Wisconsin’s Door County has long been a playground for Chicagoans in summer. We flock there for the lush green wilderness, watersports, idyllic Lake Michigan views, cozy cabins and inns, quaint small-town shopping, fish boils, breweries and wineries, cheese curds—the list could go on endlessly. But the fun doesn’t stop when the temps drop. The crowds shrink drastically in winter, which makes it perfect for a relaxing and serene getaway for those that enjoy winter play and aren’t phased by the cooler temps. Read on for a few of our favorite wintertime activities in Door County and start planning a couples-only retreat (pssst. . . perhaps for Valentine’s Day?).


Fat Tire Biking

Destination Door County

Renting a fat tire bike is a great way to kick off your morning or combat a post-lunch food coma. The traction and low pressure of a fat tire bike floats you across terrain that would otherwise be unrideable: sand, mud, wet rocks or dense snow are conquerable.

Across the street from the entrance to Peninsula State Park in Fish Creek, you'll find Nor Door Sports & Cyclery. For about $10 an hour you can rent a bike and climb Skyline Road to Sven's Bluff. The stone fences and open meadows you see on your way are remnants from long-ago farms. If you time it right, you can hit the top for golden hour in late afternoon to catch spectacular views of the winter shoreline as the sun clocks out. 

Newport State Park protects 11 miles of rugged Lake Michigan shoreline near the northeast end of Door Peninsula and offers fat bike trails. 

Fat Biking Tips:

  • Put a shot of alcohol in your water bottle to keep it from freezing if the temps are below 32 degrees.
  • Wear booties over your shoes and thick gloves. If you layer the right way, you'll stay warm even on the coldest of days. 
  • It's counter-intuitive, but stay seated even when climbing a hill. Your bike needs your weight on the back tire to keep its traction.

Ice Skating

Destination Door County

Grab your partner's hand and glide weightlessly across the ice at Sister Bay Ice Rink. The outdoor rink has skate rentals, fires going to warm fingers and toes in-between figure 8s and concessions. While in Sister Bay, we'd also recommend a stop into Wild Tomato for made-from-scratch wood-fired pizza.


Wine Tasting

Destination Door County

When you hear "Wisconsin," you likely think of beer and cheese. But wine-making is growing rapidly in the state and Door County is seeing a lot of this action. The mixture of the soil and grape varieties uniquely found in Door County creates tastes you won't find anywhere else. You can plan a whole weekend vacation around following the 8-winery Door County Wine Trail. Most are open through the winter with precautionary restrictions related to COVID, but be sure to check with each winery before planning a visit.

One of the most visited wineries, receiving over 60k guests per year, is the award-winning Simon Creek Vineyard & Winery in Sturgeon Bay. Each of their wines has received recognition and awards in international competitions. Facility tours have been halted during COVID, but you can still enjoy a tasting. 

The largest winery in Door County is Door Peninsula. Their wine tours are not currently running, but their tasting sessions with more than 60 different wines and ciders are still available. Their shop filled with jams, spreads, oils, cheeses and home accessories is a great spot to grab gifts for friends. 

We also recommend family-owned Door 44 wines for their friendly and knowledgeable ownership and staff, on top of robust and varied wine choices. They don't serve food onsite, but they do have prepacked items you can purchase and take to your table. 

A cold-weather-themed must-do is to try an ice wine from the region. The grapes for these wines are frozen while still on the vine, and then pressed while still frozen. The sugars in the grapes do not freeze, but the water does. This results in very concentrated sugars and acids being extracted and the water staying behind as frozen ice. It's labor-intensive and the yields are small, but the resulting dessert wine is well worth the trouble. 

Morning Fuel-Up

Door County Coffee & Tea

Beignets may not be the first thing that comes to mind when you think of Door County, but Big Easy Bagel and Beignet will soon change that. Make them a first stop in the morning before you head out for adventuring for this french classic dusted in powdered sugar. For something a little less sweet, their menu offers build-your-own sandwiches, breakfast burritos and pizzas, biscuit sliders and more. 

