September is our favorite time on Martha’s Vineyard. The water is still warm, the beaches are peaceful, and the sun is just right—perfect for soaking it all in. The summer crowds have gone, but the island's charm is as vibrant as ever. Whether you're paddling a kayak, casting a line, or chasing sunsets, there's no shortage of ways to unwind. Here are just some of the wonderful things to do this September on the island.

• Summer Lobster Rolls at Chilmark Community Church - Tuesday, September 2, 2025 4:30pm to 6:30pm - Enjoy a beloved summer tradition — fresh, delicious lobster rolls ready to go! Lobster roll meal includes a 4 ounce cup of lobster (lightly mixed with mayo), wrapped roll, bag of chips, fork, and napkin.
• Mocktails and Mares - Wednesday, September 3rd from 5:00pm to 6:30pm - Relax, refresh, and get your hands on a horse! Spend an early evening at the farm as a fun transition from beach time to dinner time! Light refreshments and a mocktail will be enjoyed in great company before interacting with our special herd of horses. Along with unmounted mindful horsemanship, a mounted experience will be offered. Please note Misty Meadows has a weight limit of 185lbs for riding. Plan to laugh, relax and make some new friends - both two-legged and four-legged!
• Johnny Hoy and The Bluefish - Wednesday, September 3rd at 8:00pm - Come hear a local favorite at the Ritz!
• First Friday Vineyard Haven - Friday, September 5th 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.
• Corn Shuck and Shimmy - Friday, September 5th from 5:00pm to 8:00pm - Join us Friday, September 5th, from 5–8 pm for a fun time, where summer meets fall in the most delicious way possible. It’s BYOB and lawn chairs and picnic blankets are encouraged! Enjoy an evening of farm-fresh food, corn-infused baked goods, and seasonal favorites. The fun continues with a fire pit, a corn sensory pit for kids, and classic games like corn hole. Test your skills in the Corn Shucking Competition or guess the number of kernels for a chance to win prizes. Let’s celebrate the end of summer together with good food, good friends, and a whole lot of corn!
• Drive-In Movie: Finding Nemo - Friday, September 5th at 7:30pm - Gates open 45 minutes before start time. Tickets for this screening are general-admission and pay-what-you-can. The suggested ticket price is $40. If you can pay more, we greatly appreciate it!
• Drive-In Movie: Raiders of the Lost Ark -  Saturday, September 6th at 7:30pm - Gates open 45 minutes before start time. Tickets for this screening are general-admission and pay-what-you-can. The suggested ticket price is $40. If you can pay more, we greatly appreciate it!
• 2025 80th Anniversary Derby - Begins Sunday September 14th - Come to the Vineyard and Fish The Derby! For 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
• Walking Tour in Old Westside Cemetery - Wednesdays in September from 4:00pm to 5:15pm - A guided walk among the historic gravestones in Old Westside Cemetery. The tour is an opportunity to learn about the town's past from the people who actually lived it. It includes visits to the graves of revolutionary war heroes, island missionaries, whaling captains and ordinary people who created the town through their courage and hard work.
• Trivia Night at the Black Dog Bakery Cafe - Thursdays in September from 6:00pm to 8:00pm - Come test your knowledge and play some trivia at The Black Dog Bakery Cafe! Prizes for the top three-placing teams. Maximum team size: six players. Email: bdbakerycafe@theblackdog.com to reserve your table.
• Can You Dig It: Quahog Harvesting with the Edgartown Shellfish Department - Friday, September 12th from 9:30am to 10:30am - Join us at the Katama Landing where you will get a chance to learn techniques for harvesting shellfish from the constables of the Edgartown Shellfish Department. You do not need a shellfish license to attend and observe, but a shellfish license is required for hands-on experience with harvesting and taking home quahogs. Licenses can be purchased online, click here for full details.
• Second Hand and New Art Sale - September 12th, 4:00pm to 7:00pm& 13th, 10:00am to 6:00pm - This is a unique and fun show and art sale.  In addition, we will continue our traditional fundraiser, by offering "second hand" fine art in good condition by unanimous donors to support the ongoing important work by Habitat for Humanity of Martha’s Vineyard
• The Sound of the Vineyard - Wednesday, September 3 from 5:00pm to 7:00pm - Enjoy a family-friendly evening of live music on the Grange Hall porch, featuring top local bands in a fun summer series. Produced by Mike Benjamin and Vineyard Preservation Trust—picnics welcome, food, and drink for sale.
• CnC Ole Skool Dance Cafe - Tuesday, September 2nd from 8:00pm to 11:00pm - CnC’s Ole Skool Dance Café is the best dance party on MV, featuring DJ SmoothB, spinning your favorite ole skool dance tunes, at the PA Club on Tuesday's at 8:00pm. So get your dancing shoes on and come to the PA Club every Tuesday from July 1 thru Sept. 2, 137 Vineyard Ave, Oak Bluffs. $10 at door. All are welcome!
• Chilmark Flea Market - Wednesday, September 3 & Saturday, September 6 from 9:00am to 2:00pm - The oldest outdoor flea market venue on the Island! The "Flea" has evolved into a market like no other. High quality hand made items from Vineyard artists and craftsmen, antiques, imports and vintage finds including jewelry, clothing, art, food items and more. Free parking and admission.

• Paint Party at Nomans - Wednesday, September 17th from 6:00pm to 8:00pm - Join us on Wednesday, September 17th (6-8pm), to paint "West Chop Big Pier" at Nomans in Oak Bluffs! Jasmine will be painting along with you and teaching you step by step how to create this beautiful painting while you enjoy food and drinks from the delicious Nomans menu! 
• Tivoli Day - Saturday, September 20th from 10:00am to 6:00pm- An end-of-season street fair and block party thrown in Oak Bluffs.
• Historic Cemetery Tour with Tom Dresser - Saturday, September 27th at 11:00am - Join local historian Tom Dresser for a fun, informative and not-at-all-scary cemetery tour. We will meet outside at Pacific Avenue entrance (cemetery-facing side) of the Oak Bluffs library. Tour takes about an hour and is about a mile in distance.
• Vineyard Charity Golf Classic - Monday, September 29th at 9:00am - The Vineyard Charity Golf Classic is a collaboration between MVCS and the Island’s Rotary Club. The tournament supports both MVCS programs as well as other Island charities and organizations through the Rotary Club.
• Nomans Night Market - Mondays in September from 4:00pm to 8:00pm - Come one, come all! Nomans’ weekly night market hosts many of our beautiful island’s talented local vendors. Let’s. Go. Support. Local. 
• The Jaws Experience: 50th Anniversary Escape Room - Mondays, Wednesdays, and Saturdays in September - Celebrate Jaws 50th anniversary with this uniquely Martha's Vineyard Experience Event. Create new memories with this fun event for family and friends. Jaws was filmed on Martha's Vineyard. This escape room takes place inside a replica of the boat Brody, Quint and Hooper used to defeat Jaws. In this game you are playing the role of the Jaws hunters and have to solve clues which tie in the Jaws and Martha's Vineyard themes. Your goal is to save the town of Amity by defeating Jaws within 45 minutes. 
• Women Rising Art Show - September 1-7 - Daily 12:00pm to 5:00pm - Women Rising...Where Women Gather, Power Is! This exhibition celebrates the strength and resilience of women, particularly the power that emerges when women unite. Through a dynamic selection of paintings, sculptures, installations, and mixed media works, this exhibition reflects not only the collective force of women but also the deeply personal and familial relationships that shape their experiences. At the heart of the exhibition is the idea that power grows exponentially when women come together, and these stories of connection and shared history are to