Derek Davies and Lizzie Plapinger always dreamed of hosting a music festival on Martha’s Vineyard. As best friends spending summers at the Chilmark Community Center, they shared a love of music and the Island. As they grew up, they never lost sight of their passions or their goal.

Chris Kennedy, Martha’s Vineyard superintendent for The Trustees of Reservations, has spent the past 25 years touring Trustees properties on the Island. He’s seen Wasque, Mytoi, Norton Point and Long Point in all seasons and all types of weather, watching the landscapes shift and transform over time.

There’s a paint-off going on this weekend and everyone is invited to check it out. Called Painting the Vineyard and benefiting The Trustees of Reservations, the event involves local artists painting on site at five Trustees locations on the Island and Chappaquiddick. Artists will be painting at Mytoi, Wasque Point and Cape Pogue on Chappaquiddick; Norton Point Beach (Katama) in Edgartown; and Long Point Wildlife Refuge in West Tisbury. There will be transportation available from the Chappy ferry to the Chappaquiddick sites.

Mary Steenburgen saw her first play at a community theatre in Arkansas where she grew up. It was the Music Man, performed by a travelling company and she was instantly captivated.

“I literally could not breathe,” she said in an interview with the Gazette at her home in Chilmark. “I was so transported by it, and it meant so much to me.”

Ms. Steenburgen grew up in a home with “fairly modest means,” and found refuge from family and life challenges in the audience, on the stage and in the wings of the community theatre.

Butter stained tables line the dock of Menemsha harbor where on summer evenings fresh lobsters are eaten off paper plates as the sun sets on another Vineyard day. Finger licking is required, bibs are optional. Lobsters are a celebration says Larsen’s Fish Market owner Betsy Larsen.