Join the vibrant Chilmark Road Race on Saturday, August 9, 2025 at 10:30 AM for a spirited 5 K through the rolling hills of Middle Road in Chilmark.

Celebrate the power of Black voices at the Martha’s Vineyard Black Book Festival on Saturday, August 9, 2025, from 1–7 PM at the Island Inn Conference Center in Oak Bluffs.

Step into the glow of history at Grand Illumination Night, Wednesday, August 20, 2025, in Oak Bluffs. Join the community-lit Tabernacle for hymns, prayer, and live music, then be mesmerized as hundreds of paper lanterns ignite, illuminating the iconic gingerbread cottages in a breathtaking sea of color.

Experience the Martha’s Vineyard Agricultural Fair, August 21–24, 2025, in West Tisbury! Four days of timeless tradition—livestock shows, carnival rides, delicious local fare, craft exhibits, and family‑friendly competitions.

Gather your family and friends for a dazzling night at Ocean Park, Oak Bluffs on Friday, August 22, 2025! Enjoy the Vineyard Haven Band at 8 PM, followed by a breathtaking fireworks show over the harbor at 9 PM.

Dive into diverse storytelling at the 20th Annual MV International Film Festival, September 2–7, 2025, in Vineyard Haven.

Cast your line into Vineyard tradition at the 80th Annual MV Striped Bass & Bluefish Derby, running Sept 14–Oct 18, 2025. Open to anglers of all ages and skill levels—shore or boat—with daily weigh-ins at Edgartown Harbor.

Celebrate the end of summer at Tivoli Day—Oak Bluffs’ beloved street festival—on Saturday, September 20, 2025, from 10 AM–6 PM (rain date Sunday).

Savor summer’s vibrant flavors at the Martha’s Vineyard Food & Wine Festival, June 6–9, 2025, in Edgartown.

Join us for a spooktacular day at Halloween in Oak Bluffs on Saturday, October 25, 2025!

Celebrate the start of the holiday season at Light Up Oak Bluffs, a magical tradition where the historic gingerbread cottages of the MVCMA grounds are illuminated by hundreds of colorful lanterns.