentic Swiss dining like no other! Head to downtown chalets like the Glarner Stube for traditional Swiss fondue and Rösti potatoes, or grab fresh pastries at the New Glarus Bakery. The New Glarus Hotel and Restaurant is currently under construction but promising an amazing new opening and dining experience this fall.
29. Oregon (15min.):
Oregon is a charming, tight-knit village. It celebrates its quaint downtown, abundant green spaces, and relaxed, small-town atmosphere while still being an easy commute to big-city amenities. Oregon’s top activities include the Abundant Parks & Trails. The village boasts 18 community parks. It connects directly to the Madison area’s extensive bike network via the paved Badger State trail, and borders the 625-acre Capital Springs State Recreation Area, which offers excellent hiking, biking, and cross-country skiing. Don’t miss a visit at Anderson Farm County Park; a highly popular local destination featuring beautiful rolling hills, restored prairies, and shaded walking paths. Finally, known as one of the best ice facilities in Dane County, Oregon’s Ice Arena offers open skate sessions, hockey, and camps. Check out the town’s cozy hangouts. You can grab a coffee and locally baked goods at Firefly Coffee House, or relax with a drink on the back patio at the Wine Reserve. For the best brunch ever, try Sonny’s Kitchen which is located in downtown Oregon inside a historical house built in 1908.
30. Paoli (20min.):
The historic hamlet of Paoli is famous for its riverside charm, local craft brews, shops, art, live music and artisan dairy. Paddle the Sugar River. The meandering, calm waters of the Sugar River make it perfect for kayaking or stand-up paddleboarding. You can rent equipment and arrange shuttles locally through Sugar River Outfitters. Browse Local Boutiques and listen to live music at the Mill, a historic stone mill building that houses artisan shops, local boutiques, and coffee spots in a scenic, park-like setting. The Mill also offers a variety of live music. Be sure to also check out Landmark Creamery Provisions for award-winning local cheeses and hand-shaped butter. Bike the trails. Paoli is the epicenter of the local cycling scene, lying right at the crossroads of the Military Ridge and Badger State Trails. New and unique is Paoli’s new public, permanent outdoor sauna and natural cold plunge. Experience where nature, wellness, and community meet. Best places to eat and drink are: Seven Acre Dairy Company, housed in a beautifully restored 135-year-old dairy factory. This spot is a culinary anchor and amazing experience and has outdoor seating. Enjoy farm-to-table brunch, pastries, and house-made soft serve at the Seven Acre Dairy Cafe. For a more elevated experience, book a table at their on-site restaurant, Little Cloud, known for locally inspired dishes and artisanal cheeses. Paoli Schoolhouse is another amazing culinary experience. This American bistro is located in a 1864 schoolhouse and offers a rustic fine-dining experience. You will find French and New American-inspired dishes like Prime Rib Hash and Tres Leches French Toast. Also, try The Hop Garden and enjoy wood-fired pizzas and craft brews in a picturesque outdoor beer garden. It is highly family- and dog-friendly.
31. Portage (45min.):
Portage is famously known by the phrase, “Where the North begins”. This historic city sits at the natural meeting point of the Fox and Wisconsin rivers. Portage offers a mix of rich pioneer history, outdoor recreation, and local dining. Step back in time at the Historic Indian Agency House, an 1832 interpretive site, or tour the nearby Fort Winnebago Surgeon’s Quarters. Hike the Ice Age trail and take a walk along the Portage Canal segment or climb nearby Gibraltar Rock for breathtaking 200-foot cliff views of the Wisconsin River Valley. Relax at Pauquette Park or cool off with a swim at Silver Lake during the summer. Catch a show and visit the Portage Center for the Arts to view gallery exhibits or catch a live performance in their theater. Finally, enjoy a classic Wisconsin supper club experience at Cimaroli’s, then stop by Craig’s Popcorn Corner downtown for a sweet treat.
32. Prairie du Sac (40min.):
Prairie du Sac is a picturesque riverfront community. It is best known as the “Bald Eagle Capital of the Wisconsin River,” famously drawing large numbers of wintering eagles to the open waters below its hydroelectric dam. Top things to do in Prairie du Sac include exploring the scenic Wisconsin River, visiting the historic Wollersheim Winery, and hiking the popular Great Sauk State trail, a popular, paved trail for biking and hiking that runs along the Wisconsin River and through town. This charming riverside community offers a mix of outdoor recreation and local history, often combined with neighboring Sauk City as “Sauk Prairie”. Enjoy wine tastings, distillery spirits, and dining at Wollersheim, a historic hillside winery overlooking the Wisconsin River. Visit Prairie Du Sac Dam, a historic dam providing views of the river, power house, and bald eagle spotting in the winter. The Ferry Bluff State natural area offers stunning views of the river valley and great hiking trails. A former army ammunition plant was turned into a recreational area with hiking trails and panoramic views. Visit the Sauk Prairie Area Historical Society (Tripp Memorial) Museum and learn about local history with hands-on activities for children. Explore the Culver Community Park, a large, multi-use park featuring sports fields, a skate park, a dog park, and a playground. Enjoy outdoor activities, rent kayaks or canoes at Bender’s Canoe Rental to explore the Lower Wisconsin Riverway. For dining, Prairie du Sac offers a mix of cozy local diners and scenic riverside spots. Top dining spots include the Water Street Social Club for great food and waterfront views, Que’s Bar & River Deck for pub fare and a scenic outdoor deck, and the Prairie House Food & Spirits for classic American dishes.
