Alley’s General Store
This island institution in West Tisbury opened in 1858, and is one of those adorable country stores that feels like a movie set but is totally authentic (yes, that’s the town’s post office in front, with rows of gleaming mailboxes). Every conceivable inch of the spacious store is stuffed with items ranging from fishing gear and vintage comics to homemade muffins and penny candy. Stop in for a dose of nostalgia before picking up lunch at 7a Foods next door.
Opened by a successful interior designer after years spent working on the island, Bespoke Abode sells chic nautical furnishings perfect for the elegant beach home. This isn’t, however, your typical preppy design store; the owner’s eye for the unusual comes through in her collection of vintage swimsuits reminiscent of Jackie O’s iconic summer style.
Black Sheep & Trio
By day, Black Sheep is the place to go to prep for an artisanal feast filled with enough charcuterie, pâté and fromage to feed a French village. Once night rolls around, however, Black Sheep transforms into Trio, a tapas-style restaurant serving a limited menu of cheese and charcuterie complimented with wine flights and desserts.
Bunch of Grapes Bookstore
An island institution for decades, this spacious bookstore has a well-edited selection of current titles. Don’t miss the terrific assortment of books about Vineyard life, which includes topics like beach plums, shipwrecks, beach glass and self-published fiction, essays and poetry by island authors. The shop organizes numerous readings every month; check their website for listings.
Jan Campbell was twenty-three when she founded this store in 1985, driven by a love for making fine chocolates and a commitment to hiring young people with special needs and teaching them new skills. Today the company is thriving, and the small cottage in Chilmark is a terrific place to pick up a sweet reminder of your Vineyard vacation.
The spacious two-level gallery, opened decades ago by Christina R. Cook’s parents, exhibits the works of over fifty artists (including Renoir and Cassatt) working in different mediums, from oil and watercolor to etchings. Upstairs in the back you’ll find a fascinating collection of antique nautical maps and charts, gathered by the Coast and Geodetic Survey; some date from 1844 (collecting these maps was a passion of Cook’s father).
Edgartown Art Gallery
Situated next to the Charlotte Inn, the Edgartown Gallery was originally built for renowned Martha’s Vineyard painter Ray Ellis, who is a frequent visitor. His Impressionist works set the tone in the elegant space, which is furnished with antiques and overseen by the charming and helpful assistant director.
Kara Taylor Gallery
The talented Taylor, a graduate of Maine College of Art, creates landscapes in oil and mixed media. At first the works are reminiscent of Vineyard settings—a meadow, the ocean, a field—but on second glance, morph into fantastical dreamscapes. Often using materials like wood, plaster and slate for her canvas, Taylor layers colors, textures and words, a technique she has compared to gardening, her other passion. Her lovely Chilmark gallery only sells her own pieces.
Epicures head to this Vineyard Haven gourmet shop for such artisanal products as French sea salts, Forte tea sets and fine olive oils. The island favorite is a good place to go if you’re looking to for a hostess gift for an amateur chef. Their home goods store, LeRoux at Home, is across the street, packed floor to ceiling with kitchen gadgets and gizmos.
Martha’s Vineyard Glassworks
There are daily glassblowing demonstrations at this atelier, which opened in 1992. Call ahead for the schedule.
This luminous boutique sells everything from pretty linens and glassware to bags, vintage skirts and dresses. Whimsical gifts include colorful nesting boxes, vintage matchboxes and a delightful selection of stationary.
Decorator Molly Finkelstein has created some of the lovliest interiors on the island, and luckily for the masses, her taste is accessible at her chic boutique in Vineyard Haven. The store, which sells antiques as well as women’s and children’s clothes, also doubles as a one of the best florists on the island. Almost all of the fashion and furnishings are pale—cream, white, grey or khaki, but fit in with a soothing beach life.
Vineyard Bath Co.
Inspired by the island’s bounty and made using only local ingredients, the products at Vineyard Bath Co. come in one of six scents; Edgartown, Oak Bluffs, Tisbury, Chilmark, Katama and Chappaquiddick. If that sounds cheesy, be assured their goods are not; the simply-packaged lotions, body scrubs, lip balms and more are lovely and light, and exactly what your skin needs after a long day in the sun.