Martha’s Vineyard is a dreamy New England getaway that is as rich with its historic whaling and maritime past as it is with its gorgeous beaches, quaint shops ranging from nautical novelties to high-end boutiques, eateries that are either finger-licking crab shacks or jacket-required dining and sparks of live music to work off the afternoon cocktails. “Discovered” in 1602 by English explorer Bartholomew Gosnold, he applied the name in his first published account to celebrate the mother-in-law who allegedly financed his trip and the wild grapevines that still grow rampant today. (Or, depending on who you ask, to honor his daughter, also named Martha.) The tawny but casual vibe, coupled with the beautiful low-lying nature is what attracts modern vacationers, including almost every US president of the last five decades. The evident 18th and 19th century settling of this tiny 20½-mile-long isle serves to keep the pace slow and steady.
Topographically, expect few and very slight hills, plenty of green, open spaces and houses that hardly exceed two stories and range in color from grey to grey, when not white. The graceful but simple residencies, almost all finished in cedar shakes, their abundant windows framed in crisp white, are part of the plan. You’re coming here to relax; the manmade is not superimposed upon the natural setting, rather it is harmoniously fitted into it. Ditto the crowds, which are elegant and preppy—the island has traditionally been the summer playground for Boston’s conservative blue bloods. Kennedy-philes (as well as men who wear pink) will be in heaven here. Ladies would do well to leave the stilettos home and opt for more sensible, cobblestone-friendly heels.
The preferred mode of transport is the two-wheeled variety, which keeps to the chill atmosphere and allows you to take in the island at your own, “one with the place,” pace; although the bus system is first rate and there are plenty of cabs if you really want to go that route.
Edgartown is the main “city.” To give you a sense of scale, its entire contents can be browsed in about an hour. More serious shopping will delay that, as will detours to the famous Mad Martha’s ice cream shops. To flex the charge card, The Great Put-On is thee place for fashion straight off the runways, whereas the remaining shops are more along the lines of casual surfer and après-beachwear like hometown hero Vineyard Vines (Did I say preppy?) and a smattering of stylish but relaxed clothiers and jewelers. Edgartown Books will also satisfy any craving for rare and used reading material. But the real joy is idling around the streets to take in the beautifully-restored turn of 19th century homes that are neatly manicured and bespeak the island’s whaling history. (The houses all feature square shapes, flat facades, widow’s peaks and white exteriors with black trim accessorized by unique, nautical embellishments.) Kindly refrain from wearing a patch or hollering “ahoy there.”
Oak Bluffs is more the honky tonk variety, but it’s really a stretch to say that. About an hour+ bike ride from Edgartown, and not much larger, this is where you’ll find the variety of hippie shops, Deon’s (a NoLa-like greasy spoon), the wide-open park, the campground and the circus, if it’s in town. It’s a fun and fresh lowbrow retreat. Surrounding the bluffs, you can access the local art galleries that run from “what the hell is that?” modern to friendly and traditional landscapes.
Remaining pockets of civilization are in Menemsha, the last bastion of the roughneck fishermen, and Vineyard Haven, which boasts Bunch of Grapes Bookstore and another handful of art galleries.
If it’s still warm when you come, on the water expect to see graceful, luxurious 50-foot+ sailboats, as opposed to large and loud motor and fiberglass affairs. This is a good example of the overall feeling of the place: Martha’s Vineyard is about the harmony of blue and green, the flamboyant need not apply. High season is the typical Memorial Day to Labor Day, but September and early October are the best times to take in the salty dog atmosphere without the “crowds.” Keep in mind, this New England island can be as much as ten degrees cooler than our own, especially in the evenings.
During the 1830s, religious activity began in Wesleyan Grove, which is now part of Oak Bluffs. Over the next 30 to 40 years, the congregations grew so quickly, tight knots of dormitory styled tents were covering adjacent Trinity Park. Soon, families began to lease lots on which to erect their private tents. Essentially, the prime activity was religious (the founders were Methodists) and clergy would travel from across the country to preach at the Campground where locals and visitors from ashore would flock. Over time, the tents were replaced with wooden cottages that numbered as many as 500 and looked like pristine, colorful gingerbread houses. Today, just over 300 cottages remain and are considered to be the most cherished collection of Carpenter Gothic style architecture in the world. Whiling away an afternoon in the Campground is a delightful step back in time with an Alice in Wonderland feel (how often are you almost as tall as your house?).
Getting here is easy, but it takes a little coordination. The following usual options offer reliable, albeit reduced, service after Labor Day. All times/distances are approximate.
1. Fly direct: JetBlue and Delta both operate to/from JFK. Or call a friend with an airplane (1 hr 20 min).
2. SeaStreak Ferry direct from NYC to Oak Bluffs (5 hrs 15 min).
3. Drive: NYC to Quonset Pt., RI (3 hrs 20 min), Vineyard Fast Ferry (1 hr 35 min).
4. Drive: NYC to New Bedford, MA (4 hrs), SeaStreak Ferry to MV (1 hr).
*Shortcut: Port Jefferson ferry to Bridgeport, CT and skip the city traffic.
Where to Stay
Accommodations are all about the historic B&B style lodgings. Favorites in Edgartown include pet-friendly c. 1840 Shiverick Inn with hideaway Queen Terrace room opening to the treetops and bell tower and private breakfast garden below. The 19th century Gothic revival Hob Knob eco-boutique hotel features a spa and other modern amenities. And, for something larger though no less quaint, Winnetu Oceanside Resort just steps off South Beach features the hailed oceanside Lure Grill Restaurant, kids activities and the choice of suites or private cottages.
::The Ultimate Throwback:
The Flying Horses Carousel (Oak Bluffs) is our country’s oldest operating platform carousel. For $1.50, a ride on a choice steed might lead to grasping the coveted brass ring—and a free ride!