Brewster, MA, Events

Your Year-Round Guide to Brewster, MA, Local Events

The seaside town of Brewster, MA, is a premier Northeastern vacation destination known for its fresh seafood and breathtaking views. Visitors and locals alike come together during the peak months when the weather warms up for a variety of local festivals and events. 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. That’s why we’ve chosen the best annual events to showcase and update this list often. Pick one of our favorites below and start planning your getaway with our complimentary Vacation Guide!

Discover More of Cape Cod

Our Top 3 Brewster, MA, Events

Each event and festival on the Cape has something unique for attendees to experience. Get a feel for what these events are like by reading about our favorites in each category!

Natural Beauty – Brewster in Bloom | May

This festival marks the beginning of warm weather after a frigid winter on the Cape. Brewster in Bloom began in the 1980s when businesspeople planted flowers along the famous Route 6A to celebrate the newfound warmth. Since then, it has grown into a multifaceted festival with events ranging from a parade with floats to a 5K race.

Arts & Culture – The Harwich Cranberry Arts & Music Festival | September

This festival is one of the top five Cape Cod Fairs. The Harwich Cranberry Arts and Music Festival embraces and supports the Cape and its people. The festival’s founders operate on a well-rounded mission statement to “provide events which entertain the public, sustain artists and musicians, provide voice to community organizations, and raise funds to support our youth.”

Local Flavors – Wellfleet OysterFest | October

A Cape Cod getaway isn’t complete without indulging in excellent, freshly caught seafood that’s prepared to perfection. At the Wellfleet OysterFest, you can try the Cape’s most famous seafood dishes from a variety of vendors. Enjoy live music, demonstrations, and friendly competition! 

The Best of 2020

Brewster, MA, Events

Brewster in Bloom Festival | May 2, 3, & 4, 2020

See thousands of Brewster daffodils around town when you stay at the Candleberry Inn during this weekend of local activities including a 5K run, Concert in the Park, Antiques & Arts Excursion, Fine Arts and Craft Show, Sea Captains and Treasure Parade, Golf Tournament and much more. Enjoy the marching band and parade that passes the Candleberry Inn on Main Street in Brewster, MA.

Annual Cape Cod Antique Dealers Association Outdoors Summer Antiques Show and Sale | August 2020, DATES TBA

Cape Cod attracts antique dealers and collectors throughout the year. The Cape Cod Antique Dealers Association (CCADA) annual summer antique show is a great opportunity to see and buy a wide variety of material in one visit. The event is in Orleans, just one town away from the Candleberry Inn. Plan to stay with us, attend the CCADA show, and visit the organization’s 150+ member antique shops on Cape Cod. Candleberry Inn will provide you with a complimentary antique dealer member directory. The Cape Cod Chamber of Commerce has more details for those wishing to attend.

9th Annual Kill Tide Arts and Crafts Festival | August 2020, DATES TBA

The Historic Drummer Boy Park in Brewster, just a short ride from the Candleberry Inn, hosts a variety of traditional American-made works at the Kill Tide Arts and Craft Festival. Sample specialty foods such as kettle corn, cranberry jellies, wine slushy mix, lemonade, jams, cooking oils, herbal dips, seasonings, jams, finishing sauces, BBQ sauces, gourmet pastries & more. The Kill Tide Arts & Craft Festival is free admission with plenty of free parking and held rain or shine. Friendly pets on a leash are welcome. 

Pan-Mass Challenge | August 1 & 2, 2020

The Candleberry Inn is on the event cycling route (Route 6A). Each year, the Pan-Mass Challenge brings together thousands of impassioned cyclists, committed volunteers, generous donors, and dedicated corporate sponsors. Together, they strive to provide Dana-Farber’s doctors and researchers the necessary resources to discover cures for all types of cancer. Candleberry Inn proudly donates a stay at our Inn to the Pan-Mass Challenge Fundraiser’s silent auction.

