Vineyard Haven, where the big car ferries pull in, has the salty flavor of a New England fishing town (like Gloucester, say, or New London). It can get crowded when a ferry has just arrived, but it also has some very good seafood restaurants and lots of stores (this is where island residents, particularly up-islanders, come to do their everyday shopping). 
In downtown Vineyard Haven, Owen Park Beach is a tiny strip of harborside sand just off Main Street. Adjoining a town green with swings and a bandstand, it will suffice for young children. There’s a lifeguard but no restrooms here, although it’s a quick walk from most Vineyard Haven inns. A more popular spot is Lake Tashmoo Town Beach, off Herring Creek Road. It’s also a tiny strip of sand, but it’s the only spot on the island where lake meets ocean, giving beachgoers a choice between the Vineyard Sound beach with mild surf or a placid lake beach. Parking is limited and the water is often brackish. It’s an easy bike ride from downtown Vineyard Haven.
Off Franklin Street you’ll find the West Chop Woods, an 85-acre preserve with marked walking trails.
Exploring Oak Bluffs
A popular resort town since the 19th century, Oak Bluffs is a place of Victorian gingerbread houses, a vast seaside town green, and a touch of beach-town honkytonk around the vintage Flying Horses carousel. 
Stretching along Seaview Avenue from both sides of the ferry wharf, Oak Bluffs Town Beach is a convenient place to linger while you wait for the next boat, and within easy walking distance for visitors staying in Oak Bluffs. The surf is consistently calm and the sand smooth, so it’s also ideal for families with small children. Public restrooms are available at the ferry dock, but there are no lifeguards. 
From the harborfront, turn south on Central Avenue to enter the Martha’s Vineyard Camp Meeting grounds, a neighborhood of tiny Victorian cottages grouped around a central green. First started as a Methodist Revival colony in the 1800s, this area hosted multi-week religious meetings in the summers. Back then, instead of cottages, there were tents where families would stay during the course of the meetings; some families began to decorate their tents and expand them and eventually the tents became homes. There would be three prayer services daily in the nearby 1878 Trinity Methodist Church; or the 1879 open-sided Trinity Park Tabernacle, which today is used for Sunday morning services, but also concerts and sing-alongs. The tabernacle is the largest wrought-iron structure in the country. 
Mile-long Joseph A. Sylvia State Beach, one of the Vineyard’s most popular, sits midway between Oak Bluffs and Edgartown, along the Beach Road causeway. Flanked by a paved bike path, this placid beach has views of Cape Cod and Nantucket Sound and is prized for its gentle and (relatively) warm waves. The wooden drawbridge is a local landmark—visitors and islanders alike have been jumping off it for years. The shuttle bus stops here, and roadside parking is also available—but it fills up fast, so stake your claim early. There are no restrooms, and only the Edgartown end of the beach, known as Bend-in-the-Road Beach, has lifeguards.
Exploring Edgartown
There’s more of a Colonial air to Edgartown, with its stately sea captains’ mansions, white-steepled churches, brick sidewalks, mature shade trees, and a Main Street lined with striped awnings. Divided from Edgartown by a narrow inlet, Chappaquiddick Island is a world unto itself.
A stroll around Edgartown reveals how the 19th-century whaling trade enriched this part of the world. Begin at 99 Main St. with the Dr. Daniel Fisher House, built in 1840 in Greek Revival style. Fisher, a successful whaling merchant, founded the Martha’s Vineyard National Bank. Behind the Fisher House, off Main Street between Planting Field Way and Church Street, you’ll find the oldest surviving dwelling on the island, Vincent House, a modest gray shingled Cape-style house built in 1672. Next to the Fisher House, at Main Street and Church Street, the Greek Revival Old Whaling Church (1843) was designed by local architect Frederick Baylies, Jr. It’s still a Methodist church, though its major role these days is as a performance venue. 
Continue down Main Street 2 blocks and turn left on North Water Street to admire the many grand sea captain’s homes. At 56 North Water Street, what is now the Edgartown Inn was originally built in 1798 as the home of whaling captain Thomas Worth. Converted into an inn a few years later, it is considered the longest-operating lodging on the island; in the 1830s a young Nathaniel Hawthorne lived here on and off for nearly a year while writing the short stories that would be later collected as Twice-Told Tales. At 59 North Water St., the Daggett House was built in 1750 as a conversion of a 1660 tavern. 
Edgartown is blessed with beaches—northwest of town is popular State Beach, and the 3-mile-long sweep of South Beach (Katama Beach) lies about 4 miles south of Edgartown, on Katama Road. If you have time for only one beach day while on Martha’s Vineyard, go with this popular barrier strand. It boasts heavy wave action (check with lifeguards for swimming conditions), sweeping dunes, and, most important, relatively ample parking space. It’s also accessible by bike path or shuttle. Lifeguards patrol some sections of the beach, and there are sparsely scattered toilet facilities. The rough surf here is popular with surfers. Tip: Families tend to head to the left, college kids to the right.
Felix Neck Wildlife Sanctuary, along the Edgartown–Vineyard Haven Road (tel. 508/627-4850), is an easy 2-mile bike ride from Edgartown. A Massachusetts Audubon Property, it has a complete visitor center staffed by naturalists who lead bird-watching walks, among other activities. You’ll see osprey nests on your right on the way to the center. Pick up a trail map at the center before heading out. Several of the trails pass Sengekontacket Pond, and the orange trail leads to Waterfowl Pond, which has an observation deck with bird-sighting information. 

