Martha's Vineyard Blog: Travel Tips, Guides and Island Stories

A reader planning a trip for May 2027 asked us what would actually be open. The honest year-round map: restaurants, cafes, trails, museums and services that never close, town by town, plus the calendar of when everything else reopens.

The Gay Head Cliffs are sacred Wampanoag land, not just a viewpoint. What visitors are welcome to in Aquinnah, what the rules protect, and how to be a good guest.

Shearer Cottage, Dorothy West, the Inkwell and 30 marked sites across the island: how to walk or tour the African American Heritage Trail of Martha's Vineyard.

Which Martha's Vineyard beaches are open to visitors, which need stickers or permits, and what everything costs in 2026: town by town, gate by gate.

New Woods Hole terminal, fare-free buses, new restaurants in Oak Bluffs and Vineyard Haven, a reopened lighthouse and more: everything that changed on the island in 2026.

On August 19, 1991, Hurricane Bob hit Martha's Vineyard at the height of the season: 98 mph winds, 84 boats wrecked in Edgartown Harbor alone, a sloop in the Harborside Inn pool, and a false autumn by Labor Day. The story of the storm, told through an original Vineyard Gazette storm edition we found in an island thrift shop.

Fall 2026 on Martha's Vineyard: the September 10 and October 12 deadlines, beaches that open to everyone September 16, the Derby, scalloping by town, foliage timing and honest closing dates.

Thinking about a September or October visit? Good call. A friendly heads-up on what shifts after Labor Day 2026: the ferry switch to Vineyard Haven, each boat's last day, what stays open through Columbus Day, and how far room rates fall.

The 81st Striped Bass and Bluefish Derby runs September 13 – October 17, 2026, and you don't need a rod to enjoy it. Free twice-daily weigh-ins on Dock Street, what it costs to enter, where to watch from shore, and the key-and-lock drawing where somebody wins a boat.

You can bring a rental truck to the Vineyard, but only on the Steamship Authority boat, and the booking works differently than it does for a car. What the trucks really measure, what the ferry charges in 2026, and how to reserve space.

Inside Edgartown's 4th of July: the Main Street parade with fifes, floats, classic cars and Camp Jabberwocky, then fireworks over the harbor, with photos, video and tips for doing the day right.

Take a guided Jaws tour of Martha's Vineyard with local guide Mike Currid. Walk the real Amity Island in Edgartown and book the "Amity" Walking Tour.