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Brewster Events

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View events in Brewster on or after 10/9/2025

6th Annual Fall Frolic at Chatham Bars Inn

Where: Chatham Bars Inn Farm, 3034 Main St, Brewster

When:

How Much: $10

Categories: Festival

Don't miss the 6th Annual Fall Frolic at the Chatham Bars Inn Farm in Brewster on Sunday October 12, 2025 from 11am – 5pm. Enjoy complimentary live music, lawn games and kids pumpkin painting activities.The Farm Stand will be open with plenty of pumpkins to pick from an...read more

Trad

Where: Cape Rep Theatre, 3299 Rte 6A, Brewster

When: Daily, -

How Much: $40, 25 for 25 and under

Categories: Theater

Trad is the hilarious and poignant Irish play about a son, 100-year-old Thomas, and his even older Da, who set off on a quest to find the son that Thomas thinks he fathered 70 years ago. After all that time on earth, they want to know if the family line will survive. An...read more

She Loves Me

Where: Cape Rep Indoor Theater, North Side Route 6A E. Brewster, 3299 Rte 6A, Brewster

When: Daily, -

How Much: $50, $25 for patrons 25 and under.

Categories: Theater

She Loves MeBook by Joe MasteroffMusic by Jerry BockLyrics by Sheldon HarnickBased on a play by Miklos LaszioOriginally Directed on Broadway by Harold PrinceOriginally Produced on Broadway by Harold Prince in Association with Lawrence N. Kasha and Philip C. McKennaOrigi...read more

A Grave Situation, Walking Tour of Brewster Cemetery - October

Where: Brewster Cemetery, 465 Lower Rd, Brewster

When:

How Much: $18

Categories: Historical

A Grave Situation, Walking Tour of Brewster Cemetery scripted by Sally Cabot Gunning. A Narrated walking tour of the famous, the infamous, the unknown and ignored – till now! Expect uneven terrain — and "spirited" guests. Tickets are limited, reservations required.

Dr. Frankenstein's Halloween Ball

Where: Cape Rep Barn, 3299 Rte 6A, Brewster

When:

How Much: $20

Categories: Holiday

The monster is alive… and he's throwing a party!Cape Rep Theatre presents Dr. Frankenstein's Halloween Ball—a one-night-only costume party on Friday, October 31st at 7:30 PM. Join us for a rocking night of live music, devilish dancing, and Halloween revelry in the Barn....read more

Darius Coombs presentation - 13 Moons - History of Wampanoag

Where: Brewster Ladies' Library, 1822 Main Street, Brewster

When:

How Much: Free

Categories: Historical

Coombs is a Mashpee Wampanoag tribal citizen and is the Cultural Outreach Coordinator for the Mashpee Wampanoag Education Department. Darius is the former Director of the Wampanoag Indigenous Program at Plimoth/Patuxet Museums for over 30 years. Over his career Darius h...read more


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