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Cape Cod Events
September 2021

Updated: September 6, 2021

Although summer is drawing to an end, the Cape Cod events calendar for September is still chock-full of fun things to see and do!

Shoppers at craft fair in Hyannis MAArts & Crafts Fair on the Village Green

Cape Cod Events Each Month

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August | September | October | November | December

Fairs, Festivals & Special Events on Cape Cod
September 2021

Although I do my best to keep this page up-to-date, things can still change quickly in these uncertain times. So I urge you to check the event sponsor's website or FB page to verify that the event is still on before you go!

Hyannis Labor Day Weekend Arts & Crafts Festival

When: September 4 & 5, 2021; Saturday 10am - 6pm, Sunday 10am - 4pm

Where: Hyannis Village Green, Main Street, Hyannis MA

Admission: Free

More Info: Castleberry Fairs

This Labor Day weekend, 50 talented artists and crafters will gather on the Village Green to display and sell their wares.

What's your pleasure? Fine jewelry, a new drawing or painting for your home, tasty homemade goodies, pet products, ornaments, shell craft, candles and soaps, wearable art.

You'll find all that and more at the Hyannis Labor Day Weekend Arts & Crafts Festival!

Arts Alive! Falmouth

When: September 10 - 12, 2021

Where: Falmouth Public Library lawn, Falmouth, MA

Admission: Free

More Info: Arts Falmouth

This festive three-day celebration of the arts normally happens in June. But this year, it's been moved to September.

Hosted by ArtsFalmouth, the annual event is an exuberant marketplace of handcrafted wares made by artists and artisans from around the Upper Cape, along with an extravaganza of performances from singer/songwriters to belly dancers, country music to rock bands, and musical theater to children’s story time. There is something for everyone in the family to enjoy!

"Sand Dollars for Soldiers" Benefit Event

When: September 11, 2021 from 3 p.m. to 8 p.m.

Where: Sand Dollar Bar & Grill, 50 Rt. 134, South Dennis, MA

More Info: Sand Dollar on FB

Sand Dollar Bar & Grill's annual "Sand Dollars for Soldiers" benefit combines good food and good fun for a great cause!

On September 11th, Sand Dollar will host a buffet, raffles and auctions ... and 100% of the money raised will go to Veterans on the Cape and at Walter Reid.

Let’s help the good folks at Sand Dollar make this year's event a huge success!

Seaside LeMans Race

When: September 11, 2021

Where: Mashpee Commons, Mashpee

Admission: Free for spectators

More Info: Seaside LeMans Race

"Drivers ... start your engines!"

Race fans won't want to miss this special event where teams of fearless drivers hop into European-style Formula One karts and vie for the checkered flag.

From the drop of the green flag, to pit stops, spin-outs, crashes, and the much-anticipated final lap, it's non-stop excitement for participants and spectators alike!

Friends’ Beer & Wine Grand Tasting

When: September 11, 2021, Noon - 4 p.m.

Where: Friends' Marketplace, 57 Main St., Orleans, MA

Admission: Free

More Info: Friends' Marketplace on Insta

Friends' Marketplace will have more than 60 wines and craft beers from across the country and world for you to sample and buy at their outdoor Grand Tasting. 

This event is a great opportunity to get to know some new wines and beers and have all your questions answered!

Eastham's Windmill Weekend Festival

When:  * CANCELLED * for 2021

Where: Windmill Green and other locations in Eastham

Admission: Many events are free

More Info: Eastham Windmill Weekend

Join the festivities and show off your skills at the talent show. Ooh and aah over the shiny autos at the car show. Pick up a few Holiday gifts at the arts and crafts booths. Chow down at the cookout. Tour Nauset Lighthouse.  Enter for chances to win great raffle prizes. And be sure to save time in your schedule for the Windmill Weekend Parade on Sunday. 

This is just a small sampling of the many events scheduled for the weekend. Check out the Windmill Weekend website (link above) for the full lineup!

Cranberry Cluster Dog Shows

When: September 16-19, 2021

Where: Barnstable County Fairgrounds, East Falmouth

Admission: Adults $5, children (under 12) $2

More Info: Cape Cod Kennel Club

The Cranberry Cluster Dog Shows are four days of AKC-recognized competition featuring top dogs from both the Cape Cod Kennel Club and the South Shore Kennel Club.

Events includes conformation judging, obedience trials and rally trials. Fun for all dog lovers to watch!

Celebrate Our Waters

When: September 17-19, 2021

Where: Rock Harbor and other locations in Orleans

Admission: Free

More Info: Celebrate Our Waters (event schedule)

Orleans Pond Coalition has a fabulous weekend planned at Rock Harbor and around the town of Orleans!

Events for this family friendly celebration include a sunset paddle on Pilgrim Lake, hiking around Bakers Pond, yoga on the beach, sailing on Pleasant Bay, self-guided history tours, a beach bonfire, the "Tour de Orleans" bike ride, a cranberry bog tour, fun kids activities and science explorations, and more.

Definitely a fun-filled weekend not to be missed!

Cape Cod Canal Day

When: September 18, 2021, 11 a.m. to 6 p.m.

Where: Buzzards Bay Park, Main Street, Buzzards Bay, MA

Admission: Free

More Info: Cape Cod Canal Day

This community-wide, family friendly event takes place in beautiful Buzzards Bay Park alongside the Cape Cod Canal.

