13 Coolest Wisconsin Towns For A Summer Vacation In 2025
There is enough charm in Wisconsin to go around the year, but summers are particularly special! The warm weather presents the perfect atmosphere to head out for remarkable adventures on the toasty waters of the Great Lakes. With most travelers trickling into famous destinations like Madison and Milwaukee, the smaller towns are an excellent alternative for those who appreciate a sense of privacy and an easygoing vacation experience.
Luckily, there is no shortage of options, and each destination comes with distinct charm and unique points of interest. Whether you want to attend a premier festival along Lake Superior shores in Ashland or visit the world-class water parks of Wisconsin Dells, here are the coolest Wisconsin towns for a summer vacation in 2025.
Lake Geneva
Lake Geneva has been attracting vacationers since the 1800s, and it doesn't seem to have lost its allure. The town has beautiful waterfront scenery that transforms into the perfect playground for summer tourists. Vast stretches of sand at Riviera Beach welcome you to bask on the shore and enjoy a dip in the warm waters of Geneva Lake. Alternatively, you can opt for a lazy stroll along the neighboring Lake Geneva Shore Path. Spanning about 21 miles, the scenic walking path boasts some of the most spellbinding views of the water.
Lake Geneva also hosts a lineup of exciting summer festivals to spread the warm-weather cheer across the town. The annual Venetian Festival, planned for August 2025, is one of the most anticipated and offers five days of pure fun, featuring live music, craft fairs, carnival rides, and more.
Wisconsin Dells
The warm weather in summer perfectly complements the renowned waterparks in Wisconsin Dells to deliver an unforgettable retreat for the whole family. Guests flock in droves to the Kalahari Indoor Waterpark to immerse themselves in aquatic adventures across its 125,000 square feet of lazy rivers, waterslides, and kiddie pools. Kids can have a blast encountering exotic species at the Timbavati Wildlife Park. This 25-acre sanctuary is home to beautiful animals like giraffes, tigers, and monkeys, who promise remarkable encounters.
Alternatively, they won't mind being spectators to mind-boggling illusions at the Rick Wilcox Magic Theatre. The family-friendly venues leave audiences in awe of comedic magic tricks performed by professional magicians.
Baraboo
Between its wonderful circus heritage and beautiful natural scenery, Baraboo is a fabulous location to spend a summer vacation in Wisconsin. A visit to Circus World introduces you to the community's rich circus history, featuring the Ringling Brothers' heydays in the 19th century. The museum showcases different memorabilia from the period and hosts live circus shows throughout the summer. The town celebrates the Big Top Parade to honor its circus heritage. Scheduled for June 2025, the spectacle incorporates various forms of family-friendly entertainment with a circus theme.
Baraboo provides plenty of exciting outdoor getaways for ardent adventurers, including Devil's Lake State Park. This naturally endowed reserve boasts a 360-acre lake surrounded by lush forests and picturesque quartzite bluffs, and is ideal for hikers, swimmers, campers, and sightseers.
Sister Bay
Sister Bay is an adorable waterfront village in Door County, known for its small-town feel, lake adventures, and delectable dining scene. The town spoils summer travelers with a 600-foot waterfront at Sister Bay Beach. Its sandy shores are popular among sunbathers, picnickers, and strollers looking to revel in the majestic views and soothing breeze. Meanwhile, guests can book a trip with Sail Door County to get on the water and get a unique perspective of Green Bay's unmatched beauty.
Culinary enthusiasts will relish sampling mouthwatering Swedish eats at Al Johnson's Swedish Restaurant, as festival lovers target the Sister Bay Marina Fest in August 2025 to celebrate a local tradition with live music, great food, fireworks displays, and children's activities.
Sturgeon Bay
Sturgeon Bay boasts a strategic location on the Door Peninsula, which results in a blend of scenic beauty and maritime heritage. The mild summer weather encourages excursions in the great outdoors, which you can find plenty of at Cave Point County Park. This sprawling lakeside wilderness offers miles of walking trails that let you discover rugged limestone bluffs, underwater caves, and unprecedented views of Lake Michigan. The Door County Maritime Museum documents Sturgeon Bay's storied maritime history through piles of relics, memorabilia, and artifacts.
The venue is also the site for the Sturgeon Bay Maritime Week. This Labor Day Weekend spectacle, to be held July 31-August 5, celebrates the region's nautical heritage with ceremonies, classic boat shows, and other fun activities throughout the week.
Chippewa Falls
This Chippewa County community has all it takes to make your Wisconsin summer retreat unforgettable, promising an endless supply of family-centric entertainment. Highlights include visiting the Irvine Park Zoo for rare encounters with fascinating wildlife. The small refuge provides a habitat for species like black bears, tigers, and bobcats. Elsewhere, those craving to step outside will prefer the 1,000-acre natural space of Lake Wissota State Park. Set on the shores of Lake Wissota, the park offers recreation like swimming, boating, camping, and picnicking.
Chippewa Falls hosts several festivals during summer, but the highlight has to be the Northern Wisconsin State Fair. Starting July 9, 2025, this popular annual extravaganza treats locals to five days of big-name entertainers, exhibitions, carnivals, food vendors, and more.
