Happy October! We’ve got a really good fall weekend ahead with First Friday, LadyFest, Oktoberfest, the Gay Head 10K + plenty more happening around the Island.
🗺️ What To Do This Weekend
Friday October 2, 2026
🎣 Martha's Vineyard Striped Bass and Bluefish Derby @ Derby Headquarters, Dock Street, Edgartown, Daily weigh-ins 8-10a & 7-9p / More Info All Weekend
🎨 Bass in the Grass @ The Carnegie, Edgartown, All Weekend / More Info / Free
🎨 First Friday Vineyard Haven at Downtown Vineyard Haven, All Day / More Info / Free
A day of art, shopping and activities downtown followed by food, music, a bonfire and dancing at Owen Park.🛍️ First Friday VH Passport Challenge at Participating Businesses, All Day
🎨 Daytime Art Market at Beach St. Ext., Art Hang at Althea Designs,10a-2p
10a-2p / 🎵 Live Music at 5 Corners, 12p
🎨 Evening Activities: Food Trucks, Live Painting, Beach Bonfire on the Hill at Owen Park, 5p-Dusk
🥁 Upis Land Band from Main Street to Owen Park Beach, 6-6:30p
🎵 Johnny Hoy and the Bluefish at Owen Park Beach, 7-8p
🎧 Silent DJ Party with PathwaysARTS at Owen Park Beach, 8-10p
🎨 HERitage: A Multimedia Music and Arts Festival Honoring Historic Vineyard Women at Stillpoint, West Tisbury, 3-8p / More Info + Tickets / $15–$40
Doors open at 3p for art showcases, food and henna, followed by music from 6-8p. Admission is sliding scale; advance tickets are available, drop-ins are welcome.
Saturday October 3, 2026
🥕 West Tisbury Farmers Market at Agricultural Hall, West Tisbury, 9a-12p / More Info / Free
🎸 LadyFest MV 2026 at Waban Park, Oak Bluffs, 1-9p / More Info + Tickets / $35
Outdoor music festival featuring musicians, artisans, food and other vendors, with proceeds benefiting CONNECT to End Violence. Gates open at 1p; purchasing tickets in advance is recommended.🎧 Gates Open / DJ Dolce Vita at 1p / Elda Berlin at 1:30p / Gabi at 1:45p / The Alpha Gals at 2:45p / Wolftrap at 3:45p / Sunny War at 4:45p / Island Hip Hop at 5:45p / Ali McGuirk at 6:15p / Island Hip Hop at 7:05p / Kate Taylor at 7:15p / Delanie Pickering at 8p
🍂 Fall Family Fun Day at PA, 1-4p / More Info
Community fall celebration with food, games and music, and costumes are welcome.🍺 3rd Annual Oktoberfest — Nomans Style at Nomans, Oak Bluffs, All Day / More Info / (Sun too)
Two full days of Oktoberfest in the Yard with German food, beer and live music all day. Activities include keg tapping, stein holding, pumpkin bowling, pretzel throwing, a best-dressed competition and more.🌊 Climate Conversation Chilmark: Menemsha’s Working Waterfront at Chilmark Free Public Library, Chilmark, 2-4p / More Info / Free
Panel discussion exploring Menemsha’s working waterfront, local economy and climate planning. Held in the library’s Community Room with representatives from the Fishermen’s Preservation Trust and Commercial Dock Working Group.🧵 West Tisbury Quilting Circle Show and Reception at West Tisbury Public Library, West Tisbury, 3-4:30p / More Info / Free
Meet members of the quilting circle and view their biennial show during the opening reception; refreshments will be served. The quilts remain on display in the Community Room throughout October.🕯️ Community Remembrance Event at Joseph Sylvia State Beach, Edgartown, 5:30-6:30p / More Info / Free
Sunset gathering hosted by Hospice & Palliative Care of MV to remember loved ones who have died. Meet between the two bridges at the Camp Jabberwocky parking area; the gathering is open to everyone, regardless of hospice affiliation.
Sunday October 4, 2026
🛍️ Oak Bluffs Open Market @ Washington Park, Oak Bluffs, 10a-2p / More Info / Free
🏃 Gay Head Run for the Light 10K at Gay Head Lighthouse, Aquinnah, 10a-12p / More Info + Registration / $43.40 incl. fee
🎵 Sundays In The Park Concerts @ Ocean Park, Oak Bluffs, 5-7p / More Info / Free
What’s New This Week on MV: A new Islanders-only breakfast menu, more restaurants wrapping up for the season, and newly announced October events including Fall on the Farm, Nomans’ Cornhole Tournament, Haunted Hooves + more.