September brings one of our favorite times of year to Martha’s Vineyard. As the summer crowds begin to fade, the ocean is still warm, the days are beautiful, and the sunsets are spectacular. The island settles into a more relaxed pace, but there’s still plenty to see and do. Enjoy lighthouse tours, experience the Aquinnah Powwow, or join in the excitement of the annual Martha’s Vineyard Striped Bass & Bluefish Derby. Here are some of our favorite ways to enjoy September on Martha’s Vineyard.

• Chilmark Flea Market - Wednesday, September 2nd and Saturday, September 5th and 12th from 9:00am to 2:00pm - Visit the oldest outdoor flea market on the Island, offering antiques, imports, vintage finds and high-quality handmade items from Vineyard artists and craftsmen. Discover jewelry, clothing, art, pottery and much more, all in a beautiful outdoor setting at 142 North Road.  Free entry and parking. 
  
• Family Fishing -- OB Fishing Pier - Friday, September 4th from 9:30am to 11:30am - For kids, teens and their adults. Join Librarian Jonathan on the OB fishing pier. Equipment and supplies provided.
• First Friday Vineyard Haven - Friday, September 4th from 10:00am to 10:00pm - First Friday is a free community-inspired outdoor event in Vineyard Haven, Martha's Vineyard. Your favorite artists, musicians, food trucks (+ some fun new vendors) will be back on the first Friday of each month, June - October, for a day of community and local art!
• Annual Vineyard Artisans Labor Day Festival - September 4th from 4:30 - 6:30 pm, and September 5th & 6th from 10:00 am - 4:00 pm. The largest art show on Martha’s Vineyard, featuring only Island Artists with unique furniture, clothing, ceramics, jewelry, and fine art from the Island’s top artists. Watch a weaver making a beautiful scarf from wool harvested from her own flock. Enjoy watching a young Island artist create his latest masterpiece. These and many more unique experiences, including local music, await you at this premiere show.
  
• Martha's Vineyard Jazz and Blues Summerfest -September 4th-6th - The Martha's Vineyard Jazz and Blues Summerfest is an annual Labor Day weekend festival celebrating women and top talent in jazz, blues, and contemporary arts. The 2026 festival runs from Friday, September 4 through Sunday, September 6, taking place across iconic venues like the Union Chapel and The Strand Theater in Oak Bluffs. This year's event highlights award-winning female artists and genre-blending groups.
• After The Beach Escape Room Event - September 5th, 6th, and 7th (times vary) - New limited time event. After a day spent lounging on the beach, dust the sand off your feet and create new family memories at Pirates Puzzle Escape Room in Edgartown. Work as a team to solve creative puzzles. Complete the room in 45 minutes and each member of your group wins a prize. Fun group photos emailed.
• Nomans Artisans Market - Tuesday, September 8th from 4:00pm to 8:00pm - We’re thrilled to host the Nomans Artisans Market (back again!) on Tuesday, September 8th, 2026 starting at 4pm here at Nomans. Expect an evening of local art, handmade goods, vintage finds, live music from Mike Benjamin & Co., cold drinks, good food, and community gathering in the yard as summer kicks into gear on Martha’s Vineyard.
• Edgartown Lighthouse Children’s Memorial - September 12th from 1:00 pm - 3:00 pm - Each September since 2001, families have gathered at Edgartown Lighthouse for a Ceremony of Remembrance honoring children who have died at the Children’s Memorial. More than 1,000 granite cobblestones engraved with children’s names surround the lighthouse, creating a lasting memorial at the edge of Edgartown Harbor. During this annual gathering, families return to tend the stones, leave flowers and other small remembrances, and spend time together in a community that understands the weight of their loss.
• Aquinnah Wampanoag Powwow - September 12th & 13th - Keeping Our Traditions Alive - The annual powwow is a celebration of Wampanoag culture, identity, and community. It is a time for our people to gather through song, dance, drumming, food, storytelling, and shared traditions that have been carried forward for generations. The powwow honors our ancestors, celebrates the strength and resilience of our people, and creates space to pass our teachings, values, and culture on to future generations while welcoming neighboring tribes & guests to
• 81st Derby - Begins September 13th through October - Come to the Vineyard and fish the Derby! For over 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, new friendships, and generous sponsor-donated prizes - all in support of our scholarship program.
• Potter's Bowl - Sunday, September 13th at 4:00pm -Featherstone Center for the Arts welcomes pottery (and soup) lovers to the annual Potters Bowl on Sunday, Sept. 13th, at 4 p.m. Enjoy a display and sale of beautiful handmade bowls created during the past year that are donated for this special fundraising event. Patrons select a handcrafted bowl of their choice and are served locally made soup from Island restaurants and caterers. Visit featherstoneart.org or call 508-693-1850.
• Driver’s Seat: Obsessive Compulsive Disaster - September 18th & 19th at 7:00pm - The craziest stuff happens to the funniest person in the psych ward in this "shockingly funny, refreshingly honest" solo show. Buckle up for a twisted ride through OCD, an epic break up, a major break down, coming out, and–just possibly–learning how to drive. Ellie may be scared of crashing a car, but she has no fear of crashing out.
• Poetry Reading with Billy Collins - Saturday, September 26th at 6:00pm - Please join us on Saturday, September 26th to hear U.S. Poet Laureate Billy Collins read from his work in the Francine Kelly Gallery. Dubbed “the most popular poet in America” by Bruce Weber in the New York Times, Billy Collins is famous for conversational, witty poems that welcome readers with humor but often slip into quirky, tender or profound observation on the everyday, reading and writing, and poetry itself. Presented in partnership with PathwaysARTS.
• Felix Neck Nature Stroll - Wednesdays in September from  10:00am to 11:30am
• Haunted Edgartown - Saturdays in September from 7:30pm to 9:00pm - Welcome to Haunted Edgartown, a walking tour of ghost stories, legends, and strange truths from one of the most historic (and haunted) corners of Martha’s Vineyard. You’ll explore the dark side of this charming town in this 90-minute, guided storytelling experience. Along the way, you’ll hear tales of shipwrecks and curses, spirits both restless and vengeful, and buried secrets. The route winds through shadowed lanes and historic sites, with frequent stops for storytelling, audience interaction, and eerie ambiance. Equal parts history, mystery, and theatrical flair, Haunted Edgartown is perfect for curious adults, brave teens, and anyone who enjoys a chill down the spine... served with a wink and a whisper from the other side. Designed as a "PG 13 " experience. Please wear walking shoes and prepare for uneven paths, dark corners, and unexpected guests.
• Sundays In the Park Concerts - Sundays in September from 5:30pm to 7:30pm - Shop Oak Bluffs, stroll the harbor, grab a picnic meal, bring a chair, then head to Ocean Park for live music, ocean breeze and a perfect Sunday evening.   
• Jaws at 50: An Island Story - Tues - Sun in September at the MV Museum from 10:00am to 5:00pm - Our 2025 exhibition, "Jaws at 50," was one of the Museum’s most popular exhibitions, celebrating the Vineyard’s starring role in Steven Spielberg’s classic, "Jaws." Building on that excitement, we’re continuing the story with "Jaws at 50: An Island Story." This smaller follow-up exhibition highlights the Islanders who built sets, piloted boats, and stepped in front of the camera, exploring how their creativity, ingenuity, and community spirit helped bring Amity Island to life.