Each “town” on Martha’s Vineyard has its own unique identity, style and history. Edgartown’s elegant colonial houses were built by successful whaling captains. Menemsha (in Chilmark) is an active fishing port where you can eat seafood “fresh off the boat” on the pier. Oak Bluffs has lively “Circuit Avenue”, lined with shops and restaurants as well as its famous Victorian “Campground”. Vineyard Haven (or Holme’s Hole) impresses the visitor with its animated “Main Street” and plentiful shops and services. West Tisbury has a rural feeling and is home to one of the island’s favorite summer events the “Ag” Fair. Chilmark and Aquinnah make the trip “up-island” worthwhile with dazzling views out over the Atlantic and of course a stop to see the famous cliffs and lighthouse at Gay Head.
The “down-island” towns (called “down” because of the prevailing winds which sent sailing ships “downwind” or to the east) of Oak Bluffs and Vineyard Haven are where most visitors arrive on the island, by car ferry from Wood’s Hole or by seasonal passenger ferries from Falmouth, Hyannis, New Bedford, Kingston, R.I. and even New York City.
Oak Bluffs is the town closest to Quailwood – a quick drive, a five-minute bike ride or a 15 minute walk gets you to the foot of Circuit Avenue and its shops, to restaurants, to the ferry docks or to the nation’s oldest operationg carousel “The Flying Horses”, an absolute must-do for “children” of all ages. Catching the last, “brass” ring will earn you another free ride on this living antique. Be sure to look for the different animals embedded in the horses’ glass eyes! Oak Bluffs is well-known for its picturesque “Campground”, originally a site for Methodist religious revivals in the shade of oak trees known as Wesleyen Grove. In the 1860s, revivalists pitched tents on the site and gradually started replacing the tents with more permanent structures – the hundreds of colorful gingerbread cottages we love to photograph today. The “Tabernacle” anchors the original site with its unique cast iron architecture and is home to many events including church services, weekly sing-alongs, dances and concerts. If you are lucky enough to be on the island mid-August, be sure to see “Illumination Night”, when the Campground’s residents decorate their cottages with THOUSANDS of “Japanese” lanterns. Originally the conservative Methodists built a “wall” to keep their campground separate from the bustling honky-tonk resort of “Cottage City” (later to be re-named Oak Bluffs) with its hotels, train (!) and bath houses…Easily accessible bathing beaches stretch along the Nantucket Sound waterfront. You might be able to fly a kite or catch a band concert at Ocean Park or catch a fish from the fishing pier near the ferry dock. Boat watching along the harbor front is also a fun activity… where some very snazzy sports fishing boats as well as the “party boat the “Skipper” unload their day’s catch of porgies, blues, stripers… you might even want to organize a deep-sea fishing trip on one of the specialized charter boats docked here.
Vineyard Haven is a town within the larger township of Tisbury. The harbor has been a “haven” for sailors for hundreds of years and is full of all types of craft all summer long. The Steamship Authority car ferry dock is two blocks from Main Street and shops, grocery stores, seafood vendors, the Black Dog bakery, a plethora of restaurants as well as other services are all conveniently located nearby. The town is know for the arts with galleries and The Martha’s Vineyard Playhouse. The historic Capawok cinema was recently restored and has regular summer showtimes. The Martha’s Vineyard Film Center in Tisbury Market Place hosts an annual film festival. Poetry, painting and plays all find an audience in this eclectic town. Vineyard Haven’s (infamous) five-corners intersection often comes up in conversation and is best avoided at “boat time”! The Martha’s Vineyard Hospital and Eastville Beach are on the road to Oak Bluffs (which is only three-miles away). Also nearby is the Featherstone Arts Center. West Chop, Mink Meadows Golf Club and the West Chop lighthouse (good sunset viewing out this way) are a few miles from town.
Edgartown was originally settled by whaling captains who built stately homes near the harbor on the eastern end of the island. Some of these homes are now inns, restaurants and shops while others are privately owned. Strolling through Edgartown will take you back two hundred years when the rooftop “window’s walks” might have been occupied by wives waiting for their husbands to come home from their many months or years at sea. Today you can watch yachts coming into the harbor from Lighthouse Point or from the rooftop deck on the pier next to the “Chappy” ferry. This miniscule ferry crosses the channel to the island of Chappaquiddick where you can visit the unique Mytoi Gardens, the Wasque Wildlife Sanctuary or take a tour of the remote Cape Poge Lighthouse.
See if you can find the giant Pagoda tree, brought back from China in a pot by Captain Thomas Milton in 1837 and thought to be the largest in North America. There are plenty of good restaurants and shops in Edgartown. Your nose will lead you into Murdick’s Fudge shop, an island staple, to see all sorts of delicious fudge being made.
Beaches are everywhere on the island and South Beach outside of Edgartown at Katama is one of our favorites. It’s a long, often windy stretch of sand between the Atlantic and dunes. This is a wonderful place to take a long walk, try out your boogie board or sack out on the warm sand. Katama has a tiny gem of an airfield with a popular (read: “wait”) diner where you can take a bi-plane sightseeing ride over the island. Nearby is the Farm Institute, a working and family friendly teaching farm.
West Tisbury testifies to the independent spirit of New Englanders. West Tisbury was once part of Tisbury but residents decided to break away from its parent town in 1892. It has a rural feeling and its tiny “downtown” is home to historic Alley’s General Store (motto: Dealers in Almost Everything), a local hangout and obligatory stop on your way up-island. Another must-see is the Field Gallery with its sculpture garden . West Tisbury is home to the Island’s historic Grange Hall, and to the grounds of the Martha’s Vineyard Agricultural Society, home to the popular fair held every August.
Aquinnah, at the westernmost tip of the island, is known for its famous and colorful “Gay Head” cliffs and historic lighthouse, which was moved inland from the cliffs in 2015! The town itself is less than six miles square and has only 400 year-round residents. The commonwealth’s only federally recognized Native American tribe, the Wampanoag, call Aquinnah home. Visit the Wampanoag cultural center which proposes frequent exhibits and activities. According to the Wampanoag, their ancestral giant Moshup created the colorful clay in the cliffs by smashing whales against them. The entire south coast of the island is in fact a terminal moraine, a visible remnant of the last ice age. Other signs of glacial presence are “erratics”, giant isolated boulders found around the island. Public parking ($) is available at Gay Head to visit the cliff village, cultural center, and lighthouse. From the parking lot you can follow a path to Moshup Beach (10 minute walk).
Chilmark is known for its bucolic countryside and long-ranging views. Rolling hills, stone walls, nature preserves and dramatic coastlines might make you think you are somewhere in Scotland. Sandy south coast beaches, Noman’s Land island (a federal bird sanctuary closed to the public) and pastures dotted with grazing sheep are visible from South Road. From the north shore you can see Cuttyhunk and other islands in the Elizabeth Islands chain and on a clear day, the mainland. Chilmark town center has many services including a library and general store. From Lobsterville Beach, cyclists can take a tiny bike ferry across the channel to Menemsha. Get fresh seafood at one of the fish shops or restaurants, have a take-away ice cream or chowder treat, find a treasure in one of the village shops or enjoy a dip in Vineyard Sound at the town beach which is also a popular gathering spot for sunset watchers.
Quailwood Cottage 