The Insider’s Guide to Fall Fun on the Cape & Islands
By StoryStudio on August 1, 2023
Something magical happens in the fall on Cape Cod, Martha’s Vineyard and Nantucket. After the summertime crowds die down, it may just be the best time to explore this seaside destination’s vibrant culture, locally sourced foods and jaw-dropping foliage.
Fall is festival season, and the Cape and Islands have a bounty of excellent ones coming up, as well as ongoing activities that are sure to delight every type of traveler. From culture vulture to adrenaline junkie to bon vivant, there’s a festival for everyone. Here are some of our favorites!
Foodies know that the Cape and Islands are a dream destination all year long, but fall is when the area’s world-renowned seafood is accompanied by the incredible bounties of harvest season.
The Martha’s Vineyard Food & Wine Festival (October 19-22, 2023) is the island’s annual celebration of culinary excellence, highlighting the area’s top chefs and vintners, as well as special guests from all over the world. An emphasis on local and sustainable cuisine allows guests the chance to meet these talented chefs, as well as the farmers, fishermen and artisans who collaborate to create such unforgettable food.
Bay scallops on Nantucket are harvested by hand and by boat in the waters surrounding the island in the fall, and once Nantucket Bay Scallop Season kicks off on November 1, local restaurants make this fresh seafood delicacy the star of the show. The beauty of scallops is that they can be served in so many delectable ways, and Nantucket eateries celebrate this fact through their own signature creations.
Cape Cod’s Wellfleet OysterFest (October 14-15, 2023) is a massive party that pays homage to the world-renowned Wellfleet Oyster. Seafood galore, a lively oyster shuck-off, a family 5k, live music, a local artisan fair and craft beer vendors are all part of the fun, with proceeds going back into the Wellfleet community in support of many vital enrichment programs.
For craft beer lovers, there’s plenty to celebrate. The 11th annual Cape Cod Brew Fest (September 23, 2023) highlights the best of American beers, featuring over 150 beers to sample from more than 50 breweries across the country. Also on Cape Cod, Oktoberfest comes to both Mashpee (September 30, 2023) and Chatham (October 21, 2023), where each town celebrates with authentic German music, kid’s activities, craft vendors, German fare and delightful beer gardens.
For the Foodies
Folks who proudly proclaim fall as their favorite season will have plenty of reasons to visit the Cape and Islands this year. The Nantucket Harvest Fair, hosted by the Nantucket Conservation Foundation in early October, is an all-ages weekend highlighting the best of local agriculture with enough food, fun and learning to delight the whole family. This powerhouse, a union of the Island Fair and Cranberry Festival, promises twice the excitement with glorious fall weather.
Also in October, the Living Local Harvest Festival is a celebration that brings attention to local agriculture, with a special emphasis on sustainable living. Presented by the Martha’s Vineyard Agricultural Society, the festival includes hayrides, crafts, music, food and educational workshops that cover everything from local food production and marine life to land conservation.
Yarmouth Seaside Festival (October 7-9, 2023) is a high-spirited jubilee showcasing the best of the town’s warmth and vitality. A magnificent craft fair, live music and a nonstop slate of dynamic activities – including a kayak race, beach bonfire and spectacular fireworks display - bring locals and visitors together to enjoy the best Yarmouth has to offer.
For the Harvest Lovers
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Mashpee Commons Halloween Parade in Mashpee
Brewster General Store preps for Halloween
Photo Credit: Greta Georgieva
Halloween on the Vineyard
Pumpkin People
Photo Credit: Great Georgieva
Pumpkin People in the Park
Photo Credit: Courtney Wittenstein
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For fall lovers with a special emphasis on Halloween, the Cape and Islands do not disappoint. Halloween on Martha’s Vineyard is a multi-day affair, with Halloween in Oak Bluffs bringing out young and old alike to trick-or-treat at local homes and businesses. Happy Haunting in
Edgartown draws crowds of folks in costume to pick up treats from local downtown businesses, promising delicious fun for the whole family.
Halloween on Nantucket is an unmissable experience. Festivities include a Halloween parade complete with costume contest, the Haunted Ship at Brant Point Coast Guard Station, and lots of spooky fun at the Whaling museum.
Over on Cape Cod, the town of Falmouth celebrates the spirit of the season with its Village of
Scarecrows. Downtown merchants display their best and most creative handmade scarecrows in front of Main Street storefronts, and the result is as charming as it is impressive. Over in Chatham, the whimsical Pumpkin People are on display in all their glory in Chatham’s Kate Gould Park starting October 14th. And for those in search of serious thrills, Provincetown Ghost
Tours take guests back in time with walking tours led by locals who have extensive knowledge of the area’s spooky history.
