Trolley Tours

Celebrate this holiday season by taking the heated Trolley Express to visit Santa’s cabin in the woods. Children will sit with Santa by the fire and tell him their Christmas wish list. Come join us for this fun event during this festive time of year. Seating is limited, book in advance!

Trolley guests will enjoy a cozy, horse-drawn sleigh ride through Door County’s most wintry landscapes, a wine tasting at an award-winning Door County winery and a bonus stop!

We’ll whisk you away for award winning wines, locally-crafted cheese, handmade chocolate and lunch! The perfect Winter indulgence.

Taste your way through Door County’s unique beverage scene. This tour will take you on a tasting adventure through Door County to experience the local wine, spirits, and beer. You’ll visit a winery, distillery, and microbrewery for private tastings and indulge in a delicious lunch with dessert!

Discover Door County’s award-winning wineries on our VIP Premier Wine Tour! Private tastings of red and white wines, ports, and ciders at three top wineries, and enjoy a chef-prepared lunch and dessert. This tour promises a fun-filled day of wine, food, and relaxation.

Indulge in delectable cocktails on our unforgettable Cocktail Tour! With a knowledgeable guide leading the way, you’ll visit local hotspots and enjoy handcrafted libations and a chef-prepared lunch. From refreshing fruit-infused drinks to classic favorites with a twist, this tour is a must-do for anyone looking for a unique and fun-filled experience. Cheers!

Heated holiday trolleys will chauffeur guests to 4 festive Door County establishments to consume your favorite beverages and free appetizers at one stop.

Join us in celebrating a sweet taste of Spring and the Easter holiday. We are offering Family Trolley Rides through Egg Harbor in search of what the Easter Bunny has delivered to Door County this year! Children will receive a special treat.

Welcome spring with a carriage ride, wine tasting, bonus stop & lunch! Enjoy views of the peninsula blossoms and majestic scenic overlooks that this rejuvenated season brings.

Indulge in a Wisconsin tradition – Bloody Marys and Sunday Brunch! Trolley guests will enjoy three unique stops for popular Sunday morning cocktails, Bloody Marys & Mimosas.

Experience the best of Door County on our Narrated Scenic Tour! Board our “Old Time” Trolley and be amazed by the stunning landscapes, breathtaking vistas, and charming villages. Learn about the region’s unique character and insider tips of places to wine, dine and relax from our expert local guides.

Experience the beauty and history of Door County’s most majestic landmarks. Enjoy a private tour of Eagle Bluff Lighthouse, Cana Island Lighthouse, and the Baileys Harbor Range Lights with a delicious lunch included! Enjoy entertaining narration from our local guide aboard our trolley as you soak up the breathtaking scenery.

This shortened trolley ride, perfect for young families with their children, allows the wonderful trolley experience without the full length of the adult based trolley tours.

Experience the eerie past of Door County on the Trolley of the Doomed, as expert guides share chilling tales of sunken ships, haunted lighthouses, and mysterious happenings. This one-of-a-kind tour blends history, intrigue, and fun for an unforgettable evening. Book your tickets now to explore the darker side of this spirited peninsula.

Mayhem, murder, and bone chilling fun! Step aboard the trolley as we weave through and retrace the steps of the Peninsula’s most wanted criminals, past and present.

We’ll visit a local winery, chocolatier, and enjoy an artisan cheese tasting. You’ll sample award-winning wines, handmade chocolate treats, and locally-made cheeses. You’ll also learn about the processes involved in making them. The tour includes a cozy ride in our Trolley, with the chance to purchase your favorites to take home with you. An afternoon of indulgence!

An afternoon of wine, appetizers & fun! The Uncorked Wine Tour is an afternoon devoted to wine and friends. Unwind and recharge with a few glasses of wine!

This unique haunted tavern tour will get you up close to the “spirits” of Door County. Designed for those of you who can relate to and keep up with those fun “spirited” souls.

Welcome to Door County Trolley, where luxury meets nostalgia! Step aboard our exquisite trolley and embark on an unforgettable journey in style and comfort. Our trolley boasts brass finishing, plush blue velvet curtains, and cozy booth seating, creating an ambiance of opulence and charm that will transport you back in time.