Visiting Aquinnah Respectfully: The Wampanoag Homeland at the Island's Edge (2026)
The Gay Head Cliffs are sacred Wampanoag land, not just a viewpoint. What visitors are welcome to in Aquinnah, what the rules protect, and how to be a good guest.
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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Vineyard Haven: Year-Round Main Street
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.
Bunch of Grapes Bookstore, 23 Main St
Since 1964. Publishers Weekly Bookseller of the Year 2003. Owners Molly and 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
Brickman's, 8 Main St
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
C.B. Stark Jewelers, 53A Main St
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
Other VH Essentials
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 and 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 and Dunn (closed 2011).
Oak Bluffs: Circuit Avenue's Color
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 Lazy Frog (42 Circuit Ave): games, Legos, kites, Pokémon, "Home of Vineyard-Opoly" (benefits MV Community Services)
- Craftworks (42 Circuit Ave): 400+ juried artisans, hand-blown glass/pottery/jewelry. Fodor's "must see." Since 1991
- Stefanie Wolf Designs (37 Circuit Ave): glass-tile beaded jewelry, custom MV-shaped beads, permanent jewelry. Year-round
- Glimpse of Tibet (39 Circuit Ave): Himalayan handicrafts, Buddhist sculptures, scarves
- Murdick's Fudge (5 Circuit Ave): 180–1,200 lbs daily, copper kettles, marble tables. Since 1979 on MV. ~$8–12/slice. Note: all three island shops were reported temporarily closed as of August 17, 2026, with hopes of reopening later in the summer; check before visiting
- Ben and Bill's (20A Circuit Ave): famous lobster ice cream
- Good Dog Goods (79 Circuit Ave): treats, toys, gifts for dogs
- Black Dog: General Store (35 Circuit Ave) + Dockside Outlet (12 Circuit Ave Ext)
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Edgartown: Refined Main Street
The most upscale shopping town. White-columned whaling captains' homes frame boutiques, galleries, and national brands.
Vineyard Vines, 27 North Water St (Flagship)
Brothers Shep and 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.
Edgartown Books, 44 Main St
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.
Other Edgartown Highlights
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
West Tisbury: Farms, Art and the General Store
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.
Up-Island: Chilmark, Menemsha and Aquinnah
Salt Rock Chocolate Co.: successor to beloved Chilmark Chocolates (closed 2019). Sisters Allison and 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 and Sat, 50+ years, mid-Jun–early Sep.
Practical Tips
- MA sales tax 6.25%: clothing/footwear under $175 is TAX FREE
- August sales tax holiday weekend: most items under $2,500 exempt
- Year-round shops: Bunch of Grapes, Brickman's, CB Stark, LeRoux, Rainy Day, Chicken Alley, Alley's, MV Glassworks, Granary Gallery, Edgartown Books
- Budget 20–30% above mainland prices across most categories
- Most popular souvenirs: Black Dog merch, Vineyard Vines, Murdick's fudge, CB Stark charms, MV Glassworks pumpkins, Wampanoag wampum jewelry, Vineyard-Opoly
- Parking: Easiest in VH (Veterans Memorial lot) and OB (municipal lots). Edgartown: use free shuttle from outlying lots. Or take the free VTA bus
For budget tips, rainy day activities, and restaurant guide.
Island Tip of the Day · Timing
Visit Edgartown on a Tuesday or Wednesday. Same beautiful town, maybe 30% of the weekend crowds. Most restaurants have availability without reservations.
Disclaimer: The information in this article is provided for general guidance only and was accurate at the time of writing. Beach conditions, hours, prices, lifeguard schedules, ferry fares, and business operations change frequently and without notice. Ocean swimming carries inherent risks including rip currents, undertow, and cold water shock. Always verify current conditions with official local sources before your visit. MV Vacation assumes no responsibility for any loss, injury, or inconvenience resulting from the use of this information. Swim only where lifeguards are on duty, supervise children at all times near water, and follow all posted safety signs.
