Westport Holiday Stroll
2026 dates not announced yet. Details are from 2025.
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.
All ages $
See more Christmas markets near Westport
Plan Your Visit
Last year
Neighborhood
Downtown Westport
Featured Performers
- Staples High School Orphenians
Food & Drink
Food trucks, restaurants, complimentary hot chocolate, s'mores, festive treats, wine, cocktails, and more available from various vendors and businesses.
Parking
Refer to the 'Parking + Transportation' resource link.
Location
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.
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.
Links & Contact
Run by Westport Downtown Association
Christmas Events Near Me is an independent guide, not the organizer of this event. For tickets, entries, vendor spots or questions, contact the organizer directly through their website.
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.
Browse Christmas in Westport
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. Christmas Events Near Me is an independent guide and isn't affiliated with the events we list.