Main Street TarrytownMain StreetTarrytown NY 10591
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✨Experience the Magic of the Holiday Season in Sleepy Hollow and Tarrytown✨
- Take a stroll or hop-on-and-off our FREE jolly trolleys to explore all participating businesses throughout both of our Villages
- Visit and vote for your favorite festive storefront decorations
- Put on your ugliest Holiday sweater and visit The Bucci Real Estate Team to enter their “Ugly Sweater” contest!
- Enjoy extended shopping hours, delicious treats, special discounts and festive entertainment!
❄️ Get into the holiday spirit with carolers, dancers, kids activities, theatrical performances
and more! ❄️
Find more details on Village events, participating businesses and Trolley routes below!!!
contests
UGLY HOLIDAY SWEATER CONTEST
HOW TO ENTER
- Visit The Bucci Real Estate Team: Stop by our 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 our “Ugly Sweater Contest” sign
- Share on Social Media: For bonus points, post your photo on Instagram with #uglysweater10591 and tag @buccirealestateteam.
CATEGORIES & PRIZES:
- Adult: $50 Gift Certificate to Horsefeathers
- Child: $50 Gift Certificate to Sleepy Hollow Bookshop
- Pet: $30 Gift Certificate to Bark & Meow
WINNERS:
- One winner will be selected in each category.
- Winners will be announced the night of the event and notified within 24 hours.
Receive a complimentary gift and hot cocoa just for stopping by!
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
PRIZES Sponsored by:
happenings around the villages!!!
Sleepy Hollow
- 3pm to 7pm: Holiday Vendor Village at Beekman Avenue Parking Lot (across from Firehouse)
* * Draughtwood Mobile Bar: https://www.draughtwoodmobilebars.com
*Arts & Crafts Vendors* (see list of exhibitors below) - 3pm to 7pm: Holiday Art Making including ornaments and other fun activities for kids
& Special Holiday Instagram Moments & photo ops along Beekman Avenue (courtesy of the Village & The Sleepy Hollow Project. - 3pm to 7pm: Help feed family’s in need. Stop by the Horseman’s Harvest Neighborhood Pantry table at the Holiday Vendor Village
- 3:30pm: Dance Performance by Rivertown Dance Academy at The Strand (80 Beekman Avenue)
- 4:30pm: Ice Sculputure demonstration
- 6pm: Tree lighting at Robertson Park (Chestnut Street & Valley Street)
SHOP for HOLIDAY GIFTS
- Holiday Vendor Village Exhibitors (Beekman Avenue Parking Lot/Across from Firehouse):
Bonita Bella Creations: https://wwww.etsy.com/shop/BonitaBellaCreations
dearestolive art: https://dearestolive.com/home.html
J. McKinley Brand: https://jmckinleybrand.com/
Kilaarts by Kimberly Leahey: https://www.instagram.com/kilaarts_kimberlyleahey/
Martin Munroe Art: https://www.martinmunroeart.com/
Michelle Adams Events: https://www.michelleadamsevents.com
Stitch Witch Creatives: https://www.etsy.com/shop/stitchwitchcreatives
EAT & BE MERRY
- Beekman Ale (92 Beekman Ave): special Holiday cocktails**
- Carvel & Horseman’s Bagels (276 N. Broadway): **
- Casaletto Pizza (70 Beekman Ave)*
- Coco Taqueria (84 Beekman Ave)**
- DeCicco’s Trolley Stop: serving Hot Cocoa at Lighthouse Landing Trolley Stop
- Draughtwood Mobile Bar (Holiday Vendor Village): serving Holiday cocktails and mocktails
- J&G Italian Deli (23 Beekman Ave):
- JP Doyle’s (48 Beekman Ave): special Holiday cocktails**
- Justin’s Deli & Café (86 Beekman Ave): hosting the Grinch with Greenville as their theme**
- Los Andes Bakery (180 Valley St): join Santa & other charactes for photos, cocoa and other surprises**
- Sabrosura Peruana (62 Beekman Ave)**
- Santorini Greek Restaurant (175 Valley St): Snap a photo with our merry elf serving delicious goodies and join us inside for a special holiday cocktail! **
- Sleepy Coffee Too (110 Beekman Ave): Sleepy Hollow High School Chorus, Santa from 3:30pm to 5pm; drink specials and extended hours **
- Sleepy Hollow Book Shop (95 Beekman Ave): crafting activity for kids**
- The Taco Club (31 Beekman Ave)**
SHOW YOUR SUPPORT!
