Artistic rendering – Event may differ
Sleepy Hollow & Tarrytown Winter Stroll
Free trolley service connecting two charming villages for holiday shopping.
About
Experience the magic of the holiday season with the Winter Stroll through Sleepy Hollow and Tarrytown. Visitors can enjoy free trolley rides to explore participating businesses, indulge in festive treats, and discover unique gifts. The event features an "Ugly Sweater" contest, storefront decoration voting, and live entertainment, creating a joyful atmosphere for all.
Our Take
Family Friendly
Best For
Families, shoppers, holiday enthusiasts
Vibe
Festive, community-oriented, charming
Energy Level
Moderate
Budget
$
Photo Friendly
Weather Sensitivity
Moderate
Special Events & Promotions
- Ugly Sweater Contest with prizes
- Holiday Storefront Decoration Contest
- Extended shopping hours and special discounts
- Complimentary gift and hot cocoa for contest participants
- Special holiday cocktails and treats available
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
4 hours
Ages
All ages
Neighborhood
Sleepy Hollow and Tarrytown
Timed Entry
No
Featured Performers
- Jared Nelson
- Rivertown Dance Academy
- Sleepy Hollow Arts Collective
- David Robert Brimat
Organizer
Sleepy Hollow Tarrytown Chamber of Commerce
Practical Information
Parking
Information on specific parking locations for trolleys and attendees is not explicitly detailed, but the event encourages using the free trolleys to navigate between villages.
Pet Policy
Pet-friendly for contest, service animals welcome
Food & Drink
Food trucks, special holiday cocktails, hot cocoa, festive treats, and discounts available at various participating eateries and bars.
Quick Actions
Tips & Advice
- Arrive early to take advantage of the free trolley service, as popular routes may fill up quickly, especially closer to the event's end time.
- Check the event's website for the most up-to-date trolley routes and participating business lists to plan your stroll efficiently.
- Wear comfortable shoes as you'll be doing a lot of walking and hopping on and off trolleys between Sleepy Hollow and Tarrytown.
- Bring cash for smaller vendors in the Holiday Vendor Village, as not all may accept card payments.
- Participate in the "Ugly Sweater" contest by visiting The Bucci Real Estate Team office; even if you don't win, you'll receive a complimentary gift and hot cocoa.
Frequently Asked Questions
What are the operating hours for the Winter Stroll?
The Winter Stroll takes place on Saturday, December 13, 2025, from 2:00 PM to 6:00 PM.
Is there a cost to attend the Winter Stroll?
Admission to the Winter Stroll is free, and the trolleys are also free to use.
Are there activities for children?
Yes, there are kid-friendly activities including holiday art making, photo opportunities, and the chance to meet Santa and other characters.
Where can I find more details about participating businesses and trolley routes?
More details can be found on the event's website, which includes information on village events, participating businesses, and trolley routes.
Can I bring my pet?
Pets are welcome to participate in the "Ugly Sweater" contest, with specific categories for pets. Service animals are also likely permitted.
