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Brewster for the Holidays

Becky Fischer | Updated 12/1/2024

Join us at the annual Brewster for the Holidays celebration!

The Festivities

If you’re on the Cape during the weekend of December 6 - December 8, don’t miss the merrymaking as Brewster launches the holiday season with concerts, a tree lighting, parties, pictures and breakfast with Santa, carol singing, and so much more. Luminaries glow throughout Drummer Boy Park at the annual bayside tree and windmill lighting. Santa arrives by fire truck. The Brewster Band Annual Holiday Concert will be happening December 6th at 7:00 p.m. FREE ADMISSION! Donations accepted to benefit Nauset Youth Therapeutic Alliance.

Bring an unwrapped toy for Toys for Tots! Sponsored by Brewster Historical Society, WeNeedaVacation, Brewster Chamber of Commerce and 101.5 FM Koffee Radio.

Visit Brewster for the Holidays for details and a complete festival schedule.

WeNeedaVacation's History with Brewster for the Holidays

In 2009, The Talmadge Family made the decision to purchase and plant an 8 ft. Douglas Fir tree at Drummer Boy Park. It has since grown well over 20 ft. and is warmly referred to as "The Brewster Holiday Tree." The idea to purchase and plant the tree was born after Jeff Talmadge's father, nicknamed "Bubba," passed away. The family had enjoyed many summer band concerts with him at Drummer Boy Park, which led to them proposing to the Selectmen that a permanent tree be planted for Brewster for the Holidays in his memory. 14 years later, Bubba's legacy and the Brewster Holiday Tree stand tall and proud.

WeNeedaVacation.com and the Brewster Historical Society have been sponsoring this special event for a decade. It feels poignant that we're able to work arm in arm with the Historical Society on the event, as Bubba's ancestors were on the Mayflower and were some of the very people who settled in Brewster including William Brewster.

About Becky Fischer

About Becky Fischer: I've worked for WeNeedaVacation since 2003, providing photography, video, and consultation services to vacation rental homeowners. Over the years, I've photographed more than 700 homes across the Cape and Islands. My husband and I moved to Brewster with our three children in 2006. I grew up outside Boston, spent childhood summers on Nantucket, and was married in Orleans. Some of my favorite things about Cape life include walking the CCRT, taking deep breaths at the beach, discovering new coffee shops, and supporting our schools and community events.