🗓️ My Top 10 Picks for Martha's Vineyard’s Best Events for 2025
If I could only pick 10 events to go to all year...these would be my picks!
I've attended hundreds of events across the island over the years and I VERY carefully choose the best ones to share with you each week…But I definitely have favorites!
My top picks are the ones that feel true to our community. I gravitate toward events that are easy to attend, fairly priced, and welcoming of everyone. These are the ones we keep coming back to, year after year, because they never disappoint.
🗓️ MVacay's Personal Favorite Save The Dates:
🇧🇷 Brazil Fest (June 1, 2025):
Brazil Fest is entering its second year as a celebration of Brazilian culture and the island's rural roots. The festival features live music, traditional dance performances like quadrilha, Brazilian cuisine, and family-friendly activities. / Info / Free
🌈 Martha’s Vineyard Pride Weekend (June 14 to 15, 2025):
The Oak Bluffs Pride Parade is full of color, music, and inclusivity and there are events for all ages. It’s a welcoming, affirming celebration of love and community that just keeps growing every year. / Info / Free
🎨 MV African American Film Festival (August 1 to 9, 2025):
MVAAFF draws nationally acclaimed filmmakers, actors, and thought leaders for a full week of premieres, panels, and powerful conversations. It’s one of the most influential and inspiring weeks on island and you don’t need to be an insider to be welcomed in. / Info / Single film passes around $25
🎡 MV Agricultural Fair (August 21 to 24, 2025):
This isn’t just a carnival….It’s a true agricultural fair that brings together farming, family traditions, and local pride. The first time I read the schedule I was blown away with how unique it is. To our family it's the epitome of summer and MV! / Info / $15 day pass for adults
🌟 Grand Illumination Night (August 20, 2025):
This celebration at the MVCMA includes hundreds of lanterns strung from gingerbread cottages, live music from the Tabernacle, and a rare moment where the entire island comes together to see them light up. It’s always packed, but that’s part of the magic. / Info / Free
🎣 MV Striped Bass and Bluefish Derby Weigh-Ins (September 14 to October 18, 2025):
The derby is one of the coolest fall MV experiences. You can see folks of all ages gather at the dock to weigh in their catch, cheer each other on, and quietly compete. It’s a tradition that runs deep and watching the kids haul in their fish is half the fun. / Info / Free to watch
🎉 Tivoli Day in Oak Bluffs (September 20, 2025):
A big block party where Circuit Ave closes to traffic and feels like an unofficial signoff of summer. Tivoli Day is a late summer gem with music, pop-up food stands and sidewalk sales. / Info / Free to attend
🌾 Harvest Festival at Ag Hall (October 25, 2025):
There are pumpkins and cider, but this fall celebration stands out for it’s emphasis on true appreciation of the season’s harvest. With local food vendors, games, hayrides, and community booths, it celebrates in the fall season beautifully. / Info / Free to attend
🎄 Christmas in Edgartown (December 11 to 14, 2025):
This weekend keeps getting better every year! What used to be a quiet holiday stroll has turned into a packed weekend of family programming, gorgeous lights, amazing sales, and a food tent that genuinely delivers. / Info / Free to attend
For a big picture roundup including 100+ save the dates, see this post:
📅 2025 Save the Dates - Big Events on Martha's Vineyard
This is a big picture list of the events happening this year on MV in chronological order with links to more info. Use it to guide your trip planning!
♿️ Notes on Cost, Accessibility, and Inclusiveness
I gravitate toward events that are community centered, family-friendly, and reflect the island’s diversity. The picks in this guide are free or modestly priced, with no VIP ticket needed to feel included. I prefer gatherings where you can come and go as needed, with stroller access, room to breathe, and parking that doesn’t make you sweat. You’ll find galas and golf tournaments elsewhere on my site, but they’re not what I choose to spotlight on a weekly basis.
🎶 Honorable Mentions: Recurring Events
🛍️ Artisan Fairs and Local Markets
Support Local! This guide includes dates and info for Vineyard Artisans Festival, First Fridays in Vineyard Haven, Aquinnah Artisans, West Tisbury Farmers Market, and sidewalk sales across towns:
🎤 Events at The Tabernacle
Friday and Sunday nights throughout July and August you can join Community Sings or Vineyard Sound concerts under the lights in the campground. Joyful and free!
🎸 Live Music Around the Island
Grab a drink and enjoy live sets at Noman’s, Featherstone’s music nights, and MVYRadio porch concerts. Local talent and easy fun:
What’s in your top 10 that isn’t in mine? Tell me in the comments!