There’s something magical about Door County in the winter. The summer crowds are long gone, the shoreline is covered in a dusting of snow, and the whole peninsula takes on a quiet, cozy charm. If you’ve never visited Sister Bay in the off-season, you’re missing out on one of Wisconsin’s best-kept secrets- a place where adventure meets relaxation, where you can spend your day exploring the outdoors and your evenings sipping a handcrafted cocktail by the fire.
So, if you’re looking for a weekend escape that’s equal parts cozy and adventurous, this guide is for you. Let’s dive into the best places to stay, eat, sip, and explore on a winter getaway to Sister Bay.
Where to Stay: Cozy Lodging Options
Sister Bay offers some fantastic lodging options that are open year-round, and winter rates are often more affordable than peak season. Here are a few spots that offer that perfect mix of charm and comfort:
The Dörr Hotel – This newer boutique hotel is a stunning mix of Scandinavian-inspired minimalism and cozy Wisconsin hospitality. My hubby and I stayed here in January for my birthday weekend and spent our Friday snowy evening curled up by their massive lobby fireplace with some books and a bottle of wine, and it was pure bliss. Their fireplace lounge is the perfect place to unwind after a day in the snow, and the location puts you right in the heart of Sister Bay.
Country House Resort – If you want something peaceful and tucked away, this adults-only resort offers gorgeous views of the bay, private walking trails, and even in-room fireplaces for that extra cozy factor. One of my favorite winter mornings here was sipping hot coffee on the balcony, watching the snow gently fall over the water—an experience that truly felt like a scene from a holiday movie, I mean look at that view!
Pheasant Park Resort – A wonderful year-round lodging option offering spacious suites with fireplaces, an indoor pool, and a cozy atmosphere. It’s perfect for those looking for a bit more space while still being close to all the winter activities in Sister Bay. The last time we stayed here we grabbed takeout from Wild Tomato, poured ourselves a nice cocktail, and had a cozy night by the fire in our suite- honestly, one of my favorite parts of the trip.
Where to Eat: Best Year-Round Restaurants
Many of the well-known summer hotspots close for the season, but don’t worry-there are still plenty of delicious places to grab a bite in winter. Here are some favorites that keep their doors open all year:
🥞 Al Johnson’s Swedish Restaurant – No, the goats aren’t on the roof in the winter, but this legendary spot is still worth a visit. Order a plate of Swedish pancakes (a fan favorite) with lingonberries and a side of warm, comforting glögg (Swedish mulled wine). A go to in the summer as well; next door to the restaurant they have beer garden- Stabbur (pictured above- they have lawn games and live music too in the summer!)
🍕 Wild Tomato Wood-Fired Pizza – There’s nothing better than a hot, cheesy pizza on a cold winter night. Their locally sourced ingredients and cozy atmosphere make it a must-stop. They have vegan options too! Our go to the margarita pizza with vegan sausage. A sure spot to stop in the summer as well as they have an outdoor patio and a variety of beers and ciders on tap.
🥩 CHOP – If you’re craving a steakhouse experience, CHOP offers delicious cuts of meat, seafood, and craft cocktails (a top notch old fashioned) in a warm, welcoming environment. Their bruschetta is my favorite go to appetizer!
🍝 Osteria Tre Tassi – A rustic Italian gem in nearby Ellison Bay, this farm-to-table spot offers fresh, locally sourced dishes with a cozy ambiance. Try their handmade pappardelle with wild boar ragu or the wood-fired rosemary focaccia- both are packed with rich, comforting flavors that are perfect for a chilly winter evening.
🍽️ Husby’s Food & Spirits – A local favorite with hearty pub fare, a great beer selection, delicious blood mary’s and a laid-back vibe. Perfect for post-adventure comfort food and cocktail.
☕ Skip Stone Coffee Roasters – Start your mornings here with a locally roasted coffee and a fresh pastry before heading out for the day.
