Festive Cheer at the Tarrytown & Sleepy Hollow Winter Stroll
It’s time to mark your calendars. The fourth annual celebration of the Tarrytown and Sleepy Hollow Winter Stroll will take place on Saturday, December 14th, from 3 p.m. to 7 p.m. With fall gently leaving and winter arriving, this winter stroll is a warm way to celebrate the change of seasons. These Hudson Valley villages are rolling out the holiday cheer right before Christmas with festive lights, free trolley rides, scrumptious treats, live entertainment, and, best of all, the chance to create beautiful memories with family and friends.
Come along as we guide you on all of the wonderful winter stroll festivities happening this Christmas in Sleepy Hollow and Tarrytown.
Holly Jolly Trolleys and Festive Strolls
Start your adventure by hopping on one of the free trolleys, affectionately dubbed “Holly Jolly Trolleys.” These festive rides will shuttle you between key stops, making it easy to check out everything happening at the Winter Stroll.
Prefer to walk? The streets are decorated with beautiful lights, making your walk feel festive and warm.
Contests With Holiday Cheer
Feeling competitive? There’s something for everyone to join in on the fun:
Ugly Sweater Contest
Wear your gaudiest holiday sweater and visit The Bucci Real Estate Team to enter their contest. Stop by the Bucci Real Estate Team office at 4 North Broadway, Tarrytown, between 3 p.m. and 7 p.m. Show off your holiday spirit and compete for a chance to win prizes! What are the prizes you ask? The prizes include gift certificates for adults, kids, and even pets! Just for stopping by, you get a complimentary gift and a delicious cup of hot cocoa.
Now, that sounds like a holiday contest everyone can get involved in.
Storefront Decoration Contest and Tree Lighting
Admire the creative displays from local businesses and vote for your favorite festive storefront. The winning shop gets bragging rights and prizes, too!
At 6 p.m., the tree lighting will take place at Robertson Park. This is a stunning tradition that will get you ready for Christmas and instantly put you in a festive mood.
Shop Local
This is your chance to support small businesses while checking off your holiday shopping list. Extended store hours and some really reasonable discounts make it easy to find thoughtful gifts for your loved ones. Stop by local stores like Pretty Funny Vintage and Sleepy Hollow Bookshop, all within the Winter Stroll’s vicinity.
Delicious Dining
Holiday strolling works up an appetite, and Tarrytown and Sleepy Hollow have you covered. Warm up with hot cocoa or sip a festive cocktail; it will surely put you in a festive mood. There are a few participating restaurants at the Winter Stroll where you can grab a delicious bite to eat, like Beekman Ale, Horsefeathers, and La Perla Poblanita.
Entertainment for All Ages
Visitors of all ages can enjoy live music, caroling, and theatrical performances as the Winter Stroll is packed with great entertainment. Dancers, musicians, and actors will bring holiday stories to life, while activities for kids, like ornament-making stations, add an extra layer of fun for families.
Make It a Day Trip
Getting to the Winter Stroll is pretty simple for those coming from New York City. All you’ve got to do is hop on the Metro-North Hudson Line to Tarrytown, and from there, it’s just a short walk or trolley ride to the festivities. Bundle up, bring your loved ones, and get ready to make the most of your time in these two villages.
A Holiday Tradition Worth Adding to Your List
Tarrytown and Sleepy Hollow are usually known for their spooky Halloween celebrations; however, the Winter Stroll proves these towns are just as appealing during the holiday season.
Longtime local or a first-time visitor, this is an event you won’t want to miss. So, grab your coziest coat, don your holiday best, and get ready to have fun at this year’s Winter Stroll.
Book a stay at The Sleepy Hollow Hotel to make your stay even more memorable and comfortable. There are a variety of suites, so you can find what fits perfectly for you and your friends or family.