Cape Cod is a magical place during the holidays, and one of the best ways to enjoy this time of year is to partake in Brewster for the Holidays festivities. This celebration starts in late November — usually before Thanksgiving — and ends just before Christmas.
Keep reading to learn everything about this festival, including the main events, can’t-miss events, and more!
About Brewster for the Holidays
Brewster for the Holidays is a traditional holiday celebration that offers free and paid family events and special activities for several weeks before Christmas. Sponsored by the Brewster Chamber of Commerce, it was recreated from holiday festivities of years past and has been going on for more than a decade.
The festival brings the community together in the name of the holiday spirit. Every year, it supports a different local charity with the help of sponsors and donations. A portion of the proceeds from some events benefit local, nonprofit children’s organizations.
Brewster for the Holidays’ Main Events
The main events for Brewster for the Holidays are held during the first weekend of December. During this time, the neighborhood gathers to jump-start the Christmas season, igniting the holiday spirit.
Rockin’ Round the Christmas Tree
On the first Friday of December, the town gathers at Drummer Boy Park for the Rockin’ Round the Christmas Tree event. This tree-lighting ceremony includes carolers, hot cocoa, and a Brewster PTO Toy Drive. Plus, Santa Claus comes to town in a fire truck!
The Brewster Band Annual Holiday Concert
Also on Friday, The Brewster Band performs an annual holiday concert. While the sponsors may change from year to year, the concert always includes popular singalongs. It’s free to attend, but you’re welcome to give a donation to the chosen charity for the year.
Breakfast With Santa Claus
After Santa Claus (and you) get a good night’s sleep, there’s no better way to kick-start the season than eating breakfast with him on the first Saturday morning of December. Typically, there are two breakfast times that you can reserve, and each has a maximum of 60 people.
Pictures With Santa & Storytime
After breakfast on Saturday morning, you have the opportunity to get a photo with Santa Claus and put your wish list into the North Pole mailbox. Then, kids will love the holiday storytime. Both of these events are free, and nonperishable food items will be collected for the local food pantry.
Can’t-Miss Brewster for the Holidays Events
While the main events for Brewster for the Holidays are held during the first weekend of December, other events are ongoing throughout the month. While some of the events vary from year to year, below are a handful of possibilities that you don’t want to miss.
Annual Wreath and Swag Sale
Every year, the Garden Club of Brewster holds an Annual Wreath and Swag Sale at Lemon Tree Village. It starts right after Thanksgiving and runs through the first weekend of December. All of the decorations are handmade by the club members, and the proceeds support club scholarships.
Hybrid Wine Tasting for a Cause
Friends or Relatives With Autism and Related Disabilities (FORWARD) is an organization that aims to build affordable supportive housing for adults with autism and similar disabilities, allowing them to thrive.
In 2021, the organization held a Hybrid Wine Tasting for a Cause event during the first weekend of December. The ticket proceeds helped fund its ongoing efforts.
Stuff a Cruiser
During the first weekend of December 2021, The Village Toy Store and Brewster Police Department sponsored the Stuff a Cruiser event to benefit children in need during Christmas. It involved buying a toy from the store and the store matching the purchase with the goal of filling a police cruiser.
Bayside Bright Lights Celebration
The Bayside Bright Lights Celebration was organized by the Brewster Recreation Department in 2021. The event included a drive around Eddy Elementary School to see Christmas lights, holiday-themed inflatables and lawn decorations, lit up fire engines and police cars, and Santa Claus.
Registration was required, along with a per-car fee. But, you got a goody bag at the end of the drive, and the proceeds benefited local kids and families.
Cape Rep Theatre Barn Open House & Holiday Caroling
As an artist-driven company, the Cape Rep Theatre produces a variety of stories at its historic property in Nickerson State Park. From May through December, it performs four to five plays indoors.
Around mid-December 2021, it held a Barn Open House & Holiday Caroling event to show off its progress on restoring a historic barn and provide some classic holiday music with hot drinks and refreshments for purchase. The company likes celebrating the season in some way each year, though.
More Events During Brewster for the Holidays
In addition to the above events during Brewster for the Holidays, there are tons more that occur during the month. While not all of these events are held every year, they’ll give you an idea of what to expect while you’re in town.
