What an unpredictable weekend ahead we have! I’m sending this weekend’s edition early because it includes bonus Thursday events. 🌧️
⏱️ This Week on MVacay
This week I’m showcasing FAMILY resources! Paid subscribers can access a new 23-page PDF that incorporates dozens of guides into ONE playbook. My favorite part is the by-town cheat sheets. If you don’t want to become a paid subscriber you can also buy it on Etsy here.
I updated the Ag Fair guide today to include food, vendors, maps and additional links.
🗺️ What To Do This Weekend
Thursday, August 21, 2025
🎡 Martha’s Vineyard Agricultural Fair at Agricultural Hall, West Tisbury, 10a–11p (Fri–Sun too) / More Info / Buy Tickets to the Fair / Buy Carnival Ride Passes / $15
🚌 Getting there: VTA routes 2, 3, 4, and the hourly direct Fair Bus from VH & Edg stop at the fairgrounds (fare free)
⭐️ Don’t miss: 4H Opening Day Parade @ 10:15a and LED Light Show @ 8p
🛍️ Vineyard Artisans Summer Festival at Grange Hall, West Tisbury, 10a–2p / More Info / free
🏮 Grand Illumination Night at The Camp Ground, Oak Bluffs, 7p / More Info / free
An island tradition that begins at the Tabernacle with community singing, band music, and the ceremonial lantern lighting.
Friday, August 22, 2025
🎡 MV Ag Fair at Agricultural Hall, West Tisbury, 10a–11p (Thu,Sat & Sun too)
More Info / $15⭐️ Don’t miss: Draft Horse Pull @ 1p and Pet Show @ 3p
📚 Book Signing: Carbivore by Phoebe Lapine at Edgartown Books, 2–4p / More Info / free
🦈 Jaws@50 Screening & Celebration with Wendy Benchley at Martha’s Vineyard Museum, Vineyard Haven, 5–7p / More Info / $35
🎶 Sunset Concert Series: The Jon Bates Band at 80 Trinity Park, Oak Bluffs, 6–7:30p / More Info / free
BYO picnic & chairs for this lively end-of-week concert at the Tabernacle.
🎭 Martha’s Vineyard Comedy Fest at The Strand Theatre, Oak Bluffs, 8p / More Info / cost varies
Annual festival brings top comedians to the Island for a night of laughs.
Saturday, August 23, 2025
🧺 West Tisbury Farmers Market at Grange Hall, 9a–12p / More Info / Free
🛍️ Chilmark Flea Market at Flea Market Field, Chilmark, 9a-2p (Wed too) / More Info / Free
🎡 Martha’s Vineyard Agricultural Fair at Agricultural Hall, West Tisbury, 10a–11p (Sun too) / More Info / $15
⭐️ Don’t miss: Woodsman’s Competition @ 11a and Johnny Hoy & the Bluefish Saturday night
🎭 The Fabulists: The Most Wondrous Thing at Tisbury Amphitheater (Final show of the season!), Vineyard Haven, 10a / More Info
🏃 Sullivan 5K Run at Washington Park, Oak Bluffs, 9:30–11:30a / More Info / $25
Annual fundraiser benefiting MV Hospital, open to all ages.
🎬 Highest to Lowest at MV Film Center, Vineyard Haven, 7:30p / Tickets
Spike Lee and Denzel Washington reunite for a gripping new take on Kurosawa’s classic High & Low, set in present-day New York.
🩰 Dance Theatre of Harlem: An Evening at Union Chapel at Union Chapel, Oak Bluffs, 7:30p / More Info / $35 (GA), $150 (VIP)
A powerful evening of performance and lecture-demonstration with Artistic Director Robert Garland and members of the world-renowned company.
🎆 Oak Bluffs Fireworks at Ocean Park, Oak Bluffs, 9p / More Info / free
The Island’s biggest summer fireworks show. Bring a blanket and arrive early.
Sunday, August 24, 2025
🎉 Oak Bluffs Open Market at Washington Park, Oak Bluffs, 10a–2p
🎨 Vineyard Artisans Summer Festival at Grange Hall, 10a–2p / More Info / Free
🎡 Martha’s Vineyard Agricultural Fair at Agricultural Hall, West Tisbury, 9:30a–6p / More Info / $15
⭐️ Don’t miss: Dog Show @ 10a and Women’s Skillet Toss @ 3p
🖼️ Opening: The Phil & Eileen Brown New Yorker Cartoon Collection at Featherstone Center for the Arts, Oak Bluffs, 4–6p / More Info / free
🎺 Vineyard Haven Town Band at Ocean Park, Oak Bluffs, 7:30p / More Info / free
⚠️ Events subject to change due to weather. Always check before you go! The live web version of this post will be updated with any changes or cancellations.
Behind the Paywall: a famous photographer releases island line, beach closures and alerts, MV books, ticks in the Times, Save the Dates thru September.