Bayfield, WI Is The Coolest Small Town For Midwest Winter Adventures — Here’s Our Guide

If your winter travel wish list includes staying at a luxury wellness resort, scouting the northern lights, sipping cocktails at the United States’ first Native American-owned distillery, and hiking to sea caves at a National Lakeshore, I have the place for you. And if it doesn’t include those things, well… maybe it should (in which case, I have the place for you). A tiny midwestern city with a population of just 588 people.

I’m talking about Bayfield, Wisconsin, on the southern shores of Lake Superior. The town has long been a summer tourist destination as city dwellers visit the Apostle Islands and get out on the waters of the world’s largest freshwater lake (by surface area). But local entrepreneurs have worked diligently to create spaces that draw visitors year-round. From boutique hotels to wineries, distilleries, locally sourced food, and live music, this small town in Wisconsin town might be at its coolest in the dead of winter.

Here is our winter guide:

WHERE TO SLEEP:

WILD RICE RETREAT

Wild Rice Retreat
Emily Hart

The forested shores of the “unsalted sea” are peaceful and powerful all at once – the perfect spot for a wellness retreat. I spent my time in Bayfield enjoying the almost vortex-like good energy at Wild Rice Retreat, a resort retreat Heidi Zimmer opened in the summer of 2021.

The grounds are spectacular, with views of Lake Superior and wooded surrounds that took my breath away. Whether on a guided or personal retreat, the lodging options – inspired by natural shelters – Nest, RicePods, and Treehaus — are designed in a Scandinavian modern style that connects seamlessly with the outdoors.

Wild Rice Retreat
Emily Hart

Guests can opt to participate in daily offerings from movement classes (which I very highly recommend), intention setting, journaling sessions, guided forest bathing, art and jewelry workshops, candlelight yoga, and chakra balancing – to name a few. The dining offerings are included when booking directly, and I recommend trying as much fresh food as possible. Hike directly from the property into Bayfield via the Brownstone Trail or stay put to fully immerse in nature and enjoy the sauna, cold plunge, and Peace Pod for movement or meditation.

As someone who visits hotels, resorts, and wellness properties for a living, Wild Rice Retreat truly stands out, and I can’t wait to return.

ST. JAMES SOCIAL

St. James Social
Emily Hart

While I didn’t get a chance to stay in one of the eight boutique hotel rooms at the recently renovated St. James Social in downtown Bayfield, I was utterly impressed during a property tour and promptly put it on my list for next time. The founder, owner, and designer, Annalisa Bermel, has not just brought the historic building back to life but to complete grandeur. The decor in the rooms is elevated and luxurious, with tall ceilings, Parachute linens, and original artwork. The rooms are impressively sound-proofed, with incredible attention to detail and access for guests to a gorgeous sauna just down the hall with lake views.

Possibly the best perk is the rooftop lounge. During a tour after dinner with Bermel, I was astonished at the panoramic views of downtown Bayfield and Lake Superior; amazingly, we were even treated to a show of the Northern Lights. Indeed, it was a bucket list moment I didn’t expect to have in Wisconsin, but another reason it’s described by nearly anyone who has visited as simply magical.

WHERE TO EAT AND DRINK:

COPPER CROW DISTILLERY

Copper Crow Distillery
Emily Hart

Don’t miss stopping at Copper Crow Distillery for a cocktail or two during your trip to Bayfield. As the first Native-American-owned distillery in the United States, owners Curt and Linda Basina, members of Red Cliff Band of Lake Superior Chippewa, have created incredible spirits – including whey-based gin and vodka using the Wisconsin cheesemaking byproduct – and an inviting and friendly tasting room and cocktail bar.

Try an Old Fashioned or tasting flight from their extensive menu.

WILD RICE RETREAT

Wild Rice Retreat
Emily Hart

One of the three pillars of Wild Rice Retreat is nourishment, so it’s no surprise that the dining program is a standout. Once a beloved James Beard Award-nominated restaurant, the kitchen at Wild Rice is impressive, and the team at the retreat takes nourishment seriously through pure, light flavors with a creative twist. When booking directly through Wild Rice, your stay includes a light breakfast (that I can’t stop thinking about), lunch, and dinner.

The bar is exquisitely designed and serves tonics, regional beers, ciders, and small-production natural wines.

