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Cape Cod Events Calendar
October 2021

Updated: October 15, 2021

If you're lucky enough to be on Cape Cod in October, you'll find an events calendar full of fantastic ways to enjoy the crisp, invigorating "sweater weather" that comes with autumn by the sea.

Cranberry farmers harvesting berriesWatching the Cranberry Harvest on a Beautiful October Day

Cape Cod Events Each Month

January | February | March | April | May | June | July
August | September | October | November | December

Fairs, Festivals & Special Events in October

Highfield Hall & Gardens Events

When: October 1 - 31, 2021

Where: 65 Highfield Drive, Falmouth MA

Admission: Adults $10; Seniors & Veterans $8; Members and Children under 12 free.

More Info:  Highfield Hall & Gardens

Highfield Hall & Gardens is an elegant, historic estate surround by lush gardens, lovely walking trails, and acres of conservation lands.

Throughout the month of October, Highfield Hall is offering a variety of special events including: mansion tours, estate walks, cooking and wreath-making classes, and concerts.

See Highfield Hall's calendar of events for details!


When: October 2, 2021, 10 a.m. to 4 p.m.

Where: Route 130, Sandwich, MA

Admission: Free

More Info: SandwichFest

There's a new twist to SandwichFest 2021. Instead of the "Best Sandwich in Sandwich" contest, this year's event will  feature "A Taste of Sandwich" - a food pavilion showcasing a variety of local restaurants and food trucks, along with a beer and wine tent.

In addition to all the fab food and drink, the day's festivities will also include plenty of music. And yes, the traditional dog parade will be happening, too!

Cape Cod Harvest Festival

When: CANCELLED for 2021

Where: Cape Cod Fairgrounds, North Falmouth MA

More Info: Harvest Festival

Harvest season is upon us, and it's celebrated in grand style at the annual Cape Cod Harvest Festival!

Attractions at the festival include local crafters and artisans, pony rides and amusements for the kids, farm animals, trolley rides, cider donuts and other treats, beer and wine, and of course ... the  farmers' market.

Harvest Festival is sure to be a fun event for everyone!

Looking forward to Harvest Fest's return in 2022!!

Vinegrass Music Festival

When: October 3, 2021, 11:30 a.m. to 5:30 p.m.

Where: Truro Vineyards, 11 Shore Road, N. Truro, MA

Admission: $60-$70 per person; under 12 free

More Info: Vinegrass Music Festival

This popular annual event at Truro Vineyards showcases the sounds of Americana, Bluegrass, & Folk (a/k/a "American Roots Music").  

This year will feature performances by The Wooks, The Way Down Wanderers, Jacob Joliff & Michael Daves, and Soggy Po Boys. (Haven't heard of these talented artists? No doubt you will in the years to come when they hit the big time!)

Crush Pad Food Truck will be there with their yummy eats. Truro Vineyards' wines, Twenty Boat Rum, and Dry Line Gin will also be available for purchase.

Pumpkin Day at Bourne Farm

When: October 9, 2021, 9 a.m. to 3 p.m.

Where: Bourne Farm in Falmouth

Admission: Free

More Info: Pumpkin Day

This year's event is scaled back to a "Pick Your Own Pumpkins" day.

There's no better time to find your perfect Jack-o-Lantern pumpkin!!

Yarmouth Seaside Festival

When:  October 9 - 11, 2021

Where: Various venues around town

Admission: Free

More Info: Yarmouth Seaside Festival

Yarmouth Seaside Festival is a highlight of Columbus Day weekend on Cape Cod!

This annual extravaganza has tons of fun activities for the whole family, including old favorites like an arts and crafts fair, rides and games for the kids, food vendors, a sand-sculpting contest, canoe and kayak races, a beach bonfire, and a big fireworks display at Seagull Beach.

* Fireworks postponed to Monday night, Oct. 11th. *

Taylor-Bray Farm's Fall Festival

When: October 9, 2021 (rain date Oct. 10th), 10 am to 4 pm

Where: Taylor Bray Farm, 108 Bray Farm Road, Yarmouthport

Admission: Free. Suggested parking donation $5

More Info: Taylor Bray Farm Fall Festival

Back again this year will be all the good, ol' fashioned fun Taylor Bray Farm's Fall Festival is known for: hayrides, a pumpkin patch, games for the kids, a free raffle for a giant pumpkin, yummy refreshments, and visits with all the friendly farm animals.

