Autumn events on Martha’s Vineyard

Mark Halperin flew a multi-kite rig of multi-colored kites in 2011 that measured more than 100 feet.

Martha’s Vineyard is known for its summer happenings but autumn is a beautiful time to visit and often easier, with more affordable lodging rates and less traffic. Here’s a round up of some of the off-season’s most popular events.


Friday, Sept. 1–Sunday, Sept. 3
Martha’s Vineyard Jazz and Blues Summer Festival, Oak Bluffs and Edgartown
A three-day festival celebrating jazz and blues on Martha’s Vineyard.

Saturday, Sept. 9, all day
Annual Wind & Kite Festival, Ocean Park, Oak Bluffs
All day festival with free kitemaking for children from 10:30 am–12 pm. 

Tuesday, Sept. 5–Sunday, Sept. 10 
12th Annual Martha’s Vineyard International Film Festival, Martha’s Vineyard Film Center, Capawok Theater and other locations, Vineyard Haven 
A six day festival devoted to film and culture enthusiasts from across the globe. Guests from film, media, politics, and the art worlds converge to celebrate, discuss and debate  issues presented in a selection of international films. 

Tim Peters of Oak Bluffs participates in the 2016 derby.

Sept. 10–Oct.14
Martha’s Vineyard Striped Bass & Bluefish Derby, all across Martha’s Vineyard
A longstanding tradition for fishing lovers from all over. For more than seven decades, “the Derby” has produced great fishing, rich history, new friends, and lasting memories. Derby registration is open at Island tackle shops throughout the Derby.

Saturday, Sept. 16, 10am–6pm
Tivoli Day Festival, Circuit Avenue, Oak Bluffs
The official end of the summer season. Circuit Avenue. is cleared of cars and opened up to foot traffic. Live entertainment, food, art, music and great end-of-summer shopping sales on display outside. 

Friday, Sept. 22, 12–5pm & Sat. Sept. 23, Community Supper 10am–6pm & Music from 6-10pm
The Living Local Harvest Festival, Agricultural Hall, West Tisbury
This annual festival celebrates and educates on important Island issues such as sustainable agriculture, local food advocacy and education, marine life, renewable energy, resource and land conservation and local living economies.


Non-pareils from Enchanted Chocolates.

Friday, Oct. 6–Sunday, Oct. 8
14th annual Art of Chocolate FestivalFeatherstone Center for the Arts, Oak Bluffs
This tasty festival features a Friday-night preview party, where you can enjoy the dream-come-true experience of sampling everything chocolate your heart desires, and Saturday and Sunday afternoon pay-as-you-taste events.

Sunday, Oct. 8, 10am–4pm
Vineyard Artisans Columbus Day Festival, Grange Hall, West Tisbury 
One day only to catch all your favorite Island artisans. Weaving, fine furniture, pottery, leather goods, oil paintings, pastels, mixed media, sculpture, wampum jewelry, hand knit items, clothing, photography, handmade books and much more. Indoors and outdoors, rain or shine. Free parking and free admission. Playground for kids.

Leah Littlefield paints a rainbow on Nikita Kleeman.

Saturday, Oct. 14, 11am–3pm
Morning Glory Pumpkin Festival, Morning Glory Farm, Edgartown
Pumpkin games, hay rides, live music, the fabulous trebuchet and much more, this is an annual celebration of all things pumpkin. Free admission.



Thursday, Oct. 19–Sunday, Oct. 22
Martha’s Vineyard Food & Wine Festival, various locations
Four days, three nights of unique-to-the-Island dining experiences. Rooted in the Island’s rich tradition of farming and fishing, this festival invites you to meet local culinary talent, and the farmers, fishermen, oyster producers, and artisans they work with.


Nov. 18–Dec. 18, 12–4 pm each day 
Holiday Gift Show, Featherstone Center for the Arts, Oak Bluffs
This annual event brings together the work of more than 40 local artists offering affordable handmade gifts, including apparel, scarves, cards, jewelry, pottery, paintings, ornaments, and more. Open every day excluding Thanksgiving, with a preview party on Friday, Nov. 17, from 6 to 8 pm.

Friday, Nov. 24 & Saturday, Nov. 25, 10am–4pm
Vineyard Artisans Thanksgiving Weekend Festival, Grange Hall, West Tisbury 
The largest holiday art show by Islanders, features many holiday gifts great food and live music. A $2.00 parking fee is for the Vineyard Artisans Scholarship Fund, which awards several scholarships to graduating MV High School students for studies in the Arts each year.

Nov. 29
Oak Bluffs Tree Lighting, Post Office Square, Oak Bluffs
This annual lighting of the Christmas tree.


Christina Izzo throws candy to the crowd.

Dec. 7–10 
Christmas in Edgartown, Edgartown
A winter weekend festival not to be missed, including family-friendly events that capture the magic of the holidays. In 2017 Hyline Cruises plan to run ferries from Hyannis to Edgartown especially for this event.