Shopping

Oak Bluffs

The colorful jumble of odds and ends spread throughout Craftworks (42 Circuit Ave., Oak Bluffs, 508/693-7463, www.craftworksgallery.com [1]) 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 [2]) 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 [3]) 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 [4], 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 [5], 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 [6] 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 [7], 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 [6] (36 Water St.), Edgartown [6] (Dock St.), and Oak Bluffs [8] (15 Circuit Ave.).