33. Sauk City (35min.):
Sauk City is the “birthplace of Culver’s” and the oldest incorporated village in Wisconsin. Sauk City offers an incredible blend of outdoor recreation, scenic river views, and unique local dining. Top activities include exploring the Great Sauk State Trail, paddling the lower Wisconsin River, and grabbing a bite at local favorites like the Dorf Haus or Vintage Brewing Co. Bike, run or hike the Great Sauk State trail, a paved, multi-use trail that runs along the Wisconsin River. Gab craft beers at Vintage Brewing Co. Rent kayaks, canoes, or tubes from local outfitters like Bender’s Bluff View Canoe Rentals to explore the Wisconsin River or camp on the sandbars. Treat yourself to German cuisine at the Dorf Haus or check out Wollersheim for a scenic bistro meal. Head just a few miles East to On the Rox for homemade pizza, cold drinks and great cocktails, and a large outdoor patio where goats roam freely.
34. Spring Green (45-55min.):
Spring Green is an artsy, world-class Driftless region village located just 40 miles west of Madison. It is famous for its beautiful green rolling hills. Explore the world-famous Taliesin and tour the iconic estate, studio, and school designed by legendary architect Frank Lloyd Wright. A must-see is The House on the Rock. Experience this sprawling, eccentric architectural marvel featuring the world’s largest indoor carousel and the breathtaking Infinity Room. Catch a Show at American Players Theatre and enjoy world-class classical theater under the stars at this spectacular outdoor amphitheater, which kicks off its season every spring. Hike the Spring Green Preserve and wander through a landscape of rolling sand dunes and native prairies right in the Wisconsin River valley. Canoe the Wisconsin River! Rent a kayak or canoe from local outfitters like the Wisconsin Canoe Company to explore the scenic sandstone bluffs. Best places to eat include The Shed, a local institution famous for its burgers, pizza, and Friday fish fry. A secret tip: It’s also the go-to late-night hangout for the actors from the American Players Theatre. The Reunion Family Restaurant offers a highly praised, thoughtful, and creative menu. The Spring Green General Store is a charming spot to grab a coffee, a light international/American lunch, and browse unique gifts. The Riverview Terrace Cafe at the Taliesin Visitor Center offers great sandwiches and stunning views of the surrounding valley. It is famously the only restaurant Frank Lloyd Wright ever designed. The Arthur’s Supper Club is a classic Wisconsin supper club experience perfect for getting prime rib, steak, and a traditional Wisconsin Old Fashioned!
35. Stoughton (30min.):
Stoughton is the proud birthplace of the “coffee break” and a charming Yahara River haven renowned for its vibrant downtown Opera House and rich Norwegian heritage. Stoughton is a very charming town. Best activities include catching a show at the restored 1901 Stoughton Opera House, exploring the Livsreise Norwegian Heritage Center, shopping downtown boutiques and art galleries, and finally paddling the scenic Yahara River. The river runs right through the city, making it a great, quiet spot for kayaking and canoeing. Don’t miss Cider Mill. Grab a drink or tour the grounds at Mershon’s Cidery, located right in the heart of town. Spend time at Lake Kegonsa State Park, located just a short drive from downtown. This park features forested trails, marsh boardwalks, and beaches for both people and pets. Have some family fun at Eugster’s Farm Market, perfect for a group outing or families, this working farm features a petting zoo, market, and seasonal events. Stoughton has a great dining scene with plenty of highly-rated options. Top choices are: The Feiring, offering an excellent fine dining experience in a cozy, trendy environment; the Water Street Tavern offering a classic Wisconsin supper club vibe with an incredible riverfront patio. Locals highly recommend their prime rib, fish fry, and Old Fashioned’s. Then there is Santo Tequila Stoughton, best known for Mexican food. Reviewers rave about their generous portions and excellent margaritas. Try Pota Madre! This popular spot specializes in Norwegian street food, offering delicious, loaded baked potatoes with great vegetarian options. Finally, there is Springers, directly on Lake Kegonsa, this is a laid-back dockside grill offering classic Wisconsin pub grub, fish fries, and a great lake view.
36. Sun Prairie (20min.):
Sun Prairie is the “Groundhog Capital of the World”, famous for its legendary meteorological prognosticator, Jimmy the Groundhog. Known also historically as the home of artist Georgia O’Keeffe, this vibrant, rapidly growing community just northeast of Madison perfectly combines a charming small-town feel with modern city conveniences. Catch heart-pounding dirt track races featuring midget and sprint cars during the summer months at Angell Park Speedway. Enjoy beautiful trails, disc golf, and scenic green spaces at the Creek County Park. Stroll through the local shops and grab a coffee at the Sun Prairie Chamber of Commerce plaza downtown. Best eateries include Salvatore’s Tomato Pies, famous for scratch-made pasta and award-winning craft pizzas using local ingredients; also Buck & Honey’s which has a great deck overlooking the water, serving creative American fare and great cocktails. Also try Full Mile Beer Co. & Kitchen, a cozy brewpub downtown that features wood-fired pizzas and stellar craft beers. And finally visit Meze Mediterranean Grill which is top-rated in the area for authentic Mediterranean dips, gyros, and kebabs.
