7 Autumn-Ready Wisconsin Towns For A Weekend Retreat
Fall is a magical time of year. The leaves are transforming into a glorious autumnal canopy, the crisp smell of woodsmoke fills the air, and shorter days give way to warm, cozy nights. In Wisconsin, fall creeps in slowly, spreading from north to south, with peak color occurring between mid-September and mid-October. The sunlight may be waning, but there’s still a lot going on in the state’s charming small towns at this time of year. From lively fall festivals to pumpkin parades, and from apple picking to leaf-peeping, fall activities are in full swing in the Badger State, making it the perfect time to plan a Wisconsin weekend getaway.
Sister Bay
At this time of year, the biggest, must-see event in the waterfront village of Sister Bay is Fall Fest. A lively, two-day celebration in mid-October, the annual Fall Fest includes a parade, live music, food and drink, kids’ activities, and an arts and crafts show. For more fall fun, visit Seaquist Orchards, where you can pick your own apples on October weekends. The farm also hosts an Apple Festival at the end of September. Don’t worry if you miss their events, the onsite bakery and farm market are open from May to November.
Three Springs Nature Preserve is the ideal location for a stroll on a crisp fall day. This 515-acre conservation area covers scenic creeks, springs, and wetlands, which are home to a diverse range of wildlife, including Sandhill Cranes and the rare Hine’s emerald dragonfly. Take the 1.9-mile hiking trail and check out the scenic outlooks for some beautiful fall views. Make your weekend extra special with a night at the Liberty Lodge, a charming inn that doubles as a local historic landmark. Founded in 1898, the lodge is now a luxurious bed and breakfast with old-world charm.
Eagle River
Located in the midst of 28 lakes, Eagle River sits on the largest chain of freshwater lakes in the world. Scenic and charming, this small town in the heart of Wisconsin’s Northwoods is the ideal place to spend an outdoorsy fall weekend.
Take in the autumnal foliage with a trip to Eagle Lake County Park, a recreation area on the shore of Eagle Lake which offers walking trails, a swimming pier and beach, and picnic facilities. See the lakes from a one-of-a-kind cruise with Eagle River Pirates. This family-friendly attraction sets sail across six lakes aboard a pirate ship for a unique seafaring adventure.
Eagle River isn’t just famous for its natural attractions however. The town is also a stop on Wisconsin’s ‘Cranberry Trail’ and celebrates each fall with a Cranberry Fest that takes over the town with fruit-themed games, food, drinks, and entertainment. The event takes place the first weekend of October at the Vilas County Fairgrounds.
For a true backwoods experience, stay over at Eagle River Treehouses and sleep among the fall foliage. The resort’s rustic but cozy cabins are located in woodlands between Voyageur and Eagle Lakes. Designed with families in mind, each cabin has a fully equipped kitchen, multiple bedrooms, and a family room.
North Freedom
Nestled in the Baraboo hills of southwest Wisconsin, North Freedom is beautiful at any time of year but especially colorful in the fall. The tucked-away town is the home of the Mid-Continent Railway Museum which offers one-hour Autumn Color tours onboard restored early 1900s coach cars. The leaf-peeping trip travels through a beautiful tree-covered valley, following the tracks of the historic former Chicago & North Western rail line. See more of the stunning landscapes around North Freedom at nearby Devil’s Lake State Park. The park offers biking paths, hiking trails, fishing, rock climbing, and more. There are 29 miles of trails in the park, ranging from beginner hikes to more difficult routes.
The Wisconsin Big Cat Rescue and Educational Center, just ten minutes west of North Freedom, is a nonprofit dedicated to rescuing abandoned big cats. Home to tigers, lions, and leopards, the center offers tours and feeding experiences for those who want to see these majestic felines up close. For a truly unique overnighter, book a cabin at the rescue and spend the night with the big cats. The center has two accommodations to choose from, the Family Cabin and the Spa Cabin, both of which overlook the big cat area.
Germantown
With a name like Germantown, it’s no wonder this historic community in southeastern Wisconsin is famous for its Oktoberfest. A longstanding fall tradition, the festival has been running for over 30 years and includes music, dancing, crafts, a car show, and the annual Dheinsville Dachshund Dash, when sausage dogs race for the title of champion.
The celebrations take place at Dheinsville Historic Park, which is also home to the Bast Bell Museum, a specialty museum showcasing over 5,000 bells from around the world in a restored 1870 barn. If you miss Oktoberfest, you can still enjoy a taste of fall at Apple Works Winery, which offers a selection of award-winning wines from barrel-aged reds to light and crisp whites. Relax in budget-friendly comfort when staying the night in Germantown with a room at the Best Western Germantown Inn. This Best Western property has 46 guest rooms, a pool, a spa tub, and a king suite with a whirlpool bath and fireplace.
