Labor Day weekend may mark the end of peak summer, but there’s still a lot coming up across the Island this month! Today’s full edition is free to help you plan:
⏱️ This Week on MVacay
We’re on the other end of shoulder season now! Here’s the trip itinerary I shared earlier this year if you’re planning a group trip for September/October:
Speaking of quieter season activities, reviving this hiking guide I wrote this time last year:
🗺️ What To Do This Weekend
Friday, September 4, 2026
🎨 Annual Vineyard Artisans Labor Day Festival @ Agricultural Hall, West Tisbury, Fri 4:30-6:30p; Sat-Sun 10a-4p / More Info
The Island’s largest art show features only Island artists, with furniture, clothing, ceramics, jewelry, fine art, artist demonstrations, and local music.🎷 MV Jazz and Blues Summerfest @ Union Chapel & Strand Theatre, Oak Bluffs, Fri 6-9p; Sat 6-9p; Sun 5-9p / More Info / $50 and up
Friday features Endea Owens and Dominique Smith at Union Chapel; Saturday brings The Huntertones and Uptown Royalty NYC to Union Chapel. Sunday’s finale moves to the Strand Theatre with The String Queens, Sammulous, and Affiniti NYC.🎨 First Friday Vineyard Haven @ downtown Vineyard Haven & Owen Park, 10a-11p / More Info / Free
A full day of art, music, food, shopping, and community events spans downtown.10a-2p: Daytime Art Market at Beach St. Extension, plus an Art Hang at Althea Designs.
12-9p: Live music throughout downtown and Owen Park featuring Beach Plum Jam, Tobey Sol LaRoche, Sparkestra, The Lunarchs, David Mintz, The Roundabouts, and JakeBuddy Band.
5p-dusk: Food trucks, local artists, vendors, nonprofits, and a free art activity at Owen Park.
9-11p: Silent DJ Party at Owen Park Beach with PathwaysARTS.
🎣 Family Fishing — OB Fishing Pier @ Oak Bluffs Fishing Pier, 9:30-11:30a / More Info
🫧 Bubbles and Beyond: Outdoor Sensory Play @ Edgartown Public Library, 10:30a-12:30p / More Info
🦞 Grace Church Lobster Roll Fundraiser @ Grace Episcopal Church, 3-6p / More Info / Last Chance!
🎶 Sunset Concert Series — Johnny Hoy and the Bluefish @ MVCMA Tabernacle, 6-7:30p / More Info / Free-will offering
Saturday, September 5, 2026
🎣 MVSA Used Tackle Sale @ MVRHS Parking Lot, Oak Bluffs, 8a-1p / More Info
Shop used shore and boating gear including rods, reels, lures, tackle, life jackets, kayaks, canoes, and more. Proceeds benefit MVRHS scholarships and MV veterans; cash, Island checks, and Venmo are accepted.🏃 Foot It for Felix 5K @ Felix Neck Wildlife Sanctuary, Edgartown, 8:45-11a / More Info / $32.80; Kids’ Fun Run free
The Kids’ Fun Run/Walk begins at 8:45a, followed by the 5K at 9a along Felix Neck’s pine-needle trails and pond views. 5K registration closes Sept. 4 at 12:01p; Kids’ Fun Run registration closes Sept. 3 at 12:01p.🥕 West Tisbury Farmers Market @ Agricultural Hall, West Tisbury, 9a-12p / More Info
🛍️ Chilmark Flea Market @ Flea Market Field, Chilmark, 9a-2p / More Info /
🐐 Goat Yoga MV @ Native Earth Teaching Farm, Chilmark, 11a-12p / More Info / $30
🪁 Martha’s Vineyard Wind Festival @ Waban/Alley Park, Oak Bluffs, 11a-dusk / More Info / Free
Kite-making runs from 11a-1p, followed by youth and adult flying competitions, prizes, and community kite flying through dusk. The day also includes frisbee games, food, DJ music, bubbles, and other activities; rain date is Sunday, Sept. 6.🎶 Live Music: Chris Knott & Mixt @ West Tisbury Public Library, 2:30-4p / More Info / Free
Sunday, September 6, 2026
🏃 The Inkwell Mile Community Run @ Nomans, 15 Island Inn Road, Oak Bluffs, meet 8a; run/walk 8:30a / More Info / Free
More Than A Mile presents a community run and walk, with participants meeting at Nomans at 8a before moving at 8:30a. Registration is available online.🛍️ Oak Bluffs Open Market @ Washington Park, Oak Bluffs, 10a-2p
🥁 Weekly Museum Open House and Family Samba @ Milokan Cultural Center and Drum Museum, Chilmark, 3-6p / More Info / $15 individual
🎶 Sundays in the Park Concert @ Ocean Park, Oak Bluffs, 5:30-7:30p / Free