MV shopping by town: Bunch of Grapes, Vineyard Vines origin story, Black Dog history, glassblowing, thrift shops, and no chain stores.
No Target, no Walmart, no malls — Martha's Vineyard is one of New England's last great holdouts against chain retail. Every purchase supports a local business, many run by families for generations. From the iconic Black Dog t-shirt to hand-blown glass pumpkins from a West Tisbury barn studio, this guide covers every major shopping district by town.
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The island's most reliable shopping town — many shops stay open 12 months because it's a year-round ferry port. Main Street runs uphill from the harbor.
Since 1964. Publishers Weekly Bookseller of the Year 2003. Owners Molly & Brendan Coogan (since 2022). 20,000–30,000 titles winter, expanding to 40,000–60,000 summer. Resident cat Bookmark. Author events multiple times/week in summer. Year-round. bunchofgrapes.indielite.org
Founded 1913 by Lithuanian immigrant cobbler Judal Brickman. 110+ years continuous operation. Three floors: footwear, clothing, sporting goods, toys (LEGO, puzzles), hats, proprietary "Brickred" line. Year-round. brickmans.com
Founded 1966 by Cheryl Barbara Stark. Nearly 60 years, repeatedly "Best Jeweler" on MV. Vineyard Charms, Nautical, Seaglass, Jaws 50th Anniversary collection. Sterling silver from ~$95, mid-range $195–650, fine $2,995+. Custom design and repair. Year-round VH, seasonal Edgartown. cbstark.com
LeRoux at Home (62 Main St) — 3 floors kitchen/home goods since 1998, year-round. Rainy Day (66 Main St) — "way better than touristy crap," gifts/jewelry/home, year-round. Lennox & Harvey — design-forward general store, 51% Black-owned, NYT featured. The Seven Sisters — Boston Magazine "Best of Boston." The Green Room — surf/skate/sportswear 30+ years. Louisa Gould Gallery — fine art, year-round.
Closed: Midnight Farm (Carly Simon's boutique, closed 2016 after 20 years). Bramhall & Dunn (closed 2011).
MV's most vibrant shopping strip — quarter-mile from harbor past the Flying Horses Carousel. More casual, more eclectic, generally more affordable than Edgartown.
The most upscale shopping town. White-columned whaling captains' homes frame boutiques, galleries, and national brands.
Brothers Shep & Ian Murray quit their Manhattan jobs the same day in 1998, sold 800 ties from a backpack in one MV weekend, and built a brand reaching $476M in sales and ~$1B valuation. First real store opened here July 4, 2005. Now 100+ national locations. Ties $55–85, polos $90–125, tees $40–55. Seasonal on MV.
Two floors in an 1880 Victorian building. Vineyard-author section, porch signings. Companion Behind the Bookstore café — hidden courtyard, lavender lattes, "most delicious cookies." Year-round.
Portobello Road (4 Dock St) — eclectic, packed-to-the-rafters shop, "possibly my favorite store in the world." Katydid (38 Main St) — women's boutique, MV pajamas. Eisenhauer Gallery — 40+ contemporary artists, weekly summer dance parties. Old Sculpin Gallery (58 Dock St) — MV Art Association since 1954, building was the model for Quint's shack in Jaws. Respoke — designer scarves repurposed into espadrilles.
Captain Robert Douglas sketched a building on a napkin in 1969, opened The Black Dog Tavern on New Year's Day 1971. Named for his black Lab-Boxer mix. The brand exploded when Bill Clinton was photographed jogging in a Black Dog t-shirt — then the Starr Report documented Clinton buying Black Dog merchandise for Monica Lewinsky.
Douglas died April 23, 2025, age 93. His legacy: ~7 MV locations (Tavern, bakeries, general stores across VH, OB, Edgartown). Prices: tees $34, hoodies $76–98, hats $34–48. theblackdog.com
Alley's General Store (State Rd) — "Dealers in Almost Everything" since 1858. Oldest retail on MV. Owned by Vineyard Trust since 1993. Still a functioning U.S. Post Office. Penny candy, clam rakes, peacock feathers. Opens 7 AM, year-round.
Farmers Market — 40–50+ vendors, Agricultural Hall, Sat (Jun–Oct) + Wed (Jun–Aug), 9 AM–noon. Granary Gallery (636 Old County Rd) — oldest/largest MV gallery in iconic red barn, 75+ artists including Benton, Wyeth, Eisenstaedt. Year-round. MV Glassworks (683 State Rd) — watch glassblowing live, famous glass pumpkins, year-round.
Salt Rock Chocolate Co. — successor to beloved Chilmark Chocolates (closed 2019). Sisters Allison & Sarah Flanders, mentored at original shop. Handmade at Beetlebung Farm stand (410 Middle Rd) + Farmers Market. Beetlebung Farm — expanded farmstand Nov 2024, bread from freshly milled grain, year-round.
Larsen's Fish Market (Menemsha) — since 1969, lobster rolls at sunset. Seasonal. Aquinnah Cliffs — Wampanoag-owned shops selling traditional wampum jewelry and clay items (only tribal members may mine the cliffs). Aquinnah Shop purchased back into Wampanoag ownership for $2M (2023–24).
Chicken Alley Thrift Shop (38 Lagoon Pond Rd, VH) — operated by MV Community Services, recently renovated/expanded. Clothing to furniture. Year-round. ACT TWO (66 Main St, VH) — nonprofit funding arts, $38K+ in grants distributed. Trader Fred's (249D Edgartown–VH Rd) — discount warehouse, designer jeans, beach gear, cigars. Thu–Sat only, 10 AM–4 PM. Chilmark Flea Market — Wed & Sat, 50+ years, mid-Jun–early Sep.
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