WONDERSTATE COFFEE

Stop into the Bayfield outpost of Wisconsin’s local coffee roaster, Wonderstate Coffee, for a latte and cozy vibes you can feel good about supporting, as Wonderstate Coffee is one of the world’s first 100% solar-powered roasteries and has the highest minimum price guarantee for farmers – more than 80% above Fair Trade’s conventional minimum prices. When I visited during a holiday market, the cafe was full of local indigenous creators and supporters shopping and enjoying the space. The downtown cafe serves a full coffee and tea menu, local baked goods, and seasonal specialties.

GOOD THYME RESTAURANT

Good Thyme
Emily Hart

The motto of Good Thyme Restaurant is “Eat, Drink, and Be Merry,” and I have to say – they’ve created the perfect atmosphere for all three. The restaurant is warm, inviting, and convivial in a big yellow house right outside Bayfield in nearby Washburn. Taking an artisan approach to all dishes and cocktails, making everything from scratch, and using as many local ingredients as possible, the food was some of the best I’ve had this year (and this is literally my job).

The sesame soy vinaigrette on my salad was a standout, followed by a perfectly prepared pan-fried whitefish. The service was exceptional, and it felt like dining in a friend’s home – a friend who happens to be an incredible chef.

MORTY’S PUB

Morty's Pub
Emily Hart

Head into Morty’s Pub downtown for a cozy, laid-back Wisconsin pub experience. Grab some lunch – I enjoyed a local Lake Superior whitefish sandwich – and a local brew while enjoying the friendly atmosphere (you’ll notice friendly is the best descriptor for most places in Wisconsin) and small-town charm.

ST. JAMES SOCIAL

St James Social
Emily Hart

Head into St. James Social Lobby Bar for mocktails, beer, wine, and dining on weekend nights. The recently renovated space is art deco and sleek, with beautiful furnishings, friendly staff, and inventive drinks. I was lucky enough to visit on the opening night for dinner and enjoyed a hyper-local cut of tenderloin with kimchi and sesame rice. Also on the menu: rutabaga fries, roasted bone marrow and parsley salad, local Red Cliff walleye, and house-made macarons.

The atmosphere is elevated with taste to back it up.

WHERE TO EXPLORE:

APOSTLE ISLANDS NATIONAL LAKESHORE

Apostle Islands
Emily Hart

The Apostle Islands National Lakeshore, which includes 21 islands in Lake Superior and 12 miles of mainland coast, has long been a popular summer National Park site. Kayaking to the famous sea caves is a bucket list experience, to be sure, but in the winter, the lakeshore is just as exciting. The sea caves become ice caves in the coldest months, and when conditions are just right, they occasionally become accessible from the mainland. As Lake Superior partially freezes, there are opportunities for ice fishing, ice skating on the lake, winter hiking, snowshoeing, cross-country skiing, and snowmobiling in certain areas.

If accessible, hike the mainland Lakeshore Trail to the Sea Caves overlook, just under 4 miles round trip.

DOWNTOWN BAYFIELD

Bayfield
Emily Hart

Downtown Bayfield feels like being in a Hallmark movie, Nantucket, and the Midwest all at once. On the shores of Lake Superior, the main drag offers several local restaurants, shops, and galleries – many open year-round. I recommend stopping into Apostle Islands Booksellers, Bell Street Gallery, Silverwaves Jewelry, Joanne’s Scandinavian, and Lake Superior Scandinavian, a local jewelry designer and shop where I picked up my new favorite pair of earrings.

MADELINE ISLAND

Madeline Island, an island off Bayfield in Lake Superior, is a popular tourist attraction in the summer, with beautiful beaches and hiking trails. But the small artist community, where around 250 people call home year-round, has plenty to offer winter travelers. Take the ferry until the Lake freezes and the Madeline Island Ice Road becomes accessible to the island.

Visitors must come prepared, but hiking, snowshoeing, and cross-country skiing on the island during winter are unforgettable experiences.

MT. ASHWABAY

Hit the slopes at Mt. Ashwabay, the local ski hill and recreation area. With downhill slopes and cross-country ski trails available, it’s popular with locals and winter tourists. The hill also offers plenty beyond ski and snowboarding, hiking trails, winter fat biking, and ample outdoor activities during warmer weather – like mountain biking.

