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508-693-7832
Karen M. Overtoom Logo
508-693-7832

The Best of August 2025


The very best of Martha’s Vineyard awaits you this August! It’s the height of summer, and the island is buzzing with excitement. From the iconic Agricultural Fair and spectacular fireworks to long, lazy days on the beach, August brings something for everyone. Stroll through vibrant farmers’ markets, catch live music under the stars, or savor fresh seafood by the water. Whether you’re here for a weekend or the whole month, it’s the perfect time to soak in the beauty, energy, and unforgettable charm of the Vineyard. Here are just a few of the many events happening this August on MV! 

  • 23rd Martha's Vineyard African-American Film Festival - August 1st-9th from 10:30am to 11:00pm - Join us for a captivating celebration of African-American cinema at the Martha's Vineyard Performing Arts Center. Get ready for an incredible lineup of thought-provoking films, talented filmmakers, and engaging discussions.
  • Martha's Vineyard Book Festival 2025 - Saturday, August 1st-3rd from 9am to 4:30pm - The Martha’s Vineyard Book Festival is back this summer celebrating its 20th year. This beloved community event is a vibrant celebration of literature. We will again be in Chilmark on the grounds of the Chilmark Community Center on August 1 to 3.
  • First Friday Vineyard Haven - Friday, August 1st at 4:00pm - First Friday is a free community-inspired outdoor event in Vineyard Haven, Martha's Vineyard. Started in 2016 and based on the nation-wide First Friday art walks, we celebrate the local art and culture of our island each first Friday of the month June through October.
  • Sankofa Festival : A Celebration of African American Literature and Culture - Friday, August 1st from 11:00am to 2:00pm - This program is part of OBPL’s annual Sankofa Festival celebrating Black Literature & Culture.  Join us for an engaging and thought-provoking conversation exploring the powerful relationship between Historically Black Colleges and Universities (HBCUs) and the evolution of hip hop—from its Golden Era to today’s global influence. This panel will trace how HBCU campuses served as incubators for cultural expression, activism, and musical innovation, shaping not only the sound but the soul of the genre.
  • Laughing Matters: A Comedy Fundraiser for Stillpoint - Friday, August 1st at 6:00pm - Join us for our first-ever FUNdraising event with food, drinks, stand-up comedy, and an introduction by Amy Schumer!
  • 2025 Annual Legacy Week on the Vineyard -  July 27th - August 2nd - Legacy Week on the Vineyard was created to engage, empower, and highlight the bond and value of Historically Black Colleges and Universities. This will be an ideal opportunity to relax, connect with fellow HBCU alumni and their families, and participate in events both fun and impactful. We will party with a purpose, build new bonds, and get strategic in sustaining the legacies of our great schools.
  • The Tempest at the Tisbury Amphitheater - August 1, 2, 6 & 7 at 6:00pm - By William Shakespeare. Directed by MJ Bruder Munafo. Starring Victor Talmadge as Prospero.
  • Aquinnah Cultural Center’s Wampanoag History Museum - Wednesdays-Sundays from 11:00am to 4:00pm. - Come visit the Aquinnah Cultural Center’s Wampanoag History Museum, located at the historic Vanderhoop Homestead in Aquinnah. Set on our ancestral homelands, the museum shares the long and ongoing story of the Wampanoag people on Nôepe (Martha’s Vineyard). Through exhibits and interactive displays, visitors can connect with over 12,000 years of Wampanoag history, culture, and continued presence on this Island.
  • Margot Datz: Recreator - August 1-10 from 10am to 4pm - Vineyard Preservation Trust presents a special installation showcases the process of the Island's celebrated muralist, Margot Datz, who transformed the Old Whaling Church and the Flying Horses. Meet the artist on Tuesday, August 12, from 5 to 7 p.m. Pay as you can or prepurchase for $5.
  • Chilmark Road Race 2025 - August 9th at 10:30am - The Chilmark Road Race is run on the 2nd Saturday in August in Chilmark. Since 1978, the Chilmark Road Race has been run along beautiful Middle Road. It is 5 Kilometers (3.1 miles) race. The Start is 3.1 miles east of the Chilmark Town Hall on Middle Road. The Finish Line is at Beetlebung Corner next to the Town Hall.
  • Vineyard Haven Town Band - August 3rd (VH), 10th (OB), 17th (VH) & 24th (OB) at 7:30pm - The Vineyard Haven Town Band is performing every Sunday evening throughout the summer, alternating between Ocean Park in Oak Bluffs and Owen Park in Vineyard Haven. The concerts are free to the public. Bring your beach chairs and picnic suppers and the kids and dogs march around the gazebo as they have done for the last 107 years.
  • Grand Illumination Night - August 20th - The crown jewel of the Camp Ground season is Grand Illumination Night! Thousands of Island residents and visitors enjoy Grand Illumination each summer. The evening starts in the Tabernacle, and seats fill well in advance. The program also includes a prayer, along with a  Community Sing and music by the Vineyard Haven Band, as well as the ceremonial lighting of the first lantern. The event is supported with a free will offering. We are grateful for the generosity of everyone who visits, participates, and donates what they can to make this magical evening possible.
  • Martha's Vineyard Agricultural Fair - August 21st-24th from 10:00am to 11:00pm - A 4-day old-fashioned Agricultural Country Fair held on the fairgrounds of Agricultural Hall in West Tisbury (Martha’s Vineyard Agricultural Society.) Enjoy rides, games, shucking contests, skillet toss, horse pull, woodsmen competition, dog & livestock shows.
  • Annual Oak Bluffs Fireworks and Band Concert - August 22nd at 8:00pm- Sponsored by the Town of Oak Bluffs with help from many generous donations.
  • Pans and Planks — Steel Drum and Marimba Workshop - Fridays in August from 10:00am to 11:00am - Come check out the melodic side of drumming. We’ll play our Shona style Marimbas from Zimbabwe, and Steel Drums made by Carl Chase, a master pan builder who lived in Woods Hole for a while.  Led by Rick Bausman. Stick around afterwards and explore Drummer Oo's Petting Zoo, open 10 a.m. to 2 p.m.
  • Friday Nights with Johnny Hoy and The Bluefish - Fridays in August from 6:30pm to 8:00pm - Join us and Johnny Hoy and the Bluefish this summer for Friday night musical performances on our outdoor stage under the trees! Enjoy music on our lawn while supporting musical artists and our nonprofit art center.