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
Monday, September 7, 2026
Labor Day
Brazilian Independence Day
🌱 Beetlebung Farm Tour @ Beetlebung Farm, Chilmark, 4-4:30p / More Info / $5
🌿 Garden Tasting Tour @ The Farm Institute, 5-6:30p / More Info
Today’s Full Edition is FREE!
Every week I read the newspapers, 50+ newsletters, scroll through posts from 2,000+ MV-based businesses and roll it up into this one tidy weekly email to help you plan your weekend. We take every picture you see here, and amplify events from new and minority-owned businesses. If that makes your life easier, please consider becoming a paid subscriber to help support my work, time and efforts. It makes a huge difference. ❤️
📍MVacay’s Island Updates
⛅️ Weekend Weather Outlook: Friday partly cloudy, 76°/62°, Saturday mostly sunny, 71°/58°; Sunday partly cloudy, 69°/58°, with breezier winds Saturday + Sunday (perfect wind festival weather!)
⭐️ Island + Business Updates
Boneyard Surf Co. will close its Main Street Edgartown shop after 25 years; the store will remain open while remaining merchandise sells at 50–70% off for the next few weeks. Dune will move from Winter Street to that location.
Juniper Relocation Sale: Juniper is offering 50% off everything Tuesday–Saturday ahead of its relocation; Saturday is the store’s last day at its current location, with hours 10a–5p. New location not announced.
The Gathering: Vineyard Ease: A new weeklong Vineyard experience centered on the Black Vineyard community, with community, connection, culture + rest at its core coming 7/18–7/24/27.
The Women of Chilmark Lecture Series and a collection of Chilmark oral history interviews with longtime residents are now available to watch on the Chilmark Public Library Vimeo page.
🍽️ Restaurant Updates (full post coming soon)
Art Cliff Diner is temporarily closed.
Midnight Mediterranean is closed for the season.
Smokehouse Sundays at Katama General Store: Katama General Store launches Smokehouse Sundays September 13, shifting its Coastal Smokehouse barbecue to Sundays from 11a–3p or until sold out, with brisket, pulled pork, ribs, wings, loaded mac bowls, plates + larger pre-order platters available at katamageneral.com.
🍂 Last Chances Coming Up:
9/10: Final Eisenhauer Music in the Square
9/12: Final Chilmark Flea Market
9/27: Final weekly Vineyard Artisans Sunday
10/11: Final Sundays in the Park at Ocean Park
10/31: Final Saturday West Tisbury Farmers’ Market
📅 Save The Dates - Upcoming Events
⭐️ Cool New Event Spotlights
🌸 9/6–9/27: Family Flower You Pick at Slough Farm: Pick and arrange flowers in the Horse Barn Garden on Sundays from 4–6p; bring your own container, $10.
🦇 9/8: Bat and Moth Night at Tashmoo Spring Building: An all-ages evening of moth observation and bat research with wildlife biologists from 7–10p; bring a flashlight and sturdy shoes.
🎨 9/10: The Offseason: Claymation at Martha’s Vineyard Museum: A hands-on claymation program from 5–6p exploring stop-motion animation; $25/$15.
🍯 9/12: Friends, Foraging & Fermenting at Chilmark Library: Meet from 1–3p to plan fall and winter foraging + fermenting workshops and make a fermented soda with local honey and fruit; registration required.
🎬 9/13: MV International Film Festival Closing Night: The Siege of Paradise at MV Film Center + The Wave MV: Closing night starts with The Siege of Paradise at 4:30p, followed by a party at The Wave with food, drinks, dancing + DJ Smooth B; one ticket includes both.
🎨 9/18–9/19: Habitat for Humanity Art Show & Sale at Grange Hall: Galaxy Arts MV presents a two-day art show and sale featuring Island artists from 10a–6p
🎶 9/21: Music Workshop with Darby Patterson + Sam Rothberg at Slough Farm: Rose Coloured Glasses duo Darby Patterson and Sam Rothberg lead a free, hands-on evening for musicians of all levels and curious listeners from 5:30–7p.
💃 9/24–9/26: Dance Film Festival at The Grange Hall + The Yard: Circuit Arts’ three-day festival includes international dance shorts with live performances by Abby Bender + friends, a Friday double feature followed by line dancing, and a Saturday hands-on dance-film workshop for ages 16+.
📝 10/6: At Stillpoint / The Somatics of Language: How Words Land in the Body at Stillpoint: Kate Gamble leads a workshop exploring how poetry, spoken word + personal mantras connect language with sensation, breath and emotion; $20–$35.
📖 10/12: Sweet Life Author Series: Joseph Lee at The Sweet Life: Aquinnah Wampanoag journalist and author Joseph Lee discusses Nothing More of This Land over a three-course prix-fixe dinner; $115 per ticket.
