Holiday Happenings Itinerary
© Focal Flame Photography


Madison is magical during the holidays, with the best shopping in the region, festive, memorable performances and amazing, local restaurants featuring seasonal favorites. The Holiday Tree at the Capitol and decorations along State Street add to our irresistible charm. Make this holiday one to remember with a visit to Madison.



Start your wintry stay downtown. The Wisconsin State Capitol Holiday Tree graces the rotunda, the Holiday Trolley is available to shuttle you around, and choral groups stroll State Street. Plus all the goodies you buy at local shops can be wrapped at the Holiday Open House.

The Olbrich Gardens Holiday Express showcases large-scale model trains among twinkling lights, poinsettias and miniature landscapes and The Polar Express Train Ride departs from Middleton, goes to the North Pole and returns in just an hour! Daisy Café and Cupcakery is the spot for special festive cupcakes and the Governor's Mansion tour features ten major garden areas and more than 16,000 square feet of living space.

The evening calls for a wonderful dinner at the Wonder Bar Steakhouse, Madison's oldest steak house. Follow that with the spectacular Fantasy in Lights at Olin Park. Then take the drive along John Nolen Drive to see the Capitol at night, and Monona Terrace® Community & Convention Center, designed by Frank Lloyd Wright. Finish your evening with a holiday classic, such as The Nutcracker, available at the Overture Center for the Arts, a stunning architectural landmark in the heart of Madison's downtown.



If shopping is your reason for the season, check out the newly renovated Hilldale Shopping Center, featuring an open-air concourse with new restaurants and shops ranging from designers kate spade, Michael Kors and more to local boutiques like Cornblooms.

If you want to stay near neighborhood shops and renowned restaurants, make plans to stay at The Buckingham Inn near the University of Wisconsin-Madison and Camp Randall. This bed and breakfast is near Monroe Street, which boasts many local shops, including Orange Tree Imports—the perfect place for gifts. Finish your day at Gates and Brovi, an east coast, Italian-style fish house.



Just a short drive away, our area communities host an array of festive events. Vetro Winery has been making wine for generations and often hosts events tied to wine tastings. Cambridge celebrates Country Christmas and Spring Green hosts Handmade Christmas in Wisconsin, along with other holiday events. Not to be outdone, Monona features a candlelit snowshoe hike and Stoughton's Victorian Holiday Weekend invites visitors to celebrate the holidays the old-fashioned way!

On the city's Westside is Greenway Station, a shopping mecca that features 35 stores and restaurants, an amazing Christmas tree and festive music. For lunch or dinner, try Ruth's Chris Steak House, home to USDA Prime steaks, specialty entrees, and lighter lunch options.

This is just the tip of the winter iceberg. Our Madison Winter Wonderland Itinerary gives even more possibilities for this time of year. Also view our Shopping Guide and Hotels & Accommodations page to help plan your trip.