- RHSM Life Center (32-34 Beekman Ave)**
** participating in Holiday Decoration Contest
Tarrytown
- 11am & 3pm Shows (need tickets): Tarrytown Music Hall (13 Main St): Presents Laurie Berkner: A Live Holiday Concert**
- 3:30pm: Anywhere Theatre Company presents THE WINTER ADVENTURE! (Parking Lot Entrance on Main St) The Winter Adventure is a tale of magic, fun and the cycles of nature narrated by Santa and Mrs. Claus who team up with the Winter Mother against the mischievous Krampus! Olentzero, the Spanish Christmas Giant, The Spirit of the Forest and Charles Dickens himself join in this battle of the seasons. Told with Music, Actors, Giant Puppets, Puzzles & Games.
https://sleepyhollowtarrytownchamber.com/wp-content/uploads/Logo-Anywhere-Theatre-300x400-1.png 300w" sizes="auto, (max-width: 53px) 100vw, 53px"> - 3pm & 4pm: Sinterklaas and his horse will be at Reformed Church of the Tarrytowns (42 N. Broadway) ready to meet and greet strollers and tell the story of how Sinterklaas became Santa Claus.
- 3pm-7pm: Make-A-Wish Hudson Valley accepting toys for local wish kids at The Bucci Real Estate office (4 N. Broadway)
SHOP for HOLIDAY GIFTS - All Together Now (16 Main Street) extended shopping hours**
- Bark & Meow (9 S. Broadway) stocked with Holiday wear, treats and more for your furry babies**
- Bella’s Boutique (35 N. Broadway): come by for refreshments, book signing with local author, meet & greet with local artist. Extended hours.
- Botanic Face & Body Spa (54 Main St): Stop by for hot apple cider, purchase a Gift Card & shop our organic luxury skincare brands with 20% off
- Eclipse Hair Body Nails (98 N. Broadway): 20% off select Aveda Products. Have a complimentary consultation and receive $20 off coupon for that service
- Makers Central Trolley Stop (84 Central Ave) Trolley Stop; Night market and live music**
- ONA (53 Main St) extended shopping hours
- Posh Pretzels (7 N. Broadway) Christmas and Hanukkah themed colored pretzels and gift boxes!**
- Pretty Funny Vintage (80 S. Broadway): the holidays are the perfect time to visit! The store is loaded with holidays gifts. Open 11am to 5pm.
- Tarrytown Floral Designs (51 Main St): Celebrate the season with flowers! 15% off everything in our store**
- The Hybrid Shop (51 Main St): 10% off everything in our store**
- The Purple Ostrich (7A S. Broadway) FREE apple cider & cookies. Visit our store anytime before December 14th to enter to win a 50% Off Shopping spree. Take a fun photo with your friends in front of our festive decorations. Post your photo on Instagram, tag @thepurpleostrich. The more friends in your photo, the more chances you have to WIN!**
- The Village Soccer Shop (40 Main St) come visit for Holiday Steals & Deals**
- The Swan’s House (37 N. Broadway) performance by “Sing from your Heart” carolers (5pm-7pm), exclusive in-store discounts and refreshments**
- Trilogy Consignment (54 Main Street): we will be spinning records in the shop for some live holiday cheer, and offering 10% off storewide
EAT & BE MERRY
- Eatarry (25 Main St) selling Hot Chocolate and other treats to keep Winter Strollers warm**
- 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.** - Horsefeathers (94 N. Broadway) **
- La Taqueria La Perla Poblanita (53 Main St): **
- little bs (49 Main St) $6 White Cranberry Sangrias **
- Main Street Pizza (47 Main St) **
- Main Street Sweets (35 Main St): Find the elf on the shelf for a sweet treat. Enjoy an elf size hot cocoa for $1. Egg nog ice cream and peppermint stick will be available.**
- Playa Bowls (3 Main St): $2 off any winter special bowl or winter special smoothie
- Set Back Inn (33 Main St) LIve Music; Special Holiday Cocktails **
- The Cube Inn (22 Main St) Special Holiday Cocktail **
** participating in Holiday Decoration Contest
Trolley Route and Stops:
TROLLEY ROUTE
Trolley #1: Starts route at 3pm
Trolley #2: Starts route at 3pm
STOP: Lighthouse Landing & Beekman/by Rotunda/Gate 1 (Sleepy Hollow)
STOP: Beekman Avenue & Cortlandt Street (Sleepy Hollow)
STOP: Bus Stop On Beekman Before N. Washington Street (Sleepy Hollow)
STOP: 178 Valley Street (Sleepy Hollow)
STOP: Warner Library (Tarrytown) (Tarrytown)
STOP: Broadway Avenue & Central Avenue (Tarrytown)
STOP: Tarrytown Music Hall (Tarrytown)
STOP: Makers Central (Tarrytown)
STOP: Lighthouse Landing & Beekman/by Rotunda/Gate 1 (Sleepy Hollow)
There will also be two shuttles
Shuttle 1: Starts route at Warner Library at 3pm
Shuttle 2: Starts route at Bus Stop on Beekman Avenue (before N. Washington Street) at 3pm
