Oak Bluffs
Oak Bluffs also is well-known for its Carpenter Gothic “gingerbread cottages,” brightly painted wooden houses built by visiting 19th-century Methodists. The Martha's Vineyard Camp Meeting Association (MVCMA), (508) 693-0525, offers 90-minute guided walking tours of “the Campground,” which today encompasses just over 300 of the tiny, privately owned, residential structures. Tours depart on Tuesdays and Thursdays at 10, July through August. The fee is $12; free (ages 0-9).
At the center of the MVCMA village grounds is the Tabernacle, where church services and special events are held. Built in 1879, the prominent landmark features an octagonal cupola, wrought iron arches and colored glass windows. A community sing-along and concert takes place at the Tabernacle as part of August's Grand Illumination festivities.
Shopping
You'll find one of the Vineyard's three Soft As A Grape locations along Circuit Avenue, Oak Bluffs' main commercial drag. Selling lines of men's, women's and children's clothing, the Cambridge-born chain's most well-known collection is made from a super-plush, ring-spun combed cotton.Also on Circuit Avenue is another Massachusetts chain, Black Dog General Store , the first of which opened in Vineyard Haven in 1992. The Martha's Vineyard original is filled with sailing attire, rain jackets, water bottles, tote bags and a vast array of other products bearing the image of a Lab-boxer mix named after Black Dog, the character from Robert Lewis Stevenson’s “Treasure Island.”
Craftworks (42 Circuit Ave.), a contemporary sales gallery, sells whimsical pieces fashioned by both local and national artisans (think garden ornaments, handmade jewelry and decorative wood sculptures). For more unique keepsakes, walk to the Oak Bluffs Arts District (just west of Circuit Avenue at Dukes County and Vineyard avenues), home to Alison Shaw Gallery (88 Dukes County Ave.), Lucinda Enamels (11 Vineyard Ave.) and other artsy independent businesses.
Along the Circuit Avenue Extension, the Dockside Marketplace & Marina on Oak Bluffs Harbor features several restaurants and bars as well as another Black Dog General Store, the Black Dog Premium Outlet, The Christmas Cottage, Dockside Jewelers and Martha's Gifts.
Nightlife
Out-of-towners soaking up rays and slurping down oysters pack the second-floor patio bar at Nancy's Restaurant (29 Lake Ave.), a local institution since 1960. Downstairs, in-the-know natives hit up the Vineyard's favorite bartender, Donovan, whose signature Dirty Banana—made with vodka, Bailey's Irish Cream and Kahlúa—packs a real punch. With frozen drink in hand, you're ready to watch the sunset. Phone (508) 693-0006. Next door to Nancy's, you'll find more of the same (refreshing beverages, fresh seafood and outdoor seating) at the string of buzzing Dockside Marketplace & Marina hangouts overlooking Oak Bluffs Harbor.The Lampost (6 Circuit Ave.) offers a little of everything, including a large dance floor and performance space for up-and-coming music acts. You can also shoot some pool or play a game of darts at the divey, multilevel club; phone (508) 693-4032.
Boisterous patrons catch up with old friends at casual Offshore Ale Co. (30 Kennebec Ave.), a brewery/restaurant popular with craft beer lovers. Perhaps not so coincidentally, Offshore's tasty IPA just so happens to be the perfect accompaniment to the delicious wood-fired brick oven pizzas coming out of the open kitchen. Phone (508) 693-2626.
Just across the street from Offshore Ale is an Oak Bluffs must: Back Door Donuts. Beginning at 7:30 p.m., the back door of Martha's Vineyard Gourmet Café & Bakery opens for business, with heavenly baked goods sold out of a sketchy parking lot filled with hungry late-night carousers until about 12:58 a.m. The line is usually long, but trust us, the wait for a fresh apple fritter the size of your head is so worth it. Cash only.