Luck
A historic community in rural Wisconsin, Luck was originally founded by Danish settlers. It takes its name from loggers who passed through the area in the 1800s on their way to the St Croix River. If they made it as far as Butternut Lake, where the town is situated, they considered themselves lucky. Luck is the gateway to Straight Lake State Park, home of some of the best fall hiking in Wisconsin. See the colorful canopy with amazing views along the Ice Age National Scenic Trail or Rainbow Lake Trail. The trees aren’t the only scenic attraction; watch out for some of the park’s resident wildlife, which includes bald eagles, trumpeter swans, and river otters.
Dive into Luck’s long history at the Luck Historical Museum on Main Street. The museum tells the story of the town, including its association with Duncan Yo-Yos and how it came to be known as the ‘Yo Yo Capitol of the World' from 1945 to 1963. If you’re looking for hometown entertainment on Friday or Saturday night, head to the Bunnycup Winery for some live music and locally-made wines. The winery also hosts an ‘Unfussy Fall Fest’ on the first Saturday of October, which includes a vendor fair, alpaca petting, BBQ, live music, pumpkin sale, and mulled wine.
Luck is the perfect town to indulge in another seasonal favorite — fall camping. There are ten hike-in campsites at Straight Lake State Park but you can also camp in comfort at Lazy Luck Cabins, a secluded four-cabin resort on Butternut Lake. The cabins are equipped for year-round use with full kitchens and bathrooms.
Fish Creek
Something very special happens in the charming waterside town of Fish Creek at the end of October. The town comes together for a quirky tribute to the fall season with Jack O’Lantern Days. This hometown Halloween includes a costume parade, games, trick or treating, and the Fish Creek Haunted Trail, a spooky walk through the town park’s trails and bridges at dusk. Enjoy more fall-themed hiking, but without the scares, at nearby Peninsula State Park. Known as a prime destination for fall foliage, this huge preserve contains a sand beach, a lighthouse, sky-high bluffs, a nature center, and 8 miles of shoreline.
Spend a crisp fall afternoon wandering around the Edgewood Orchard Galleries, a unique outdoor art gallery. The property features a restored fruit barn, sculpture garden, and original artwork from over 150 artists. Edgewood Orchard Galleries is open daily until October 27. Fish Creek has a charming and walkable downtown that overlooks the harbour. Stay at the centre of the action with a room at the Main Street Motel, conveniently located within walking distance of the beach, shops, and restaurants.
Bayfield
Wisconsin’s smallest city, Bayfield, is a vibrant harbor town on the shores of Lake Superior. Known as ‘the berry capital of Wisconsin’ thanks to the large number of berry farms in the area, Bayfield is famous at this time of year for another fruit. At the start of October, the town hosts the Bayfield Apple Festival. This three-day event first began in 1962 and has grown into a beloved fall tradition which features live music, food vendors, carnival, and apple orchard tours. The festival highlight is a grand parade and the crowning of the Apple Festival King and Queen.
Bayfield’s proximity to Lake Superior means the fall colors come a little later in the season, typically around mid-October. The best way to see them is to take a drive on Highway 13, the Wisconsin Lake Superior Scenic Byway, also known as the Fruit Loop, as it winds past orchards, cideries, and wineries.
For more dazzling autumnal views, visit the Apostle Islands National Lakeshore, located on the northern tip of the Bayfield Peninsula. The park covers 21 islands, sea caves, cliffs, and the highest concentration of lighthouses in North America. See it at its autumnal best with a cruise from Apostle Island Cruises. The company’s 55-mile Grand Tour cruises around the park’s many highlights and lasts 2.5 to 3 hours. Make your trip to Bayfield especially memorable with a stay at the Artesian House Bed and Breakfast. Nestled in 25 wooded acres, this contemporary eco-lodge offers a luxurious yet rustic retreat with stunning views and a spacious outdoor patio from which to enjoy the fall scenery.
Fall Fun In Small Town Wisconsin
Fall is the perfect season to take a weekend getaway. The summer crowds have gone, the scenery is ablaze with colour, and you can relax, recharge, and reset before winter roars in. Everyone has their own idea of the perfect weekend, but whether you’re looking for somewhere to take the family, a romantic break, or a chilled out retreat, the Badger State’s small towns have it all. Celebrate the season with these charming communities and get a true Wisconsin welcome.
