Your Fall Getaway Guide
Planning your next vacation? Turn here to find Wisconsin destinations near and far.
Dollar Lake Retreat
Right on the lakefront and just minutes from downtown Eagle River, Dollar Lake Retreat offers a cozy, design-forward escape for year-round visitors. With space for up to 14, the cabin feels cozy for couples and spacious enough for group vacations. “It’s not your typical Northwoods rental,” says owner Angie McGuire. “It’s curated, not kitschy – designed with intention, warmth and vintage charm that feels both elevated and welcoming.” Guests rave about the inviting spaces, warm hospitality and optional sauna experience that make it a true Northwoods destination. dollarlakeretreat.com
The La Crosse Region
Discover the beauty of La Crosse and Southwestern Wisconsin with a Bluff to Bluff Trolley Tour. It starts in historic downtown La Crosse before venturing into the bluffs in the surrounding
region. Visitors will descend through the Coulee Region and cross the Mississippi River into Minnesota, all the way to La Crescent, aka our neighboring state’s “Apple Capital.” The four-hour trek finishes with an orchard visit and tasty bites at La Crosse’s French restaurant, Le Chateau. explorelacrosse.com
The North Shore of Milwaukee
Fall colors come alive in Milwaukee’s North Shore neighborhoods. Options are plentiful. Sample local beers and sodas at the famous Sprecher Brewery. Take a walk through the Schlitz Audubon Nature Center or one of the area’s many parks and trails. Make sure to stop at Milwaukee’s Original Oktoberfest at Old Heidelberg Park on the grounds of Bavarian Bierhaus, where they are celebrating every weekend from Sept. 5-Oct. 5. Staying overnight? Glendale has seven hotels, each with free overnight parking. discoverthenorthshoremke.com
Mount Horeb
There’s no shortage of adventure in Mount Horeb, located in Wisconsin’s beautiful Driftless Area. Tie up your laces and head out to Dane County’s oldest county park, Steward Lake, for a hike, or camp at the highest point in Southwestern Wisconsin, Blue Mound State Park. Known as the “Troll Capital of the World,” Mount Horeb offers plenty of fun inspired by the mythical Scandinavian creatures – follow the town’s online Troll Map to find all 40 troll statues spread across the village (trollway.com/trolls). Visit local gems like Duluth Trading’s flagship store and Scandinavian-inspired Open House Imports, or Driftless Chocolates for a sweet treat. trollway.com
Greater Richland Area
Colorfest Weekend returns to Richland Center from Oct. 3-5. This three-day festival draws visitors from across the region, with events including the spectacular Canyon of Lights Nighttime Parade and the Wheels of Time-Hill Country Classic Power Show, showcasing classic trucks and tractors. Plus, the area is home to other autumnal experiences to enjoy throughout the season, like a visit to Oakwood Fruit Farm orchard, the Driftless Area views of Wild Hills Winery, or the numerous activities and pumpkin patch at Chicken Ridge Farm. greaterrichlandtourism.com
Sheboygan
The “Malibu of the Midwest” is just kicking off surf season this month. Surfers from all over the world visit Sheboygan’s sandy shores through fall and winter to catch a wave on Lake Michigan. Watch the action or get out on the water yourself with one of Sheboygan’s many rental options. Sheboygan’s Kohler-Andrae State Park is a popular destination, one of the last natural preserves on the lake, and was recently awarded a Wonders of Wisconsin designation from Travel Wisconsin. On top of its natural beauty, Sheboygan boasts the title of “bratwurst capital of the world.” Consider a stop by Sly’s Midtown Saloon, famous for its brat plate. visitsheboygan.com
• Curated Northwoods charm, spotlessly clean, locally owned
• A chef-worthy kitchen designed for cooking & gathering
• 300 feet of private lakefront
• 5 minutes from Eagle River
• Add a mobile sauna for next-level relaxation
“I love feeling like you are truly in the Northwoods while simultaneously being spoiled with every modern comfort.”
Whitewater
This autumn, take a leaf-peeping trip down the Kettle Moraine Scenic Drive, only an hour southwest of Milwaukee. Consider stopping to hike the region’s segment of the historic Ice Age Trail as part of the 2025 Mammoth Hike Challenge, in which hikers are invited to explore 44 miles of scenic trails to earn a challenge patch. And as we enter spooky season, you might want to book a Spirit Tour with Discover Whitewater, which will take you through the many haunted sites that earned Whitewater its nickname, “Second Salem.” discoverwhitewater.org ◆
Staycations
You don’t have to go far to enjoy a getaway. Consider paying a visit to one of these local spots.
Harley-Davidson Museum
This monument to motorcycle history is a must-see visit for bike enthusiasts and history buffs. The museum has over 100,000 square feet to explore, so you can easily spend an entire day learning about the creation of the iconic brand and checking out the extensive collection of motorcycles both old and new. harley-davidson.com/us/en/museum
The Plaza Hotel
Step back in time with a staycation at the Plaza Hotel, an art deco East Side spot that has drawn visitors and guests for 100 years. Start a day of exploration with brunch at Café at the Plaza, one of Milwaukee’s most beloved spots, with a horseshoe breakfast counter and a vine-covered outdoor patio. Modern accommodations round out the charming vintage rooms, perfect for a night of relaxation after a day exploring Downtown. plazahotelmilwaukee.com
Potawatomi Casino Hotel
This local casino just launched a new sports betting app. It allows guests on-site to place bets from anywhere in the casino. That means you can drop a bet while enjoying a meal at Dream Dance Steakhouse, sipping a latte at Cream City Coffee Co., walking between floors, or even playing a different game. potawatomi.com
