Spring Offerings

wine festival
Courtesy Martha’s Vineyard Wine Festival

May and June are the warm-up to summer on Martha’s Vineyard. Temperatures are more inviting, beaches are bare, and parking is plentiful. Not to mention there’s no lack of events and activities – Vineyarders and visitors alike are excited to get out and about, see their friends, and celebrate the start of the season. There’s something for all ages, and here are some our favorites:

1. Raise your glass. The Island welcomes a new culinary event to its spring lineup. For four days, May 9 to 12, restaurants and private residences will host the Martha’s Vineyard Wine Festival, showcasing a global selection of wines with food pairings by Island chefs. For a very Vineyard experience, the Farmer’s Table dinner on Saturday in Chilmark will feature a farm-to-table Island menu served with wine from Napa Valley’s organic Frog’s Leap Winery ($150). On Sunday, Détente will host a Bottomless Mimosa and Endless Bloody Mary Brunch at 11 a.m. in Edgartown ($45). For tickets and a full schedule of events, visit By dedicating a portion of proceeds to support the Local Wild Food Challenge and Martha’s Vineyard Boys & Girls Club, this event’s organizers leave nothing to whine about.

2. Hats off to tea time. Lavish hats aren’t just for British royalty – in May on Martha’s Vineyard, at least. Wear your most elaborate hat and celebrate Mother’s Day weekend in style at the Garden Tea Party and Fashion Show at Featherstone Center for the Arts in Oak Bluffs on Saturday, May 11, from 2 to 4 p.m. Tea sandwiches, sweet treats by Cakes by Liz, and of course, hot tea, are served alongside a runway showcasing spring and summer designs from Vineyard boutiques such as Laughing Bear, Bananas, and Bryn Walker. The fundraising event coincides with Featherstone’s Art of Flowers show, curated by Holly Alaimo. This party draws a big crowd, so make your advance reservation early by calling 508-693-1850. Tickets are $40. Oh, and what to wear? Make it fancy – there are contests for best hat and most creative outfit.

3. Choice art. What have Island artists been doing all winter? They’ve been making art! The Friends of Family Planning Art Show over Memorial Day weekend at West Tisbury’s Agricultural Hall is often considered the kickoff event of the season. With some 125 artists exhibiting, the non-juried show has become an essential fundraising (and social) event. Even high school students get involved, entering a contest to design the promotional poster. The Gala Preview Party is Thursday, May 23, from 6 to 8 p.m. and tickets are $50. The show runs Friday through Sunday from 10 a.m. to 6 p.m. and is free. For information, visit Board member Jennifer Knight sums it up: “For us, it’s really crucial – it’s what enables us to support the clinic.”

river rocks

4. Oh, the places you’ll go. When you live on an island, there is only so far you can travel without traversing the water. But after the annual Cross-Island Hike on Saturday, June 1, you won’t feel that way. The route clocks in around twenty miles, and every year for the past twenty years, rain or shine, Island adventurers put on their best hiking shoes, pack water and snacks (and rain gear), and hit the trails. About fifty people start, with a third making it all the way. Led by Martha’s Vineyard Land Bank staff, the hike route changes each year, exploring conservation trails and properties that are part of the Island’s extensive trail system. Start at 8:30 a.m. and walk the whole route, or choose a section of it. A detailed map with meeting points will be posted at in late spring. If this isn’t already on your bucket list, it should be – for bragging rights alone!

cliffs lighthouse

5. To the lighthouse. Quick! Grab a friend and see how many lighthouses you can visit in one day during the Annual Lighthouse Challenge on Saturday, June 8, from 10 a.m. to 4 p.m. Make your way around the Island to explore the Edgartown, East Chop, and Aquinnah lighthouses, as well as the grounds at West Chop. For the complete experience, take a trip to Chappaquiddick to visit Cape Pogue (for an additional fee; reservations required). Sponsored by the Martha’s Vineyard Museum, Chamber of Commerce, and The Trustees of Reservations, this event raises funds to help maintain the Island’s beacons of light. The challenge is free for museum members, $15 per non-member adult, and $25 per non-member family. Visit With erosion threatening the future stability of the Gay Head Light, and plans to move it underway, make sure to put that one at the top your list.