There’s something magical about visiting a city in the winter that sits near hundreds of acres of frozen lakes, so it comes as no surprise that some of the best things to do in Madison, WI, this winter are outdoors in the snow! The wintertime softens the edges of the neighborhoods near the Wisconsin State Capitol, restaurants lean into hearty and satisfying menus, and the city feels easier to explore without summer crowds. On a winter escape, Madison offers plenty of walkable attractions, thoughtful entertainment and seasonal events, and easy access to thrilling outdoor recreation.
One of the most popular things to do in Madison this winter is the Frozen Assets Festival. It begins with a 5K race run entirely on the ice, followed by a full day of winter activities. Visitors can join pond hockey games, try snowshoeing, skate on the Edgewater Ice Rink, watch curling demonstrations, drop in at craft stations, and fly kites on the ice. And not to worry, if you’re more inclined to explore indoors during the winter in Wisconsin, Madison has plenty in that respect as well!
Before you fill your itinerary with the best things to do in Madison, you’ll want to choose a cozy and welcoming place to stay. The Buckingham Inn, a highly-rated Bed and Breakfast in Madison, is such a lovely space for your winter retreat. As a small-boutique property, we can offer a more personal experience than larger hotels, with warm common spaces, thoughtful amenities, and hosts who know the city well. Plan your next getaway and book your lodging today!
Best Things to do in Madison, WI: Winter Adventures in the City
Whether you are visiting for a long weekend or planning a quick weekday getaway, there are plenty of memorable things to do in Madison during the winter months. From classic Wisconsin experiences to events that only happen this time of year, winter gives the city a different personality, and with the stunning frozen lakes as a backdrop, you’ll love curling up in the evenings after a busy day in the winter wonderland.
Our Bed and Breakfast in Madison is centrally located, so the best adventures are just a quick drive away, or you can bundle up and explore on foot. Monroe Street is our neighborhood shopping area, and our guests love discovering the boutique shops and cafes, including Orange Tree Imports, Bloom Bake Shop, and Madison Chocolate Company (where The Buckingham Inn chocolates are made!). Browsing on this charming street is just the start of the best things to do in Madison.
Our favorite winter adventures to add to your itinerary:
- Plan your vacation around the seasonal winter festivals. The Frozen Assets Festival in early February, as well as the Wisconsin Union’s Winter Carnival, spans several days and features a packed schedule of activities. Highlights include skiing and snowboarding contests, ice fishing, snowshoeing, ice mini golf, hot cocoa stands, and fireworks over the lake. Toward the end of February, Bockfest celebrates a seasonal beer tradition in nearby Middleton. Capital Brewery hosts this event with live music, food, and the release of its winter bock lager.
- Whatever you do, on a visit to Madison in the winter, don’t forget to pack your warmest coat, hats, and gloves! The city’s extensive trail system remains active all year, and winter transforms familiar paths into quieter spaces. The Lakeshore Path, sections of the Capital City State Trail, and the Arboretum offer opportunities for winter walks, snowshoeing, and cross-country skiing.
- Cold weather is a good excuse to explore Madison’s dining scene. Winter menus tend to feature comfort-driven dishes, seasonal ingredients, and thoughtfully crafted cocktails. Many restaurants near downtown and the Capitol Square are easy to reach on foot, making it simple to plan an evening out without worrying about driving in winter conditions. From an eclectic meal at Everly and a classic Italian feast at Fabiola’s to immersive Wisconsin supper clubs like Tornado Club Steak House, there are so many options within two miles of our Bed and Breakfast in Madison.
- The Bolz Conservatory at Olbrich Botanical Gardens is a tropical paradise year-round. Housed in a glass pyramid, tour the toasty structure to see more than 650 warm-weather plants; don’t miss the rare orchids. The outdoor trails are also open, winding through the perennial gardens and the Royal Thai Pavilion.
- Winter is an ideal time to focus on Madison’s museums and educational spaces. The Chazen Museum of Art offers an impressive permanent collection along with rotating exhibits, and admission is free. The University of Wisconsin campus adds another layer of indoor attractions, including lectures, exhibits, and performances that are often open to the public.
Choose our Bed and Breakfast in Madison, WI, as Your Cozy Home Base
After a day exploring things to do in Madison, whether that means walking the Capitol Square, visiting a museum, or attending one of the city’s winter events, returning to a quiet residential street just minutes from downtown feels like a reset. Snow settles softly along the sidewalks and nearby historic homes, and our Bed and Breakfast in Madison itself feels warm and inviting without being formal. Evenings tend to revolve around good conversation, a glass of wine, and the sense that there is nowhere else you need to be, then settling into your cozy guest suite.
Mornings begin slowly, which is exactly the point of a winter getaway in Wisconsin. A homemade breakfast kicks off the day before heading out to discover what to do in Madison, WI, during the colder months. Guests often plan their itinerary around nearby Madison events, a winter walk through the university area, or a drive beyond the city to see other places to go in Wisconsin while the landscape is dressed in snow.
Choosing a Bed and Breakfast in Madison, WI, during winter adds a layer of comfort that larger hotels cannot offer. The Buckingham Inn feels personal, thoughtful, and well-suited for couples seeking a relaxed escape. Winter in Wisconsin encourages staying in just as much as going out, and the Inn supports that rhythm beautifully. Comfortable rooms, peaceful common spaces, and attentive hosting create an experience that feels intentional rather than rushed, making a winter stay in Madison something guests often remember long after the snow has melted. Book your next escape today!
