- Insider guide to Martha’s Vineyard, with local perspective on Up-Island and Down-Island, scenic outdoor spots, and the island’s understated luxury.
- Roundup of Martha’s Vineyard restaurants and the best places to eat Martha’s Vineyard favorites for breakfast, beach picnics, lobster rolls, and dinner.
- Travel inspiration featuring Tradewind Aviation and convenient flights to Martha’s Vineyard from the New York and Boston areas for an easy island escape.
Martha’s Vineyard has long held a singular place in the American imagination: elegant but unfussy, exclusive but never ostentatious. For decades, it has drawn those who prize privacy, beauty, and a certain understated ease, captivated by its pristine beaches, rolling hills, picturesque small towns, and the quiet coastal rhythm of life lived largely outdoors.
Reaching the Vineyard has become even more seamless with Tradewind Aviation’s new scheduled service from the Boston area, departing from Hanscom Field (BED) in Bedford. The route offers a direct link from Boston and its suburbs to the island, eliminating the usual friction of travel. For travelers coming from the New York area, Tradewind also operates scheduled service from Westchester County Airport (HPN) to Martha’s Vineyard, making the journey feel less like commercialized transit and more like celebrating the start of the trip itself.
On both routes, scheduled flights depart from private FBO terminals, allowing guests to arrive just 30 minutes before departure and bypass crowds, security lines, and ferry logistics in favor of a smooth, direct flight aboard Tradewind’s modern Pilatus PC-12 aircraft. For travelers considering flying to Martha’s Vineyard, Tradewind is an especially appealing way to begin an island stay.
For those who want to experience the Vineyard beyond the standard summer playbook, it helps to begin with the island’s geography of six distinct towns, each with its own character.
Broadly speaking, those towns fall into two worlds. Down-Island, on the eastern end, is home to the livelier towns of Edgartown, Oak Bluffs, and Vineyard Haven. This is where much of the island’s visible bustle unfolds in season. Up-Island, by contrast, feels quieter, greener, and more removed from the summer crowds and commercial activity. The western communities of Aquinnah, Chilmark, and West Tisbury move at a gentler pace, and it is here that the island reveals its more private side. Even the name carries a maritime sensibility, drawn from the old nautical expression for sailing westward, or “up” in longitude.
To know the Vineyard like a local is to spend time Up-Island, where the landscape opens and the crowds thin. But the island’s insider pleasures are not limited to its western end. Down-Island, too, has its own quieter pockets and lesser-known charms.
Up-Island in Aquinnah, Squibnocket Pond Reservation (opened last year on land that once belonged to Jacqueline Kennedy Onassis) offers a less-traveled kind of beauty, with trails winding through an ecologically rare habitat of woodland and coastal plain. Nearby, Philbin Beach remains one of the island’s more peaceful stretches of sand, its relative seclusion preserved by limited parking access. Those willing to arrive on foot are rewarded with dramatic Atlantic views and the sight of surfers riding the breaks offshore. Walk along the beach to the Aquinnah Cliffs, a stretch of towering, multi-colored clay bluffs topped by the historic lighthouse, Gay Head Light.
Inland, in West Tisbury, Manuel F. Correllus State Forest offers miles of hiking and biking trails through fragrant scrub oak and pitch pine, with wild blueberries and blackberries appearing in season. Shop for local produce and food items at the West Tisbury Farmers Market, the island’s oldest and largest open air market, which runs from June through October. Nearby is Field Gallery and Sculpture Garden with rotating exhibits of local and regional painters, sculptors and photographers.
Down-Island in Oak Bluffs, Eastville Beach near the drawbridge offers a less busy shoreline with views of the outer harbor and a calm inner lagoon. Stroll through the Oak Bluffs Campground to see an enchanting historic enclave of brightly painted nineteenth-century gingerbread cottages. The area dates from 1835 when Methodist summer retreats were organized in tents, later evolving into the whimsical wooden cottages seen today.
From Edgartown, take the “On Time” ferry across the channel to Chappaquiddick and visit Mytoi, the fourteen-acre Japanese-style garden. There’s also a nine-hole golf course, The Royal and Ancient Chappaquiddick Links, a quirky, laid-back island institution beloved for its offbeat charm. Back in Edgartown, the Felix Neck Wildlife Sanctuary offers walking trails, salt marsh views and guided kayak tours on Sengekontacket Pond.
And then there is the food, which is one of the island’s great pleasures.
Martha’s Vineyard is an exceptional dining destination thanks to its working farms which shape the island’s farm-to-table culture, and fishermen who bring in lobster, sea scallops, black sea bass, and other delectable treasures from surrounding waters. As a result, Martha’s Vineyard restaurants, whether a little fish market or gourmet restaurant, feature the freshest seafood and just-picked produce from the island.
For repeat visitors, the real pleasure lies in knowing where locals actually go, because to know the Vineyard is to know the best places to eat. These are among some of the best places to eat in Martha’s Vineyard for diners who want to experience something more insider than the obvious choices.
Start the morning at Dock Street Coffee Shop in Edgartown, a vintage diner that has been an island staple since 1975. With old photographs lining the walls, a screen door at the entrance, and red-cushioned stools at the counter, it offers an easy familiarity. Order a bacon, egg, and cheese, settle in, and take in the local chatter. Another dependable favorite in town is Among the Flowers, where patio dining offers a leisurely start to the day, especially over homemade corned beef hash, avocado toast, or fruit-topped Belgium waffles.
If planning a beach day, pick up lunch to-go. Katama General Store, just south of Edgartown, is a classic stop for provisions before heading to the shore, while Morning Glory Farm offers prepared foods and market-fresh ingredients for the perfect beach picnic.
Heading Up-Island, 7a Foods in West Tisbury is the place for great sandwiches. Chilmark General Store features salads, island-grown produce, freshly baked baguettes, cheese, charcuterie, and other picnic essentials.
Lobster rolls, of course, are part of the Vineyard’s culinary language, and every regular has their preferred version. But to indulge in a local tradition, go to Grace Church in Vineyard Haven. On Friday summer evenings from 4 to 7 p.m., the church sells lobster rolls as a fundraiser, and the result is one of the island’s simplest and most beloved rituals.
For dinner, State Road restaurant in West Tisbury is a contemporary tavern serving farm-to-table American cuisine. Surrounded by herb, vegetable, and fruit gardens, they also draw from regional farmers, fishermen, and food artisans. In Vineyard Haven, Beach Road restaurant offers another perspective on island dining, overlooking Lagoon Pond. Their crispy fried chicken is an island favorite, as are the beautifully roasted seasonal vegetables.
Photo courtesy of The Outermost
For something more remote and dramatic, head Up-Island to Aquinnah. Perched on the western edge near Gay Head Light and the Aquinnah Cliffs, The Outermost feels blissfully far from everything. Start with a glass of wine to watch the sunset over the Atlantic from the Adirondack chairs, then linger over a raw bar and prix fixe dinner.
With Tradewind making the Island so easy to reach, there has never been a better moment to book your next flight and experience it like a local.
To learn more about Tradewind’s scheduled flights to Martha’s Vineyard, please visit our website. For questions regarding scheduled flights, contact our scheduled service team at scheduledservice@flytradewind.com or 1-800-376-7922 option 1. To receive a private charter quote, please submit an inquiry here or contact our specialists at sales@flytradewind.com or 1-800-376-7922 option 3.
Featured Image Courtesy of The Edgarton Collection