Holiday Shop Crawl, Carolers + Window Display Competition

Date and Time

Saturday Dec 13, 2025
3:00 PM - 5:00 PM EST

Saturday, December 13th - 3-5pm
Note: Carolers are from 3-5pm, but participating Retailers will have special offers, treats, and family friendly activities throughout the day!

Location

The Village of Rhinebeck
🛍️ Participating Stores & Restaurants:
Kick off: Foster's Coach house
Fireside finale: The Beekman Arms

MONTGOMERY ROW:
Foster's Coach House • Paper Trail • Oblong Books • Pause Dog Boutique • Gigi’s Trattoria • Hammertown • J. McLaughlin

GARDEN STREET:
Twin Tides Tattoo, High Score Arcade, ME Hair Studio

East Market St:
Rhinebeck Mercantile • Winter Sun Summer Moon • Land of Oz Toys • Pegasus Shoes • Rhinebeck Artist's Shop • John Jack’s

West Market St:
Rain Spa • La Tua Bella Salon
and more to be announced!

1 East Market Street Rhinebeck NY 12572

Fees/Admission

Free community event! Stroll, explore, and find your holiday gifts from your favorite local Rhinebeck Village shops. #ShopLocal

Website

http://www.rhinebeckchamber.com/

Contact Information

Liana Galardi
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Holiday Shopping, Carolers + Window Display Competition

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Description

🎄 Rhinebeck Holiday Shop Crawl + Strolling Carolers! 🎶
Kick off the season with a festive afternoon of shopping, singing, sipping, and strolling through the village! Enjoy joyful holiday vibes as our Professional, Victorian Dress-Clad caroling group make their way through town, stopping at featured locations for mini-performances you won’t want to miss. Bundle up, bring friends + family, and soak in the magic! ✨

🎤 Caroler Route & Timeline

(Highlighted stops at top!)

⭐ Fosters – 3:00pm Kickoff
⭐ Twin Tides Tattoo – 3:15–3:30pm
⭐ Oblong Books (Montgomery Row) – Time TBD
⭐ Land of Oz Toys – 3:30–3:45pm
⭐ Winter Sun Summer Moon – 3:45–4:00pm
⭐ Rhinebeck Mercantile – 4:00–4:15pm (approx.)
🔥 Fireside Finale at the Beekman Arms – 4:30pm

🎅✨ Shop local, support small businesses, catch every stop on the caroling trail, and discover the most charming holiday windows in town. It’s the perfect way to welcome the season!