Plenty of Holiday Activities in Southeast Wisconsin for Travel Groups

Every year as the weather turns cold, Southeast Wisconsin heats up with festive lights, wintery landscapes, and unique holiday traditions. This three-day itinerary takes you through Milwaukee’s historic sites, Lake Geneva’s lakeside magic, and the cozy charm of Janesville and Madison. Whether you are exploring grand mansions, wandering botanical gardens, or enjoying holiday-themed shows and cruises, this guide offers a memorable holiday experience in the heart of the Midwest during the most wonderful time of the year.

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Rotary Lights in La Crosse, Wisconsin.

Rotary Lights in La Crosse, Wisconsin.

Enjoy These Great Attractions and More:

  • Pabst Mansion
  • Holiday Lights Festival
  • Boerner Botanical Gardens
  • Old World Wisconsin
  • Rotary Botanical Gardens’ Holiday Light Show

Veterans Park, Milwaukee

Veterans Park, Milwaukee

Day-to-Day Wisconsin Holiday Itinerary


Day 1: Holiday Activities in the Milwaukee area

Start your Southeast Wisconsin adventure in Milwaukee, a city known for its vibrant history and festive holiday spirit. Stop one: Pabst Mansion, a stunning remnant of 19th-century architecture. Once home to beer baron Captain Frederick Pabst, this meticulously-restored building gets gussied up for the holidays, enhancing its Victorian splendor with glittering trees and elaborate garlands. Christmas at the Pabst Mansion, an annual tradition, features self-guided tours from mid-November to early January, while special evening tours from Thursday to Saturday include live holiday music and purchasable drinks like spiced wine and hot pecan whiskey cider. Giving guests a glimpse into Milwaukee’s opulent past, with intricate woodwork and lavish holiday decorations, Pabst Mansion can be counted on to create a sense of seasonal charm.

Next, head over to the Mitchell Park Domes for a lush escape from the chilly weather. These unique domed conservatories house diverse ecosystems, including a tropical rainforest and desert, providing a colorful contrast to the snowy landscape outside. During the holidays, the Domes are adorned with lights, making Milwaukee’s most exceptional botanical wonderland even more enchanting.

As the evening approaches, immerse yourself in the magic of Milwaukee’s Holiday Lights Festival. This event transforms the city’s downtown area into a sparkling wonderland, with light displays lining streets and parks. Be sure to stroll through the city’s parks, admire the glittering chandeliers suspended over Wisconsin Avenue, and hop on a jolly Jingle Bus ride. Finally, end your first day with a peaceful drive through the illuminated Boerner Botanical Gardens, where the Winter Wonders Holiday Light display casts a beautiful glow across the gardens, offering a serene and festive close to your Milwaukee exploration. This attraction features over a million LED lights along 1.4 miles, making it a popular attraction every winter.

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Baker House Lake Geneva

Lake Geneva’s Baker House, dressed
in holiday lights, delights December
visitors.

Day 2: Lake Geneva Area Holiday Attractions

On day two, journey to the picturesque Lake Geneva, where the holiday magic continues with the Santa Cruise. As part of this adventure, guests board a glowing boat and enjoy a scenic cruise across Lake Geneva, complete with stories about Santa and his elves—not to mention heated boat decks and a reading of the “Nice List.” Along the way, you will pass by elaborate light displays on the shore, making for an unforgettable holiday experience for all ages.

Old World Wisconsin is up next: it is a living history museum that recreates the lives of19th-century settlers. During the holiday season, the museum hosts “Home for the Holidays,” where costumed interpreters lead visitors through old-fashioned holiday traditions. Enjoy horse-drawn wagon rides, sip warm cider, and discover how early Wisconsinites celebrated Christmas. Finish the evening with a holiday performance at the Fireside Theatre in nearby Fort Atkinson, just a 45-minute drive northwest of Lake Geneva. Known for its dinner shows, the Fireside will present a magical rendition of “Miracle on 34th Street” this holiday season. Enjoy a delicious meal while watching the heartwarming story unfold, creating the ideal capstone for your second day.

ITP HD MadisonFallShopping

Downtown Madison
Credit: Visit Madison

Day 3: Holiday Attractions in Janesville and Madison

On your final day, venture over to Janesville and take in the spectacular Rotary Botanical Gardens’ Holiday Light Show. This annual event features more than one million lights spread across the gardens, creating a magical winter wonderland. Walk through tunnels of twinkling lights, illuminated sculptures, and themed displays, altogether a perfect daytime or evening stop.

From Janesville, head to Madison, Wisconsin’s capital city. Begin your visit with a trip to the Wisconsin State Capitol, where the holiday tree is erected every holiday season in the grand rotunda. Reaching towering heights and showcasing ornate decorations, the Capitol tree is a beloved tradition for locals and visitors alike. It’s a perfect opportunity to take in some history and holiday cheer in the heart of Madison.

Before the day ends, make your way to the Henry Vilas Zoo for their spectacular Zoo Lights display. Wander through the zoo’s festively illuminated pathways and enjoy seasonal treats, crafts, and a visit with Santa. The Zoo Lights offer a fun and family-friendly way to wrap up your three-day tour of Southeast Wisconsin.

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