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Cape Cod Events Calendar
October 2025

Updated: February 24, 2025

Watching the Cranberry Harvest on a Beautiful October Day

[*Note: Event details may be changed or events may be postponed or canceled by the sponsors at any time without my knowledge. Be sure to confirm all information directly with the event sponsor before making plans to attend.]

Fairs, Festivals & Special Events
October 2025

Cranberry Harvest Season

When: Throughout the month of October 2025

Where: Multiple cranberry bogs on Cape Cod

Admission: Free to watch on your own; cost varies for guided tours

More Info: See link below.

October is cranberry harvest time on Cape Cod!

If you've never seen acres of crimson berries floating on our local bogs, now's your chance to get out and watch our hard-working Cape Cod cranberry growers bringing in their crops.

It's a fascinating thing to see, and the photo opps are spectacular! 

* Read about: When & Where to See the Harvest  (and maybe wade into the bog with the berries, too.)

Falmouth Jazz Stroll

When: October 2025 date - TBA

Where: Various locations along Main Street, Palmer Ave, and Queen’s Buyway in Falmouth MA

Admission: Free

More Info: Falmouth Jazz Stroll

Head downtown this Saturday for the ever-popular Falmouth Jazz Stroll.

If the weather is hot, meander over to the cool jazz performances. If it’s chilly, the hot jazz will warm you up!

This is a great way to enjoy some incredible music, meet friends old and new, and enjoy the liveliness of downtown Falmouth. Come early to shop, and stay late to enjoy a meal!

Again this year, there'll be a special After-Stroll event with the Bart Weisman Jazz Group at The Vine Restaurant from 6:30 to 9:30 p.m. It’s the perfect ending to a delightful evening!

SandwichFest

When: October 2025 date - TBA

Where: Water Street, Sandwich, MA

Admission: Free

More Info: SandwichFest

SandwichFest features lots of fabulous food, a beer and wine tent, juried artisans and crafters, activities for the kids, and plenty of music. 

No doubt SandwichFest will be a fun time for all again this year - as it always is!

Vinegrass Music Festival

When: October 5, 2025

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

Admission:  $55

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.

Provincetown Town Crier Competition

When: October 2025 date - TBA

Where: Bas Relief Park, Provincetown, MA

Admission: Free

More Info: Provincetown Town Crier Competition

Looking for something truly unique to add to your must-see list?

It doesn't get much more unique than Provincetown's Town Crier Competition!

Come cheer on 15 talented Town Criers from the USA, Canada, and the UK as they bellow their best in hopes of winning top prizes.

Each crier will have two chances to impress the judges with  cries about 'My Hometown' and a key event in Provincetown's history.

This event is free and open to the public. Don't miss it!

Barktoberfest

When: October 2025 date - TBA

Where: Agway of Cape Cod, 686 Route 134, South Dennis MA

Admission: $15 for humans; pups are free

More Info: Barktoberfest

Bring your pups, kids and your favorite costumes for a fun fall party at Dennis Agway!

Grab your four-legged bestie, dust off those dog costumes (or pick one up at Agway), and get ready for the ulti-mutt fall festival!  From wags to witches and paws to pumpkins, it'll be a  tail-wagging good time filled with:

• Live Music & Food Trucks: Groove to some tunes while munching on delicious bites and sipping adult beverages (for humans, of course—dogs, you’re on treat duty).
• Pet Portraits by Sue Unleashed: Capture your spooky (or silly) side with professional portraits of your fur baby.
• Pumpkin Decorating: It’s not just for the kids! Show off your creative side—just try to keep the slobber off the pumpkins.
• Puppy Picasso: Your pup can create it’s very own art masterpiece to take home! (mess-free).
• Fur Painting: Like face-painting but on their coats!
• Door Prizes: Snag pawsome goodies just for showing up
• Costume Contest: Does your dog have the best costume? Funniest costume? Special prizes awarded throughout the night!

All proceeds benefit The Sampson Fund, a fabulous organization that provides financial assistance for veterinary care for critically ill or injured dogs and cats on Cape Cod and the Islands when owners can't afford to pay for their pet's treatment.

It’ll be a howlin’ good time for a very worthy cause!

A Different Drummer Craft Fairs

When: October 4 & 5, 2025, 10 a.m. to 4 p.m.

Where: Drummer Boy Park, 773 Old Kings Highway (Rt. 6A), Brewster MA

Admission: Free

More Info: A Different Drummer Craft Fairs

A Different Drummer Craft Fairs feature more than 40 of Cape Cod and New England's best crafters and artists.

What will you find at these fairs? A wonderful selection of artwork, books, candles, clothing, fiber arts, glass, jewelry, metal work, mixed media, pet items, photography, soaps, pottery, toys, woodwork, and much more!

Taylor-Bray Farm's Fall Festival

When: October 11, 2025

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, old-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.

