The Classic Town On Martha's Vineyard With A Posh But Leisurely Blend Of Shops, Beaches, And Nightlife

Cast seven miles off the coast of Cape Cod, Martha's Vineyard is one of America's most beloved islands, renowned for its historic harbors, rolling farmlands, and sweeping beaches. The island's oldest town is Edgartown, which was settled in the mid-17th century and became the main hub of the country's whaling industry. After the end of the whaling trade by the early 20th century, the town transformed into a popular summer colony. Perfectly capturing the charm of an English village, Edgartown still appears like a time capsule, with elegant Greek Revival mansions side by side with shingled cottages. The idyllic harbor bobs with boats, ranging from sleek sailboats to grand yachts. Cozy inns and chic boutiques line the cobblestone streets, as well as refined seafood restaurants and convivial bars. Just a short walk from town is the historic Edgartown Lighthouse and Lighthouse Beach, a golden slip of sand lapped by the calm waters of Katama Bay.

You can easily visit Martha's Vineyard via both ferries or air travel. There is a ferry service during the summer months between Falmouth on Cape Cod and Edgartown. Direct flights from major East Coast cities, including New York, Boston, Philadelphia, and Washington, D.C., land at Martha's Vineyard Airport, which is just five miles from Edgartown. The high season for Martha's Vineyard is the summer when hundreds of thousands of visitors come to the island for long beach days, sailing adventures, and shopping and dining. However, spring and fall are also quieter and more affordable times to enjoy the island's charms.

Martha's Vineyard's small size makes it perfect for an easy three-day vacation weekend every traveler needs to take, and there's plenty to keep both adventurous travelers and leisure lovers happy. For a lay of the land, roam around Edgartown's charming streets to discover its stylish boutiques and art galleries. Stop in at Salte for chic home decor and fashion accessories or Nell for breezy beachwear and whimsical jewelry. Don't miss the Black Dog General Store for clothing emblazoned with the iconic Black Dog logo. Art lovers will want to browse The Christina Gallery, a curated collection of island-inspired paintings, maps, and shell art, or the North Water Gallery for both traditional and contemporary fine art, including works by late local artist Ray Ellis.

Discover the island's stunning natural landscape, which is also on view close to town. Walk to the picturesque Lighthouse Beach, which is presided over by the 19th-century Edgartown Lighthouse, and boasts a small sandy beach lapped by the calm waters of Katama Bay. The most popular beach on the island is the beautiful South Beach, a three-mile sandy stretch on the Atlantic Ocean where travelers can swim, surf, and boogie board in the waves, as well as embark on beach walks or fish in the surf. For a different perspective on Edgartown, board a sailing cruise, such as a ride on the Mad Max catamaran, for a trip around the harbor. From Edgartown, you can also take the short five-minute ferry over to Chappaquiddick, the quiet, trail-laced island that is perfect for hiking and biking, as well as visiting remote beaches and the Mytoi Japanese gardens.

To immerse yourself in the charms of Edgartown, check in to one of the town's quaint inns or family-friendly resorts. Couples will adore the romantic Charlotte Inn, which was built in 1864 in the Greek Revival style. The luxurious interiors, complete with fine antiques and sumptuous furniture, recall a bygone age, and the gardens transport guests to an elegant English garden. Families with young children will be happy at the Winnetu Oceanside Resort, one of the 10 best beach resorts in the U.S. for family vacations. The grand oceanfront property boasts spacious suites and cottages for families and larger groups, as well as swimming pools and tennis courts, and hosts weekly clambakes.

Edgartown offers the island's top dining scene, from iconic harbor-front institutions to relaxed seafood shacks. Don't miss a meal at the popular Atlantic Fish & Chop House in a large shingled building overlooking the Edgartown harbor docks. The menu features delicious seafood specialities like lobster vol au vent with caviar and dover sole, as well as prime steaks. After dinner, stop for a nightcap at the restaurant's Island Social Club, which opens at 10 p.m. Another excellent restaurant in town is Alchemy, a sophisticated Main Street dining room with innovative Mediterranean-inspired cuisine featuring local ingredients. For fresh seafood in a more casual setting, try the classic Seafood Shanty, which also turns into a party later at night with DJs and live music.