The Cape Cod Bay seaside town of Brewster MA is a premier vacation destination known for its fresh seafood and breathtaking views. When you visit this historic town, you’ll find tons of things to do. You can even attend some fantastic events in Brewster Massachusetts if you come at the right time.
Come visit during one of these Brewster MA events to experience the best of Cape Cod with us. At Candleberry Inn, we want our guests to arrive as visitors and leave feeling like locals.
Brewster events and festivals are unique, and we’ve put together a list of more than a dozen for you to enjoy in each season. Pick one of our favorite Cape Cod events in Brewster below and start planning your getaway with our complimentary Vacation Guide!
Cape Cod’s Brewster Events in the Spring
Brewster in Bloom Festival
Late April to Early May
The Brewster in Bloom Festival is the biggest event in Brewster during the spring. It all started when a group of businesspeople planted daffodils along Route 6A, marking the beginning of the season. When the flowers bloom brilliant yellow, the town comes alive with live music, arts and crafts, a lawn display contest, a kid’s carnival, and a parade through town.
By the Bay Fine Art & Craft Show
Late May (and more)
Considered the largest “Little Show on Cape Cod,” the By the Bay Fine Art & Craft Show represents local and regional artists and craftspeople. Visit Drummer Boy Park for folk art, photography, leather, oils, watercolors, antiques, fabrics, glass, handcrafted jewelry, and more.
By the Bay hosts multiple shows throughout the year. The first is in the spring in late May, and the others are in early July, early September, and early October.
Summer Events in Brewster Massachusetts
Drummer Boy Open Air Antiques Fair
Late June
Featuring antique dealers from across the Cape, the Drummer Boy Open Air Antiques Fair is the ultimate event for finding hidden treasures. This annual outdoor event is held at the scenic Drummer Boy Park and will include free tours of Windmill Village, blacksmith shop demonstrations, and a classic car show.
Our Lady of the Cape Summer Fair
Late June
Every year, Our Lady of the Cape Catholic Church hosts a summer fair that makes a huge splash in Brewster. The “Whale of a Fair” has a variety of items for sale — baked goods, household items, themed baskets, gifts, art, antiques, collectibles, jewelry, and so much more. Plus, it has barbecue, kids’ face painting, a lottery tree, cash sweepstakes, and a silent auction.
Cape Cod Hydrangea Festival
Mid-July
The Cape Cod Hydrangea Festival is a Cape-wide event of garden tours from Bourne to Falmouth to Chatham to Provincetown. The Garden Club of Brewster hosts a garden in Brewster, while the Cape Cod Hospital Auxiliary Orleans Branch hosts four other gardens throughout town. The Candleberry Inn gardens have been part of these tours.
The 10-day festival is a celebration of the blue, white, and pink hues of hydrangeas. The garden tour fees support local nonprofit organizations.
Pan-Mass Challenge
Early August
If you like to cycle for a cause, you can participate in the Pan-Mass Challenge. This event brings thousands of cyclists and more together.
There are 16 cycling routes — ranging from 25 miles to 211 miles in length — from Sturbridge, Wellesley, and Bourne to Provincetown (and routes in between). Brewster Massachusetts is on the cycling route, so even if you don’t participate, you can watch the cyclists whiz by on Main Street.
Annual Brewster Brew Run
Mid-August
This 5.2-mile run in Brewster finishes at the Woodshed Bar on Route 6A, across the street from the Candleberry Inn. The popular Brewster Brew Run is known for its huge prize giveaway after the event. It is co-sponsored by the Brewster Rescue Squad and The Woodshed Bar to benefit The Brewster Rescue and Safety.
Against the Tide
Mid-August
Benefiting the Massachusetts Breast Cancer Coalition, Against the Tide is a multi-sport event held at Nickerson State Park. You can participate in several sports — kayaking, running, swimming, and walking — to raise funds for the fight against breast cancer. Everyone who registers will receive a bib, T-shirt, and/or swim cap.
Kill Tide Arts and Crafts Festival
Late August
More than 100 juried artisans gather at the Kill Tide Arts and Craft Festival in late August to show off their jewelry, fine art, quilts, pillows, candles, toys, clothing, and tons more. The event is held at Drummer Boy Park.
And, arts and crafts aren’t the only things you’ll find. You get to enjoy specialty food samples too — jellies, jams, barbecue sauces, herbal dips, kettle corn, gourmet pastries, and more.
Brewster Cape Cod Events in the Fall
Harvest Bazaar at Windmill Village
Early October
The Harvest Bazaar at Windmill Village is one of the biggest events in Brewster Massachusetts during the fall. Along with free village tours and blacksmith demonstrations, there’s a farmer’s market with artisans and crafters of all kinds.
The event features free kid’s activities, including pumpkin painting, face painting, a scavenger hunt with prizes, a prize for wearing a costume, and more.
