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Cape Cod Events Calendar
October 2023

Updated: October 6, 2023

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

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Fairs, Festivals & Special Events in October

Cranberry Harvest Season

When: Throughout the month of October 2023

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 Cape Cod our hard-working cranberry growers bringing in their crops.

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

>> Read all about: Harvest Time at Cod Cranberry Bogs

Wampanoag Cultural Celebration

When: October 1, 2023, 11 a.m. to 3 p.m.

Where: 65 Highfield Drive, Falmouth MA

Admission: Free

More Info:  Highfield Hall & Gardens

This annual celebration of Cape Cod's native Wampanoag culture and history is a free, family friendly event featuring something for all to enjoy!

The Wampanoag Singers and Dancers will once again be the highlight of the day, along with hands-on activities for kids, story sharing, food trucks specializing in traditional native fare, and vendors selling Native American crafted items.

Vinegrass Music Festival

When: October 1, 2023, 11 a.m. to 6 p.m.

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

Admission:  General admission $49 (plus small online convenience fee)

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.


When: October 7, 2023, 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!

Taylor-Bray Farm's Fall Festival

When: October 7, 2023 (rain date: October 8)

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.

Pumpkin Day at Bourne Farm

When: October 7, 2023, 9 a.m. to 3 p.m. *Cancelled due to weather. No rain date.*

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 7 & 8, 2023

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 7 - 9, 2023

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.

Fall Frolic & Pumpkin Patch

When: October 8, 2023, 11 a.m. to 5 p.m.

Where: Chatham Bars Inn Farm, 3034 Main Street (Rt. 6A), Brewster, MA

Admission: Free

More Info: CBI Fall Frolic & Pumpking Patch

Head out to Chatham Bars Inn Farm for the annual Fall Frolic & Pumpkin Patch event. Enjoy hot apple cider, pick pumpkins, listen to live music, enter a pie contest, and explore the beautiful eight-acre farm.

The Farm Stand offers seasonal goodies like apples and squash. Find your perfect pumpkin, savor seasonal treats, and take home a custom fall bouquet. (All food, beverages, and farm items are available for purchase.)

The event is free, but parking is limited. Leashed, well-behaved pets are welcome.

Nauset Newcomers

When: October 11, 2023, 8:30 a.m. Social Hour; 9:30 a.m. Brief Member Meeting; 10 a.m. Jane Paradise, speaker

Where: 51 Route 6, Wellfleet, MA

Admission: Free to members & non members alike

More Info: Nauset Newcomers

Ever wonder about the intriguing dune shacks in Provincetown? Unlock the mystery as you listen to author and photographer Jane Paradise talk about her latest book,"Provincetown Dune Shacks". Built in the 1920s and 30s, these shacks, originally life-saving huts, became havens for artists and writers. Nineteen shacks remain on the dunes, many still rented out during the summer in all their non-modern glory.

Come to this month's Nauset Newcomers’ meeting and learn what it's like to live in one of the shacks and experience the magic of the dunes.

This event is open to everyone and free to attend!

Autumn Gathering at Nye Museum

When: October 14, 2023, noon to 4 p.m.

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

Admission: Free

More Info: Nye Museum Autumn Gathering

Discover the rich history of East Sandwich and one of its founding families at the Nye Museum's Autumn Gathering.

This is a great event for kids and families to get a dose of local history! Enjoy open hearth cooking demos, kids activities, a roaming fiddle player, artisans, pizza for sale, a colonial doctor reenactor, museum trails to explore, and more. Come celebrate autumn at the Nye Museum!

Wellfleet OysterFest

When:  October 14 & 15, 2023, 10 a.m. to 5 p.m.

Where: Main Street, Wellfleet, MA

Tickets: $23 per adult; children under 12 Free; free tickets for Wellfleet residents to attend on Sunday

More Info: Wellfleet OysterFest 

The ever-popular OysterFest is back for 2023, 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 15, 2023, noon to 4 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: October 14, 2023, 2 p.m. to 5 p.m.

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.

Outermost Contra Dance

When: October 20, 2023; doors open at 6:30 p.m., dancing begins at 7 p.m.

Where: Wellfleet Preservation Hall, 335 Main Street, Wellfleet, MA

Admission: $15 general admission; $10 for those under 30; $5 with student ID

More Info: Outermost Contra Dance

Put on your dancin' shoes for this fun event at Preservation Hall!

Contra dancing is the older cousin to the square dance. No fancy footwork is needed – if you can walk, you can contra dance!

All the dances are taught and called. If you're new to contra dance, join the free "Contra Basics Workshop" at 6:30 p.m. to learn the basic moves. (No need to bring a partner; there are plenty of friendly people in this welcoming dance community.)

Come to dance or come just to listen. All are welcome!

Harwich Cranberry Arts & Music Festival

When:  October 21 & 22, 2023, 9 a.m. to 4 p.m.

Where: Harwich Community Center Field, 100 Oak Street

Admission: Free

More Info: Harwich Cranberry Festival

This two-day event features more than 100 talented artists and crafters displaying their wares for sale. (A little early Holiday shopping, anyone?)

When you hear the music, it's time for some toe-tapping live entertainment at CranJam Music Festival, also held behind the Community Center. And when the music stops on Saturday evening, the fireworks display begins

*Note: This festival was rescheduled from its usual September dates because of impending bad weather. Due to rescheduling,  there'll be no live music or alcohol at the festival this year.

Oktoberfest in Chatham

When: October 21, 2023, 10:30 a.m. - 4:30 p.m. (rain or shine)

Where: Kate Gould Park and Town Hall Lot, 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 two stages of live music, beer and wine, food trucks and tents, artist village, kids zone, Pumpkin People in the Park.

Tap time is 11 a.m. with last pour at 4 p.m.

*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, 2023, 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!