The day features arts and crafts vendors, live entertainment, kids activities, a 5K road race (registration required), food vendors, and the "Cape Cod Canal Cup Cornhole Tournament". 

Canal Day is a fun-for-all event for visitors and locals alike!

Cape Cod St. Patrick's Parade

When:  September 18, 2021, starting at 11 a.m.

Where: Along Rt. 28 from South Yarmouth to West Yarmouth

Admission: Free

More Info: Cape Cod St. Pat's Parade

St. Paddy's Day parade in September??? Yes!

Postponed from it's normal time in March, this popular Cape Cod event has been re-scheduled to September. (Warm weather! Yay!!)

Come out and celebrate the Irish at this 2 mile-long parade featuring floats, marching bands, and plenty of parade beads to go around!

This year's Cape Cod St. Patrick's Parade is dedicated to the essential workers, first responders and front-line personnel who have worked tirelessly to get us all through the pandemic. They well deserve the honor!

Harwich Cranberry Arts & Music Festival

When:  September 18-19, 2021

Where: Harwich Community Center Field, 100 Oak Street

Admission: Free

More Info: Harwich Cranberry Festival

This two-day event features more than 100 talented artists and crafters displaying their wares for sale. (A little early Holiday shopping, anyone?)

When you hear the music, it's time for some toe-tapping live entertainment at CranJam Music Festival, also held behind the Community Center. And when the music stops on Saturday evening, the fireworks display begins!

Tennessee Williams Theater Festival

When: September 23-26, 2021

Where: Various venues in Provincetown

Admission: Ticket prices vary by event

More Info: Tennessee Williams Festival

Theater buffs from far and wide come to Cape Cod each year just to attend the  fabulous Tennessee Williams Theater Festival.  

Festival events are held at different venues around Provincetown and include performances of Williams' works, opportunities to meet the artists, and get togethers for Williams aficionados at coffee hours, mixers and parties.

Cape Cod Brew Fest

When: September 25, 2021, 2 p.m. - 5:30 p.m.

Where: Cape Cod Fairgrounds, 1220 Nathan Ellis Highway (Rt. 151), East Falmouth, MA

Admission: $50-60 per person (adults 21+ only)

More Info: Cape Cod Brew Fest

Beer lovers, this one's for you!

This popular annual event features craft brewers from Cape Cod to California and everywhere in between. 

Your admission ticket gets you an afternoon of live music and unlimited samples of some of the best, most creative beers you'll ever taste, along with a commemorative pint glass to take home.

* Tip - If you're going to be drinkin', don't be drivin'!!! Designated Driver tickets are available, too. They include reduced-cost admission to the festival, non-alcoholic beverages, snacks and a souvenir branded pint glass.

Cape Cod Doxie Day

When: September 25, 2021, 12 p.m.

Where: Behind the Barnstable County Courthouse, 3195 Main Street, Barnstable Village, MA

Admission: Free

More Info: Cape Cod Doxie Day

A Cape Cod tradition continues this fall, celebrating everything dachshund in historic Barnstable Village.

Join the Wiener Waddle and Waggin’ Parade, and cheer on your favorite doxie in the Doxie Dash.

Think you have the longest dachshund or teeniest weenie? [Dee's Disclaimer: Those aren't my words. The sponsor wrote it that way! LOL!] Enter contests to win prizes and bragging rights.

Funds raised from this event benefit Cape Wildlife Center. Donations of pet food and kitty litter for Red's Pet Pantry will be gratefully accepted.

Autumn at The Manse

When: September 25, 2021, 1 p.m. to 4 p.m.

Where: Josiah Dennis Manse, 16 Whig Street, Dennis Village, MA

Admission: Free (donations greatly appreciated!)

More Info: Dennis Historical Society

Step back in time to the early 1700s as period-costumed docents show you around the home of the Reverend Josiah Dennis - the man for whom the town of Dennis was named.

This special annual event is a wonderful opportunity to see a treasure trove of historic artifacts and learn about life in Dennis is the 18th century.

Cape Cod Vintage Motorcycle Show

When: September 26, 2021, 10 a.m. - 2 p.m.

Where: Barnstable County Courthouse Complex, Rt. 6A, Barnstable Village, MA

Admission: Free

More Info: Vintage Motorcycle Show FB page

Motorcycle aficionados, this is your chance to check out some of the coolest rides from the "olden days"!

Make your way to scenic Main Street (Rt. 6A) in Barnstable Village for this popular, family friendly event where vintage and collectible motorcycle owners show off their treasures.

Love Local Fest

When: September 26, 2021, 11 a.m. to 5 p.m.

Where: Aselton Park on Hyannis Harbor

Admission: Free

More Info: LoveLiveLocal

The autumn Love Local Fest at Aselton Park brings the Cape Cod community together for free, family-friendly fun while also supporting local business.

This popular event features local artists, brands, makers and the small businesses that sell them, along with food trucks, a craft beverage garden and kids activities - all overlooking the beautiful Hyannis Harbor.

There'll be live music, too. And Cape Cod Maritime Museum will host maritime-themed activities for families and kids from 12-4pm on their back patio.

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Important Note: The date, time, place, admission charges, etc. of the events on this page may be changed by the event sponsor at any time, without my knowledge. Please be sure to confirm all information directly with the sponsor before you make any plans!