SIDE TRIPS:

One thing that makes Bayfield magical is its remoteness, but this can also be a transportation challenge. Duluth, Minnesota, is within a 2-hour drive, but with limited flight options, many visitors will make the 4-hour drive from Minneapolis – like I did.

As someone who has visited all 50 states, I can confidently say that Wisconsin has more to offer than the majority of them, so if you have the time, here are some side trips I’d take on the way.

PERLICK DISTILLERY

Perlick Distillery
Emily Hart

Situated about 2 hours between both Bayfield and Minneapolis is the completely unassuming but extremely impressive Perlick Distillery. Established in 2014, the distillery is owned and operated by the sixth-generation family who has farmed their 3,000-acre property where it sits since 1920. The grains grown on the farm are used to create their American Yeoman Vodka, Yeoman Maple Syrup Flavored Vodka, and a 5-year American single malt whiskey.

The tasting room, in a beautifully repurposed quonset shed with views of the rolling farmland powered by a solar array, is bustling year-round with inventive cocktail lists and tastings. I loved my maple vodka-based old-fashioned, and be sure to try “The Odd Couple,” a creative and delicious cocktail mixing vodka, grapefruit juice, and coconut cream.

LEINENKUGEL’S

Leinenkugels
Emily Hart

Grab a Summer Shandy from the source at Leinenkugel’s brewery in Chippewa Falls. Once only an upper Midwest favorite, the 155-year-old brewing company has grown and expanded to distribute in all 50 states – primarily the aforementioned extremely popular Summer Shandy. But for a look behind the scenes – and a taste of some of the 15+ brews on tap (some exclusive to the tasting room) – take a pit stop to visit the Leinie Lodge and tour the brewery.

I loved spending an afternoon learning about the brewing process and history of the sixth-generation family business before tasting some new beers with Wisconsin cheese curds in the expansive and lively Leinie Lodge Tasting Room.

EAU CLAIRE:

Eau Claire
Emily Hart

Eau Claire is an excellent spot to spend a night between Bayfield and Minneapolis. With a growing arts and music scene, a walkable downtown, nearby state parks, and a cool musician-owned boutique hotel with an on-site bar and live music – it’s a stopover that will keep you busy.

STAY AT THE OXBOW HOTEL

Oxbow Hotel
Emily Hart

The Oxbow Hotel, just steps from downtown Eau Claire, is a boutique hotel with an on-site bar, live music, an outdoor outfitter, and woodsy vibes. Adding to the cool factor of this music-centric hotel, the Oxbow counts Bon Iver frontman and Eau Claire local Justin Vernon as one of the group of local owners. I loved the Wisconsin-made art along the hallways and in my suite, along with record players in every room – and a vinyl library for guests to check out their favorites.

The style of the hotel is cozy and modern, with a courtyard and patio that hosts regular activations and an art gallery off the lobby that invites conversation and connection for visitors and locals alike.

DINE AT THE INFORMALIST

The Informalist
Emily Hart

A quick walk from the Oxbow, inside The Lismore Hotel, is the sleek farm-to-table restaurant The Informalist. The vibe is upscale yet friendly, with an extensive beer, wine, and cocktail menu, regionally-inspired dishes, and wood-stone pizzas. The Informalist prides itself on paying its staff a liveable wage plus benefits while keeping the prices and quality approachable. I enjoyed the Yellow Jacket pizza topped with red sauce, mozzarella, cheddar, pepperoni, and house-made spicy honey paired with a wine selected by my amiable server.

WALK TO BREAKFAST AT EC DC

EC DC
Emily Hart

Before returning to the airport, I stopped at EC DC in downtown Eau Claire for an Americano and The Bec Sandwich – bacon, garlic aioli, two fried eggs, and American cheese on ciabatta bread. The vibe was relaxed and understated yet cool and vibey, with a diverse group of patrons working, socializing, and grabbing breakfast before heading out into the snowy Wisconsin weather.

The service was friendly, and my sandwich was the perfect choice after a night out at The Lakely.

ENJOY LIVE MUSIC AND COCKTAILS AT THE LAKELY

The Lakely
Emily Hart

Head to The Lakely for some grub or drinks inside The Oxbow Hotel. Sitting at the bar with some wine and listening to live jazz music in a packed house, I had a blast. The cocktail lounge is proud of its Midwestern vibes and friendly culture for gathering travelers and locals.