37. Verona (20min.):
Verona is known as “Hometown U.S.A.”, a charming, bike-friendly suburb. It offers the perfect mix of peaceful, small-town living and bustling big-city convenience, best known for its outdoor recreation and as the headquarters of medical software giant Epic Systems. Verona has lots to offer for nature lovers. Hike the Ice Age Trail! The Ice Age Junction pathway and terminal moraine segments run right through Verona. It is heavily wooded and excellent for a scenic hike or run. Check out the Military Ridge State trail. This 40-mile paved route is perfect for biking and hiking, running right through the heart of town. If you golf, try the PGA-recognized University Ridge Golf Course, which hosts the annual American Family Insurance Championship. You have to schedule a free, self-guided tour of the amazing EPIC campus, a sprawling, 1,100-acre fantasyland where healthcare technology meets pop culture, featuring heavily themed office buildings inspired by Alice in Wonderland, Harry Potter, and The Wizard of Oz. The EPIC campus is something not just unique for here but one of a kind in the world. Unwind with a local pint at the massive Wisconsin Brewing Company or Hop Haus Brewing Company in downtown Verona or refuel after a day on the trails by grabbing lunch or dinner at Sugar River Pizza. For coffee lovers, check out Alice Good Specialty Coffee. It is highly regarded as the top coffee shop in Verona, and known for its high-quality, 100% Colombian coffee, airy atmosphere, and a lovely outdoor porch.
38. Waunakee (25min.):
Waunakee offers a great blend of rural charm and modern dining, just north of Madison. Best things to do and explore include Schumacher Farm Park which is a beautiful, historical farm park, offering walking trails, heritage buildings, and seasonal community events. Visit the Bolz Conservancy which features a peaceful one-mile loop trail that rewards hikers with beautiful views of the State Capitol. Finally, stroll down Main Street to check out the Arts on Main steel art displays and visit local boutiques.Top experiences include enjoying a local brew on a rooftop patio, hiking peaceful conservancies, and dining at cozy supper clubs or modern cafes. Visit the Lone Girl Brewing Company, known for its local craft beer and an excellent rooftop patio offering a great view of downtown. Go to Rex’s Innkeeper, a classic Wisconsin supper club featuring a great Friday fish fry and a famous salad bar. Visit Era Cafe, a local favorite for brunch and lunch, offering unique dishes like Avocado Bacon Benedict, skillets, and craft cocktails. Finally, check out the Red & White Wine Bar, a trendy, self-serve wine bar featuring a stunning second-level loft and a great patio.
39. Waterloo (40min.):
Waterloo is a charming town known as the birthplace of Trek Bicycles and for its access to the scenic Glacial Drumlin State trail. Also, explore Waterloo Regional Trailhead, the central hub for biking and hiking in the area, offering a well-kept facility and easy access to trails. What’s more, visit Waterloo’s Firemen’s Park, a premier spot for family activities with playgrounds, fishing, and a picnic area and finally, Dr. J.S. Garman Nature Preserve which is perfect for a quiet hike to enjoy nature, featuring several trails and restored mounds. For family fun, head out to Little Amerricka, located just 10 minutes away in Marshall, this spot is perfect for families with younger kids looking for classic amusement rides. For dining, visit Hubbleton Brewing Company, a highly-rated local brewery featuring craft beers as well as the MT Bar, a local favorite for casual dining. Finally, we love Stubby’s Bowl, a fun spot for bowling and social activities and Hartwig’s Waterloo Diner, a classic spot for a local Wisconsin meal.
40. Windsor (25min.):
Windsor is a growing, upscale suburb, famously described as “a place to get away from the Madison area a little bit, that has so much community life. Top things to do in Windsor include exploring the natural trails at Token Creek Conservancy, enjoying family-friendly activities at Windsor Community Park, and visiting local favorites like the Mousehouse Cheesehaus. Outdoor activities and parks include the Token Creek Conservancy; 190 acres of land, excellent for hiking, bird watching, and snowshoeing; the Windsor Fireman’s Park: A central community park with playground equipment and picnic areas; the Windsor Gardens Park, known for its unique bicycle training path for children; Elmer and Edna Culver Wetlands Conservancy: A quiet, park-like area popular for hiking. Finally, the Cherokee Marsh Conservation Park offers extensive wetlands and trails with scenic views. For dining, check out The Bar Next Door for burgers, sandwiches, and great cocktails; the Rodeside Grill, known for fast service and popular American dishes like barbecue Mac n’ cheese and the Branch & Daughter, a local market known for having excellent pizza.
