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Cape Cod Events Calendar
October 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 Harvests

When: Throughout the month of October 2025

Where: Multiple cranberry bogs on Cape Cod

Admission: Free to watch on your own; costs vary 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

Barktoberfest

When: October 3, 2025, 4:00 p.m. to 6:00 p.m.

Where: Agway of Cape Cod, 20 Lots Hollow Road, Orleans MA

Admission: $10 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).
• 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 MSPCA.

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

SandwichFest

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

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 a live music PorchFest extravaganza. 

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

Tunes & Tales on the Trail

When: October 4, 2025, 1:00 - 4:00 p.m.

Where: Wellfleet Bay Wildlife Sanctuary, 291 State Highway (Route 6), South Wellfleet MA

Admission: Free with Mass. Audubon membership or regular sanctuary admission

More Info: Tunes & Tales on the Trail

Celebrate the magic of fall with music, storytelling, and nature at Wellfleet Bay Wildlife Sanctuary. As you wander the sanctuary’s scenic trails, discover live, trailside performances by beloved local musicians, poets, and storytellers. At each stop, let soulful melodies, captivating tales, and powerful poetry deepen your connection to the season and the landscape. Trail maps will be provided—just pack your imagination and adventurous spirit.

Bring the whole family. Kids (and kids at heart) will love the nature-themed puppet show, self-guided story walk, the Nature Play Area, and a well-earned stop at the Ice Cream Café cart, ready with sweet treats!

Witches on the Water Costumed Paddle Event

When: October 4, 2025, 3:00 p.m. - 5:00 p.m. (paddling parade starts at 4 p.m.)

Where: Oyster Pond Beach, 80 Stage Harbor Road, Chatham, MA

Admission: Free for spectators; $50 entry fee and $250 fundraising minimum for paddlers

More Info: Witches on the Water

Witches on the Water ("WOW"), one of Cape Cod's premier non-profit organizations, definitely puts the fun in fundraiser!

Paddleboarders: Here's your chance to help WOW raise funds for a very special cause — NAMI Cape Cod & The Islands, a grass-roots non-profit organization serving the families and friends of people with mental illness, as well as the individuals who have a mental illness themselves on Cape Cod and The Islands.

Come dressed in your finest witchy regalia (or whatever character you choose to be), bring your own SUP (or kayak or paddle boat or any other self-powered aquatic vehicle). This isn't a race, it's just a fun paddle parade!

Spectators: Prefer to stay on dry land? Not a problem! Everyone is welcome to watch the fabulously-costumed paddlers parade around Oyster Pond. No admission fee is required for spectators. (Donations are always welcomed and gratefully accepted!)

In addition to a whole bunch of magical witches on SUPs, the event will also feature the ever-enchanting DJ Stephanie Viva from X 102.3 FM, spellbinding live music, fantastical food trucks, mysterious raffles, and lots more! 

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!

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.

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.

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.

Oktoberfest in Chatham

When: October 18, 2025

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!

Autumn Gathering at Benjamin Nye Homestead

When: October 18, 2025, noon to 4 p.m.

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 history reenactors, a strolling fiddler, open hearth cooking, and guided tours by docents in period costumes.

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!

Pink Pumpkin

When: October 23, 2025, 5:00 p.m. to 7:00 p.m.

Where: Sandwich Glass Museum, 129 Main Street, Sandwich, MA

Admission: $25

More Info: Pink Pumpkin

During October’s Breast Cancer Awareness Month, Sandwich Glass Museum is holding an evening of information, sisterhood, and glassblowing.Special Guests Speakers Jennifer Rako, founding member of the Cape Cod Women's Cancer Prevention and Early Detection Fund and Dr. Naomi Kalliath, Breast Surgeon at Cuda Breast Care Center and Falmouth Breast Care Center, will be discussing overall breast wellness and strategies for managing breast cancer.

Open Artist Studio: Watch leading women glassblowers showcase their talents with live demonstrations. You'll have the chance to ask questions of both the artists and medical experts!

Halloween Fun: Party, Parade & Trick or Treat

When: October 25, 2025 from 11 a.m. to 5 p.m.

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 include 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!

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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!