Plymouth Holiday Stroll and Town Tree Lighting (Downtown Plymouth) — official source imageFree
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Plymouth Holiday Stroll and Town Tree Lighting (Downtown Plymouth)

Save-the-date only so far; no tickets mentioned. Check the organizer's page for the updated schedule.

Fri, Dec 4December 4-6, 2026. Town Tree Lighting on the first day (page says Thursday, December 4) and Cookie Trail on the last day (page says Saturday, December 6). See Plymouth lists the stroll on December 5, 2:00-7:00 pm.

Downtown Plymouth and the waterfrontWater Street, Main Street and Court Street, Plymouth, MA 02360 · 34.3 mi approx. from BostonDirections

Family-friendly; all ages

Free

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About this adventure

Plymouth's Downtown Waterfront District opens the holiday season with the Holiday Stroll, a three-day downtown open house along Main Street, Court Street and the Water Street waterfront. Shops stay open late with refreshments and one-night-only deals, the harbor is lined with luminaria, and carolers move from corner to corner through the evening, which makes it an easy outing for families who want to walk, window-shop and hear some carols downtown. The weekend starts with the Town Tree Lighting and ends with a Cookie Trail. The district also plans Light the Night, a month-long lighting installation that turns storefronts, streetlamps and the waterfront into a backdrop for evening walks and family photos from December 5 through New Year's Eve. The organizer's page is still a save-the-date: check it, or the See Plymouth listing, for the final schedule before you go, because the weekday labels on the page do not match the 2026 calendar.

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