- Saturday, June 1st at 8:30 am - Annual Cross-Island Hike! This years hike starts at Blackwater Pond Reservation and ends at Big Bridge, Edgartown. The route is 15.2 miles.
- Saturday, June 8th from 9:00 am to 12:00 pm - West Tisbury Farmers’ Market! - Outdoor farmers market featuring locally grown produce, meat & locally made products. Wed & Sat throughout the summer.
- Saturday, June 8th from 5:30 pm to 7:00 pm - Cheese Talk & Tasting at The Grey Barn! Head to the farm and learn about the cheese making process. BYOB if you like. More dates in the summer
- Saturday, June 8th at 7:00 pm - Schonberg Fellows/Chicagoland: The Era & Joanna Furnans at The Yard!
- Sunday, June 9th from 10:00 am to 2:00 pm - Vineyard Artisans Summer Festival! - A Vineyard summer tradition. Thurs & Sun throughout the summer.
- Monday, June 10th at 6:30 pm - MV Sharks vs. Mystic Schooners! Enjoy the Island’s own collegiate summer baseball team as they take on the Mystic Schooners.
- Thursday, June 13th from 6:30 pm to 10:00 pm - The Taste of the Vineyard Gourmet Stroll!
- Saturday, June 15th from 10:00 am to 4:30 pm - Cape Pogue Lighthouse Tour! Enjoy an over-sand vehicle adventure to the remote Cape Pogue lighthouse.
- Sunday, June 16th from 11:00 am to 1:00 pm - Car-B-Q Classic! Procession of classic cars followed by a classic car show on the lawn of the new MV Museum!
- Saturday, June 22nd from 10:00 am to 6:00 pm - Harbor Festival! - Oak Bluffs Annual Street Fair!
BONUS! June 22nd Strawberry Festivals! Morning Glory Farm 11-3, WT Church 12-4! Don’t miss the islands best strawberries!