For the Fright Lovers
For outdoor lovers, there’s plenty to do on the Cape and Islands to make the most of the area’s abundant wildlife and scenic surroundings. The Martha's Vineyard Striped Bass and Bluefish
Derby (September 10-October 14, 2023) is a rollicking good time, making the most of the glorious fall weather to spend quality time outdoors in nature engaging in one of the area’s most beloved activities. Fishing is a great, immersive way to experience the island, and this derby, full of friendly competition, helps create lasting memories in support of local scholarships.
Thrill-seekers aren’t confined to festival timelines to make the most of the Cape and Islands’ gorgeous natural terrain; there are more than enough outdoor activities to keep any adventurer happy. Hiking and biking are ideal during this time as temperatures cool and trees are vibrant with fall color. Kayaking and paddleboarding are also exceptional ways to survey the area ― harbors, coves, ponds and even the ocean offer varying levels of intensity to suit any traveler’s needs.
For the Adventurers
Fans of live music have much to celebrate this fall. The Harwich Cranberry Arts & Music Festival (September 16-17, 2023) presents a stellar lineup of musicians in a variety of genres, celebrating the best of local, national and international artists in a fun atmosphere that also features the wares of local crafters and artisans.
Nantucket’s Cisco Brewers keeps the party going in every season with a steady roster of live events and pours of their exceptional craft beers. Levitate Flannel
Jam in October has become one of the brewery’s staple autumn events, featuring a weekend of rotating live musical acts along with food trucks, special fall beers and ciders and kids’ activities.
The Vinegrass Music Festival in early October is the yearly culmination of the Vinegrass Organization’s work raising awareness and support for the American Roots music scene. Regional and national artists will put on stellar shows in the genres of Americana, Bluegrass and Folk music.
For the Music Lovers
Travelers who love to bring home treasures will find no shortage of shopping opportunities on the Cape and Islands. The Love Local Fests (September 24, 2023 and December 2, 2023) in Hyannis are a terrific chance to experience the best the Cape has to offer. Artisans, farmers, artists and other local businesses are able to showcase their wares alongside live entertainment and fun activities that bring folks together in support of the community.
Cobblestones & Cranberries (October 6-9, 2023) is a Nantucket tradition that rewards folks for shopping locally. Participating stores will give shoppers a chance to win incredible prizes ― the more stores visited, the greater the chance of winning. This fun and festive challenge is all in support of the #ShopNantucket initiative, encouraging people to take advantage of the incredible products that are available locally.
The Featherstone Holiday Gift Show (November 13-December 17, 2023) on Martha’s Vineyard is the ultimate holiday shopping experience, with a spectacular array of goods from local artists. The perfect gift for everyone is waiting at this special show that supports the area’s artistic community.
For the Shoppers
Fall on the Cape and Islands is a rich bounty of food, fun, cranberries, culture and nature—and festival season is the perfect time to experience it all. For more information on Cape Cod, visit CapeCodChamber.org. Find more information on Nantucket at NantucketChamber.org. More information on Martha’s Vineyard can be found at MVY.com.
Martha's Vineyard Food & Wine Festival
Cape Cod’s Wellfleet OysterFest
Cape Cod Brew Fest
Yarmouth Cranberry Bog
West Chop Lighthouse
Fall Stroll on the Beach
Fishing Derby
Kayaking on Cape Cod
Fall Golf Outing
Levitate Flannel Jam at Cisco Brewers
Vinegrass Music Festival
Fall on Cape Cod - credit Sveta Damiani
Featherstone Holiday Gift Show
Brewster General Store
Pumpkin People in the Park
Halloween on the Vineyard
Mashpee Halloween Parade
Bay scallops on Nantucket are harvested by hand and by boat in the waters surrounding the island in the fall, and once Nantucket Bay Scallop Season kicks off on November 1, local restaurants make this fresh seafood delicacy the star of the show. The beauty of scallops is that they can be served in so many delectable ways, and Nantucket eateries celebrate this fact through their own signature creations.
Cape Cod’s Wellfleet OysterFest (October 14-15, 2023) is a massive party that pays homage to the world-renowned Wellfleet Oyster. Seafood galore, a lively oyster shuck-off, a family 5k, live music, a local artisan fair and craft beer vendors are all part of the fun, with proceeds going back into the Wellfleet community in support of many vital enrichment programs.
For craft beer lovers, there’s plenty to celebrate. The 11th annual Cape Cod Brew Fest (September 23, 2023) highlights the best of American beers, featuring over 150 beers to sample from more than 50 breweries across the country. Also on Cape Cod, Oktoberfest comes to both Mashpee (September 30, 2023) and Chatham (October 21, 2023), where each town celebrates with authentic German music, kid’s activities, craft vendors, German fare and delightful beer gardens.
@visitcapecod
@visitmarthasvineyard
@ackchamber