🀄 10/17: Mah Jongg Tournament for Dementia & Caregiver Services on MV at The Grange Hall: The MV Center for Living hosts a Mah Jongg tournament from 10a–3p supporting Dementia & Caregiver Services; registration opens after Labor Day, with tournament updates available from katiev@mvcenter4living.org
🎃 10/31: Murder! On the Dance Floor: A Ghostly Gala at Red Cat Kitchen: A 21+ Halloween night hosted by Zest with performances, dancing, games + a costume contest; doors at 9p.
Now for ALL the Save the Dates combined…
September 8 - Bat and Moth Night at Tashmoo Spring Building
September 8–13 – Martha’s Vineyard International Film Festival (MV Film Society)
September 9 - Improv for Adults at Grange Hall
September 10 - The Offseason: Everything You Ever Wanted to Know About Claymation at Martha’s Vineyard Museum / Can You Shuck It: Shellfish Shucking with Chris Look at Edgartown Public Library / Music in the Square: Mike Benjamin and the Keepers at Eisenhauer Gallery / Noman’s Tiki Party
September 11 - MoGlo Corn Shimmy at Morning Glory Farm / MV Football vs. Mashpee Home Opener at MVRHS / Rosh Hashanah begins at Martha’s Vineyard Hebrew Center
September 12 - Run for Hope with Millers Foundation at MVRHS / Children’s Memorial Ceremony of Remembrance at Edgartown Lighthouse / Vineyard Vanguards with Tom Dresser at Oak Bluffs Public Library / Friends, Foraging & Fermenting at Chilmark Library
September 12-13 - Aquinnah Wampanoag Powwow
September 13 - MV Striped Bass + Bluefish Derby begins / Burgers & Bubbles at Daniel Fisher House / Potter’s Bowl at Featherstone Center for the Arts / MV International Film Festival Closing Night: The Siege of Paradise at MV Film Center + The Wave MV
September 16 - Author Dinner with Emma Brodie: Into the Blue at Sweet Life / The Giving Garden: Fall Tour, Taste, and Take-Home with Roxanne Kapitan at Ag Hall
September 17 - 2026 Great Reads Community Discussion: “Nothing More of This Land” by Joseph Lee at Vineyard Haven Public Library / Community Sound Bath at Oak Bluffs Public Library / Open Mic Night at Vineyard Haven Library
September 18-19 - Habitat Art Show and Sale at Grange Hall (West Tisbury) / DRIVER'S SEAT: OBSESSIVE COMPULSIVE DISASTER at Martha’s Vineyard Playhouse / Behind the Curtain With the Nashville Hit Makers at The Strand Theatre
September 19 - Tivoli Day / An Evening With Music City’s Rising Stars at The Strand Theatre / Maritime Felting at Oak Bluffs Public Library
September 20 - Hospice of MV Memorial Golf Tournament / Derby Kids Day at the OB Pier / Young Eagles Rally at Katama Airfield / Yom Kippur at Martha’s Vineyard Hebrew Center
September 21 - Music Workshop with Darby Patterson + Sam Rothberg at Slough Farm
September 24 - Bass in the Grass Opening at The Carnegie Heritage Center / Dance Film Festival at The Grange Hall + The Yard begins (thru 9/26) / 29th Annual MANHATTAN SHORT Film Festival at MV Film Society begins (thru 9/27)
September 25 - Fly Fishing Film Tour + Sage Fly Rods Demo at Kismet Outfitters / Poetry Workshop with Billy Collins at Featherstone Center for the Arts
September 26 - Seed Cleaning and Storage Basics with Brittany Clark at Polly Hill Arboretum / Back Door Dinner at Beetlebung Farm at Beetlebung Farm / Cultivating a Writer’s Mindset with Allison Alsup at Featherstone Center for the Arts
September 27 - Camp by the Sea at Slough Farm / Elie Wiesel: Soul on Fire at MV Film Society
September 30 - Barney Zeitz Open Studio
October 2 - First Friday Vineyard Haven
October 3 - Family Day at The PA Club (rain 10/4) / Misty Meadows Ponies & Pumpkins / Ladyfest
October 6- Martha’s Vineyard Chamber of Commerce State of the Island Tourism Breakfast / At Stillpoint // The Somatics of Language: How Words Land in the Body at Stillpoint
October 10-11 - Vineyard Artisans Fall Festival
October 12 – Indigenous Peoples’ Day / Sweet Life Author Series: Joseph Lee at The Sweet Life
October 15 - Venus Speaks: Women of Comedy at MV Film Society
October 16–18 – Women in Film Festival (MV Film Society)
October 17 – Pumpkin Festival at Morning Glory Farm / Mah Jongg Tournament for Dementia & Caregiver Services on MV at The Grange Hall
October 18 - Derby Awards Ceremony at Farm Neck
⭐️ Also see Save the Dates for 2026 & MVacay Mobile App