Oak Bluffs

The colorful jumble of odds and ends spread throughout Craftworks (42 Circuit Ave., Oak Bluffs, 508/693-7463, www.craftworksgallery.com) is actually a dream team of artwork, all handmade by contemporary American artists. The highlights include nearly life-size papier-mâché cows, funky butterfly garden benches, and exquisitely carved and painted wooden plaques.

Located a short drive north of town, the Book Den East (71 New York Ave., Oak Bluffs, 508/693-3946, www.bookden.com) is a musty old barn filled to the eaves with secondhand books; check out their collection of vintage postcards.

Vineyard Haven

Owner Carly Simon (who’s also been known to sing a tune from time to time) sees to it that Midnight Farm (18 Water-Cromwell Ln., Vineyard Haven, 508/693-1997, www.midnightfarm.net) is stocked with a smorgasbord of high-end, quasi-bohemian wares: beaded moccasins and sequined dresses, handmade honey and soaps, etched antique cocktail glasses, and shabby-chic furniture.

Opposite the Black Dog Tavern, on the dead-end lane headed toward the harbor, is stina sayre design (13 Beach St. Extension, 508/560-1011, www.stinasayre.com, year-round by appointment or chance), a small atelier of women’s couture. If you’re on the island around Thanksgiving you can catch Sayre’s annual fashion show at the Mansion House, but she welcomes drop-ins, too, as she enjoys meeting potential clients in person.

The very presence of The Devil’s Dictionary (9 Main St., 508/693-0372, 10 a.m.–10 p.m. Mon.–Sat., noon–7 p.m. Sun. mid-June–mid-Sept.; off-season hours vary; closed Feb.–Mar.) on Main Street is one of those defiant gestures proving that the Vineyard is not just your parent’s family resort.

If you must have something emblazoned with a Black Dog, B.D. Gear (11B Water St., Vineyard Haven, 508/693-7381, www.theblackdog.com, 10 a.m.–5 p.m. daily April–Dec.; 12 p.m.–5 p.m. daily March–April; closed Jan.–Feb.) sells T-shirts, mugs, backpacks, and tennis balls that sport the Labrador profile.

Edgartown

Awash in Edgartown’s pink-and-green sea of preppy boutiques, The Great Put On (Dock St., Edgartown, 508/627-5495, 10 a.m.–6 p.m. Mon.–Sat.; 11 a.m.–5 p.m. Sun. May–Oct.; 12 p.m.–5 p.m. Mon.–Sat.; closed Sun. Nov.–April; hours vary in Jan.) is a refreshing blast of innovative women’s clothing from designers like Moschino and Vivienne Tam.

Up-Island

The bluefish icon of casual clothing store Menemsha Blues (Basin Rd., Menemsha, 508/693-9599, www.menemshablues.com, 10 a.m.–5 p.m. daily in summer; closed Nov.–May) has replaced the black dog as the island symbol of choice. The shop also has branches in Vineyard Haven (36 Water St.), Edgartown (Dock St.), and Oak Bluffs (15 Circuit Ave.).

© Michael Blanding and Alexandra Hall from Moon New England, 2nd Edition