Join us for a magical evening at the Tarrytown and Sleepy Hollow Winter Stroll! Experience the charm of the season as our historic towns come alive with festive lights, warm treats, and joyful celebrations.
The 4th annual Tarrytown and Sleepy Hollow Winter Stroll takes place Saturday, December 14th! Extended shopping hours, outdoor dining, story telling, Holly Jolly Trolleys, holiday treats, carolers, ugly sweater contest, live entertainment and other special events!
Festive Lights & Decorations: Wander through beautifully decorated streets and enjoy the enchanting holiday displays.
Delicious Local Cuisine: Savor seasonal delicacies from local restaurants and vendors offering everything from hot cocoa to gourmet bites.
Live Music & Entertainment: Enjoy performances from local musicians, carolers, and festive entertainment for all ages!
Unique Shopping: Explore local shops and find perfect gifts for your loved ones while supporting small businesses.
Don't miss this opportunity to create lasting memories with family and friends. Bundle up, bring your loved ones, and immerse yourself in the winter wonderland of Tarrytown and Sleepy Hollow!
2024 date: December 14. 3 pm to 7 pm.
Where: throughout the downtowns of Tarrytown and Sleepy Hollow!
For info: https://www.sleepyhollowtarrytownchamber.com
Ugly sweater contest
It’s that time of year again, when cute fall sweaters give way to your ugliest holiday creations…
- Visit The Bucci Real Estate Team: Stop by their office at 4 North Broadway in Tarrytown (corner of Broadway & Main) during the Winter Stroll (3 pm – 7 pm).
- Strike a Pose: Take a photo wearing your sweater in front of the “Ugly Sweater Contest” sign
- Share on Social Media: For bonus points, post your photo on Instagram with #uglysweater10591 and tag @buccirealestateteam.
Receive a complimentary gift and hot cocoa just for stopping by!
TIC TAC TOE contest
Fuel Hub (37 Main St) Extended shopping hours. TIC TAC TOE the day of the winter stroll.
5 categories: 7-10 year olds; 11-15 year olds; 16-25 year olds; 25-40 year olds; 40+ year olds
Winner from each category will get a coupon for a free Holiday Edition Specialty smoothie through December 30th and will receive a unique gift the day of the event. Participants need to show up with a partner WITHIN THEIR AGE category.
Holiday Storefront Decoration Contest
Stroll or take the trolley to participating businesses from December 7th through December 14th – the day of the Winter Stroll. Click HERE to take a look at the storefront decorations pictures and cast you vote for your favorite.
PRIZES: Grand Prize: $250 Second Prize: $150 Third Prize: $ 100