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Celebrate the Holidays with the Ugly Sweater Trolley Pub Crawl in Wisconsin Dells

Celebrate the Holidays with the Ugly Sweater Trolley Pub Crawl in Wisconsin Dells

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  4. Celebrate the Holidays with the Ugly Sweater Trolley Pub Crawl in Wisconsin Dells

Adventure Brief

Hop aboard Wisconsin Dells’ Ugly Sweater Trolley Pub Crawl for a festive night of music, local bars, and holiday cheer. Don your quirkiest sweater and enjoy a moving celebration through this lively Midwestern town.

3–4 hours
moderate
Family Friendly

Keep the Adventure Going

More ways to explore the area's outdoor wonders

No Experience Required

Experience the holiday season like never before on the Ugly Sweater Trolley Pub Crawl, a spirited journey through the heart of Wisconsin Dells. This unique, festive adventure blends the fun of a trolley ride with the vibrant nightlife of one of Wisconsin’s most popular tourist destinations. Wisconsin Dells, known as the 'Waterpark Capital of the World,' transforms during the winter months into a playground of holiday cheer, and the trolley pub crawl is a one-of-a-kind way to soak it all in.

The experience kicks off as participants board a charming vintage trolley, decked out for the holidays and rolling through the snow-dusted streets. The best part? Everyone is encouraged to wear their most outrageous ugly Christmas sweaters, turning the crowd into a sea of quirky, festive fashion. The trolley stops at some of the city’s favorite bars, giving riders multiple opportunities to mingle, dance, and enjoy Wisconsin’s local brews and festive cocktails. This social ride is perfect for those looking to meet new friends or celebrate with old ones in an energetic, inclusive environment.

Unlike typical pub crawls, the trolley provides a cozy, mobile venue that keeps the party moving, all while allowing revelers to enjoy the crisp winter air and twinkling holiday lights that adorn the city. Wisconsin Dells itself is famous for its stunning sandstone formations sculpted by the Wisconsin River and its bustling entertainment scene, making it an ideal backdrop for any adventure. Though this experience is centered on fun and camaraderie, the trolley crawl also offers a chance to explore the town’s winter charm safely and comfortably.

Whether you’re a local or visiting for the holidays, the Ugly Sweater Trolley Pub Crawl turns an ordinary night out into a memorable celebration on wheels. Bring your own drinks and snacks to personalize your festive experience, making it both cost-effective and uniquely yours. This event is not just about the drinks; it’s about community spirit, the allure of holiday traditions, and celebrating the season in a setting that only Wisconsin Dells can offer.

This tour is a standout in Wisconsin Dells’ winter activity lineup, combining elements of cultural festivity, spirited socializing, and scenic exploration. Perfect for groups, couples, or solo travelers, it offers an accessible, moderate activity level that anyone in average physical shape can enjoy. So grab your ugliest sweater, gather your friends, and prepare for a night full of laughter, music, and holiday magic on Wisconsin Dells’ most festive trolley ride!

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Trip Details from the Operator

Frequently Asked Questions

Yes, attendees are encouraged to bring their own drinks and snacks for a personalized experience.

This event is typically for adults 21 and over due to alcohol consumption at bars.

Accessibility may vary by location; please contact the operator for specific accommodations.

Key Highlights

Difficulty

moderate

Duration

3–4 hours

Fitness Level

Suitable for most people comfortable with light walking and standing for moderate periods

Local Insights

Wildlife

  • White-tailed deer visible on town outskirts
  • Winter birds like chickadees and cardinals

History

Wisconsin Dells developed around dramatic sandstone formations carved by glacial meltwaters and grew into a major tourism hub by the mid-20th century.

Conservation

The local tourism industry actively promotes sustainable business practices, encouraging visitors to respect nature and minimize waste during their stay.

Related Adventures & Guides

  • See other trips from Wisconsin Dells Trolley Service
  • Explore more Wisconsin Dells adventures
  • Browse more land adventures experiences

Operated By

Wisconsin Dells Trolley Service

Hop aboard Wisconsin Dells’ Ugly Sweater Trolley Pub Crawl for a festive night of music, local bars, and holiday cheer. Don your quirkiest sweater and enjoy a moving celebration through this lively Midwestern town.

About Wisconsin Dells Trolley Service

Wisconsin Dells Trolley Service provides curated trolley tours and shuttle transportation in Wisconsin Dells, Wisconsin. The company offers a range of themed experiences including private customizable tours, family rides, brewery and bar crawls, culinary excursions, winery tastings, brunch tours, tubing transfers, and airport shuttle services. Tours are designed for groups and individuals seeking convenient, local transport with guided, time-efficient routes.

Private tours allow customers to select date, time, and destinations to create a tailored itinerary. Family-friendly options include a condensed 30-minute City Express Family Tour ideal for young children. Food- and drink-focused experiences include a Mexican Fiesta TOUR featuring multiple Mexican restaurants, a Beer Lover's Brewery TOUR through the Driftless area, a Bloody Mary/Mimosa Brunch Bus visiting multiple establishments, and a Dive BAR Extravaganza with relaxed, offbeat stops.

Additional services include round-trip transportation to Point Bluff or Sandy Shores for tubing, and an Evening Wine Adventure that combines winery tastings, a lakeside bar stop, and an alpaca encounter. The Airport Shuttle accommodates groups of 1 to 100, using vehicles ranging from a BMW X5 to multiple buses, with tailored amenities and professional drivers.

Reservations and specific pickup or drop-off details for tubing trips are handled via email at [email protected]. By focusing on safe transportation, customizable scheduling, and local knowledge of Wisconsin Dells attractions, Wisconsin Dells Trolley Service offers a practical option for visitors and groups exploring the region. Online booking guidance and detailed tour descriptions help guests choose suitable experiences and confirm logistics before arrival.

Group tubing down river on inflatable rafts, outdoor water fun
Friends picnic outdoors under trees sharing food and laughter

Tours Offered

11 tours

Variety of themed experiences

Group Capacity

1–100 passengers

Vehicles from BMW X5 to buses

Flexible Scheduling

Private & set times

Customizable private tours

Service Area

Wisconsin Dells

Local pickups & drop-offs

CTA Section Background Image

Reserve a Private Tour or Shuttle in Wisconsin Dells

Book customizable tours, tubing transfers, or airport shuttles — email [email protected] to confirm pickup, drop-off, and group details.

Adventure Tips

Dress Warmly and Festively

Wear your ugliest Christmas sweater plus layers to stay warm during trolley stops or outdoor mingling.

essential

Bring Your Own Snacks and Drinks

Personalize your experience by packing snacks and drinks to enjoy throughout the crawl.

info

Plan for Moderate Walking

Be prepared for short walks between bars and the trolley; comfortable shoes are recommended.

info

Book Early During the Holidays

This popular event fills up fast during the holiday season—reserve your spot in advance.

warning

Recommended Gear

Ugly Christmas Sweater

Key for joining the festive spirit and blending in with fellow crawlers.

winter

Essential

Warm Jacket

Necessary for comfort when waiting between stops and riding the trolley.

winter

Essential

Comfortable Walking Shoes

Ideal for short walks between trolley stops and standing in bars.

Essential
  • Read our Wisconsin Dells travel guide
  • Reusable Drink Cup

    Helps you safely carry drinks onboard the trolley.

    winter