Best events in

Brewster

Tied to the tides and seasons, the calendar of events and things to do in Brewster, MA offers a relaxed pace. Activity centers along historic Main Street, where preserved sea captains' homes host local gatherings and community programs. Much of life here unfolds outdoors, from craft fairs at Drummer Boy Park to walks along the expansive Brewster Flats at low tide.

• Follow the low-key evening scene to spots like The Woodshed, a classic dive bar known for its nightly live music.
• Explore community-focused programming at the Brewster Ladies' Library, which hosts concerts, book clubs, and educational talks.
• Find seasonal outdoor events at Drummer Boy Park, the setting for annual traditions like the Brewster Summer Craft Festival and Kill Tide Arts & Craft Festival.