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Cape Cod Events Calendar
October 2024

Updated: September 9, 2024

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 2024

Cranberry Harvest Season

When: Throughout the month of October 2024

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.)

SandwichFest

When: October 5, 2024, 10 a.m. to 4 p.m. (rain or shine!)

Where: Water Street, Sandwich, MA

Admission: Free

More Info: SandwichFest

This year's SandwichFest will include 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 - as it always is!

Witches on the Water Costumed Paddle Event

When: October 5, 2024, 2:30 p.m. - 5:30 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 - Dream Day on Cape Cod, the Brewster-based non-profit that brings respite and joy to the lives of children with serious and/or life-threatening illnesses and their families.

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! 

Vinegrass Music Festival

When: October 6, 2024

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 12, 2024, 11 a.m. to 3 p.m.

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 12, 2024, 9 a.m. to 3 p.m.

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 12 & 13, 2024

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 12 - 14, 2024

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 19 & 20, 2024, 10 a.m. to 5 p.m.

Where: Main Street, Wellfleet, MA

Tickets: TBA

More Info: Wellfleet OysterFest 

The ever-popular OysterFest is back for 2024, 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 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.

Hyannis Open Streets

When: October 20, 2024, noon to 4 p.m. (rain date October 27)

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: October 2024 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 19, 2024, 11 a.m. to 4:30 p.m.

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!

Halloween Safe Trick or Treat in Hyannis

When: October 31, 2024, 4 p.m. to 6 p.m.

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!