Brewster Events and Things to Do

View events in Brewster on or after 8/26/2025

Tour of Brewster's Ancient Burial Ground

Where: Chowder House parking, 1993 Main Street, Brewster

When: Thursday, August 28, 2025, 9:30 AM - 10:30 AM
Saturday, September 20, 2025, 9:30 AM - 10:30 AM

How Much: $15

Categories: Historical

Tour of Brewster's Ancient Burial Ground located behind First Parish Brewster Unitarian Universalist Church on 6A. A Brewster Historical Society guide provides the history, sharing highlights of some of the townspeople buried underneath these centuries' old headstones. ...read more

Jessica Sheppard presents "Women Pirates!"

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

When: Thursday, August 28, 2025, 6:00 PM - 7:30 PM

How Much: Free

Categories: Historical

Aye, listen up ye swabs! 1718, she were a wild year, she were! Pirates, they ruled the seas, from the Caribbean to New England! But did ye know, some o' them scurvy dogs were lasses? Ye've heard o' Blackbeard and his Queen Anne's Revenge, Calico Jack and the Kingston, b...read more

By The Bay Shows Labor Day Weekend Fine Art and Craft Show

Where: drummer boy park , 733, Brewster

When: Friday, August 29, 2025 10:00 AM - Sunday, August 31, 2025 4:00 PM

How Much: Free

Categories: Festival

The biggest Little Show on Cape Cod - come out and see the best that Cape Cod can offer. Come and visit with us. You wont be disappointed. By the Bay Fine Art & Craft Show 24th Annual Fine Art & Craft Shows 2024 at drummer boy field Brewster Our 25th year of quality fi...read more

All Our Best

Where: Indoor Theater, 3299 Rte. 6A, Brewster

When: Friday, August 29, 2025, 7:30 PM - 10:00 PM

How Much: $50

Categories: Theater

CAPE REP THEATRE presents ANNUAL BENEFIT REVUE ALL OUR BESTCape Rep Theatre is excited to announce the return of our beloved annual benefit celebration All Our Best, directed and designed by Scott Storr. Performances will be held in Cape Rep's Indoor Theater August 29 &...read more

Trad

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

When: Daily, Wednesday, September 17, 2025 7:30 PM - Sunday, October 12, 2025 9:00 PM

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

A Different Drummer Craft Fair at Brewster Drummer Boy Park

Where: Drummer Boy Park, 773 Old Kings Highway, Route 6A, Brewster

When: Saturday, September 6, 2025, 10:00 AM - 4:00 PM
Sunday, September 7, 2025, 10:00 AM - 4:00 PM

How Much: Free

Categories: Festival

A Different Drummer Craft Fair at Drummer Boy Park Route 6A Brewster Hours 10 to 4. Featuring select craftspeople from Cape Cod and New England, over 40 booths will be at Drummer Boy Park Saturday and Sunday. You will find a wide variety of quality handcrafted items ma...read more

Brewster's Historic Main Street Walking Tour

Where: Meet at , 1993 Main St, Brewster

When: Wednesday, September 10, 2025, 9:30 AM - 11:00 AM
Wednesday, October 8, 2025, 9:30 AM - 11:00 AM

How Much: $15, $12members/15 non-members

Categories: Historical

Join us for an hour-long journey through history along Brewster's iconic Main Street, also known as the Old Kings Highway! Take a step back in time as our guide leads you through this charming street, brimming with stories of brave sea captains, antique homes, and long-...read more

A Grave Situation, Walking Tour of Brewster Cemetery

Where: Brewster Cemetery, 465 Lower Rd, Brewster

When: Thursday, September 18, 2025, 5:00 PM - 6:15 PM

How Much: $18, member $15/non-member $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.

Moscow Pianist Polina Osetinskaya in Concert

Where: Performing Arts Center, 95 Southern Eagle Cartway, Brewster

When: Wednesday, September 24, 2025, 7:00 PM - 9:00 PM

How Much: $35, Seniors $30

Categories: Music

Mark your calendars for an unforgettable opportunity to hear Polina Osetinskaya, "one of the most acclaimed Moscow pianists in the world" (Morellino Classica Festival, ITALY) playing Bach and Tchaikovsky in concert at Arts Empowering Life's Performing Arts Center. Known...read more