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Island flying adventures: New England to Chesapeake Bay

Pilots don't need to travel to the Bahamas or Caribbean for some island time. Check out this list of fun islands to visit from New England to the Chesapeake Bay.

Plum Island Airport, looking northwest. Photo by Alex Hasapis.

Plum Island, Massachusetts: About 27 nautical miles northeast of Boston’s Logan International Airport you’ll find the Plum Island Airport. From here it’s an easy walk to what many say are the best “lobstah” rolls in New England at Bob Lobster, also a fresh seafood market. A barrier island, Plum Island is home to large tidal marshes that provide outstanding waterbird habitat—bring your binoculars! A mile east of the airport is the Plum Island Grille, upscale dining in a casual atmosphere, and the resort town of Plum Island.

Nantucket Island, Massachusetts: A treasured place to get away from it all—Nantucket’s cranberry bogs, cobblestone streets, lighthouses, working windmill, and rose-bedecked cottages will take you back to a simpler time. Much of the island has been left in its natural state, and it’s easy to explore the windswept moors and pristine beaches. Fly to Nantucket Memorial Airport and grab a shuttle, taxi, or rental bike; you won’t need a car! Play on the beaches (which are all public), rent a boat, sail on a gorgeous sloop, or book a whale-watching tour. Visit the whaling museum to see artifacts from the ship that inspired Moby Dick. Inns, B&Bs, and waterfront cottages abound, as do both upscale and casual eateries.

Martha’s Vineyard, Massachusetts: Martha’s Vineyard Airport gets you quick access to this famous summer colony for the affluent and influential. Visit the town of Oak Bluffs, home to rows of gingerbread cottages and some of the island’s best night life. Pick up fresh cod in Menemsha, the fishing village memorialized in a Carly Simon song (the singer has a home on the island). Menemsha is where Steven Spielberg filmed Jaws and also where you’ll find New England’s best sunsets. Walk the windswept beach at Gay Head or take a spin on the Flying Horses Carousel, America’s oldest platform carousel, constructed in 1876, and don’t forget the lighthouses and museums.  

Block Island, Rhode Island: Situated about 9 nm off the coast between Long Island and Martha’s Vineyard, Block Island State Airport sits on an unspoiled, sparsely inhabited refuge island that has escaped the ravages of overdevelopment. Walk the nature preserve just south of the airport or scour the beaches for one of 550 glass fishing floats made by a local artist and hidden in early June 2017. Rent a bike or moped, visit the lighthouses, go fishing or kayaking, or join in the nightlife in Old Harbor.

      Morning on Tangier Island in the Chesapeake Bay. Photo by J. Albert Bowden II via flickr.                         Tangier Island, Virginia: Fly to Tangier Island Airport in the Chesapeake Bay to experience a tiny, long-isolated community seemingly immune to invasion by the densely packed Eastern Seaboard that surrounds it. Many of the 750 or so residents are related and most speak with a unique accent they call “Hoi Toider” (as in “High Tider”). Shops are generally open between May and October. Some residents combine services by offering places to stay, dine, and shop; others are happy to give you a neighborhood tour. Soft-shell crab is a local specialty, along with crab cakes and unique ice cream shops.
  • Thai Seafood Stew, courtesy Plum Island Grille.
  • Private boats and homes in Nantucket. Photo courtesy Wikimedia commons.
  • Gay Head Cliffs, on the western side of Martha’s Vineyard, offers uncrowded beaches. Photo courtesy Wikimedia commons.
  • The Flying Horses Carousel on Martha’s Vineyard is America’s oldest platform carousel. Photo courtesy Martha’s Vineyard Preservation Trust.
  • Block Island lies 9 nm off the Rhode Island Coast. The airport is at the island’s center. Photo by Timothy J. Quill.
  • New England Airlines serves the Block Island Airport. Photo by Timothy J. Quill.
  • Crescent Beach is a popular spot for sunbathing on Block Island. Photo by Timothy J. Quill.
  • Tangier Island ingenuity: this crab shack also offers a gift shop and golf cart rentals. Photo courtesy Virginia State Parks Youth Conservation Corps (VSPYCC).
  • Tangier Island residents take pride in their island—even the garbage cans are unique. Photo courtesy VSPYCC.
Crista Worthy

Crista V. Worthy

Crista V. Worthy has been flying around the United States with her pilot-husband Fred and their children since 1995, and writing about fun places to fly since 2006. She has single-engine land and sea ratings. Her favorite places to explore are the backcountry strips of Idaho and Utah's red rock country. She currently lives in Idaho and serves as editor of The Flyline, the monthly publication of the Idaho Aviation Association.
Topics: U.S. Travel

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