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September 2022 Events on Cape Cod

Josie Cataldo | 8/25/2022

Second summer is here! The beginning of fall brings with it a cool breeze, the soft glow of new-season sunshine, and a long list of exciting events for you to choose from!

By the Bay Fine Arts & Crafts Show, Brewster

Happening the weekend of September 2nd at beautiful Drummer Boy Park in Brewster, the By the Bay Arts & Crafts Show is back and better than ever! Explore the enchanting work of Cape Cod's finest artists and artisans. It's the perfect place to visit if you're looking to find meaningful gifts for friends and family back home. Photography prints, paintings, and pottery for the artists. Jewelry and leather goods for the fashionista.

Brewster Band Concert

Sit back, relax, and drift away to the tune of live music at Drummer Boy Park on the evening of September 4th. Set the soundtrack to a new season and appreciate the cool breeze as you sit beneath the setting sun.

24th Season of Great Music on Sundays at 5, Provincetown

Great Music on Sundays at 5:00 is back for its 24th season of summer concerts! Sit back and enjoy some live music in the heart of the hustle and bustle of Provincetown.

Saturday Night Cruise-In, Dennis

The Cape Cod Classic Car Club welcomes all vehicles and all years at Patriot Square Shopping Center. Stroll through and admire these unique antique cars from 4:30pm to dusk.

Dennis Festival Days

Celebrate the conclusion of another sensational summer on Cape Cod at an end of summer Beach party with the Dennis Chamber of Commerce! Happening Sunday September 4th on West Dennis Beach, there will be a beach fire, fireworks display, and live music.

RAD Comvert Series RideAway Adventures, Sandwich

Live music, food trucks, kayaking, and paddle boarding...what more could you want? Happening 5:30 - 8:00 p.m. on September 14th, celebrate the end of summer outdoors with RideAway Adventures at Lawrence Pond in Sandwich!

Hyannis Open Streets on Main Street

It's not very often you get to storm the streets of Cape Cod on foot without having to frantically look both ways first! On Sunday September 18th, Main Street in Hyannis will be closed to vehicular traffic. Spend the afternoon shopping and soaking up the early fall sunshine all while strolling freely through the street.

Seaside LeMans Kart Race

Ready, set...start your engines! The Seaside LeMans Kart Race kicks off with an opening ceremony at noon and concludes with awards immediately after. This highly-anticipated event is free for spectators, and the close race will have you shaking with excitement! Spend the rest of the day exploring the wonderful shops and restaurants that Mashpee Commons has to offer.

Community Health Center 22nd Annual Golf Tournament

At beautiful Pocasset Golf Club on September 12th, Mashpee Community Health Center will be holding their 22nd annual golf tournament. This event helps the Community Health Center address issues such as housing insecurity, food insecurity, transportation challenges, employment challenges, language barriers, and access to affordable health care.

Cape Cod Canal Day

Celebrate the start of fall on Cape Cod with a FREE festival located right by the breathtaking Cape Cod Canal. This festival features something for everyone..craft beer and wine for the adults, arts & crafts vendors for creative minds, children's activities for the little ones, and the Cape Cod Cornhole Tournament and 5k Road Race for the athletes!

Rubber Duck Regatta, Dennis

The rubber ducks are making their highly anticipated return to Corporation Beach! From the "decked out duck contest" to the "duck race," attending this event will make you as happy as the ducks floating on the calm bay waters of Cape Cod!

CCYP Back to Business Bash, Hyannis

Cape Cod's most highly anticipated networking event is set for September 22nd! Each year, the CCYP Back to Business bash attracts close to a thousand individuals looking to expand their professional reach and network. Don't miss out on this incredible business opportunity if you're going to be on Cape!

Cape Cod Doxie Day

"A Cape Cod tradition continues celebrating everything dachshund in charming Barnstable Village. Join the Wiener Waddle and Waggin' Parade, cheer on your favorite doxie in the Doxie Dash. Think you have the longest dachshund or teeniest weenie? Enter contests to win prizes and bragging rights. Your dog will want to sit and stay at the pop-up Dachshund Café. Check out unique vendors. raffles and more. So come on out and sing the official Dachs-song, mingle and meet other doxies to benefit local animal organizations. Bring along packaged pet food and kitty litter for local shelters."