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Armchair Adventurer: Vacation on Martha’s Vineyard with Chances Are…

In Pulitzer Prize winner Richard Russo’s latest novel, Chances Are . . . three college friends in their sixties, Lincoln, Teddy, and Mickey, gather to spend Labor Day weekend on Martha’s Vineyard. Though they haven’t kept in touch as much as they would have liked, they are forever bonded not just to each other, but to the island itself, where forty-five years earlier on a similar weekend celebrating the start of summer, their best friend, Jacy, disappeared. While the men reckon with growing older and the mystery of what happened to their friend, they explore the island looking for clues and answers to their pasts and futures.

Martha’s Vineyard plays such a huge part in this story that we wanted to explore the island ourselves. We hope you enjoy this guide to the different areas and attractions a summer on the Vineyard has to offer.


Vineyard Haven
Home to the only ferry terminal open all year long, Vineyard Haven is likely the first stop on any visit to Martha’s Vineyard. Once you disembark, you can’t miss the Vineyard Haven Harbor Cultural District. This mile-long Main Street offers museums, shops, and restaurants and is the go-to spot for anything related to the performing arts or shipbuilding. Don’t get confused if you hear locals referring to the area as Tisbury—that’s the name of the town the village of Vineyard Haven is in, and the two are used interchangeably.

Chilmark, where Lincoln’s house is located, is on the southwest side of the island. It is known for its beautiful scenery, general store, and community center, which is famous for The Martha’s Vineyard Film Festival. Be sure to visit nearby Menemsha for some seafood from an authentic fishing village.

Known as Gay Head until 1977, Aquinnah is in the far west of Martha’s Vineyard and is where Teddy and Jacy visit the stunning striped cliffs and lighthouse. The beach is now off limits, even if you’re wearing your swimsuit, but you can still experience breathtaking views, especially if you climb to the top of the lighthouse. Take time to learn more about the Aquinnah Wampanoag at the cultural center or exhibit kiosk, do some souvenir shopping, and grab a bite to eat—perhaps a crab roll?

On the other side of the island is Edgartown, where you’ll find more boutiques, restaurants, and museums. Its lovely harbor and history as a whaling village where many captains had their homes, gives this eastern section its unique architecture. Edgartown is also home to the Vineyard Gazette, the premiere source for any type of news about the island—and where you’d go to dig up information, maybe even on a cold case.

Oak Bluffs
Oak Bluffs is the place to be if you’re looking to get out and have fun on Martha’s Vineyard. Located on the north side of the island, just east of Vineyard Haven, come here for the quirky gingerbread cottages, ride on the historic Flying Horse Carousel, eat, drink, shop, and be sure to check out live music on Circuit Avenue. We imagine you could find a Mick on Pots set at The Ritz Cafe, the most iconic dive bar on the island.