As summer fades and Wisconsin’s landscapes shift into shades of gold and red, September becomes the perfect time to sneak away for a cozy escape! Dreaming of mornings on the lake, nights under the stars, or waking up to the sound of farm animals? Every corner of Wisconsin has a stay perfect for you! From treetop hideaways to historic inns, here are a few handpicked spots where fall feels extra special.
Bayfield County: A Treetop Stay
Sometimes, the best way to experience fall in the Northwoods is from up above! And at Bayfield’s Boulder Ridge Treehouse, you’re invited to stay among Bayfield County’s towering pines. This unique stay offers an enchanting, panoramic view of the colorful canopy that sweeps across the hills each September.
Spend your mornings sipping coffee on the wraparound deck, then fill your afternoons with adventure. Paddle out to the famous sea caves along Lake Superior’s shoreline, or wander through nearby apple orchards that come alive during harvest with crisp picking, warm donuts, and fresh-pressed cider. A few local favorites include Apple Hill Orchard and Hillcrest Orchards, to name a few.
To experience the season at its fullest, plan your stay around the Bayfield Apple Festival, a beloved fall tradition for 63 years, featuring parades, tastings, live music, local artisans, and, of course, the Spectrum Carnival. Mark your calendars for October 3, 4, and 5, 2025!
After a day full of fun, whether you’re paddling the pristine waters of Lake Superior or celebrating the fall harvest, there’s truly no better place to curl up with a good book than your private treetop nook at Boulder Ridge.
La Crosse County: A Farm Stay
If you’re craving a simpler, slower pace, Rainbow Ridge Farms is the perfect September stay! Nestled on 35 beautiful acres in La Crosse County’s Driftless Region, this family-run working farm invites you to roll up your sleeves and dive into true country living.
As a guest, you can jump right into farm life—from milking dairy goats and feeding baby animals to collecting fresh eggs for breakfast—all while surrounded by rolling hills and peaceful pastures that are especially stunning this time of year.
Up for a hike? Don’t miss the famous “Monkey Tree,” where more than 50 friendly goats love to gather and greet visitors. And it’s not just goats—heritage pigs, chickens, turkeys, sheep, and llamas also call this farm home, all raised with lots of love and freedom to roam.
When you’re not playing farmhand, kick back in cozy rooms with views of the bluffs, or gather around the big dining table for an unforgettable game night. Ready to experience farm life your way? Check it all out at Rainbow Ridge Farms Bed & Breakfast!
Brown County: A Historic Stay
For history lovers, there’s nothing cozier than spending a night in a Victorian-era inn. The Astor House Bed & Breakfast, nestled in Brown County’s historic Astor neighborhood, offers a glimpse into Wisconsin’s past—with a warm welcome that feels just like home.
As the innkeepers lovingly call it, “Everyone’s House,” The Astor House is a place where guests become part of the story. Built in the 1880s, the inn is full of incredible historic details—from antique furnishings and exquisite woodwork to unique, character-filled guest rooms, each with its own personality.
Planning your visit in September? Perfect timing! Feel the buzz of a Packers game just three miles away at Lambeau Field, or find tranquility walking, running, or biking along the colorful Fox River Trail. For a more leisurely afternoon, explore local shops and cafés like LoCo WisCo or Bhava Coffee—two fan favorites. If you prefer a quiet day in, cozy up in The Astor House.
No matter what’s on your itinerary, each morning you’ll be treated to a hearty homemade breakfast, served with classic Wisconsin hospitality. It’s the perfect start to a day of adventures or a slow-paced unwind in this historic haven. Start planning so you can step into this timeless treasure firsthand!
Walworth County: A Lakeside Stay
The lake is calling, and fall is absolutely the perfect time to answer! With summer crowds gone, Walworth County slows down and fills the air with crisp breezes, vibrant foliage, and, of course, stunning sunsets. Lake Geneva Lodge offers cozy lakeside accommodations just steps from the water—so you can easily enjoy both relaxation and adventure.
Pack your walking shoes and hit the famous Geneva Lake Shore Path, a scenic 21-mile trail lined with historic estates that are spectacular against the backdrop of colorful fall leaves. Or hop on a boat cruise to see the kaleidoscope of autumn reflected in the calm, glassy lake.
If you’re more of a land explorer, downtown Lake Geneva beckons with boutique shopping, delicious dining, and fun fall events like the Geneva Lakes Antique and Classic Boat Show (September 26–28, 2025).
When the sun dips below the horizon, head to local favorites like Pier 290 for tasty food, handcrafted cocktails, and an unforgettable lakefront ambiance. Come see why this lakeside escape is a beloved yearly tradition!
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September is the perfect time to escape to one of the state’s cozy retreats! From treetop hideaways and working farms to historic inns and lakeside lodges, these handpicked spots across Bayfield, La Crosse, Brown, and Walworth counties offer unforgettable fall experiences. Embrace the crisp air, stunning scenery, and warm hospitality that make Wisconsin truly special. Your perfect fall getaway awaits!
*This article is brought to you with support from the Wisconsin Counties Association.
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Hailey Marien: Writer for Discover Mediaworks. A born & bred Wisconsinite with a love for fishing, hunting, and enjoying the great outdoors.
