Candy pink, turquoise, lilac, mint green: Oak Bluffs' first colours appear even before the tender touches the dock. It is through this gateway that most cruisers reach Martha's Vineyard, the most sought-after island off the Massachusetts coast, a summer refuge for presidents, artists and loyal families for generations. Ships anchor offshore and land their passengers right in the centre, a five-minute walk from the main attractions, on flat ground well suited to strolling.

The Gingerbread Cottages

Behind the main street hides the neighbourhood that made the town famous: the Campground of the Martha's Vineyard Camp Meeting Association. In the 1860s and 1870s, Methodists who came to camp for their summer meetings gradually replaced their tents with tiny Victorian cottages, vying with one another in wooden lacework, ornate porches and bright colours. More than 300 remain, arranged in circles around an iron tabernacle where concerts and services are still held. You can wander freely along the paths, keeping in mind that these dollhouses are lived in every summer — their owners, sitting on the porch, are in fact happy to answer curious visitors' questions.

The Country's Oldest Carousel

At the corner of the street leading to the dock, the Flying Horses Carousel has been turning for generations, considered the oldest carousel in continuous operation in the United States. Its wooden horses with real manes and glass eyes still delight children, who try to catch the brass ring that earns a free ride. The line moves quickly, a ticket costs a few dollars, and many adults give in with a laugh, under the eyes of regulars who know the organ music by heart.

Circuit Avenue and the Waterfront

The main shopping street, Circuit Avenue, lines up island boutiques, galleries and fudge counters in a joyful summer bustle. Heading back down to the water, the harbour is lined with terraces where local oysters are enjoyed facing the sailboats. On the other side, Ocean Park spreads its large lawn ringed by Victorian homes around a bandstand. Close by lies the beach known as the Inkwell, a place of memory for African American vacationing: for more than a century, Oak Bluffs has been one of the great vacation spots of the Black American middle class, and this history is fully part of the town's identity.

Toward Telegraph Point

For an after-lunch walk, the coastal promenade climbing toward East Chop passes grand homes facing the sound and leads to the small white cast-iron lighthouse guarding the point. The walk, about thirty minutes round trip from the harbour, offers open views of the sailboats and, on clear days, of the Cape Cod coast.

And the Rest of the Island?

A full day lets you go further: island buses and guided excursions connect to Edgartown, a village of former whaling captains with white homes, as well as the coloured clay cliffs of Aquinnah, at the western tip, territory of the Wampanoag Nation. Cyclists will find rentals near the dock and a network of well-designed bike paths along the lagoons. Those who stay in Oak Bluffs won't feel they have missed the essentials, however: the town alone captures the spirit of the island.

Time to Head Back

As the tender pulls away from the dock, the cottages shrink until they look like toys set on the lawn. Martha's Vineyard leaves that particular feeling of a preserved world, where the wooden lacework is repainted every spring and the brass ring still awaits the next outstretched hand. Few ports of call make you want so much to come back with more time — and perhaps a bicycle.