Winter Stroll

Sleepy HollowTarrytown
6th Annual Winter Stroll

SATURDAY, DECEMBER 12th, 2026 | 1PM TO 5PM

Grateful to our Presenting Sponsors:

 

Stroll, Shop & Be Jolly!

✨Experience the Magic of the Holiday Season in Sleepy Hollow and Tarrytown✨

• FREE Transportation:  Take a stroll or hop-on-and-off a FREE jolly trolley or luxurious
  Party Bus to visit participating businesses in both Villages 
• Contest:  Visit The Bucci Real Estate Team to enter their “Ugly Sweater” contest!
• Festive Fun:  Vote for your favorite festive storefront decorations
• Local Treats: Enjoy extended shopping hours, special discounts, delicious treats
  and festive entertainment!
• Live Performances:  Get into the holiday spirit with carolers, dancers, kid’s
  activities & performances featured throughout the villages! 
• Take Photos and Tag us!      @sleepyhollowtarrytownchamber

❄️ Find more details on Village events, participating businesses and Trolley/
Party Bus routes below!!!

UGLY HOLIDAY SWEATER CONTEST
HOW TO ENTER:

HOLIDAY STOREFRONT DECORATION CONTEST 

1. Stroll or take FREE transportation to participating businesses
2. Participating businesses noted with  **
3.  Vote for your favorite decoration the day of the Winter Stroll

Winner in each category will be announced within 24hrs on Instagram @sleepyhollowtarrytownchamber

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

PRIZES: Grand Prize: $250  Second Prize:  $150  Third Prize:  $ 100

Sponsored by:  

HAPPENINGS AROUND BOTH VILLAGES

SLEEPY HOLLOW

• 2 to 6pm: Holiday Vendor Village at Beekman Avenue Parking Lot (across from Firehouse):
  * Shop for unique gifts atLocal Shops and Arts & Crafts Vendors (see list below)
  * Choir performance from the Salvation Army Music Programs
• 2 to 6pm: Andean Pan Flute Music player will be stationed on Valley Street between
  Los Andes Bakery and Santorini
• 5 to 6pm:  Celebrate the Sleepy Hollow High School football team for their championship
  season!  Team players will walk from the High School (5pm) to Village Hall for a 5:30pm ceremony. 
  After the ceremony, the team will attend the annual Tree Lighting at Robertson Park.
• 6pm:  Tree lighting at Robertson Park (Chestnut Street & Valley Street) 

Shopping 

• Cozy Coven (31 Beekman Ave): singer/guitarist Jared Nelson will perform holiday songs 2pm to 6pm**
• Honey & Gold Flowers Shop (74 Beekman Ave):  Join our Gingerbread House Workshop—a fun, festive experience for families and kids, set to lively Christmas music**
• Quality High Cannabis Shop (25 Beekman Ave)**
• Sleepy Hollow Bookshop (95 Beekman Ave): Stop by to have John A. Rice sign his beautifully illustrated edition of the Christmas Carol. Grab your holiday gifts, a steaming cup of hot chocolate, and even to shop the Sleepy Hollow Middle School and High School Book Fair in the Bookshop.**

   

   Holiday Vendor Village (Beekman Avenue Parking Lot/Across from Firehouse)

• PHOTO OPP:  Headless Horseman will be at the Holiday Vendor Village

• TESLA: Experience the Future of Transit!
  Tesla is joining the Winter Stroll with exciting activities and transportation! Look for two exclusive Cybertrucks circulating the villages, offering rides to the business districts. Stop by the Tesla tent in the Winter Village to explore a display vehicle, enter raffles for Tesla merchandise, and sign up for a demo drive that night!

• Holiday Vendor Village Exhibitors:

  ArtHousebySusie: https://www.instagram.com/SusieBrubaker
  Cursed Objects Vintage: https://www.instagram.com/cursedobjects.vintage
  Dicentrose: https://www.instagram.com/dicentrose/
  Gioia by Gianni: https://www.instagram.com/shopgioiabygianna
  Jewelry by Mystical Meghan:  https://www.instagram.com/mysticalmeghan/
  Jimmy’s Soft Serve: https://www.instagram.com/jimmysoftserve/  
  Manor Sangria: https://www.instagram.com/manorsangria/
  Pride of the Hollow: https://www.instagram.com/prideofthehollow/
  Stitch Witch Creatives: https://www.instagram.com/stitchwitchcreatives/
  Tilly’s Tassel:  https://www.instagram.com/tillystassel
  Time to be a Candle: https://www.instagram.com/timetobecandlecompany/
  Walter’s Hot Dogs: https://www.instagram.com/waltershotdogs

   

   

