MARTHA'S VINEYARD, Mass. — During the 37-minute flight from Boston to Martha's Vineyard, I asked myself at least 37 times what I was doing on this nine-seat toy plane in unusually heavy winds with a pilot who looked barely old enough to drive a car, much less have a pilot's license.
Looking out the window as we made our bumpy approach, I realized what I was doing here. I forgot about the bumps and concentrated on the beauty. Below me was an artist's palette of colors: green fields dotted with flecks of summer pink and yellow, blue sea, and at the edge of the island, the burnt umber of Gay Head cliffs. The colors dazzled in their intensity.
The island resembled a canvas framed by the sea. An Impressionist blur from the plane, it came into focus on the drive from the airport. Sand dunes strewn with cobalt-blue beach morning glories gave way to gleaming white clapboard Colonial houses. Harbors crammed with fishing boats and lobstermen checking their traps were juxtaposed against the occasional solitary lighthouse, its giant cyclops eye looking out to sea.
Martha's Vineyard, which includes the neighboring island of Chappaquiddick, has six communities, each with a distinctive personality, surrounding an interior largely comprised of the Manuel F. Correllus State Forest.
Never miss a local story.
The history of Martha's Vineyard is as fascinating as its geography. There really was a Martha: She was the daughter of English explorer Bartholomew Gosnold, who sailed to the island in 1602, but she died in infancy, so it's unlikely she ever had a vineyard.
But before the English arrived, there was another sailor: a member of the Wampanoag tribe who, according to legend, floated ashore on a sheet of ice, accompanied by his dog. To this day, islanders refer to mainlanders who come here to live as "wash-ashores."
Every town is different
Most visitors headquarter in Edgartown, the island's first colonial settlement (1642), and with its stately Greek Revival mansions built by prosperous 19th-century whaling captains, it is one of New England's most elegant communities.
For the best perspective, wander the town's picturesque streets, stopping to visit the Old Whaling Church on Main Street and the Vincent House, the oldest home on the island, now a museum.
North Water Street has a row of captain's houses, many complete with "widow's walks" facing seaward, from which many a captain's wife watched for her husband's safe return.
On South Water Street, the main attraction is the enormous pagoda tree that was brought from China as a seedling in the early part of the 20th century. The house behind the tree belonged to Capt. Valentine Pease, on whose whaling ship Herman Melville made his only voyage. Many think that Pease was the model for Ahab in Moby Dick.
Another slice of history can be found in the Newes From America Pub, just a few blocks from the harbor. Dating from 1742 and once a popular gathering spot for Colonials, the tavern has retained its original rough-hewn beams, ballast brick walls and cozy hearth. Now a restaurant, it specializes in food from both sides of the Pond: You can get burgers and fries or bangers and mash.
If Edgartown is Colonial in feel, Oak Bluffs' ambiance is pure Victorian. A staggering number (312) of brightly painted and ornately trimmed gingerbread cottages, with charming names such as Five Gates, Judy's Jewel and Time Remembered, surround 34-acre Wesleyan Grove. Today a park listed on the National Register of Historic Places, the Grove began in 1835 as a Methodist campground, where the faithful attended religious revivals. The cottages are all privately owned, but you can tour the Cottage Museum at the entrance to the park.
If it started out catering to the pious, today Oak Bluffs is considered the liveliest of the island's towns, as seen in the number of restaurants and bars lining the picture-postcard harbor.
Like Edgartown, Oak Bluffs has a storied whaling heritage and an impressive Colonial history. Pay a visit to the Old Schoolhouse Museum and note the Liberty Pole standing in front of it. The tall white pole is a replacement for the original and commemorates the daring of three teenage girls who, in 1776, inserted gunpowder into the original pole's base and blew it up to keep it from being used as a spar on a British warship.
West of Oak Bluffs is Vineyard Haven, a shopper's paradise (the stores Bunch of Grapes and Midnight Farm are well worth a browse), a diner's delight (the famous Black Dog Tavern next to the ferry dock serves breakfast, lunch and dinner) and a great place for celebrity-spotting: among those who live year-round or part-time on the island are Carly Simon, Meg Ryan, Mike Nichols and Diane Sawyer, Mike Wallace, Bill Murray, Ted Danson and Mary Steenburgen, and Caroline Kennedy, who inherited the estate that belonged to her mother, Jacqueline.
Head 'up island'
Heading west, or "up island," the landscape changes from beach resort to rural small-town America. By the time you reach West Tisbury, the island's second-oldest community (1670), you realize that this is quintessential New England. At the intersection of two country roads, the tall spire of West Tisbury Congregational Church welcomes parishioners just as it has since 1865.
Alley's General Store has been here even longer (since 1858), and it is still the gathering place for "up-islanders." If you're looking for something a bit more cosmopolitan, walk across the road to the Field Gallery, whose sculpture garden is one of the most charming I've ever seen.
Chilmark is known for rolling hills and stone fences, reminders that this was once an area of sheep farms. Now, it's more likely to be the setting for luxurious summer homes. Its companion village, Menemsha, might be familiar to moviegoers who remember being scared out of the water while watching Jaws; many of the film's scenes were shot here.
Keep going until you get to the western end of the island and you will be rewarded with one of its most spectacular sights. Gay Head Cliffs, with a picturesque lighthouse and bands of multi-colored clay, tower over the blue-green waters of Vineyard Sound in the tiny village of Aquinnah.
Aquinnah — which in the Algonquin tongue has several translations, among them "colors by the sea" and "land below the cliffs" — is home to a small community of Wampanoag Indians who are descended from that original "wash-ashore."
This is nature at its best, with white beach plum blossoms in the summer, and cranberry bogs along Moshup's Trail turning a fiery crimson in the fall. The trail is named for the legendary Wampanoag hero who is said to have captured whales with his bare hands.
As I sat on the deck of the tiny café overlooking the cliffs, savoring a bowl of clam chowder, I decided it would be very easy to become a "wash-ashore."