Martha’s Vineyard

Photo by Tom Dussault

Martha’s Vineyard Itineraries

Martha’s Vineyard for First-Timers

A tiny island (seven miles offshore) known worldwide

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For such a small place, Martha’s Vineyard has a huge reputation. Roughly triangular in shape and about 25 miles by nine miles big, this hallowed island is agrarian and quiet off-season (mid-October to mid-June) and celebrity-choked in the summer (when you need to have made car reservations six months in advance). Down-island towns (Edgartown, Oak Bluffs, and Vineyard Haven) are the most developed. Up-island refers to the less developed, hilly western end (including West Tisbury, Chilmark, Menemsha, and Aquinnah).

Martha’s Vineyard ferries arrive into Vineyard Haven and/or Oak Bluffs from Cape Cod (primarily Woods Hole, Falmouth, and Hyannis) and the nearby island of Nantucket (the latter in summer only).

Martha’s Vineyard: Down-Island


Elegant Edgartown is chock-full of grand white Greek Revival ship captains’ houses, with fanlights and widows’ walks. Many of these private homes are clustered on North and South Water streets, while elsewhere downtown you’ll find chic shops, galleries, and restaurants.

Vineyard Haven

Although it’s less showy than Edgartown, Vineyard Haven maintains a year-round level of activity that Edgartown doesn’t. It’s the commercial center of the island, where “real” people live and work. The harbor is home to more wooden boats than any other harbor of its size in New England. For an experience straight out of the 19th century, stop in at Gannon and Benjamin Boatbuilders on Beach Road; it’s one of the few remaining wooden-boat rebuilding shops in the country. Literary and journalistic personalities have all called Vineyard Haven their second home.

Oak Bluffs

Oak Bluffs today is at once charming and honky-tonk. It has a long history of welcoming and attracting prominent African Americans; the most recent influx began during Bill Clinton’s presidency. In 1835, Wesleyan Grove was the site of the Methodist congregation’s annual summer-camp meetings. The campers’ small tents became family tents; then primitive, wooden, tentlike cottages; and finally, brightly painted cottages ornamented with fanciful trim. Cupolas, domes, spires, turrets, and gingerbread cutouts make for an architectural fantasyland. The whimsical, precious, and offbeat cottages are worlds away from Edgartown’s traditional houses. So are Oak Bluffs’ nightclubs and the baggy-pants-wearing, pierced youth.

Martha’s Vineyard: Up-Island

Aquinnah Cliffs; by Kindra Clineff/MOTT

West Tisbury

West Tisbury is often called the Athens of the Vineyard because of its fine New England Congregational Church, Town Hall, and Grange Hall. Music Street, where descendants of the island’s 19th-century ship captains still live in large houses, was so named because many of these families used whaling profits to purchase pianos. Over the years, West Tisbury summer residents have included Washington Post owner-publisher Katharine Graham, cartoonist Jules Feiffer, and historian David McCullough. Other A-list celebs clamoring for their place in the Vineyard sun (in Hollywood East) have included Ted Danson and Mary Steenburgen, Larry David, film mogul Harvey Weinstein, John Cusack, and Michael J. Fox.


Chilmark is a peaceful place of rolling hills and old stone fences that outline 200-year-old farms. You’ll find dozens of working farms up-island, some still operated by descendants of the island’s original European settlers. Travel down North Road to Menemsha, a small (truly picturesque) village and working harbor that you may recognize as the location of the movie Jaws. The surrounding area is crisscrossed by miles and miles of unmarked, interconnected dirt roads, great for exploring. (Alas, many are private. Such are the increasing ways on Martha’s Vineyard.)

Chilmark is sparsely populated, to the tune of 850 or so year-rounders, and they aim to keep it that way. In order to limit growth they issue the island’s only three-acre-minimum building permits. Chilmark (among the 50 wealthiest towns in America) has hosted such disparate personalities as photographer Alfred Eisenstaedt and John Belushi.


Aquinnah, which occupies the western tip of Martha’s Vineyard, is home to the Wampanoag Indians,  who own the brilliantly colored bluffs and the face of the Clay Cliffs of Aquinnah. Of the 1,100 members listed on the Wampanoag Indian tribal rolls, approximately 300 still reside on the Vineyard, half in Aquinnah. Tribal legend holds that the giant Moshup created the Vineyard, taught the Wampanoag how to fish and catch whales, and remains a protector.

Explore a Martha’s Vineyard Itinerary

Never been to the Vineyard? Get started with this Martha’s Vineyard itinerary for first timers.

Adapted from the perennially favorite guide to the region, Cape Cod, Martha’s Vineyard & Nantucket, An Explorer’s Guide, and available from Amazon.


Thanks to an efficient network of public transportation, it’s easy to get around up-island and down-island, terms leftover from the days when the island was populated by seafarers — i.e. as you travel west, you move up the scale of longitude.

Getting There

By boat

From Woods Hole

The Steamship Authority (508-477-8600 for advance auto reservations; 508-548-3788 for day-of-sailing info from Woods Hole; don’t count on getting lucky with latter).

The Steamship is the only company that provides daily, year-round transport—for people and autos—to Vineyard Haven and Oak Bluffs. The Vineyard is 7 miles from Woods Hole, and the trip takes 45 minutes. About 9 boats ply the waters daily.

The Steamship annually carries upwards of 2 million people to the Vineyard. Make car reservations as soon as possible. Auto reservations are mandatory/essential year round. Otherwise, the Steamship has a standby policy that’s first come, first served.

Roundtrip car prices: More than $150 in-season and about $100 off-season. If you are not taking your car, the Steamship Authority provides free, frequent buses between the parking lots and the ferry dock. Each bus has a bike rack that holds two bikes.

