- Vineyard Artisans Labor Day Festival - September 1st from 10 am to 5:00pm
- The Martha's Vineyard Jazz and Blues Summerfest 2024 - Sunday, September 1st from 5:30pm to 9pm - Since its inception, the annual Martha’s Vineyard Jazz & Blues Summerfest has played host to music lovers from all over the United States and Europe. Sheila Baptista, Summerfest producer and President of Lewis and Kirk Music, Inc., believes that great music and medicine can radically change the course of one’s life, a family’s future and a community’s well-being. Baptista launched Summerfest in 2008 to support regional breast cancer initiatives with a monetary donation and to also spread a vital message regarding breast cancer, early detection, courses of treatment and positive recovery.
- Gay Head Lighthouse - September 1st-4th from 10:00am to 4:00pm - The Gay Head Lighthouse was the first lighthouse constructed on Martha’s Vineyard. In 1799 The Commonwealth of Massachusetts deeded two acres and four rods to the federal government for the site of the Gay Head Lighthouse. On November 7, 1799 the light was turned on for the first time. After the building was completed, Paul Revere provided some copper and tin used to augment the weatherproofing of the Light.
- The 19th Annual Martha’s Vineyard International Film Festival - September 3rd-8th
- Bite Me! Stand-Up Comedy - Wednesday, September 4th from 7:00pm to 8:30pm
- Author Talk: A Culinary History of Martha’s Vineyard - Thursday, September 5th from 4:30pm to 5:30pm - Local authors Thomas and Joyce Dresser will discuss their newly released book, A Culinary History of Martha’s Vineyard. Books will be available for purchase and signing.
- First Friday VH - Friday, September 6th from 4:00 PM to 11:00 PM - An outdoor arts and culture community event on the First Friday of every month through December. Owen Park + Main St Vineyard Haven. Festival atmosphere, outdoor vendors, live music, and delicious food.
- Martha's Vineyard Wind Festival - Saturday, September 7th from 10:30am to 3:30pm - Enjoy a day in beautiful Ocean Park. Bring a kite, buy a kite, or make a kite. Activities include kite making and kite flying for young and old. Free kite making workshops for kids from 10:30 a.m. to noon. Flying competition for anyone up to age 12 from 12 to 1 p.m., followed by prizes awarded at 1 p.m. Adult flying competitions 1 to 3 p.m. followed by prizes awarded at 3 p.m. Community kite flying until dusk.
- Aquinnah Powwow - Saturday, September 7th and Sunday, September 8th at 11am - The Aquinnah Powwow celebrates a Native American tradition that brings together many different tribes and communities. Powwows are cultural celebrations that include dancing, singing, socializing, crafts, arts, and food. Gates open at 11 a.m. Grand entry at 12 p.m. Admission: Aquinnah tribal members free with tribal ID; adults $10 or $15 for two days; children (13 and under), seniors (65+), veterans $5 or $7.50 for two days.
- Art Stroll - Saturday, September 7th from 4:00pm to 7:00pm - The final art stroll of the summer, celebrating island artists and galleries in the Arts District in Oak Bluffs. Enjoy strolling down the closed street, enjoy live musicians and meet the artists.
- TBD Improv - Friday, September 13th at 7pm - The comedy is To Be Determined...by you! Unscripted and spontaneous, this nevertheless polished and expertly hosted show will have you rolling on the floor! Vineyard-based improvisers from New York, Chicago, Philadelphia, and beyond compete for your laughs by using their wits and suggestions from the audience. These performers create scenes right on the spot, in a highly interactive and highly entertaining night of fast, smart, and hilarious comedy.
- Martha's Vineyard Striped Bass & Bluefish Derby - Beginning Sunday, September 15th at 8:00am - Come to the Vineyard and Fish The Derby! For almost eight decades, "The Derby" has been a time to renew friendships, share a hot cup of coffee and create memories that fuel the winter's exaggerated fish tales. It is a time for all to refocus on the natural beauty of this Island sanctuary. So come and join us, to experience great fishing, rich history, meeting new friends, and generous sponsor-donated prizes - all in support of our scholarship program. Remember: Registration is open throughout the Derby. Daily Weigh-In Hours: Dock St. Edgartown: Mornings: 8:00-10:00 AM. Evenings: 7:00-9:00 PM
- Behind the Curtains With the Nashville Hitmakers - Friday, September 20th from 7:30 PM - 10:30 PM - Nashville songwriters CJ Solar, Ben Williams, Rick Huckaby, Paul Sikes, & Dave Kuncio sing the hit songs they wrote for superstar artists like Morgan Wallen, Selena Gomez, Lainey Wilson, Ty Dolla $ign, Trace Adkins, Alicia Keys, Government Mule, Megan Maroney, Thomas Rhett, Steve Aioki Justin Moore, Jameson Rodgers, Cody Johnson, Jason Aldean & tell the stories behind them!
- Tivoli Day Celebration - Saturday, September 21st at 10:00am - An annual celebration of summer’s end on Circuit avenue, featuring live music, arts, crafts, great food and family fun.
- Island Alpaca Yoga - Sundays in September at 11:00am - Enjoy a 45-minute session of relaxing yoga, held in our pastures among our friendly alpaca with our instructor, Jason Mazar-Kelly (YogiJay).
- Sunday in the Park Concert Series - Sundays in September from 5:30pm to 7:30pm
- Gossip, Ghosts, and Downright Scandal Walking Tours - Thursdays in September from 7pm to 8:15pm
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