Brewster Baptist Church Holiday Fair
Early to mid-October
If you want to start your holiday shopping early, head to the Brewster Baptist Church Holiday Fair. You’ll find jewelry and handbags, wreaths and floral arrangements, baked goods, handmade crafts and knits, and other holiday gifts and treats. Best of all, the proceeds are donated to local charities.
Brewster Artillery Company Drill
Late October
At Windmill Village in Brewster (next to Drummer Boy Park), the Brewster Artillery Company Drill is a colonial militia drill reenactment. You get to learn about colonial life during the performance, and there are kid-friendly, hands-on activities for kids.
Halloween Haunted Mansion
Late October
As the fall season turns spooky, stop by the Crosby Mansion for the Halloween Haunted Mansion. The historic mansion is full of stories and lore, and for an eerie weekend, it’s transformed into a haunted mansion with goblins, ghouls, and ghosts.
The Halloween Haunted Mansion is a popular attraction in Brewster, so we recommend that you register ahead of time for a guided tour. This haunt is suitable for children 7 years and older.
Top Winter Event in Brewster Massachusetts
Get into the holiday spirit when you stay at Candleberry Inn during Brewster for the Holidays! This holiday festival comes to town during the first weekend of December and continues for several weeks leading up to Christmas.
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. Watch the Illumination Ceremony, tour the Cape’s art galleries, shop around for presents, and more. The Holiday Party ends the weekend with treats and even a visit from Santa!
This traditional holiday celebration offers an array of free and paid family events and activities, such as:
- Rockin’ Round the Christmas Tree
- The Brewster Band annual holiday concert
- Breakfast and pictures with Santa Claus
- Annual swag and wreath sale
- Bayside Bright Lights Celebration
What makes this event even more unique is the exclusive holiday ornament collection. It’s a collaboration between the Brewster Chamber of Commerce and a different local artist each year. Every ornament is signed and numbered, and only a limited number are available.
More Big Annual Events in Nearby Cape Cod Towns
The events in Brewster Massachusetts aren’t the only Cape events worth attending. Here are a handful of other festivals that we recommend.
Cape Cod Maritime Days
May
A month-long celebration of Cape Cod’s rich maritime history, including lighthouse and walking tours, nautical art exhibits and lectures on maritime lore, boat-building exhibits, kayaking excursions, and the Maritime History Symposium. Check out the full lineup of activities to learn more.
Harwich Cranberry Arts & Music Festival
Mid-September
Held behind the Harwich Community Center, the Harwich Cranberry Arts & Music Festival is a two-day event with more than 150 vendors who sell handcrafted items. The event includes the CranJam Music Festival with live tunes, a wooden dance floor, and fireworks.
ALA Autumn Escape Bike Trek
Late September
Supporting the American Lung Association (ALA), the Autumn Escape Bike Trek routes takes bikers on a breathtaking journey through Cape Cod after the madness of the summer season has passed. As a participant, you’ll enjoy the Rail Trail – Cape Cod’s bike path, known for its beautiful views of the quaint seaside towns and Nickerson State Park. At the end of your ride, relax and pamper yourself at the Candleberry Inn.
Wellfleet OysterFest
Mid-October
Since 2001, the Wellfleet OysterFest has celebrated the town’s deeply rooted history of shellfishing — Wellfleet is known as having some of the best shellfish in the country. This event plays a major role in the local community with the proceeds supporting local businesses and students.
There are a lot of activities to enjoy during the oyster festival, including a Shuck Off, food demonstrations and tastings, oyster farm tours, beer and wine, live entertainment, and more. Plus, there’s a family fun area with crafts, face painting, and educational displays to name a few.
Eastham Turnip Festival
Mid-November
Celebrating the turnip, the Eastham Turnip Festival is an event where you can purchase locally grown turnips and taste various turnip dishes at participating restaurants. You can even try out some turnip ice cream — it’s better than it sounds!
Also, there’s a Turnip Cook-Off, live music, and turnip-themed entertainment — such as a juggling act, balloon and magic show, face painting, Henna body art, temporary turnip tattoos, and turnip games. You can buy turnip-themed merchandise as well.
Gardens Aglow
November to December
At the Heritage Museums & Gardens in Sandwich, Gardens Aglow is one of the biggest winter attractions on Cape Cod. From right after Thanksgiving until a couple of days before Christmas, the gardens are decorated in festive seasonal decor and thousands of holiday lights.
Themed activities include going on a reindeer scavenger hunt, roasting marshmallows, playing lawn games, and eating seasonal treats. Making the event even more magical, you can ride on the 1908 Looff Carousel and visit with Santa & Mrs. Claus.
A Luxury Bed and Breakfast in the Heart of Brewster Cape Cod
Whether you plan your trip around specific events in Brewster Massachusetts or just happen to be visiting at the right time, make Candleberry Inn your retreat. Our inn is a short drive or walk from most of the events on this list. And, the other Cape town events are only about a 30-minute drive away.
When you stay with us, you can expect world-class amenities, a gourmet breakfast every morning, and luxurious rooms and suites. Plus, we’re close to the best Brewster restaurants. Take a look at the rooms available for your next travel dates!