Door County Coffee & Tea is located across the street from Door Peninsula Winery and is open for breakfast and lunch, or when you just need a quick caffeine jolt. Their shop is filled with gourmet foods and home decor and you can watch the roasting process in action on most weekdays. 

Lunch & Dinner Joints

Community-style fish boils are a decades-long tradition in Door county. Locally caught whitefish is boiled on an open fire in a large metal kettle and is typically served alongside potatoes and onions. It's a must-do while in the region to get the full local experience and The White Gull Inn, with it's warmth and charm dating back to 1896, is a great place to indulge.

For a taste of home, Sonny's Italian Kitchen & Pizzeria in Sturgeon Bay holds the title for the #1 spot in Door County for Chicago-style pizza. They also serve Napoletana-style pizza and have an impressive selection of pasta and salads. After dinner, we recommend a stop into Bridge Up Brewing Co., a small-batch brewery on the 1st floor that uses local ingredients with a wide range of flavor profiles.


Plum Bottom Gallery

Destination Door County

A fun way to remember your trip for years to come is by purchasing something special for your home from a local artist. Plum Bottom Gallery is a family-run art gallery that sits on 20 acres in Egg Harbor. They represent 100 artists from across the county that specialize in hand-crafted jewelry, paintings, pottery, metalwork, fiber, glass and printmaking. In addition, their resident artists have studios onsite where they create their one-of-a-kind pieces. 


Door County Cabins @ Plum Bottom


Door County Cabins at Plum Bottom offers three different sleeping options in Egg Harbor, a cabin, a cottage and a treehouse located on 20 acres amidst rolling prairies and woods. The 3-bedroom cabin is a great option for multiple couples as it features two king suites and a queen bedroom with an attached bathroom.

When in Egg Harbor, be sure to stop into Big Easy for fresh beignets that will make you feel like you woke up in New Orleans. 

Landmark Resort

Landmark Resort

The Landmark Resort is hidden in 40 wooded acres sprawling along a wooded bluff with panoramic views of the Bay of Green Bay. Their one-, two-, and three-bedroom suites are spacious and comfortable and include a fully-equipped kitchen, living room and a deck or patio. For summertime visits, they have 3 outdoor pools and 1 indoor pool that is open 24/7, year-round.

Located on the north end of the property is Landmark's onsite restaurant, Carrington Pub & Grill, where you'll find a good dinner selection of salads, steaks, fish and American classics. 

The White Gull Inn

Destination Door County

The White Gull Inn is a picturesque bed and breakfast loaded with charm and character located in the bayside village of Fish Creek. The property features meticulously maintained rooms, suites and cottages, some with fireplaces and whirlpools. They're famous for their traditional fish boil featuring Lake Michigan whitefish. Even if you don't stay at the Inn, stop in for breakfast, lunch, candelight dinners and the fish boils which are open to the public year-round.


Plan Your Route

Door County is on the Lake Michigan Circle Tour, which follows state highways around Lake Michigan through Illinois, Indiana, Wisconsin and Michigan. The tour is roughly 1,100 miles long and would take roughly 14.5 hours without stops. While that might be ambitious for a quick weekend away, you can enjoy bits of the tour on your way to Door County.

For a taste of the tour, we recommend jumping off 43 in Manitowoc and driving old 42 along the lake through Two Rivers, Kewaunee and Algoma. It adds a few minutes to your trip, but the drive through classic midwestern waterfront towns is worth the minor inconvenience. 

Mike Romer Photography

Pack your weekend full of snow-filled activities, or just enjoy the calm, quiet beauty of Door County. For more help crafting your perfect trip, visit doorcounty.com.

— Maria Chambers

Photos courtesy of Destination Door County. This trip was paid for by Door County Visitor Bureau but all opinions belong to the author. 


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