Martha’s Vineyard is as classic New England as it gets, with its quaint port towns, white-sand beaches, lighthouses (one of them, the historic Gay Head, was moved from the edge of the Aquinnah Cliffs to a new location 135 feet inland last year), and general fondness for water sports. There’s never a shortage of quality places to eat and drink, which has made the island a popular summer hangout for Northeasterners looking for a little respite.
Where To Stay
Two (New-ish) Sister Hotels
In May, New England-focused boutique hotel group Lark Hotels opened The Christopher and reopened The Sydney, which underwent a major redesign last year. The 15-room Christopher looks stately and Victorian on the outside, but borrows its interior design elements from the French Caribbean, with rattan furnishings, pops of bright coral, and batik prints. Book the Lark Suite (from $330), which comes with two private balconies (24 S. Water St., Edgartown; 508-627-4784; thechristophermv.com). The smaller and more private Sydney is just a few steps away and features a more typical New England aesthetic, plus a well-kept lawn and midcentury furniture (22 N. Water St., Edgartown; 508-939-9299; thesydneyhotel.com).
Originally a tavern that housed sailors in 1742, the 60-room Kelley House got a new general manager in May. Stockholm-born Patrick Cabido, who has worked for The Pierre and Soho House in New York, as well as Montauk’s storied Surf Lodge, is set to breathe a little life into this aging member of the Historic Hotels of America. 23 Kelley St., Edgartown; 508-627-7900; kelley-house.com.
Where To Eat
Just opened in May, Down Island features communal-style, five-course set dinners in the basement of a building in Oak Bluffs. Chef Scott Cummings, who also runs the kitchen at much-lauded sister restaurant 20byNine, serves homemade pasta and local seafood on his rotating menu. 6 Circuit Ave., Oak Bluffs; downislandmv.com.
Behind the Bookstore
Tucked behind indie bookstore Edgartown Books is a quaint mega-stop serving breakfast, lunch, dinner, as well as baked goods, Chemex-brewed coffee, and cocktails. The kitchen welcomes Chez Panisse alum Molly Levine as the new head chef this season, who brings flavors of California and Nashville to the menu (squid a la plancha, ancho chili short ribs). 46 Main St., Edgartown; 774-549-9123; btbmv.com.
Eating at the Aquinnah Circle
Having just won the distinction of a historic district by the Massachusetts Cultural Council, the westernmost tip of Martha’s Vineyard, called The Aquinnah Circle, has witnessed a crop of new businesses: The community-favorite Orange Peel Bakery opened a separate café in the Circle serving tacos, clam chowders, and lobster rolls in June (37 Aquinnah Circ.; 508-645-2025); and Cliffhangers, a take-away joint that also opened in June, specializes in stuffed quahogs (round clams) and serves soft-serve ice cream (21 Aquinnah Circ., Aquinnah; 508-955-9163).
What To Do
Atria Summer Wine Dinners
On select Wednesdays until the end of August, the chefs at fine-dining outfit Atria in Edgartown team up with vintners and importers to host a series of special dinners, open to the public, focused on wine. 137 Upper Main St, Edgartown.; atriawine.com.
Martha’s Vineyard Summer Concert Series
In addition to performances by musical acts like NOLA’s Preservation Hall Jazz Band (July 19), Chadwick Stokes (July 30), and the Taj Mahal Trio (August 5), this concert series also features non-musical acts—most notably David Sedaris (July 26 and 27), Alan Cumming (July 14), and storytelling podcast The Moth (August 3). mvconcertseries.com.
Martha’s Vineyard International Film Festival
Drawing from the world’s top festivals—including Sundance, Berlin, and Cannes—Martha’s Vineyard International Film Festival returns to Vineyard Haven just at the end of the summer rush, from September 6–11, for another showcase of roughly 40 films from around the world at the island’s Film Center. 79 Beach Rd.; 5008-696-9369; mvfilmsociety.com.