Donations are greatly appreciated and go toward upkeep of the farm, feeding and care of the animals, and the farm's educational programs. So please chip in $5 for parking - and a little more, if you're able!

*Note - No dogs are allowed at the farm on festival day.

Wellfleet OysterFest

When: CANCELED for 2021

Where: Main Street and other venues in Wellfleet

More Info: Wellfleet OysterFest 

OysterFest brings together locals and visitors from near and far for a celebration of the salty, succulent, world-renowned Wellfleet oyster. Fresh seafood is the star of the show, with fresh oysters, homemade chowder, and plenty of other delicacies purveyed in venues from the quaint town center to restaurants throughout town.

Fest-goers of all ages also enjoy arts and crafts, cooking demonstrations, nature walks and talks, live music, kids activities, and much more ... including the weekend's feature event: an oyster-shucking contest where competitors vie to win the $1000 first prize by properly shucking 24 oysters in the quickest time.

Fingers crossed that OysterFest will return in 2022!

Hyannis Open Streets

When: October 17, 2021, noon to 5 p.m. (weather permitting)

Where: Main Street and Village Green, Hyannis

Admission: Free

More Info: Hyannis Open Streets

Remember when your parents warned you, "Don't play in the street!"? Well, this is one day when it's okay - encouraged, actually - for you to do just that.

Beginning at noon, Main Street in downtown Hyannis will be closed to auto traffic, allowing everyone to walk, run, bike, dance and play in the street!

There'll also be lots of family friendly activities on Main Street and at the Village Green, along with food, shopping, and live performances. Fun for all on an October day!

Turtle Walk Story Hour

When: October 22, 2021, 4-5 p.m.

Where: Margaret Wyman Wildlife Sanctuary, 194 Meadow Lane, West Barnstable, MA

Admission: Suggested donation $5 per person

More Info: Orenda Land Trust

Follow the footsteps of a turtle’s journey through the seasons as depicted in the children’s book Turtle Walk by Matt Phelan.

Participants will stroll through the Turtle Sanctuary, making stops at signs displaying the book’s pages along the way, while the text is read aloud. The book is written for young children but the signs are augmented with additional information for older kids and adults, making it fun and educational for all ages.

All proceeds from this event directly support Orenda’s Diamondback Terrapin Protection Program that identifies, monitors and protects these threatened creatures.

(*Note: COVID safety protocols including social distancing and mask wearing requirements will be followed.)

Trick or Treat with the Animals

When: October 28, 29 and 30, 2021, 3 p.m. to 8 p.m.

Where: Meeting House Farm, 333 Quaker Meetinghouse Road, East Sandwich, MA

Admission: $10 per person; reservations required

More Info: Meeting House Farm on FB

Meeting House Farm in East Sandwich hosts the best, most unique Halloween event of the year!

For these three days, the farm will be all decked out in Halloween decor ... and the horses will be in costume!!

There'll be music, photo ops, and plenty of candy for the kids, too.

Don’t miss your opportunity to sign up for this super-cool "Trick or Treat" event! Last year, tickets sold out within the first 48 hours.

Cape Cod Marathon Weekend

When: October 30 & 31, 2021

Where: Falmouth MA

More Info: Cape Cod Marathon

There's good reason that Runners' World named this as one of the "Ten Most Scenic" marathons in the world!

Beginning and ending at the beautiful Village Green in Falmouth, the loop course takes runners along the shoreline, through farmlands and cranberry bogs, and past the imposing Nobska Light.

Choose your spot along the course, and help cheer the runners on as they pass by!

Halloween Safe Trick or Treat in Hyannis

When: October 31, 2021, 4 to 6 pm

Where: Main Street in Hyannis

Admission: Free

More Info: Hyannis Main Street

Head to Main Street in Hyannis for a fun, family friendly trick or treat experience! The street will be closed to traffic, and businesses will be passing out candy.

Come in costume, and dress your 4-legged friend up, too. (Yes, pets are welcome!) This is sure to be a fun event for the entire family.

Want to Add An Event To This Month's Calendar?

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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!