The Beachy Charm of Chappaquiddick Island - Accessible by ferry from Edgartown (see below), quiet Chappaquiddick is home to two sizable preserves run by the Trustees of Reservations. The Cape Poge Wildlife Refuge and Wasque Reservation, covering much of the island’s eastern barrier beach, have 709 acres that draw flocks of nesting or resting shorebirds, including egrets, herons, terns, and piping plovers. Also on the island, 3 miles east on Dyke Road, is another Trustees of Reservations property, the distinctly poetic and alluring Mytoi, a 14-acre Japanese garden that is an oasis of textures and flora and fauna.
Within Wasque (pronounced Way-squee) Reservation are two fine beaches. Half-mile-long Wasque Beach, is the easier to get to and has all the amenities—lifeguards, parking, restrooms—without the crowds. If you are not a Trustees member you must pay at the gatehouse; it’s $5 to park your car here and go to the beach. East Beach, is one of the Vineyard’s best-kept secrets, and rarely crowded, since few people make the effort to hike or bike this far. Most people park their car near the Dyke Bridge and walk the couple hundred yards out to the beach. Admission is $5 per person. Because of its exposure on the east shore of the island, the surf here is rough. Pack a picnic and make this an afternoon adventure. Sorry, no facilities.
Biking on Chappaquiddick is one of the great Vineyard experiences, but the roads can be sandy and are best suited for a mountain bike. You may have to dismount during the 5-mile ride to Wasque. 
The On-Time ferry (tel. 508/627-9427) runs the 5-minute trip from Memorial Wharf, on Dock Street in Edgartown, to Chappaquiddick Island (a distance of about 500 ft.) from June to mid-October daily, every 5 minutes from 6:45am to midnight. Passengers, bikes, mopeds, dogs, and cars (three at a time) are all welcome. A round-trip is $4 per person, $12 for one car/one driver, $6 for one bike/one person.

Exploring Up Island
The western half of Martha’s Vineyard feels completely different from the eastern half—hilly, rural, and rugged. The town centers of West Tisbury and Chilmark are little more than a cluster of modest buildings; the fishing hamlet of Menemsha, a 5-minute drive northwest of Chilmark, has an end-of-the-road quality. North of West Tisbury, State Road splits into three equally lovely country roads, somewhat prosaically named North Road, Middle Road, and South Road; with very little car traffic, they are wonderful for cycling. The three roads reconvene at the Chilmark crossing, beyond which State Road winds past Menemsha and Squibnocket Ponds to wind up at the spectacular Aquinnah cliffs (formerly known as Gay Head, before adopting the name of the native peoples). It’s a lot of scenery packed into just a few square miles. 
Most of the up-island shoreline is privately owned or restricted to residents and thus off limits to transient visitors. Renters in up-island communities, however, can obtain a beach sticker (around $35–$50 for a season sticker) for those private beaches by applying with a lease at the relevant town hall: West Tisbury, tel. 508/696-0147; Chilmark, tel. 508/645-2100; or Aquinnah, tel. 508/645-2300. Also, many up-island inns offer the perk of temporary passes to residents-only beaches such as Lucy Vincent Beach. 
Menemsha Beach, next to Dutchers Dock in Menemsha Harbor, is a small but well-trafficked strand, with lifeguards and restrooms. Popular with families, in season it’s virtually wall-to-wall colorful umbrellas and beach toys. The nearby food vendors in Menemsha are a plus (get a lobster dinner to go at the famous Home Port restaurant) and it’s an ideal place to watch a sunset.
Down by Aquinnah, you have two beach options. The 2-mile beauty Lobsterville Beach, at the end of Lobsterville Road on Menemsha Pond, has calm, shallow waters that are ideal for children. It’s also a prime spot for birding—just past the dunes are nesting areas for terns and gulls. Parking, however, is for residents only—it’s a great beach for bikers to hit on their way back from Aquinnah. Just east of the colorful cliffs, Aquinnah Beach (Moshup Beach), off Moshup Trail, is a peaceful half-mile beach. Parking costs $15 a day (note that the lot is small and a bit of a hike from the beach); in season, shuttle buses from down-island stop at the parking lot at the Aquinnah cliffs, from which you can walk to the beach. Although it is against the law, nudists tend to gravitate here. Remember that climbing the cliffs or stealing clay for a souvenir here is against the law, for environmental reasons: The cliffs are suffering from rapid erosion. Restrooms are near the parking lot.
In this woodsy area, it’s not surprising that there are some wonderful nature preserves. The 300-acre Cedar Tree Neck Sanctuary (tel. 508/693-5207) on State Road in Tisbury, has several trails leading through ponds, fields, woods, and bog to a picturesque bluff overlooking Vineyard Sound and the Elizabeth Islands. To get there, take State Road to Indian Hill Road to Obed Daggett Road and follow signs. The 633-acre Long Point Wildlife Refuge, off Waldron’s Bottom Road in West Tisbury (tel. 508/693-7392), offers heath and dunes, freshwater ponds, a popular family-oriented beach, and interpretive nature walks for children. In season there’s a $10 parking fee, plus $5 per person ages 16 and older. The Menemsha Hills Reservation, off North Road in Chilmark (tel. 508/693-7662), encompasses 210 acres of rocks and bluffs, with steep paths, lovely views, and even a public beach. 

West Tisbury Farmers’ Market - This seasonal outdoor market (tel. 508/693-9561), open Wednesdays and Saturdays 9am to noon, is among the biggest and best in New England, and certainly the most rarefied, with local celebrities loading up on prize produce and snacking on pesto bread and other international goodies. The fun starts in June and runs for 18 Saturdays and 10 Wednesdays. It’s located at the Old Agricultural Hall, West Tisbury, just up the road from Alley’s General Store.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.