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508-693-7832

29 Things to Add to Your Summer on Martha's Vineyard Bucket List 2019


As the days get longer, the weather warms up and the official start of summer is just days away, it’s time to get serious about summer. This is the time of year Martha’s Vineyard really comes to life - and we want to soak up every second of it. So we’re making a bucket list and ticking off each item as we enjoy the sun, sights, and sand on our favorite island. Making your own bucket list? Here are some thought starters:

  1. Taste of the Vineyard - Thursday, June 13th, 2019 - Come taste more than 90 local fine food and beverage participants. www.tasteofthevineyard.org
  2. Oak Bluffs Harborfest - Saturday, June 22nd from 11am to 8pm. Local artists, craftsmen and antique dealers, as well as non-profit organizations offering a tempting array of baked goods, raffles and information.
  3. 4th of July parade and Fireworks in Edgartown. Parade begins on Main Street at 5 pm, Fireworks on the harbor at dark.
  4. Tisbury Annual Street Fair - July 8th, 6:30-9:30 - Come join the fun when Main Street closes for food, music, shopping and more.
  5. Meals in the Meadow - Saturday, July 13th from 5-9 pm - The annual farm to table dinner and dancing to support the Farm-Based Education Program at The FARM Institute. www.thetrustees.org
  6. Vineyard Cup - July 12-14 - Three days of sailing races, a harbor side party in the Race Village at the Martha’s Vineyard Shipyard in Vineyard Haven with locally sourced cuisine, live music, daily awards, sponsored activities and giveaways.
  7. Possible Dreams - July 28th at Tilton Farm, 52 Middle Rd., in West Tisbury
  8. Built on Stilts August 8-11 August 15 August 17-18. The community dance party that takes up residence at Union Chapel in Oak Bluffs.
  9. The Grand Illumination of the Oak Bluffs Campground, a.k.a. “Illumination Night,” August 14th at 7:30 pm. An annual tradition, the gingerbread cottages in the Camp Ground are festooned with colorful lanterns that are illuminated all at once after sunset. Dating from the turn of the 19th century, Grand Illumination is a crowd pleasing event that attracts visitors from all over. 
  10. The 157th Martha’s Vineyard Livestock Show and Fair - August 15th - 18th. Come to the Fair!! Rides, games, shucking contests, skillet toss, horse pull, woodsmen competition, fiber-arts tent, dog & livestock shows. www.marthasvineyardagriculturalsociety.org
  11. Fireworks and Band Concert - August 16th, 6pm - Oak Bluffs harbor. Don’t miss the best fireworks show on the island.
  12. Dock Dance in Edgartown from 7:30-10:00 pm every Wednesday in July and August. Free live dance music on the dock at Memorial Wharf starting just before sunset. Check https://calendar.vineyardgazette.com for exact times and dates.
  13. Artisan Festivals - Thursdays and Sundays. 10:00-2:00 at the Grange Hall in West Tisbury. www.vineyardartisans.com
  14. Jaws at the beach - Take a day at the beach to another level. MV Film Festival hosts Jaws at the beach. www.tmvff.org
  15. Menemsha sunset - EVERY night! Grab a picnic or takeout at one of the Menemsha restaurants and head to the beach. Don’t miss this applause worthy sunset!
  16. Jaws bridge jump - Take a leap! Go at high tide for a shorter jump!
  17. Mytoi Gardens on Chappy - Enter a secluded world of designed Japanese elegance in this garden environment of exotic and native plantings that encircle a serene pond. www.thetrustees.org
  18. Cape Poge Wildlife Refuge - Enjoy a day on the secluded Chappy beach or join a guided kayak tour of Chappy! The Trustees of the Reservation will take care of all your outdoor activities. www.thetrustees.org
  19. Felix Neck Wildlife Sanctuary - Take a hike, spot owls, join the moonlight kayak tour! Felix Neck is worth the trip. www.massaudubon.org
  20. Farmer’s Market - Wednesdays and Saturdays 9:00 am - 12:00 pm throughout the summer at The Grange Hall in West Tisbury. Outdoor farmers market features locally grown produce and meat and locally made products. www.wtfmarket.org
  21. Polly Hill Arboretum - Stroll the gorgeous grounds daily from sunrise to sunset. www.pollyhillarboretum.org
  22. Aquinnah - Take a walk around the cliffs at Philbin beach, and then climb on the top of the cliffs for a spectacular view. Don’t miss a tour of the Aquinnah lighthouse.
  23. Lighthouse tours around the island - Enjoy an over-sand vehicle adventure to the remote Cape Pogue Lighthouse. Edgartown light, East Chop light and West Chop light are open sporadically throughout the summer. www.calendar.vineyardgazette.com
  24. Donovan’s Reef and Nancy’s Restaurant - Grab a famous “Dirty Banana” cocktail at Donovan’s and add some of the islands best Fried Clams.
  25. Flying Horses - Ride the nation’s oldest platform carousel. Try to grab the Golden Ring!
  26. Alley’s General Store - Purveyors in almost everything, Alley’s General Store is the island’s oldest retail business. When it opened in 1858, it provided householders and local farmers and fishermen with basic staples and as a retail outlet for their goods. Today, Alley’s is a gathering spot for locals and visitors alike.
  27. Beach Picnic - Hit one of the many delicious take-out spots and then head to one of the many spectacular beaches! Our favorite take-out spots? Shepherd’s Provisions, 395 State Rd, VH. Black Sheep, 17 Airport Road, Edg. 7a Foods, 1045 State Rd, WT.
  28. Concerts at The Carnegie - North Water St, Edgartown - Wednesdays throughout the summer 6-7 pm. Bring your beach blankets and folding chairs to the lawn at The Carnegie and join us for a toe-tapping evening of lively jazz, bluegrass, folk, and rhythm and blues during our free weekly outdoor concerts. Featured performers from PickPocket Bluegrass, Jeremy Berlin Jazz, and Missus Biskis are sure to have everyone humming along and might even inspire some grooving and two-stepping
  29. .Chilmark Road Race - August TBA, Chilmark. Since 1978, the Chilmark Road Race has been run along beautiful but oh-so-hilly Middle Road.