A Chocolate-Lover’s Holiday Dream on Wheels: My Night Aboard the Fannie May Jolly Trolley
Last night felt like stepping straight into a Chicago holiday movie—except this one came wrapped in twinkling lights, vintage charm, and the irresistible aroma of chocolate.
I was invited to an exclusive influencer preview of the Fannie May Jolly Trolley, and let me tell you: this festive ride is pure magic.
A Warm Welcome on Michigan Avenue
Our evening began at the beautifully decorated Fannie May flagship store at 343 N. Michigan Ave. (at Wacker), where the team greeted us with contagious enthusiasm and trays of nibbles and chocolate tastings. Before we even boarded the trolley, we had fallen headfirst into the holiday spirit.
And yes—because I wondered, too—the trolley is fully enclosed and heated. A must during Chicago December!
A Holiday Experience That Moves (Literally)
Once aboard, the trolley came alive with shimmering garlands, nostalgic holiday décor, and the kind of cozy glow that makes the city feel like home. It’s a moving winter wonderland, and it’s impossible not to smile.
What makes the Jolly Trolley special is that it’s not just a ride—it’s a guided chocolate experience. Along the route, we stopped at four “Chocolate Stops” to sample some of the brand’s most iconic treats:
✨ Vanilla Buttercream — Fannie May’s very first candy, created by founder H. Teller Archibald in 1920 right here in Chicago
✨ Peanut Butter Truffle — made with their own house-made peanut butter
✨ Pixies® — their beloved take on the classic turtle
✨ Trinidad® — my personal favorite, with that perfect hint of coconut
Between tastings, we were treated to stories, music, and delightful surprises. The “Taste Conductor” guiding the experience added a joyful energy that made the ride feel intimate and whimsical all at once.
The Best Part? It’s FREE.
Yes—you read that right. The Fannie May Jolly Trolley is entirely free and runs now through December 21, Wednesdays through Sundays.
You can:
• Hop on and off at any of the designated Chocolate Stops
• Enjoy free samples along the way
• Explore iconic Chicago sights
• Make memories
If you prefer guaranteed boarding, you can reserve a spot on Eventbrite—but walk-ups are welcome when space allows.
A Perfect Outing for Locals & Visitors
Whether you’re planning a festive night with friends, entertaining out-of-town guests, or simply wanting a moment of holiday joy in the middle of the city—this experience is a must.
And before you leave Michigan Avenue, be sure to visit the flagship store to browse their gorgeous holiday gifts. The selection this year is exceptional—beautifully boxed chocolates, seasonal treats, corporate gifts, stocking stuffers, and classic favorites that never disappoint.
Chicago, This Is One You Don’t Want to Miss
The Jolly Trolley captures everything we love about the holidays here: community, nostalgia, creativity, and of course… chocolate. It celebrates Fannie May’s 105 years as a Chicago icon—and invites all of us to be part of that story.
All aboard the sweetest ride in the city!
For schedules, reservations, and pop-up locations:
👉 https://FannieMayJollyTrolley.eventbrite.com
Follow: @FannieMayChocolates
