Holiday Shop & Carolers Crawl
Date and Time
Saturday Dec 5, 2026
Saturday, December 5th - 3-5pm
Note: Carolers are from 3-5pm, but participating Retailers will have special offers, treats, and family friendly activities throughout the day!
Location
2026 Locations TBA
Lineup from 2025 For Reference Only
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!
Fees/Admission
Free community event! Stroll, explore, and find your holiday gifts from your favorite local Rhinebeck Village shops. #ShopLocal
Website
Description
🎄 Rhinebeck Holiday Shop Crawl + Strolling Carolers! 🎶 2026 TBA ⭐ Fosters – 3:00pm Kickoff 🎅✨ 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!
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
Last year's stops for reference 2025
(Highlighted stops at top!)
⭐ 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
