Artistic rendering – Event may differ
The Peppermint Trail
A festive holiday trail with peppermint-themed specials and activities.
About
Experience the festive magic of The Peppermint Trail, a vibrant holiday event transforming The Avenues of Ingersoll & Grand and the Roosevelt Cultural District. Discover unique peppermint-themed window displays, enjoy live ice carving, and indulge in special holiday treats from local businesses. Meet Santa, browse artisan crafts, and ride the free Bee-Merry-Line trolley for a truly enchanting holiday celebration.
Our Take
Family Friendly
Best For
Families, shoppers, foodies
Vibe
Festive, cheerful, community-oriented
Energy Level
Moderate
Budget
$
Photo Friendly
Weather Sensitivity
Moderate
Special Events & Promotions
- Peppermint-themed window displays by local artists
- Toys for Tots collection
- Gingerbread House Decorating Contest
- Photos with Santa Claus
- Carolers from Roosevelt High School Choir
- Live Ice Carving demonstrations
- Free Bee-Merry-Line holiday trolley rides
- Various restaurant and retail specials
- Peppermint-themed cocktails and treats
- Brilliant Craft & Wares Fair
- Winter Wellness Market
- Disney's Beauty & the Beast performances
- Holiday play activities
- Gift card deals and discounts
- Spin the Wheel game with prizes
Always check the official website for the most current information.
We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly.
Location
Event Details
Pricing
$
Duration
All day
Ages
All ages
Neighborhood
The Avenues of Ingersoll & Grand, Roosevelt Cultural District
Timed Entry
No
Featured Performers
- Venus Hartman (artist)
- Roosevelt High School Choir
- Bill Gordish (ice carver)
Organizer
The Avenues of Ingersoll & Grand
Practical Information
Parking
On-street parallel parking stalls are available along Ingersoll Avenue (2-hour limit between 9 AM-4 PM). Some businesses have private, off-street parking lots. Parking a few blocks away is encouraged to allow for exploration. Bike parking is available throughout the corridor.
Pet Policy
No pets allowed
Food & Drink
Food trucks, beverage vendors, and restaurant specials available. Includes peppermint-themed cocktails, hot chocolate, baked goods, and more.
Tips & Advice
- Arrive early to enjoy the full day of activities, especially if you plan to meet Santa or participate in popular decorating contests.
- Utilize the free Bee-Merry-Line trolley to easily navigate between the Ingersoll & Grand and Roosevelt Cultural Districts, saving time and parking hassle.
- Check the event map and business listings beforehand to plan your route and prioritize the shops and activities you want to experience.
- Dress in layers as you'll be moving between indoor shops and outdoor activities, and the weather in December can be unpredictable.
- Bring cash or be prepared for various payment methods, as some smaller vendors or pop-up shops might prefer it.
Frequently Asked Questions
What are the main areas for The Peppermint Trail?
The event spans two main areas: The Avenues of Ingersoll & Grand and the Roosevelt Cultural District.
Is there transportation available between the event areas?
Yes, a free holiday trolley called the Bee-Merry-Line operates between the two districts, with stops at key locations.
Are there activities for children?
Absolutely! Activities include gingerbread house decorating, cookie decorating, photos with Santa, and caroling.
What kind of food and drinks can I expect?
Expect a variety of festive treats, including peppermint-themed cocktails, hot chocolate, baked goods, and specials from local restaurants and food vendors.
Where can I find a map of the event?
A map of the event, including trolley routes and business locations, can be downloaded from the event's website.