68th Annual Society of Cape Cod Craftsmen Craft Fair | August 4, 5, & 6, 2020

You can visit this fine juried craft show just a short drive from Candleberry Inn that features the work of the Cape Cod Craftsmen. This year’s celebration will include select Cape Cod artists. The show is held rain or shine under a big white tent at Drummer Boy Park in Brewster. Come support this talented group of professional local artists and craftspeople!

42nd Annual Brew Run | August 8, 2020

This 5.2-mile run in Brewster finishes at the Woodshed Bar on Route 6A, across the street from the Candleberry Inn. The popular 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 | August 15, 2020

Swim, kayak, walk, run, or paddle to fight breast cancer at Nickerson State Park, just moments from the Candleberry Inn. Against the Tide is a family-friendly, multi-sport event to benefit the Massachusetts Breast Cancer Coalition (MBCC). MBCC is the only non-profit in the state dedicated to the prevention of breast cancer from environmental causes. You may participate in several events to fundraise on behalf of MBCC and its important mission to change the legacy of breast cancer for future generations. 

ALA Autumn Escape Bike Trek | September 25, 26, & 27, 2020

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. 

Brewster for the Holidays | December 2020, DATES TBA

Get into the holiday spirit when you stay at Candleberry Inn during Brewster for the Holidays! This three-day festival comes to town during the first weekend of December. 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. You won’t want to miss this!

Cape Cod Events

Cape Cod Maritime Days | May 1-31, 2020

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.

Annual Heritage Auto Show | June 2020, DATES TBA

One of the most unique and impressive collections of antique cars you’ll ever experience at the Sandwich Heritage Museum and Gardens. Browse through their incredible exhibitions before you go!

Cape Cod Hydrangea Festival | July 10-19, 2020

An annual celebration of the Cape’s signature flowers! This ten-day festival’s main attractions are the daily tours of private gardens, each designed and maintained by the individual homeowners carrying a unique charm. You will surely enjoy such special garden spaces. This event supports a variety of local nonprofits.

Annual Harwich Arts & Music Cranberry Festival | Sept. 2020, DATES TBA

With over 375 cranberry farms in Massachusetts, cranberries are an integral piece of not only the state’s economy but also its culture. The Harwich Arts and Music Festival embraces this culture every September for two days as it hosts live music, food trucks, and over 150 local craft vendors.

Cape Cod Roots and Blues Festival | September 2020, DATES TBA

The Cape Cod Roots and Blues Festival is a celebration of music, family, and community that you won’t want to miss! Listen to live music on one of Cape Cod’s best beaches, Nauset Beach. If this year’s festival is anything like its previous iterations, a good time is guaranteed.

Chowder Festival | June 2020, DATES TBA

Rich, creamy, and delicious, New England clam chowder is a staple of Massachusetts cuisine. It practically rains clam chowder on Cape Cod, and the Chowder Festival is the best place to get a taste. Join the party every June to sample chowder from the talented local chefs and vendors.

Wellfleet OysterFest | October 17 & 18, 2020

One of the most essential fall events on Cape Cod is the Wellfleet OysterFest. Every October, this festival offers a taste of one of Massachusetts’ most iconic dishes. Stop by Main Street and enjoy some of the best oysters, clams, and shellfish in the entire country!

Eastham Turnip Festival | November 2020, DATES TBA

In addition to buying delicious locally grown turnips, enjoy a Turnip Cook-Off, live band music, fun contests and turnip-themed games, and artisan vendor handcrafts and gifts in time for holiday shopping at the Eastham Turnip Festival.

Stay at Candleberry Inn During Your Cape Cod Getaway

Exterior dining area at Candleberry Inn

Candleberry Inn is the perfect choice for relaxing after attending a Brewster, MA, festival. After you fill up on clam chowder or run a 5K race, come back to Candleberry Inn for some of the most relaxing and luxurious accommodations on Cape Cod. Our quaint inn is right next to Cape Cod Bay and features world-class amenities, a friendly atmosphere, and a gourmet breakfast that’s included with your stay!

Explore all of Cape Cod’s upcoming events and book your stay today!