Artistic rendering – Event may differ
Westport Holiday Stroll
Downtown holiday market with over 100 participating businesses and Santa's headquarters.
About
Experience the magic of the 5th Annual Holiday Stroll in Westport, CT, co-sponsored with Dan Woog's '06880'. This festive event on December 6, 2025, transforms downtown Westport into a winter wonderland. Discover unique finds at the Holiday Winter Market, enjoy children's activities like face painting and Santa photos, and be entertained by live performances. The Elm & Main complex is the central hub, buzzing with Santa, music, and photo opportunities.
Our Take
Family Friendly
Best For
Families, shoppers, holiday enthusiasts
Vibe
Festive, community-oriented, cheerful
Energy Level
Moderate
Budget
$
Photo Friendly
Weather Sensitivity
Moderate
Special Events & Promotions
- Participating retailers and restaurants offering deals and promotions.
- Activities for children including face painting, s'mores, and Santa photos.
- Performances by the Staples High School Orphenians.
- Elm & Main complex as headquarters with Santa, DJ, and photo booth.
- Holiday Winter Market with a variety of vendors.
- Toy drive hosted by the Westport Police Department.
- Complimentary hot chocolate, samples, discounts, and giveaways from various vendors.
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
2 hours
Ages
All ages
Neighborhood
Downtown Westport
Timed Entry
No
Featured Performers
- Staples High School Orphenians
Organizer
Westport Downtown Association
Practical Information
Parking
Refer to the 'Parking + Transportation' resource link.
Pet Policy
No pets allowed (inferred, as not specified)
Food & Drink
Food trucks, restaurants, complimentary hot chocolate, s'mores, festive treats, wine, cocktails, and more available from various vendors and businesses.
Tips & Advice
- Arrive early to secure parking and enjoy the full two-hour event, especially if you plan to visit Santa or popular vendors.
- Check the event map beforehand to plan your route and identify specific vendor locations or performance times.
- Bring a new toy for the Westport Police Department's toy drive to spread holiday cheer.
- Many participating businesses offer special promotions and discounts; have your phone ready to capture any deals you're interested in.
- Dress warmly in layers, as the event takes place outdoors and in various indoor locations throughout downtown.
Frequently Asked Questions
What are the main attractions at the Holiday Stroll?
The event features a Holiday Winter Market with numerous vendors, activities for children like face painting and Santa photos, and performances by the Staples High School Orphenians. The Elm & Main complex acts as a central hub with Santa, a DJ, and a photo booth.
Where is the Holiday Stroll located?
The event takes place throughout downtown Westport, with the Elm & Main complex at 136 Main Street serving as the main headquarters. The Holiday Winter Market is located on Elm Street in the Sigrid Schultz parking lot.
Are there any special offers from businesses?
Yes, many participating retailers and restaurants offer exclusive deals, promotions, and complimentary treats or samples during the event. It's recommended to check the 'View All Promotions' link for details.
Is there a toy drive at the event?
Yes, the Westport Police Department is hosting a toy drive. Attendees are encouraged to bring a new toy to donate.
What time does the Holiday Stroll take place?
The Holiday Stroll is scheduled for Saturday, December 6, 2025, from 5 PM to 7 PM.
