Martha’s Vineyard, the camelback-shaped Massachusetts island off the coast of Cape Cod, is often connected with political names (Kennedy, Obama) and with other bold-faced ones (Carly Simon, Spike Lee). My Vineyard is a quieter spot. Although I spend a good part of the year in New Orleans, I have been journeying to the island every summer for more than six decades. My father had the good sense to buy a house in Oak Bluffs, one of the Vineyard’s six small towns, in 1957, and as an only child I didn’t have to kill anyone to inherit it. Being the high season, summer is always social. So in September when the weather starts to turn autumnal, I often breathe a sigh of relief. The M*A*S*H-style signpost outside of the Vineyard Vines store on Narragansett Avenue, with arrows pointing toward Memphis, Georgetown, Nashville, and Palm Beach, always reminds me that though the island is cooling down, many of my friends in the iced-tea zone are still wrapped in summer’s sticky embrace and craving a cool breeze.
The delights of the Vineyard come September are some of the island’s best-kept secrets. The crowds have thinned, the shops are filled with end-of-season sales, the bike paths are manageable again, and tee times can be had. Islanders are relaxed, thankful for having survived summer. Sadly, my home in Oak Bluffs is only one board thick—the inside wall is the outside wall—so when the chillier evenings arrive, I shutter it for the off-season. But this time of year is perfect for exploring the island. Before heading back south on a recent trip, I indulged my Downton Abbey fantasies and booked a room at the Charlotte Inn, where stepping beyond the wrought-iron fence is like time traveling to an Edwardian English country house—with plumbing that actually works.
Located next to Oak Bluffs in Edgartown—a patrician hamlet that recalls Nantucket (a.k.a. that other island!)—the imposing white clapboard inn with green-and-white awnings and dark green shutters brings to mind Baudelaire’s luxe, calme, et volupté (“luxury, calm, and voluptuousness”). At the quiet entrance, just off busy Main Street, a sign informs guests that public use of cell phones is frowned upon. I checked in at the mahogany front desk amid antiques and enough polished silver and brass to keep an army of house elves employed full-time. My room had a chintz-dressed four-poster bed, a sitting area with reading lamps, a selection of books on the decorative arts (I was tickled to note a copy of Charleston Style), and a luxuriant bathroom with an oversize tub.
For old times’ sake, I secured a table in the inn’s conservatory-style restaurant, the Terrace, the same space where I supped weekly with my mother more than twenty years ago. Following a dinner of heirloom tomato salad and a perfectly prepared spaghetti Bolognese, I retired to dream of living in this sumptuous manor house—after all, if the new Duchess of Sussex can live in Kensington Palace, I can dream too.
The next day’s bright sunlight lured me beyond the library-like breakfast room and out into the streets. The three towns on the island’s east end, which locals refer to as “down island”—Edgartown, Vineyard Haven, and Oak Bluffs—can all easily be toured in a weekend. There are purple-and-white island buses, taxis, and the usual Web-based transportation options, but to really soak up the charm, head over to Wheel Happy on South Water Street, around the corner from the inn, to rent a bicycle. During the off-season, the island becomes a bike rider’s or stroller’s paradise, where each corner turned marks the beginning of a leisurely adventure.
Vineyard Haven, the island’s main port of entry, has few true tourist lures. For me, a visit to the town is often an evening endeavor because the island’s Film Society is headquartered there. The International Film Festival runs September 4–9 this year with an array of documentaries and full-length features. Typically, I will try to snag a postfilm reservation at the nearby Beach Road restaurant, where my meal might include an overflowing lobster roll on a butter-toasted bun or a mammoth hot dog served with house-made kimchi and whole-grain mustard. Despite the name, there’s no beach at Beach Road; rather, the casually elegant dining room offers a spectacular view of Lagoon Pond, one of the island’s many inlets.
Oak Bluffs, my summer roost, combines the sacred and the secular. Originally a Methodist camp meeting site, the community has historically been an African American summer spot for almost a century—everyone from Martin Luther King, Jr., to Harlem Renaissance writers summered within its limits. The town’s picturesque homes with their wide porches and rocking chairs that invite friends to “set a spell” have a distinctly Southern air. Stroll through the campgrounds and get lost in the labyrinth of alleyways lined with nineteenth-century gingerbread cottages that delight photographers with their brightly colored facades and postage-stamp gardens. After your walk, take a nostalgic turn on the Flying Horses, the oldest operating platform carousel in the country. Don’t let nearby Linda Jean’s location amid the souvenir shops on Circuit Avenue fool you—the lavender-hued diner is a local favorite, serving a hearty New England breakfast until 11:30 a.m. and reasonably priced Vineyard staples such as fish and chips and fried clams for lunch and dinner.
Just around the corner from Linda Jean’s, restaurateur and chef Ben deForest, who can now boast of owning the largest and smallest bars on the island, helms the minuscule Red Cat Kitchen on Kennebec Avenue. The menu changes daily, but look out for his signature “big-ass” scallops. Across the street, his considerably larger Cardboard Box, which opened in May, expands not only the space and menu but also the fun with a bar that’s quickly become a popular late-night hangout in a town that’s known for its party mode.
Back in Edgartown, with its white picket fences and tumbling hydrangeas, run the retail gauntlet before savoring what I call my “South of France moment”—sipping rosé and watching the yachts from the deck at the Atlantic. Then amble down the lanes and peek into the windows of houses once owned by whaling captains. Make a pit stop at the Martha’s Vineyard Museum to learn about the island’s seafaring past before heading back to the Charlotte Inn for a preprandial glass of champagne. For dinner, I can never resist a farewell taste of island lobster at upscale L’Etoile or Atria.
To say my final goodbyes at the end of each season, I like to take one last meander through the Vineyard’s narrow streets, when the leaves are just beginning to turn. I wrap my shawl around me, knowing that I’ll soon be shedding it when I return home to the New Orleans heat.