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Upcoming Cape & Islands Fairs and Festivals

The following is a list of upcoming events to be held this fall on Cape Cod, Martha’s Vineyard, and Nantucket

Fall fairs and festivals on the Cape & Islands


Harvest Festival

Saturday, September 12
10 a.m. – 2 p.m.
Briggs-McDermott House,
22 Sandwich Road, Bourne Village

This old-time harvest event offers live music, crafts and games, a country store, an attic treasures sale, miniature petting ponies and horse rides, fun photo opportunities, blacksmith demonstrations, a traditional puppet show, and more. General admission is $6; Children ages 4-12 cost $3.

Scallop Fest

Friday to Sunday,
September 18 – 20, 10 a.m. – 9 p.m.
(closes Sunday at 6 p.m.)
Cape Cod Fairgrounds,
1220 Nathan Ellis Highway, Falmouth

Hosted by the Cape Cod Canal Region Chamber of Commerce, this popular annual event features rides and games, music, and a juried arts and crafts show—in addition to its signature fried scallops and herb-roasted chicken dinners. Rain or shine. General admission costs $7; children 6-12 cost $2; children under 5 are admitted free of charge.

Pumpkin Day at Bourne Farm

Saturday, October 10, 9 a.m. – 3 p.m.
Bourne Farm, 6 North Falmouth
Highway, North Falmouth
This fun event at lovely Bourne Farm includes hayrides, face painting, a bounce house, a petting zoo, crafts, and a pick-your-own pumpkin patch. Admission and parking is free. Lunch options are available and a bake sale will be held.


Labor Day Weekend

Arts & Crafts Festival
Saturday and Sunday,
September 5-6, 10 a.m. to 5 p.m.
John Simpkins Field,
Route 28, South Yarmouth

More than 75 artisans will display and sell their American-made wares at this free event. Holiday bonus: there will be specialty food sampling, craft demonstrations, and live music.

Cape Cod Wildlife Festival

Saturday, September 12
10 a.m. – 3 p.m.
Mass. Audubon’s Long Pasture Wildlife Sanctuary, 345 Bone Hill Road,
Cummaquid (Yarmouth)

Environmental organizations from around the Cape and beyond host discussions, presentations, and interactive exhibits on this day of celebrating and learning about wildlife. Local authors and wildlife photographers will be on hand to answer questions and sign books.

Yellow Dog Music Fest

Saturday, September 12
12 p.m. – 9 p.m.
Craigville Beach Association,
Craigville Beach Road, Centerville

This event brings together music and nature to benefit the Barnstable Land Trust. Students from Berklee College of Music will perform original music all day Saturday for an epic beach party.

Cape Cod Bird Festival

Friday to Sunday, September 18-20

The third installment of this unique festival, sponsored by the Cape Cod Bird Club, consists of field trips, workshops, and lectures by renowned guests including Dr. Miyoko Chu and Richard Crossley.

Osterville Farmers

Market Fall Festival
Saturday, October 3, 9 a.m. – 1 p.m.
Osterville Historical Museum,
155 West Bay Road, Osterville

The best of sea and land come together at this event to celebrate the fall harvest. Enjoy breads, fruit, vegetables, flowers, jams, honey, butter, meats, pasta, cheese, cookies, kettle corn, soaps, and more. An apple dessert contest will benefit the Hyannis Food Pantry.


6th Annual Celebrate

Our Waters Festival
Friday to Sunday, September 18-20
Various locations in Orleans

In an effort to showcase the region’s beautiful water bodies—from lakes and creeks to beaches and bays—this festival offers activities including walks, bike rides, guided tours, kayak trips, catboat sailing, aquaculture events, a sand sculpture contest, and a bonfire on Nauset Beach.

Harwich Cranberry

Arts & Music Festival
Saturday and Sunday,
September 19-20, 9 a.m. – 6:30 p.m.
(closes 5:30 p.m. on Sunday)
Brooks Park, at the corner of Oak Street and Route 39, Harwich

This free event sponsored by WMOR/WFMR offers great food, 130 unique craft vendors, live music, and more.


Saturday, October 25,
12 p.m. – 4 p.m.
Kate Gould Park,
Main Street, Chatham

The main attraction of Chatham’s annual Oktoberfest, as always, is the “Pumpkin People in the Park,” a display of pumpkin carvings created by local businesses, groups, and residents. At the festival, families can view the pumpkins and celebrate the fall in German style, with old-fashioned games, tasty food and a beer tent, all sponsored by Chatham’s Merchants Association.


Afterglow Alternative

Performing Arts Festival
Monday to Sunday, September 14-20
Various events and times
Crown & Anchor Complex,
247 Commercial Street, Provincetown

This festival is a celebration of Provincetown’s roots as an iconoclastic community in the sphere of performance art. Innovative artists, both renowned and some that are under the radar, will perform 17 different shows and events.

Truro Treasures Grape Stomp & Music Fest

Sunday, September 20,
2 p.m. – 6 p.m.
Truro Vineyards
11 Shore Road, North Truro

With live music, wine tasting, and a food truck from BlackFish of Truro, this event—the finale of Truro Treasures weekend—is sure to be a blast. The annual Grape Stomp takes place at 3 p.m.

Vinegrass Music Festival

Sunday, October 4, Begins 11 a.m.
Truro Vineyards
11 Shore Road, North Truro

This event offers a relaxing day of music, wine, and a food truck. Performers include Nemes, Dead Winter Carpenters, and Caribou Mountain Collective. Tickets cost $40.

Wellfleet Oysterfest

Saturday and Sunday, October 17-18
10 a.m. – 5 p.m.
Town Center, Wellfleet
$5 for 1-day; $8 for 2-day pass

The famous Wellfleet Oysterfest celebrates its 15th anniversary this October. Sponsored by Wellfleet SPAT (Shellfish Promotion and Tasting, Inc.), the event is held for everyone to come celebrate and enjoy the Cape’s favorite shellfish: the oyster. Educational games, cooking demonstrations, walking tours, live music, a road race, and of course the annual Oyster Shuck-Off Competition will bring locals and visitors together for a weekend full of hometown flavor.


38th Annual Tivoli Day

Saturday, September 19
12 p.m. – 5 p.m.
Circuit Avenue, Oak Bluffs

This popular event offers live entertainment, food, raffles, arts and crafts, and a display of antique bicycles.

Food & Wine Festival

Thursday to Sunday, October 15-18
Events are held at various
locations and times

More than 20 different 21-plus events enliven Edgartown for four days during this annual festival. Local culinary talents as well as chefs and vintners from around the world will come together to celebrate food and drink and give guests a true taste of The Vineyard.


Artists Association of Nantucket Wet Paint Weekend

Friday to Sunday, October 9-11
Various events and locations
in Nantucket

A Friday night cocktail party celebrating the Artists Association of Nantucket (AAN) Permanent Collection kicks off this weekend of art appreciation. On Saturday and Sunday, member artists will be painting at different spots around the island for visitors to observe. The weekend concludes with a silent auction and benefit dinner at Le Languedoc (24 Broad Street).

Nantucket Cranberry Festival

Saturday, October 10,
11 a.m. – 4 p.m.
Milestone Cranberry Bog, 118 Cliff Road

Attendees can learn about the history of cranberry farming on the island, observe the harvesting process, take part in several family activities, buy some berries for the coming holiday season, or simply listen to the music and take in the lovely fall foliage at this Nantucket Conservation Foundation event.

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