Although a summer resort, much of what the island has to offer is enjoyable and accessible in early autumn after the summer hoards have gone.
Harvest festivals, fishing derbies, cycling events and open air markets add to the mix during a time of year that many locals say is the island's best.
With six towns, and a dose of fame and notoriety, the 100-square-mile island has become known as a summer colony beloved by writers, artists, musicians and presidents Bill Clinton and Barack Obama. Its year-round population of about 15,000 can swell upwards of 100,000 on peak summer weekends.
Reuter correspondents with local knowledge help visitors enjoy the island's highlights during a quick trip.
FRIDAY
5 p.m. - Arrive via Steamship Authority ferry (www.steamshipauthority.com for schedules) after a 45-minute trip from Wood's Hole. The only other travel options are plane, private boat or a few longer ferries from other locations. Boats debark in either bustling Oak Bluffs or more staid Vineyard Haven. First-timers are advised to make their base in youth-oriented Oak Bluffs or Edgartown - the only two of the Vineyard's six towns that are not dry. Set out to explore the charming harbor after checking in.
8 p.m. - A wealth of both fine dining and casual seafood joints awaits. Dine at the Lobsterville Bar and Grill (8 Circuit Ave., lobstervillemv.com/) and try to score a table on the second floor porch overlooking the marina before tucking into local specialties such as hand-dug steamed Vineyard clams and steamed lobster.
10 p.m. - Check out the Flying Horses, a national historic landmark that is the country's oldest platform carousel and still has brass rings to grab, then take a stroll up Circuit Avenue, Oak Bluffs' main thoroughfare, which is populated with bars, boutiques and ice cream parlors, most of which are open late on weekends.
Midnight - Listen to some live music and mix with the locals at the Ritz Cafe (2 Circuit Ave., 508 693-9851), or if something more low-key is in order, stroll over to the Oak Bluffs campground, which isn't a campground at all. Here you'll be met with a truly unusual site - hundreds of Victorian gingerbread cottages in a riot of confectionary hues, all impeccably maintained and decorated.
SATURDAY
9 a.m. - Many people consider Linda Jean's (25 Circuit Ave., 508 693-4093) a must for breakfast. Locals like to pair their eggs or pancakes with linguica - a spicy, red-hued Portuguese sausage.
11 a.m. - The best, and by far most economical, way to see the island is by the Martha's Vineyard Transit Authority bus system (www.vineyardtransit.com), which traverses the island and costs just $1 per town (i.e. $2 from one town to another). Invest in a $7 day pass and you can ride all day and night on any of the 13 routes which run year-round.
Start with the longest trek, taking the #5 past scenic tidal pools and over rolling hills to Aquinnah, which the locals still refer to by its former name, Gay Head. If time allows, stop off in West Tisbury for a stroll through the Farmer's Market (here) and pick up some snacks for the rest of the afternoon.
Once at Aquinnah, a short walk past a line of seasonal shops and clam shacks leads to your reward from the top of the brilliant, clay streaked cliffs down to the sea. Gay Head Light beckons photographers, while the more intrepid hike down the path to the beach far below. Most of the casual shacks offer similar menus and vibes. Feast on local classics such as chowder, fried whole belly clams and requisite onion rings. A typical restaurant is the Aquinnah Shop (www.theaquinnahshop.com/, 508 645-3867).
2 p.m. - Take the bus, transferring to the #4, to Menemsha, a quaint village where parts of the classic film "Jaws" were filmed. Tiny shops, clam shacks, a sturdy jetty and incomparable sunsets beckon many to this quiet hamlet.
4 p.m. - Next stop Vineyard Haven, which along with Edgartown houses many of the Vineyard's more upscale shops. But for a late afternoon drink go elsewhere because like most of the island's towns, alcohol is not served.
7 p.m. - For a truly special Vineyard dining experience, reserve a table at the waterside Lure Grill near South Beach. Take the free water taxi (in high season) from Edgartown Harbor, where you'll cruise right past lavish homes owned by "Lord of the Dance" creator Michael Flatley and, until his death a few years ago, newsman Walter Cronkite.
9 p.m. - Stroll the streets of Edgartown, where you'll notice all homes are painted white or gray, or have natural shingles. It's a law. Galleries welcome browsers and place a heavy emphasis on local artists and seaside motifs. Cap off the night, as everyone seems to do, with the requisite ice cream cone.
SUNDAY
9 a.m. - Back in Edgartown, enjoy a coffee at Espresso Love (17 Church St., 508-627-9211), and a breakfast of muffins and other delectable morning pastries.
11 a.m. - After a stroll around the harbor and stops to admire the pristine, lush gardens that adorn the tidy homes, stop at Black Sheep Fromage and Charcuterie (18 North Summer Street, 774-549-9118) for a picnic lunch, then head to Wheel Happy, (8 South Water St, 508-627-5928) where $20 covers a half-day rental, which is plenty of time to explore beautiful Chappaquiddick.
Board the Chappaquiddick ferry "On Time," which runs more like a shuttle, eschewing schedules and travel past the beautiful waterside vistas.
5 p.m. - For a last bite, try the Quarterdeck (29 Dock St., 508 627-5346) by the Chappy ferry for a classic New England meal of clam chowder and fried whole belly clams. Alternatively, grab a last beer and chowder at Nancy's (29 Lake Ave., 508 693-0006) in Oak Bluffs, which is popular with tourists, locals and presidents, before boarding the ferry back to the mainland. (Editing by Patricia Reaney and Andre Grenon)
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