Christmas Boutique Event
Each year, Sea Captains’ Thrift Shop hosts its Christmas Boutique event. It starts before Thanksgiving and ends a couple days before Christmas. The shop has everything that you need for the holidays — from wreaths and ornaments to home decor to gifts and holiday clothes and jewelry.
Half-Price Original Artwork
At the Underground Art Gallery in 2021, many of the shop’s original works on display were half price for the entire Brewster for the Holidays celebration. You received a free greeting card and could enter to win a gift raffle too.
Brewster Ladies’ Library Fundraiser
The Garden Club of Brewster hosted a silent auction for about a week and half in 2021 to benefit the Brewster Ladies’ Library. The auction included a boxwood tree, decorated wreath, lichen wreath, one painting, and other items. Library members had the chance to enter to win a gift card to a local establishment too.
Holiday of Giving
The Holiday of Giving event started at Lemon Tree Village the day after Thanksgiving 2021. Along with the Garden Club’s Wreath and Swag Sale and the Stuff a Cruiser fundraiser, the event included a coat drive to support a local charity. There were also raffles and refreshments to thank customers.
Club Tanuki Holiday Open House
The Japanese-themed Club Tanuki art gallery held a Holiday Open House event during most of the Brewster for the Holidays festivities. The gallery featured handmade local gifts, Japanese antiques, fine art, and Japanese-themed refreshments.
Holiday Book Signing
The Brewster Book Store hosts book signings throughout the year. But, it spices up these events during the holidays. For 2021, it featured author Amy Pershing signing copies of her books, including “An Eggnog to Die For.” The shop set up a holiday tent with eggnog and other holiday treats as well.
Shop Small Saturday
The Saturday after Thanksgiving is Shop Small Saturday across the United States, including Brewster Cape Cod. It’s the perfect time to shop the local stores and support their businesses for the holidays.
Gift Certificate Raffle
For three weeks during the Brewster for the Holidays celebration, Heart Pottery & Peru Photography hosted a raffle for a gift certificate that the winner could use toward purchasing Mark’s fine scenic and nature photography or Diane’s raku pottery and wheel-thrown porcelain.
Holiday Refreshments & Free Gift
The Cape Cod Bag Company hand crafts beach bags, wine bags, travel bags, totes, and other bags. It also sells candles and home decor items that are made by local artisans. All of these make fantastic gifts for loved ones.
While shopping there during the first weekend of December 2021, customers were treated to holiday refreshments. If they spent $50, they were awarded a free whale key fob.
Discount Handcrafted Goods
Every year, HandCraft House has a three-day sale during the first weekend of December. For the 2021 holiday season, everything in the store and online was 10% off! This art and gift gallery sells handcrafted creations by local, regional, and national artisans.
Windmill Meadows Decorating Event
If the Rockin’ Round the Christmas Tree event isn’t enough for you during Brewster for the Holidays, you could have the chance to help decorate Windmill Meadows at Drummer Boy Park. The Brewster Conservation Trust hosted a decorating event in 2021, featuring twinkling lights, hot cocoa, mulled cider, treats, and a Solstice Storytime.
Annual Scholastic Book Fair
Every holiday season, the Brewster PTO holds a Scholastic Book Fair during the first weekend of December. Stop by to look for children’s books as gifts, or bring your kids to make ornaments. It’s a great way to support the schools in Brewster too.
Write & Mail Letters to Santa
Cape Cod 5 — The Brewster Banking Center — held an event on the first Saturday of December to mail Christmas wish lists. The elves were on hand to help write letters to Santa and put them in the North Pole mailbox. Special holiday treats and takeaways were given out as well.
Special Brewster for the Holidays Ornament Collection
To commemorate the holidays, the Brewster Chamber of Commerce collaborates with a local artist to create a series of ornaments. Each ornament is numbered and signed by the artist. Since only a limited number are made, it’s the perfect souvenir to memorialize a visit to Brewster Cape Cod.
In 2021, it launched the Cape Cod Sea Shells series. The ornaments could be ordered via a mail order form or purchased at various Brewster shops.
Where to Stay for Brewster for the Holidays
Since Brewster for the Holidays extends over a weekend, you’ll need comfy accommodations for your visit. Candleberry Inn has luxurious accommodations with modern amenities for your comfort. We’re also located in the heart of Brewster, a short walk or drive from many of the festivities.
Book a guest room now for the first weekend of December and the kick off to the holiday season in Brewster Cape Cod!