Eat & Be Merry

• Beekman Ale (92 Beekman Ave):  special Holiday cocktails**
• Bridgeview Tavern (226 Beekman Ave):  join us for Holiday drinks and dinner in our cozy, heated beer garden**
• Casaletto Pizza (70 Beekman Ave)**
• Coco Taqueria (84 Beekman Ave)**
• DeCicco & Sons (1 Legend Dr):  Get the perfect holiday photo! Stop by for a festive photo op featuring our Headless Horseman Bench & Giant Christmas Tree. Warm up afterward with a delicious Holiday Cocktail!**
• JP Doyle’s (48 Beekman Ave):  special Holiday cocktails**
• J&G Italian Deli & Catering (23 Beekman Ave)**
• Justin’s Deli & Café (86 Beekman Ave): take your picture with Santa Claus and The Grinch and bring the kids for a serving of popcorn and cotton candy**
• Los Andes Bakery (180 Valley St):  join Santa & other characters from 4pm to 6pm 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 treats and a special holiday cocktail! **
• Sleepy Coffee Too (110 Beekman Ave):  Sleepy Hollow High School Chorus, Holiday pictures with Bear, our unofficial therapy dog, drink specials and extended hours**
• The Taco Club (31 Beekman Ave): enjoy fun Holiday cocktails with a Mexican twist**

** participating in Holiday Decoration Contest

TARRYTOWN

• 2:30pm, 3:30pm, 4:30pm & 5:30pm @ Main Street Parking Lot (next to River View
  Wine & Spirits)  Lovely Calamity Productions presents a 30-minute play, Christmas at
  Bracebridge Hall,based on the classic stories of Washington Irving. Catch the magic!
  Starring Billy Arrowsmith & friends.
  

  

•  4pm & 8pm Shows (tickets needed) @ Tarrytown Music Hall (13 Main St)  Cherish the Ladies
  – extremely popular all-female Irish band
• Visit The Bucci Real Estate Team (4 N. Broadway) & donate a new, unwrapped gift for Make-A-Wish Hudson Valley wish kid to spread joy this season. Receive candy gram, with personal note from local wish kid. Your generosity helps bring hope  & smiles to children battling critical illnesses

  Shopping

• All Together Now (16 Main Street):  We’re hosting a “Make Your Own Putty!” experience for
  $20 per putty. Pre-sales are open, but we’ll have extra spots for walk-in kids!**
• Bark & Meow (9 S. Broadway): 10% OFF all Holiday items during the Winter Stroll**
• Bella’s Boutique (35 N. Broadway): Get into the holiday groove! Enjoy festive holiday tunes from saxophonist T.C. while you sip on refreshments and take advantage of our special in-store discounts! Extended shopping hours.**
• Corcoran Legends Realty (38 Main St):  hosting its 2nd Annual Holiday Pop Up Shop featuring local vendors. Sweet treats for visitors as well! **
• EZ Fix (8A Main Street):  20% OFF ALL phone accessories the day of the Stroll!
• Harnik Brothers Jewelers (6 N. Broadway): 20% OFF on the day of the Stroll (some exceptions apply)**
• Holston Jewelers (28 Main St): 20% OFF all jewelry when you spend $100 or more, day of the Stroll**
• Hudson River Eye Care: 20% OFF any frame or lens purchases (offer not valid with insurance);
  A FREE eye-themed cookie; photo with life-sized Grinch.  Open from 2pm to 4pm.  
• Marquee Records (13 Main St, 2nd Floor):  score some vinyl for a good cause! Records available for just $2 each, with all proceeds benefiting the nonprofit Tarrytown Music Hall!
• Mindset Cannabis Shop (51 Main St): 10% OFF everything in our store; extended shopping hours**
• 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): we’ve been shopping all season to offer special finds in both vintage and contemporary HOLIDAY gifts, all of which will be offered at 10% OFF for the stroll!**
• Shaylula Jewelry & Gifts (23 Main St):  Stop in for a Holiday Candle Trunk Show (2-6 pm)! Meet local designer Anat from Midnight Embers and discover our two new “scentsational” exclusive holiday candles. Stock up on special gift sets perfectly priced for teachers and quick holiday grabs!
• Tarrytown Floral Designs (51 Main St): Celebrate the season with flowers! 15% OFF storewide**
• The Purple Ostrich (7A S. Broadway) FREE Hot Apple Cider & Purple Salt Water Taffy!!   Come meet, and get your photo taken with, The Purple Ostrich himself!  Be sure to tag us with your fun photos on Instagram @the_purple_ostrich**
• The Swan’s House (37 N. Broadway):  Exclusive in-store discounts and refreshments**
• Trilogy Consignment (54 Main Street):  Time to shop! Enjoy 10% off storewide during the Winter Stroll. Plus, every customer who visits between 2 pm and 6 pm will be entered to win a $100 gift certificate! Wear a past Trilogy purchase for an extra raffle entry!** 
• VSS: A Soccer & Lifestyle Joint (40 Main St):  10% OFF everything in our shop**

