Planning a Labor Day Weekend Trip to Martha’s Vineyard

Many visitors flock to Martha’s Vineyard to Martha’s Vineyard, making for one of the most anticipated weekends on the Island. While Labor Day unofficially marks the end of the summer season there’s still so much to see and do and the weather is usually ideal for travelling and sightseeing. If you’re heading this way here’s some Labor Day weekend highlights you won’t want to miss!

Photo: L.A. Brown

Explore our Island Farms
There’s over forty working farms on Martha’s Vineyard where you can get fresh produce, meat, and dairy, while mingling with local livestock and barnyard buddies, and Labor Day weekend is the perfect time to explore them. On Friday August 31, from 10-10:45am and again on Monday September 3, from 10-11am, the FARM Institute in Katama offers a guided tour to visitors. “Whether you’re a family with a few wee farmers eager to check out the chickens, seasoned farmers curious about island agricultural techniques, farm-to-table enthusiasts wondering how artichokes grow, backyard gardeners, or anything in between – stop by for a visit.”

The Grey Barn farm in Chilmark, home to the Island’s most delicious (and award winning!) cheeses, offers a couple different tours throughout the weekend on their beautiful sprawling property. Take a Cheese Tasting and Milking Tour on Saturday, September 1 at 5:30 pm and meet the cows that produce their beautiful cheeses before feasting on a large cheese board at the end of the mini tour and talk. Or on Monday, September 3 at 10am visit the farm for a walking tour and learn the history of this important farm and how it’s been brought it back to life in recent years.
For the animal loving yogis in town be sure to stop by Island Alpaca on Monday from 3:30-4:30pm for Alpaca Yoga. There you’ll get to enjoy a one hour session of relaxing yoga held in a pasture among friendly fuzzy alpaca, what could be more stress relieving than that?

If you’re looking to get a taste of many Island farm’s pop into the West Tisbury Farmers Market on Saturday September 1 at the Grange Hall in West Tisbury for a DIY food tour of the Island’s freshest food.  

Photo: Monique Beliar

Shop the old, the new, and everything in between
Shopping on Martha’s Vineyard is a sport, especially if you’re looking for on-of-a-kind treasures that have a special meaning or a storied past. Over Labor Day weekend you’ll find several markets selling locally made and locally found objects. On Friday August 31 from 9am to 3pm the Grange Exchange Antiques and Art Sale returns to the West Tisbury Grange Hall for their last sale of the summer. There you’ll find historical artifacts, vintage art, maps, jewelry, Island memorabilia, decorative objects, and more.

Then there’s the Chilmark Flea Market, the oldest outdoor Flea Market on the Island, which returns to the Chilmark Church on Saturday, September 1 from 9am-2pm. The "Flea" features high quality handmade items from Vineyard artists and craftsmen, antiques, imports and vintage finds, including jewelry, clothing, art, food items and more.

If you’ve never visited the Vineyard Artisans Festival Labor Day weekend is the time to do it, and you have three opportunities to get there. The largest art show on Martha's Vineyard features Island artists with unique furniture, clothing, ceramics, jewelry and fine art from the Island’s top artists and it happens at the Ag Hall in West Tisbury on Friday, August 31, from 5-8pm; on Saturday, September 1 from 10am-5pm; and again on Sunday, September 2 from  10am to 5pm. 

The Oak Bluffs Open Market will also be alive on Sunday, September 2 from 10am-2pm in Oak Bluffs’ Washington Park with an ever-changing mix of local produce, specialty foods, arts, crafts, antique and vintage dealers, massage, tarot and more.

Photo: David Welch

Get down with local, and international, live music
Martha’s Vineyard loves their music. Most night of the week you’ll find musicians playing local bars, outdoor concerts and various venues around the Island. On Friday August 31, enjoy the final Sunset Concert Series of the season, which brings local favorite the Pickpocket Bluegrass Band to the Tabernacle Green in Oak Bluffs from 6-7:30pm. Take in the sounds of the band and bring a picnic, or dance along, while admiring the adorable gingerbread houses nearby.

Labor Day weekend also brings big talent from near and far for the Martha’s Vineyard Jazz and Blues Summerfest series which takes place on Friday, August 31, September 1, and Sunday, September 2. This annual music festival plays host to music lovers from all over the United States and Europe, and offers a weekend of concerts featuring women in jazz including Jazzmeia Horn, Sage, Alyson Williams, Maysa and more.​

For those night owls the Ritz, the Seafood Shanty, the Atlantic, and the Port Hunter all offer nightly live music and entertainment during Labor Day weekend and most nights throughout the summer.  

Dance, dance, dance
If you’re looking to be inspired by a riveting dance performance you’ve picked the right weekend to be on Martha’s Vineyard. On Saturday, September 1 at 7pm The Yard in Chilmark presents the Schonberg Fellows their residents from the The Bessie Schonberg Boston Choreography Residency. Alex & Joy Davis - The Davis Sisters of Junk Drawer explore “the intersection of things in their lives that don't quite have their own place, but are too essential to keep hidden from sight” while Marsha Parilla Danza Orgánica of Melaza II performs a dance theater piece based on the colonial relationship between the Caribbean and the United States of America.
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Also on Saturday at 7pm the Vineyard Arts Project, an arts and wellness retreat space on Martha’s Vineyard, brings us the Black Iris Project a ballet collaborative and education vehicle that creates “new, relevant classical ballet works that celebrate diversity and Black history.”
 
Now the challenge is where to start! Be sure to check out our sample itineraries of other ways to spend your time on Martha’s Vineyard along with can’t miss sights and attractions. Have a safe and happy Labor Day weekend wherever your travels take you!