From Falmouth

Island Queen (508-548-4800), 75 Falmouth Heights Road. This passengers-only service (smaller and more comfortable than the Steamship Authority’s boat) operates late May to mid-October. The trip takes about 35 minutes; departures are from Falmouth Inner Harbor to Oak Bluffs. There is plenty of parking near the Island Queen’s dock.

Falmouth–Edgartown Ferry (508-548-9400), 278 Scranton Avenue. From late May to mid-October, this service plies the waters three to five times daily between Falmouth and Edgartown (Memorial Wharf).

From Hyannis

Hy-Line Cruises (508-778-2600), 220 Ocean Street Dock. Two to five passenger boats to and from Oak Bluffs from May to late October. If you haven’t purchased advance tickets, it’s wise to arrive an hour early in July and August. The trip takes 55 minutes.

From New Bedford

Seastreak Ferry (866-683-3779) operates passenger boats from 49 State Pier to Vineyard Haven from late May to mid-October. The ferry takes 1 hour. For visitors coming from the south, New Bedford is a more convenient departure point than Woods Hole. Even those driving from points north may wish to consider taking the New Bedford ferry to avoid Cape Cod Canal bridge traffic. From I-195, take Exit 15 (Route 18 South) to the second set of lights, turn left, and follow signs to ferry parking.

From Nantucket

Hy-Line Cruises (508-778-2600 Hyannis; 508-693-0112 Oak Bluffs; 508-228-3949 Nantucket) offers interisland service between Oak Bluffs and Nantucket from mid-June to mid-September. The trip takes 1¼ hours; there is only one trip daily.

From New York City

Seastreak Ferry (866-683-3779) offers this 5-hour trip during summer months.

By bus

Bonanza/Peter Pan (888-751-8800) provides daily year-round service to Woods Hole from Boston, New York, Hartford, and Providence. Buses are scheduled to meet ferries, but ferries won’t wait for a late bus.

By air

Cape Air (866-227-3247 flies to the Vineyard from Boston, Providence, Nantucket, New Bedford, Hyannis, and White Plains.

Getting Around

By car

The infamous Five Corners is the trickiest and most dangerous intersection on the island. It’s also the first thing you’ll encounter as you disembark from the Vineyard Haven ferry terminal. If you’re going to Oak Bluffs, Katama, Edgartown, and Chappaquiddick, take the left lane. For West Tisbury, North Tisbury, Lambert’s Cove, Menemsha, Chilmark, and Aquinnah, enter the right lane and turn right.

When making plans, consider these sample distances: Vineyard Haven to Oak Bluffs, 3 miles; Vineyard Haven to Edgartown, 8 miles; Oak Bluffs to Edgartown, 6 miles; Vineyard Haven to Aquinnah, 18 miles.

Unfortunately, summertime traffic jams are commonplace in down-island towns. Try to park outside of town and take shuttles into town (see below). Why would you want to stop and crawl in a picturesque village on a vacation day?

In-season, expect to pay more than $100 daily for the least-expensive rental car and upwards of $200 daily for four-wheel-drives and minivans. A word of note: rates change according to weekday, weekend, and holiday rentals. Before heading out, invest a few bucks in the very detailed gold-and-orange Martha’s Vineyard Road Map produced by Edward Thomas (508-693-2059; Box 1354, Vineyard Haven, 02568.). It’s an excellent, accurate resource and even lists mileage between intersections. It’s available at most bookstores, grocery stores, and liquor stores.

Car rental companies include Budget (508-693-1911), Adventure Rentals (508-693-1959); Island Hoppers (508-696-9147). Gas is usually cheapest at the airport, but Mobil (North Line Rd, Edgartown) and Up-Island Automotive (1074 State Road, West Tisbury) have decent prices too.

By moped

If most Vineyarders and emergency-room doctors had their way, mopeds would be banned. Sand, mopeds, winding roads, and speed do not mix. Take a look at the mopeds you might be renting; many of their plastic hulls have been cracked from accidents.

Having said that: Many rental agencies are located near the ferry terminals in Oak Bluffs and Vineyard Haven. Adventure Rentals and Ride-on Mopeds (508-693-2076) have mopeds (often $100/day). Extra training, yellow diamond road signs (at notorious intersections), and maps (with danger spots and distances between points) should help reduce casualties.

By shuttle

Martha’s Vineyard Transit Authority (VTA) (508-693-9440) operates an excellent system of buses. Twelve buses travel among Vineyard Haven, Oak Bluffs, Edgartown, West Tisbury, Chilmark, Menemsha, and Aquinnah year-round. Buses seem to stop everywhere you want to go; you can also flag them down. They even have bike racks. Get a copy of the very helpful VTA map with stops and routes clearly listed. Carry it with you wherever you go.

Exact change is strongly suggested since change is given only in the form of credit vouchers for future trips. All routes run year-round except Edgartown Park & Ride and South Beach; the latter operate May to mid-October.

By bus tour

Gay Head Sightseeing and M.V. Sightseeing (508-693-4681) offer tours from mid-April to late October. The clearly marked buses meet incoming ferries. The Gay Head tour covers all six towns, but makes only one stop—at the Clay Cliffs of Aquinnah—where there are small food stands, souvenir shops, public restrooms, and a wonderful view of the cliffs and the ocean. The only potential drawback: You may tire of hearing the constant running commentary about which celebrities live down which dirt roads. They also offer charter tours for large groups.

By taxi tour

Most taxis conduct island sightseeing trips for a price, but you don’t want to go with just anyone. I highly recommend Jon’s Taxi (508-627-4677) for one to six people.

Adam Cab (508-627-4462) is also very good and gives a general 2½-hour tour twice daily from Edgartown from late May to early September.

By bicycle

Bicycling is a great way to get around, but it requires stamina if you’re heading up-island.



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