Winthrop Cottage

Oak Bluffs, located on the northeastern shore of Martha's Vineyard, is a charming seaside town that offers a delightful mix of history, culture, and beachside relaxation. Known for its picturesque gingerbread cottages, Oak Bluffs is a visual feast with its vibrant Victorian architecture that harks back to the town's origins as a Methodist camp meeting site in the 19th century. The whimsically painted cottages, with their intricate trim and fairy-tale-like charm, encircle the historic Tabernacle, which remains a central gathering place for community events and concerts. The town's harbor area is a bustling hub of activity, where visitors can watch boats come and go, dine at waterfront restaurants, or simply enjoy a leisurely stroll along the docks. The Flying Horses Carousel, the oldest operating platform carousel in the United States, is a beloved Oak Bluffs landmark that delights both children and adults with its hand-carved horses and classic charm. Oak Bluffs is also a gateway to the island's natural beauty. With several beaches easily accessible from the town, including the popular Inkwell Beach, visitors can bask in the sun, swim in the clear waters, or partake in water sports. For those who prefer land-based activities, the town offers an array of boutique shops, art galleries, and eateries that showcase the local flavor and artisanal talent of Martha's Vineyard. The town's nightlife is lively and welcoming, with a variety of bars and clubs that feature live music and entertainment. During the summer months, Oak Bluffs comes alive with festivals and events that celebrate the town's rich cultural heritage and community spirit. For a touch of nature, the nearby Manuel F. Correllus State Forest provides miles of trails for hiking and biking, allowing visitors to immerse themselves in the serene woodland environment. The state forest is also a prime spot for birdwatching and observing the island's diverse wildlife. Oak Bluffs' combination of historic charm, recreational activities, and natural beauty makes it a quintessential New England coastal town. Whether you're seeking a family-friendly vacation, a romantic getaway, or a solo adventure, Oak Bluffs on Martha's Vineyard offers a memorable experience for every type of traveler.