New Glarus
Christened "America's Little Switzerland," New Glarus maintains its small-town charm throughout the year, and summer is no exception for those lured by its rich Swiss heritage. Tourists love to explore the quiet downtown streets and interact with friendly residents. The Chalet of the Golden Fleece Museum stands out for its unique chalet-style architecture, a staple in downtown New Glarus. Meanwhile, culinary connoisseurs can indulge in savory traditional eats at the New Glarus Bakery, featuring Swiss pastries and other baked goods in a lovely atmosphere.
Also, you can attend the annual New Glarus Polkafest for a more immersive cultural experience. This two-day fair, from June 13-14, 2025, encourages you to bring your favorite dancing shoes for nonstop polka music and dancing.
Bayfield
This relaxed Bayfield County community serves as an entry point to the Apostle Islands National Lakeshores and welcomes tourists to explore Lake Superior's best-kept secret. Thanks to the Apostle Islands Cruises, guests are treated to a once-in-a-lifetime boat excursion into the heart of the lake, with a chance to marvel at dramatic coastal bluffs, hidden lake caves, and storybook islands. The clear summer skies are perfect for a golf session on the peaceful greens of Apostle Highlands Golf Course.
Bayfield's Concerts by the Lake make it one of the coolest Wisconsin towns for a summer vacation in 2025. This is because vacationers enjoy free music concerts every Tuesday and Thursday from June through August in a delightful outdoor setting overlooking the water.
Cedarburg
Cedarburg's location, about twenty miles from Milwaukee, provides an excellent reprieve from the busy city scene. The town has a storied and colorful heritage that guests can learn more about at the Cedarburg History Museum. This has a vast collection of relevant archives and artifacts, and so does the Cedarburg Cultural Center. Meanwhile, the Cedarburg Museum of Art presents a look at the local art scene. It exhibits sculptures, paintings, and other creations by different local artisans.
The community takes pride in a lively winery scene. One of the best times to sample this culture is during the Cedarburg Strawberry Festival. Scheduled for June 28 & 29, 2025, this fun spectacle allows attendees to indulge in all things strawberry, from sweet-tasting strawberry wines to delicious strawberry cakes.
Waupaca
Waupaca has a delightful setting in the Chain O' Lakes of Wisconsin, opening doors to amazing water-based adventures for summer vacationers. Many of these await at Hartman Creek State Park, whose 1,400-acre territory provides ready access to the water. Activities here range from fishing and boating to camping and water skiing. When hungry from all the adventure, consider stopping by Clearwater Harbor Waterfront Restaurant & Bar for a nice meal. The romantic eatery serves sumptuous American fare with a fine selection of craft cocktails and beers.
Elsewhere, tourists interested in local history can tour the Hutchinson House Museum. This Victorian-era home offers a window into the period with a rare exhibit of artifacts and furnishings depicting the life of early settlers.
Ashland
Ashland is a magnificent getaway on the serene shores of Lake Superior, known for its laid-back personality and pleasant lake beaches. The summer weather is tailored for unplugging along the sandy stretches of Maslowski Beach. This popular outdoor space presents over 1,400 feet of waterfront with shallow waters, attracting swimmers, sunbathers, and picnickers. Guests can also spend their time watching compelling live presentations at the Chequamegon Theatre, featuring talented performers from the community.
Meanwhile, festival lovers are in for an entertaining experience during Ashland Bad Days. This well-attended event is set for July 18-19, 2025, and unravels along the shores of Lake Superior. Tourists can look forward to an exceptional lineup of arts, crafts, food, live music, and games.
Hayward
Hayward made a name for itself with a storied fishing heritage, promising warm-weather travelers exciting fishing adventures. It is home to the National Freshwater Fishing Hall of Fame, whose exhibits chronicle the region's freshwater fishing history. However, the main attraction at the site is the 143-foot fiberglass muskie exhibited outside the museum, which always makes for an unmissable photo opportunity. Golfers of all skill levels can try their hand at the Hayward Golf Club, while those with kids can take them to Hayward City Beach for a swim.
Hayward celebrates its fishing heritage annually during the Musky Festival. This family-centered event incorporated arts and crafts, kids' games, live music, a beauty pageant, a carnival, and fishing contests to entertain all ages.
Washington Island
Vacationers seeking solitude for their summer getaway will entertain the idea of escaping to the secluded Washington Island. With almost five miles separating them from the mainland, the island is perfect for letting your hair down while walking on the smooth, rounded pebbles of SchoolHouse Beach Park. The Washington Island Farm Museum is an excellent stop for history buffs. The fascinating venue showcases rare exhibits of old farm implements, kitchen items, and tools originating from the late 19th century.
Visitors with a soft spot for the arts can stop by Trueblood Performing Arts Center to watch a moving stage presentation. Alternatively, the town will host the Washington Island Music Festival in August 2025, a great time to enjoy weeks of continuous music concerts.
Final Thought
If you are contemplating spending your summer in the Badger State, there is no shortage of fun spots to plan your trip. The mentioned coolest Wisconsin towns for a summer vacation in 2025 are only a fraction of the fun awaiting holiday makers and promise an authentic feel of the countryside. From the beautiful lakeshore in Ashland to the cozy small-town atmosphere in Sister Bay, each destination has the ingredients to guarantee you and your family a fantastic retreat.
