This Month’s To-Do List

July is jam-packed with fun events and activities. Here are a few you won’t want to miss.

1. Artsy Monday nights. The Vineyard Playhouse in Vineyard Haven brings back its popular Monday Night Specials, featuring original scripts and well-known performers on the main stage. Tickets go fast, so reserve yours in advance ( Over in Oak Bluffs, Featherstone Center for the Arts, in its fifteenth season, presents Musical Mondays, with Island bands and musicians on the outdoor stage ( Bring a picnic, bug spray, and your dancin’ feet!

2. Shooting hoops. Seconds left, players scramble, a bounce pass, a hook shot, and score! Onlookers cheer, and the next teams step up. It’s the ninth annual Vineyard Streetball Classic, a three-on-three tournament held at Niantic Park Courts in Oak Bluffs all day Saturday, July 2. Interested players (ages ten to eighteen) or sponsors can sign up online at, and fans just need to bring their spirit.

3. Pond swimming. The ocean isn’t the only place to catch a dip and cool off on a summer’s day. Consider Ice House Pond or Uncle Seth’s Pond (both in West Tisbury off Lambert’s Cove Road) for a change of scenery from coastal to sylvan, or to rinse off after a salty swim. Be forewarned: Parking at both locations is very limited, so if you’re traveling by bike or by bus, you’ve got an advantage getting in.

4. An Old World festival. Celebration is in full swing at the Portuguese American Club July 16 and 17 for the Holy Ghost Feast. A fair crops up on the club’s Oak Bluffs property Saturday from 5 p.m. on, with live music, dancing, games and crafts for the kids, and of course kale and linguica soup, among other good eats. The festivities hit the streets on Sunday morning with a parade starting from the Oak Bluffs wharf at 11:30 a.m., followed by traditional dancing at the club.

5. A sailboat spectacle. To us beach bums, the flocks of sailboats offshore make an iconic Vineyard backdrop. July sees some fierce competition take to the seas. Keep an eye out for circumnavigating vessels on Saturday, July 9, during the ’Round the Island Race. The Edgartown Regatta, July 14 to 16, and the Vineyard Cup in Vineyard Haven, July 15 to 17, bring sailors from around the world to compete in Island waters.