Eat, Shop, Enjoy

Winter Stroll

calling all WINTER STROLLers!


3rd Annual Winter Stroll  Jolly Trolleys, carolers, dancers, storefront decoration & UGLY SWEATER contests, extended shopping hours…. GEt strollers throughout Tarrytown and Sleepy Hollow into the holiday spirit!

5pm-9:30pm  FREE pair of hop-on-and-off holy jolly trolleys will shepherd strollers around both villages. 

7pm-9:30pm Onboard performance by The TAT Troubadours.


START/END: Patriot’s Park/College Ave

1 N. Broadway & Central Ave/Tarrytown

2 Main St & N. Washington St/Tarrytown

3 Central Ave/Makers Central/Tarrytown

4 Wildey St @ Central Ave/Tarrytown

5 Beekman Ave & Hudson Anchor/SleepyHollow

6 Beekman Ave & Cortlandt/SleepyHollow

7 Washington & Chestnut/SleepyHollow

END/START: Patriot’s Park/College Ave


  • 11am & 3pm Tarrytown Music Hall Laurie Berkner Band (Sold Out)
  • 2pm–6pm  TaSH Holiday Market Patriots Park
  • 4pm-5:30pm Tarrytown Tree Lighting carolers and performance by Music Hall Academy.  Make-A-Wish Hudson Valley wish kids and families will light tree, Patriots Park
  • 6pm- 7pm Sleepy Hollow Tree Lighting Performance by Sleepy Hollow High School Chorus (Gail Persad’s direction).  Make-A-Wish Hudson Valley wish kids and families will light tree.  Washington & Chestnut St
  • 6pm & 7pm Rivertown Dance Academy will demonstrate a selection of tap dance exercises & short performance pieces with their youth students on S. Washington, next to the Tarrytown Firehouse
  • 6pm-8pm Santa will be greeting strollers at the Tarrytown Firehouse
  • 6pm – 8:00pm Sinterklaas will be ready to meet and greet starting at 6 p.m. Storytelling of how Sinterklaas became Santa Claus is at 6:30 p.m. and 7:30 p.m. Cookies and hot cocoa will be served after each show. Reformed Church of the Tarrytowns
  • 6:30pm to 8:30pm horse drawn carriage rides at the Sleepy Hollow Village Hall Municipal Parking Lot, courtesy of the Village’s Recreation Department (Pelham Bit Carriages, Inc.)
  • 6pm to 9pm Valley Street, Sleepy Hollow will be closed to host DJ Tommy Lee,  Draughtwood Mobile Bar, Santa & the Headless Horseman as well as 3 surprise characters on horseback (Corinthian Equestrian Center)
    Headless Horseman and other characters on horseback/Photo Opportunities Sponsored by
  • 7pm to 9pm S. Washington & Main Street, performances by Saxophonist Radamsey music and Rivertown Dance Academy 
  • 7pm Tarrytown Music Hall Comedian Eric D’Alessandro performs

ugly sweater contest

Enter the 3rd Annual UGLY SWEATER Contest sponsored by The Bucci Real Estate Team 

PRIZES: One winner from each category (Adult, Child, Pet) will win a prize. Prizes are as follows: $100 Tarry Tavern Gift Card (Adult) | $50 Healthy Sugar NYC Gift Card (Child)| $30 Bark & Meow Gift Card (Pet)

To Enter the Contest – 

1. Stop by the Coldwell Banker Realty office at 4 North Broadway, Tarrytown on the day of the Winter Stroll and take a picture in front of the Ugly Sweater poster in their window.
2. Post your photo on Instagram using the hashtag #UglySweater10591 and tag @buccirealestateteam @sleepyhollowtarrytownchamber for bonus points!
3. Winners will be chosen by 12pm on Sunday, December 3rd. 

cast your vote for your favorite Holiday storefront decoration 

Scan QR Code below or click  HERE!!!! to vote for your favorite  

Sponsored by Dalia Valdes/Julia B. Fee Sotheby’s International Realty  PRIZES:  Grand Prize:  $250  Second Prize:  $150  Third Prize:  $ 100

Holiday balloon display

Take a pic in front of this gorgeous ballon display at Patriot’s Park sponsored by Rey Insurance  Created by HudsonValley Balloon Girl

chamber member activities & holiday decoration contestants


  • Bark & Meow already stocked with Holiday wear, treats and more for your furry babies**
  • Corcoran Legends Realty giving away kids’ color your own winter ornament’ kit and refreshments**
  • Eatarry selling Hot Chocolate and other treats to keep Winter Strollers warm**
  • Fuel Hub Extended shopping hours, FREE Greens Shots for tagging us on social media when visiting our store **
  • Horsefeathers the horned Krampus will be making an appearance**
  • Make-A-Wish Hudson Valley accepting toys for local wish kids at TASH Holiday Market and Bucci Real Estate Team/Coldwell Banker office at
    4 N. Broadway, Tarrytown.
  • Makers Central Holiday market and live music by The Barn Vultures Band**
  • ONA extended shopping hours
  • Playa Bowls any 20 ounce smoothie for the price of a 16 ounce and/or a Free Crushed Candy Cane topping on any bowl purchase
  • Posh Pretzels Christmas and Hanukkah themed colored pretzels and gift boxes!**
  • Rivertown Dance Academy 10-15 minute intro swing dance lessons + ONEHOPE wine tasting
  • Set Back Inn Christmas cocktail specials
  • Tarry Tavern selling Hot Chocolate and other treats to keep Winter Strollers warm**
  • Tarrytown Music Hall performance by Tarrytown Music Hall Academy (6:30-6:45pm)**
  • The Village Soccer Shop 15% Off Veja sneakers and other exclusive in-store sales**
  • The Swan’s House performance by “Sing from your Heart” carolers (5pm-7pm), exclusive in-store discounts and refreshments**

Sleepy Hollow

  • Beekman Ale special Holiday cocktails**
  • Carvel & Horseman’s Bagels**
  • Draughtwood Mobile Bar spiked & regular cider, winter sangria (Valley Street)
  • DW Balloon Boutique extended shopping hours, Santa will be greeting children and their families**
  • Hudson Anchor Seafood & Grill boozy hot chocolate and apple cider**
  • JP Doyle’s special Holiday cocktails**
  • Justin’s Deli & Cafe will be hosting the Grinch with Greenville as their theme**
  • KensiGo Kitchen and Deli**
  • Los Andes Bakery will be hosting Santa, hot cocoa and other surprises**
  • Santorini Restaurant serving hot food, mini baklava and apple cider outdoors**
  • Sleepy Coffee, Too extended hours with special beverages – hot chocolate and warm spiced apple cider **
  • Sleepy Hollow Bookshop kids’ crafts, extended hours**

**Holiday Storefront Decoration Contestants


For more events on December 2nd visit our partner website:  VisitSleepyHollow




Why Join the Chamber?

We're bringing businesses & our community together!

The Sleepy Hollow Tarrytown Chamber of Commerce is here to connect, support, represent and elevate our members via dynamic networking events, social media promotion, the organization of popular annual events like the street fair, and active collaborations with the Villages themselves.