48 Hours in Oak Bluffs

Make the Most of Your 48 Hours in Oak Bluffs

As one of Martha’s Vineyard’s most vibrant ports of arrival, Oak Bluffs buzzes with energy and traditional charm. Step into a fascinating blend of history and lively entertainment, where every day brings a new adventure, from guided history tours to sunny beach days. We consider it a privilege to sit at the center of this nostalgic town, close to a delightful mix of shopping, dining, and even a timeless carousel. Here’s how to spend 48 hours in Oak Bluffs.

Foodies

Oak Bluffs is a melting pot of cuisines, but true to our New England heritage, seafood takes center stage. Whether you’re craving fried clams from Coop de Ville, a lobster roll from Martha’s Vineyard Chowder Company, or raw oysters from The Oyster Bar, Oak Bluffs delivers the best bites from the sea. Meat-eaters can’t miss the steaks at Red Cat Kitchen and juicy, wood-smoked meats at Sea Smoke. If you’re searching for something on the lighter side, MV Salads, Nancy’s, and the Pawnee House are our go-tos. We also have Jamaican eats at Vineyard Caribbean, Thai and Southeast Asian flavors at Bangkok Thai, and south-of-the-border dishes at Sharky’s, Dilly’s, and Dos Mas. Wherever you decide to dine in Oak Bluffs, know that you’re in for a treat from the hard-working restaurant owners who call the island home.

Beach Aficionados

On Martha’s Vineyard, the beaches are the belle of the ball, and you’ll find some of the island’s best sandy stretches in Oak Bluffs. We love Inkwell Beach, with strong links to the island’s African-American heritage. It’s the beach to see and be seen, relax with friends and family, and enjoy the perfect beach day. Joseph Sylvia State Beach, a 2-mile swath of sand and shallow water, served as the main shooting location in the popular film Jaws. At Bend in the Road Beach, find family-friendly calm waters with easy parking (or a short bike ride from the hotel). Eastville Beach, with views of the Steamship ferries coming and going and Vineyard Haven Harbor, is also family- and stroller-friendly with on-site parking.

History Buffs

Oak Bluffs is steeped in rich history, and you could spend an entire vacation learning, discovering, and exploring our story. The African-American Heritage Trail recognizes the contributions made by people of African descent to the history of the island. Mariposa Museum explores American history and experiences through a diverse lens and the creativity of artists, scholars, and other creatives. The Martha’s Vineyard Camp Meeting Association, with its historic gingerbread cottages, is well-known and well-loved for its unique charm–a local gem ideal for early-morning walks with your coffee. Nearby, The Flying Horses–the nation’s oldest platform carousel–has been delighting visitors since 1884. Each horse is brightly painted and fixed to the rotating platform by a metal post. Try your luck at grabbing the brass ring–fun for all ages!

Make the Most of Your 48 Hours in Oak Bluffs

Foodies

Beach Aficionados

History Buffs

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