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Cape Cod Events Calendar
October 2022

Updated: May 26, 2022

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, 2022

Where: 65 Highfield Drive, Falmouth MA

Admission: Adults $10; Seniors $8; Active Military, Veterans and Children under 17 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 autumn months, Highfield Hall offers a variety of special events including mansion tours, estate walks, cooking and wreath-making classes, and more.

See Highfield Hall's calendar of events for details!


When: October 1, 2022, 10 a.m. to 4 p.m.

Where: Route 130, Sandwich, MA

Admission: Free

More Info: SandwichFest

This year's SandwichFest will once again 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 include plenty of music, too!

Cape Cod Marathon Weekend

When: October 1 & 2, 2022

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!

Cape Cod Harvest Festival

When: 2022 date - TBA

Where: Cape Cod Fairgrounds, North Falmouth MA

More Info: Harvest Festival

Harvest season is 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.

We're all looking forward to Harvest Fest's return in 2022!!

Vinegrass Music Festival

When: October 2, 2022, noon to 6 p.m.

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

Admission:  General admission $50

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's festival features performances by up-and-coming, talented artists - along with lots of yummy eats and Truro Vineyards' wines, Twenty Boat Rum, and Dry Line Gin available for purchase.

Pumpkin Day at Bourne Farm

When: October 8, 2022, 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 8 - 10, 2022

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.

Taylor-Bray Farm's Fall Festival

When: October 8, 2022

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, tasty 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:  September 19 - October 16, 2022

Where: Multiple venues in Wellfleet

More Info: Wellfleet OysterFest 

The ever-popular OysterFest is back this year, once again bringing shellfish lovers from near and far to celebrate the salty, succulent, world-renowned Wellfleet oyster.

OysterFest 2022 will be a nearly month-long event with fun, tasty, and educational pop ups for all to enjoy.

(*Note: All OysterFest events will be ticketed, and pre-registration is required.)

Hyannis Open Streets

When: October 16, 2022, 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!

Trick or Treat with the Animals

When: 2022 dates - TBA

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.

Halloween Safe Trick or Treat in Hyannis

When: 2022 details - TBA

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!