Pumpkin Day at Bourne Farm

When: October 2025 date - TBA

Where: Bourne Farm in Falmouth

Admission: Free

More Info: Pumpkin Day

There's plenty of autumn fun at the farm on Pumpkin Day.

Bring the kiddos, and have your camera at the ready to capture those memories, as your youngsters choose their perfect Jack-o-Lantern pumpkin!!

Cape Cod Marathon Weekend

When: October 11 & 12, 2025

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!

Yarmouth Seaside Festival

When:  October 11 - 13, 2025

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.

Wellfleet OysterFest

When:  October 18 & 19, 2025

Where: Main Street, Wellfleet, MA

Tickets: General Admission - TBA

More Info: Wellfleet OysterFest 

The ever-popular OysterFest is back for 2025, once again bringing shellfish lovers from near and far to celebrate the salty, succulent, world-renowned Wellfleet oyster.

What about the famous "Shuck Off"? It's back again this year - along with lots of local cuisine, a fine art and craft fair, educational non-profit booths, children’s activities, and live music.

*Note: Everyone attending must pre-register and show a ticket for entry to the event.

Halloween Extravaganza: Trick or Treat with the Animals

When: October 2025 date - TBA

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

Admission: $10 per person; $20 per pony ride (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!

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. So reserve your spot soon.

Oktoberfest in Chatham

When: October 2025 date - TBA

Where: Kate Gould Park, 549 Main Street, Chatham, MA

Admission: Free; food and beverages for purchase

More Info: Oktoberfest in Chatham

Chatham's popular Oktoberfest is a free, family friendly day in downtown Chatham featuring live music, beer and wine, food trucks and tents, family activities and Pumpkin People in the Park.

*Tip: If you plan to enjoy an adult beverage or two, please don't drive!

"Haunted Hathaway's"

When: October 2025 date - TBA

Where: Hathaways Pond, Phinney's Lane, Barnstable MA

Admission: $40 for pumpkin carving dive; $75 for haunted house dive; $100 for both. Spectators can watch from shore for free.

More Info: Haunted Hathaway's Dive Event

Get ready for some underwater spook-tacular fun at the 2nd annual Haunted Hathaway's dive event. This year promises to be bigger, better, and definitely more spine-chilling! 

Two dives await brave souls at Hathaway’s Pond:

• an Underwater Pumpkin Carving dive where you can create jack-o'-lanterns and enter the contest for the best design;  and
  
  
• an Underwater Haunted House dive, complete with a lit pathway, haunted attractions, and fun photo ops. Don your best, most creepy costume to win awesome prizes!
  

Whether you’re a diver or just coming along for the fun, there'll be plenty of treats and refreshments on the shore.

Call United Divers at (617) 666-0410 to sign up for your spooky dive!

Autumn Gathering at Benjamin Nye Homestead

When: October 2025 date - TBA

Where: Benjamin Nye Homestead Museum, 85 Old County Road, East Sandwich, MA

Admission: Free

More Info: Nye Homestead Autumn Gathering

It's time again for the autumn get-together at historic Benjamin Nye Homestead. 

This popular event is filled with fun activities including vendors selling sweet confections, blacksmithing demonstrations, a genealogy hour, history reenactors, a strolling fiddler, open hearth cooking, and a guided museum tour.

Whether you’re a fan of history or just enjoy the crisp autumn air, this event is perfect for everyone!

Hyannis Open Streets

When: October 19, 2025, noon to 4 p.m. (rain date October 26)

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!

Halloween Fun Parade & Trick or Treat

When: October 2025 date - TBA

Where: Mashpee Commons, 22 Steeple Street, Mashpee MA

Admission: Free

More Info: Halloween Fun at the Commons

Save this date for the annual Halloween Fun event at Mashpee Commons. 

The day's festivities will include a pre-party on the Village Green with live music, kids activities, dancing, treats and a costume contest, followed by a parade down to Central Square and trick or treating at the shops.

No doubt, a fun time will be had by all!

Cotuit Witch Walk

When: October 2025 date - TBA

Where: Cotuit Town Docks, Oyster Place Rd., Cotuit MA

Admission: $10 donation to benefit Mills River Rescue & Sanctuary

More Info: Cotuit Witch Walk

Join the SandWitches for their annual performance of the Witch Dance at the Cotuit Town Dock.

Dress in your finest witchy gear and join the walk, or just cheer them on as they make their way up School Street, stopping for pictures by the village green and trick or treating with witchy ponies!

The walk continues down School Street to Cotuit High Ground Golf Club for more festivities and raffles to benefit Mills River Rescue & Sanctuary.

Your $10 donation gets you a raffle ticket and lots of witchy fun!

Halloween Safe Trick or Treat in Hyannis

When: October 2025 date - 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.

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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!