1. Dockside Inn
City: Oak Bluffs, MA
Category: Accommodations
Telephone: (508) 693-2966
Address: 9 Circuit Ave.
Description: Overlooking the busy harbor and located in the heart of Oak Bluffs, this Victorian inn has recently been totally revamped in the clean, modern style that is practically de rigueur for new lodgings. Each of the 21 rooms is done up in an ocean-inspired palette of soft blue and plum and features high-end linens and toiletries, a flat-screen TV, and free Wi-Fi. All rates include a continental breakfast. This inn is more child-friendly than many Vineyard inns and some suites have kitchenettes. Other extras include ice cream and snacks in the afternoon and complimentary beach gear to borrow. You’ll love sitting out on the front veranda in a rocking chair as the world passes by.
2. Pequot Hotel
City: Oak Bluffs, MA
Category: Accommodations
Telephone: (508) 693-5087
Address: 19 Pequot Ave.
Description: Blessed with a prime location close to Oak Bluff’s Camp Meeting Grounds (the “gingerbread cottages”) and just 1 block from State Beach, this Victorian inn offers 32 charmingly quirky rooms (all with private bath) spread across 3 buildings. Room rates are affordable and include an expanded continental breakfast and afternoon cookies. Free Wi-Fi is available in the hotel’s common areas. Children are welcome.
3. Martha’S Vineyard Gourmet Cafe & Bakery (And Home Of Back Door Donuts)
City: Oak Bluffs, MA
Category: Restaurants
Telephone: (508) 693-3688
Address: 5 Post Office Sq.
Description: One of the Vineyard’s best spots for coffee, breakfast treats, and cupcakes, this bakery is best known for its “after-hours” activity. For the best doughnut-eating experience you’ll ever have, join the late-night line (beginning at 7 p.m.) behind the shop for doughnuts that are served warm out of the fryer until the wee morning hours. The apple fritters reign supreme here; enormous, deep-fried to a crisp, dark brown with bits of apple and a heavy sugar glaze, they are indeed the finest fritter anywhere. The bakery is open year-round; Back Door doughnuts are available Apr through Oct (cash only).
4. Martha’S Vineyard Chowder Company
City: Oak Bluffs, MA
Category: Restaurants
Telephone: (508) 696-3000
Address: 9 Oak Bluffs Ave.
Description: As you would expect from the name, the chowder is the thing to order here. Their clam chowder is made without butter or flour—just clams and fresh, creamy broth. Fast, friendly servers bring terrific sandwiches and salads, including the standout lobster tail salad. In the evening the menu includes various seafood specials. It’s located across the street from the Flying Horses Carousel, so don’t be afraid to bring your kids—everyone else does!
5. Vineyard Vines
City: Oak Bluffs, MA
Category: Shopping
Telephone: (508) 687-9841
Address: 56 Narragansett Ave.
Description: Sporty, summery, preppy. Clothing retailer Vineyard Vines was founded in Edgartown in 1998 by brothers Shep and Ian Murray and is the embodiment of all that is the Vineyard. The brand is best known for its whimsical ties, including ones with whales, lighthouses, and Red Sox logos. Real New England weddings always have the groom and groomsmen wearing Vineyard Vines ties! The company has since expanded to well beyond ties with a full line of men’s, women’s, and children’s clothing that brings fun updates to traditional New England staples. The Edgartown store is the brand’s original location, but the Oak Bluffs store is open year-round. Additional location information is available on the Vineyard Vines website.
6. Hostelling International–Martha’s Vineyard
City: Oak Bluffs, MA
Category: Tours & Attractions
Telephone: (508) 693-2665, (888) 901-2087
Address: 25 Edgartown–West Tisbury Rd.
Description: If you weren’t paying about $32 a night, you’d think you were staying at the quaintest of country inns. This cedar-shake saltbox, now more than five decades old, sits at the edge of the Manuel F. Correllus State Forest. The hostel has a fireplace in the common room, a volleyball court, a sheltered bike rack out back, and a spacious kitchen that awaits budding gourmets. Five dorms house 74 beds; check-in is between 8 a.m. and 10 p.m. daily. The hostel fills up quickly; we suggest you make reservations (especially during the season) at least two weeks in advance. The hostel is open from late Apr through early Oct.
7. Vineyard Scuba
City: Oak Bluffs, MA
Category: Tours & Attractions
Telephone: (508) 693-0288
Address: 110 South Circuit Ave.
Description: The waters around the Vineyard were unlucky for many a sailor in the 18th and 19th centuries. With the help of Vineyard Scuba, you can now visit these sunken ships and lost schooners. They offer equipment rentals so you can explore the Vineyard’s undersea world.
8. Martha’S Vineyard Hospital
City: Oak Bluffs, MA
Category: Tours & Attractions
Telephone: (508) 693-0410
Address: 1 Hospital Rd.
Description: This full-service hospital has an emergency room, inpatient/outpatient service, operating rooms, a day surgical suite, a radiology department, a three-bed dialysis unit, a psychiatry department, and a cardiac rehabilitation program—basically all the services available at the mainland hospitals. There are 45 staff physicians available at the hospital. A new $50 million hospital on Beach Road was expected to be complete in 2010.
9. Cottage Museum Shop
City: Oak Bluffs, MA
Category: Tours & Attractions
Telephone: (508) 693-7784
Description: Just behind Oak Bluffs’s main street, the “Campgrounds” is a neighborhood of some 300 gaily painted Victorian summer cottages with ornate gingerbread trim. The cottages date from the 1860s and 1870s and were built by members of Oak Bluffs’s summer Methodist retreat colony. The houses are all privately owned, but you can peek inside the Cottage Museum Shop, which has been set up with period furniture and artifacts.
10. Joseph Sylvia State Beach
City: Oak Bluffs, MA
Category: Tours & Attractions
Address: 180 Beach Rd.
Description: Located between Oak Bluffs and Edgartown, along Vineyard Sound, this 2-mile beach has pearly white sand along with calm, temperate waters. It’s a favorite spot for families with young children. The parking tends to fill early, but the beach is easy to reach by the VTA shuttle or by the bike path, which runs its length.
11. Flying Horses Carousel
City: Oak Bluffs, MA
Category: Tours & Attractions
Telephone: (508) 693-9481
Address: 15 Lake Ave.
Description: There’s plenty of old-time fun to be had on this vintage carousel located inside a quaint red barn. The carousel itself dates from 1876 but was almost scrapped in the 1980s. The Martha’s Vineyard Preservation Trust rallied to save the carousel and have it designated a National Historic Landmark. Now the 1923 Wurlitzer band organ plays and the 20 hand-carved horses have been beautifully restored, each featuring real glass eyes and a horsehair mane and tail. Open Easter Saturday through Columbus Day; check for times.