  
  Eat & Be Merry

• Coffee Labs Roasters (7 Main St)**
• Eatarry (25 Main St):  Warm up with festive cheer! Serving up the smooth White Christmas Martini and rich Egg Nog (for adults), plus comforting Hot Cocoa for the kids!**
• Fuel Hub (37 Main St) Extended shopping hours.  TIC TAC TOE (day of the Winter Stroll)
  Categories: 7-10 year olds; 11-15 year olds; 16-25 year olds; 25-40 year olds; 40+ year olds Winner from each category gets coupon for free Holiday Edition Specialty smoothie thru 12/30 & receives gift day of event. Participants need to show up with a partner WITHIN THEIR AGE category.**
• Grass Roots Kitchen (124 Wildey St) **
• Horsefeathers (94 N. Broadway)**
• 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**
• Mint Premium Foods (19 Main St):  Enjoy Main Street’s ONLY Michelin Gide restaurant and gourmet store.  Savor our premier selection of artisanal cheeses & charcuterie or enjoy a satisfying cup of our famous Belgian Hot Chocolate while you stroll!  Enjoy Holiday cocktails while you dine from our Mediterranean inspired menu.  Brunch. Lunch. Dinner
• Osaka Japanese Restaurant  (134 Wildey St):  Enjoy a taste of Japan! Receive a FREE appetizer with any dine-in or takeout order on the day of the Winter Stroll.
• Playa Bowls (3 Main St): $2 off any winter special bowl or winter special smoothie
• Pik Nik BBQ (45 Main St): Home of the BEST BBQ in New York… yeah we said it!  Come taste our freshly smoked brisket, ribs, pulled pork, smoked & fried chicken.  Add our signature sauces, sides & desserts and we guarantee you’ll stay warm AND full while you stroll! Wine, Beer, Sangria.  You’re welcome!
• Set Back Inn (33 Main St): Live Music; Special Holiday Cocktails **
• Susuru Ramen (21 N. Broadway):  Warm up with ramen! We’re offering a FREE appetizer with your dine-in or takeout order during the Winter Stroll
• Sweet Grass Grill (24 Main St):  We’re hosting a live jazz trio and shaking up special holiday cocktails to fill your stroll with festive cheer**
• Taqueria La Perla Poblanita (53 Main St): Dine in or take out & receive FREE champurrado (warm, traditional Mexican drink served during the Holidays) on us! **
• The Cube Inn  (22 Main St):  Special Holiday Cocktails **
  
• The Sailhouse (238 Green St): Special Holiday Cocktails**

Pamper Yourself or a Loved One!

• Diamond Nail Spa (1 Neperan Rd): FREE gift (lotion) for in-store customers on the day of the Stroll!
• Eclipse Hair Body Nails (98 N. Broadway):  20% off select Aveda Products.  Have a complimentary consultation and receive $20 off coupon for that service**
• JN Town Nails (4 Main St):  Treat yourself for the season! For the entire month of December, we are offering 20% off all waxing services—the perfect self-care stop during the month of December!

FREE & Festive Transportation

This year, getting around the villages is part of the fun. In addition to our FREE Jolly Trolley and luxurious Party Bus, we are thrilled to feature three Holiday-Decked Tesla Cybertrucks transporting guests to all the stops!

TROLLEY
STOP (Starts Route Here at 2pm):  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:  Holiday Vendor Village (Sleepy Hollow)
STOP:  Warner Library (Tarrytown)
STOP:  Broadway Avenue & Central Avenue (Tarrytown)
STOP:  Tarrytown Music Hall (Tarrytown)
STOP:  Lighthouse Landing & Beekman/by Rotunda/Gate 1 (Sleepy Hollow)
ROUTE:  https://maps.app.goo.gl/JXoHSNk2XRDb1jfZ9

PARTY BUS 
STOP:  (Starts Route Here at 2pm): Tarrytown Music Hall (Tarrytown)
STOP:  Lighthouse Landing & Beekman/by Rotunda/Gate 1 (Sleepy Hollow)
STOP:  Beekman Avenue & Cortlandt Street (Sleepy Hollow)
STOP:  Beekman Avenue & N. Washington Street (Sleepy Hollow)
WALK TO:  Holiday Vendor Village (Beekman Parking Lot, Sleepy Hollow)
STOP:  Valley St (Los Andes Bakery/Santorini Greek Restaurant (Sleepy Hollow)
STOP:  Tarrytown Station Center (Grass Roots Kitchen & Osaka (Tarrytown)
STOP:  Broadway Avenue & Central Avenue (Tarrytown)
STOP:  Tarrytown Music Hall (Tarrytown)

SHUTTLES:
STOP: Starts route at Tarrytown Train Station at 3pm 
STOP: Pretty Funny Vintage (Tarrytown)
STOP  Warner Library (Tarrytown)
STOP  Holiday Vendor Village (Beekman Parking Lot, Sleepy Hollow)
ROUTE:  https://maps.app.goo.gl/A2hdoYp5w7sA7dsx8
(no stop after 6pm at Pretty Funny Vintage)

TESLA CYBERTRUCKS 

Look for the festive Cybertrucks stationed at these key hubs:

• Tarrytown Train Station

• Sleepy Hollow Holiday Vendor Village (Beekman Lot)

• Lighthouse Landing & Beekman Rotunda