This is a beach town that happens to have serious history. Behind the harbor bustle, more than 300 tiny Victorian cottages cluster around an iron tabernacle, their Gothic trim painted in colors that shouldn't work together but somehow do. The neighborhood has been a National Historic Landmark since 2005, but most visitors come for simpler pleasures—warm sand, cold beer, and the particular freedom of an island where the car stays on the mainland.

The Flying Horses Carousel has been spinning on Circuit Avenue since 1876, making it the oldest platform carousel in America, and the horses have real horsehair manes. Grab a mount on the outer ring and try for the brass ring; catch it and you win a free ride, just as generations of children have before you. From there, Circuit Avenue stretches uphill with shops, ice cream parlors, and the buzz of a beach town on a good day.

The Martha's Vineyard Camp Meeting Association cottages reward a quiet wander. These 318 tiny Victorians, built for Methodist summer revivals in the 1860s and 1870s, cluster in neat rows around the 1879 wrought-iron Tabernacle. The elaborate wooden trim that earned them the nickname "gingerbread houses" comes in every color imaginable. On Grand Illumination Night, held the third Wednesday of August since 1869, residents hang paper lanterns on their porches and light them simultaneously after a community sing at the Tabernacle. The whole neighborhood glows pink and yellow and green, and the island feels like it belongs to another century.

For meals, the options stay casual and close. Back Door Donuts serves warm apple fritters late into the night; follow the smell to find the line. Offshore Ale pours local beer. Nancy's offers fried seafood with harbor views. Camp Canteen at Summercamp stocks provisions for beach days. State Beach stretches toward Edgartown along a flat bike path, and the clay cliffs at Aquinnah make a worthy day trip where you pack lunch and stay for sunset.