This month is the culmination of the Island’s delightful summer mayhem.

Simone McCarthy

1. Get your snorkel on.

Simone McCarthy

The Island sheds her winter cocoon in May and June. Nascent summer weather livens the tempo in the towns and outdoors – the fish start to bite, the flora to bloom, and the ferry to bustle. Hibernation is ceding quickly to congregation, but it’s still possible to find parking in Edgartown. Or at the cliffs.

Simone McCarthy

So we survived the hustle, bustle, and heat of the summer season, and now we find ourselves on the other side, free from traffic and crowds but – nothing to do? Au contraire, hardy ones! The winter Island is too good to stay inside. Whether you’re in the mood to tuck into some hearty food, sit back and be entertained, or venture into the bracing outdoors, there are plenty of ways to get out and appreciate the other season.

Simone McCarthy

September and October are two of the Island’s best months. By the time summer fades, that famed New England autumn is in full swing, and it’s warm enough to enjoy it. This time of year is also the unofficial Island festival season – with several weekend-long events to suit a variety of interests. Our picks for these months remind us why we love the Island’s shoulder season.

Simone McCarthy

1. A week of Kahoots. The popular (and prolific) Vineyard band Kahoots is hitting the road, and luckily for us, it’s an around-the-Island tour. The band will be jamming its indie rock sound in all six towns and Chappaquiddick from August 1 to 7, playing through its twelve albums in chronological order. The newest, “Play Something You Know,” is timed for release at the Saturday performance. Tickets are $5, on sale at the door, and shows are for fans of all ages (except those at bar venues). For a full schedule, visit the Kahoots Facebook page.

Simone McCarthy

This year marks the 150th anniversary of the Island’s beloved Ag Fair, which honors the Vineyard’s agricultural traditions, fosters community participation, and offers all kinds of fun food, games, and carnival rides.

Karla Araujo

The people responsible for garnering and escalating bids at charity auctions can significantly impact the bottom line of Vineyard nonprofits, some of which are now hiring professionals.

Kate Feiffer

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