Holiday Shop Crawl, Carolers + Window Display Competition

🎄 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! ✨

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🎤 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

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🎅✨ 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!