Outdoor Adventures: Embracing the Winter Wonderland
Winter in Door County means embracing the elements, and there are plenty of ways to do just that in Sister Bay and beyond:
🎿 Cross-Country Skiing & Snowshoeing – Peninsula State Park (just a short drive from Sister Bay) has beautiful trails for both activities. Rent gear from Bay Shore Outfitters in Sister Bay if you need equipment.
❄️ Ice Skating & Hockey – The Teresa K. Hilander Community Ice Rink in Sister Bay is a fun spot to lace up some skates and enjoy a classic winter activity.
🌲 Winter Hiking – Head to Newport State Park, Wisconsin’s only designated Dark Sky Park, for a peaceful winter hike. If you’re lucky, you might catch a stunning sunset or a sky full of stars.
⛸️ Sledding at Hill 17 – A hidden gem for some classic winter fun, this sledding hill in Peninsula State Park is a blast for kids and adults alike.
Shopping in Sister Bay
If you’re looking for a more relaxed indoor activity, shopping in Sister Bay offers a mix of charming boutiques, local crafts, and cozy finds:
🛍️ Spot – A trendy boutique featuring a carefully curated collection of stylish clothing, accessories, and home goods. Whether you’re looking for a unique sweater or a handcrafted candle, Spot offers a shopping experience that blends modern fashion with Door County charm.
🏡 Space – A beautifully designed shop showcasing Scandinavian-inspired home décor, minimalist furniture, and locally made artisan pieces. If you’re a fan of clean lines and cozy aesthetics, Space is a must-visit for design lovers looking to bring a touch of hygge into their home.
🛍️ On Deck Clothing Company – A great place to grab high-quality, classic apparel, perfect for layering up in the Wisconsin winter.
🕯️ Ecology Sports – This shop specializes in sustainable and outdoor gear, along with books, gifts, and cozy winter wear.
🛍️ Kindgoods – A charming boutique offering a mix of eco-friendly products, self-care items, and locally made goods- perfect for finding unique and thoughtful gifts.
Sip & Savor: Wine, Beer & Spirits Tastings
A winter getaway wouldn’t be complete without some delicious local drinks to warm you up. Luckily, Door County has some fantastic spots for tastings:
🍷 Door Peninsula Winery – One of the most well-known wineries in the area, offering a huge selection of fruit wines and classic reds and whites. Their winter spice wine is a must-try!
🍺 Door County Brewing Co. – Located in Baileys Harbor, this brewery has a fantastic taproom with live music on the weekends and a great selection of craft beers.
🥃 Hatch Distilling Co. – If you’re a fan of small-batch spirits, this is the place for you. Try their bourbon, gin, mead or one of their unique honey-based spirits.
🍎 Island Orchard Cider – For something a little different, visit this Ellison Bay cider house for French-style hard ciders made from locally grown apples.
Final Tips for a Perfect Winter Getaway
✔️ Dress in Layers – The winter weather in Door County can be unpredictable, so pack warm layers, waterproof boots, and all the cozy essentials.
✔️ Check Winter Hours – While many businesses stay open year-round, some have reduced winter hours. Always double-check before heading out.
✔️ Embrace the Slow Pace – Part of the beauty of a winter trip here is the peacefulness. Take it slow, enjoy the scenery, and savor the quiet moments.
✔️ Bring a Blanket & Thermos – Whether you’re watching a winter sunset over the bay or stargazing at Newport State Park, a warm blanket and a thermos of hot cocoa or mulled wine will make the experience even cozier.
The Best of Both Worlds
A winter getaway to Sister Bay is the perfect mix of cozy and adventurous. Whether you’re exploring the snowy trails, indulging in comfort food, or sipping on local wine by the fire, this charming Door County town offers a winter experience like no other. So pack your warmest sweater, grab your favorite travel buddy, and escape to the quiet beauty of Sister Bay this season-you won’t regret it. ❄️🔥
Have you visited Door County in the winter? What are your favorite spots? Let me know in the comments!
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