Travel Destinations

Island Hopping Around the Chesapeake Bay


A trip to the islands — the phrase itself conjures up thoughts of a getaway to serenity, fun and adventure. The Chesapeake Bay envelops a number of islands, some so anchored to the mainland, like Kent or Solomons, that we hardly think of them as islands. Others are connected by a single bridge creating a more isolated lifestyle for residents. Hart-Miller and Pleasure Islands are seasonal boating destinations. Many, like Tangier, are threatened by the slow but steady erosion of the Bay’s waves.

Island time has a different meaning for each of them... on some islands, time has stopped, or even appears to have reversed. For a few, it’s party time, and for many, time is running out. Here are the stories of eight Chesapeake islands off the shores of Maryland and Virginia. How many can you explore this summer?


Hart-Miller Island

Hart Miller Island aerial | Will Parson-Chesapeake Bay Program on Flickr

Lat/Long: 39.24 -76.36

Begun in the early 1980s as a dredge containment area filled with underwater materials from Baltimore Harbor and the region, Hart-Miller Island has reached full capacity at 1,200 acres. Located near the mouth of Middle and Back rivers, the island is only accessible by boat.

Park Ranger Robin Reed says, “It’s hard to recreate nature,” but working together, Maryland’s Department of Natural Resources, Environmental Services and Port Authority have successfully turned the site into a viable island and protected haven supporting birds and wildlife. More than 275 bird species, some found only on Hart-Miller, call the island home.

Its western shore offers safe mooring, wading, a 3,000-foot beach, concessions, picnic area and restrooms, making it a favorite destination for weekend boaters from May 1 to Sept. 30.

Where to Dock: Hart-Miller Island State Park

Pleasure Island

Lat/Long: 39.23 -76.39

Originally developed in the late 1940s as Bay Shore Park, a very popular amusement destination for Baltimoreans with a gala casino for dancing, a five-acre midway and about seven glorious miles of lovely white sandy beach. Pleasure Island was connected to Millers Island via a wooden bridge that was destroyed in a 1964 hurricane.

Pleasure Island is now part of Hart-Miller Island State Park, which also includes Hawk Cove and offers recreational opportunities and camping. The park complex is well-known for its abundant migrating bird populations.

Where to Dock: Hart-Miller Island State Park

Taylors Island

Lat/Long: 38.46 -76.30

When the Taylor brothers took ownership of 400 island acres in 1662, they named it Taylor’s Folly. Once connected on the north to James Island and on the south to Hoopers Island by way of Meekins Neck, Taylors has lost about 1,500 acres in the last 100 years to erosion washing away most of James Island and all traces of the road to Hoopers. It’s connected to the mainland by a concrete bridge over Slaughter Creek.

During its early history, Taylors Island was an important center for farming, shipbuilding and seafood. Island shipyards built pungies, schooners, bugeyes and sloops. This, along with the lumber industry, nearly decimated the trees on the island. Talented decoy carvers lived on the island back in the days of market hunting. An old Taylors Island working decoy is priceless.

With an abundance of waterfowl, the island is a hunter’s paradise. For those who shoot with cameras, Frank M. Ewing Robinson Neck Preserve is a gorgeous hidden gem with an undisturbed waterfowl habitat and sanctuary for bald eagles. A 1.25-mile, one-way nature trail winds through the tall pines and tidal marshes of this Nature Conservancy preserve that’s open year-round.

Where to Dock: Slaughter Creek Marina

Hooper Island work boats | Matt Rath-Chesapeake Bay Program on Flickr

Hoopers Island

Lat/Long: 38.29 -76.19

Just 25 miles yet worlds away from Cambridge, Hoopers Island encompasses three islands with authentic working watermen villages. Upper Hooper and Middle Hooper are connected to the mainland by high arched bridges.

Henry Hooper settled here in 1669. At various periods, islanders farmed, built ships and canned tomatoes. Hoopers Island has historically housed many of Maryland’s crab processing facilities. Today the tradition of “working on the water” continues as a hub for crab-picking operations, oyster aquaculture facilities and charter sport fishing.

Dock at Old Salty’s, a classic Bay restaurant drawing people from all over for traditional fresh seafood recipes: delectable crab cakes, soft shells and various seafood dishes, plus a bustling tiki bar. For early risers, Hoopers Island General Store (open at 5:00 a.m.) has everything from groceries to sporting supplies and a deli known for homemade cheesesteak subs, crab cakes and desserts.

Deal Island

Lat/Long: 38.14 -75.94

Deal Island, Chance and Wenona, the three communities on this three-mile stretch off Tangier Sound, are inhabited by watermen, wildlife and waterfowl; and on Labor Day weekend, skipjacks.

For more than 60 years, skipjacks have traveled from around the Bay to compete and celebrate these iconic Chesapeake wooden vessels at the Deal Island Skipjack Race & Festival. Activities include a parade, fishing and boat-docking contests, music, crafts, food and skipjacks on display. On race day, yard sales line the 16-mile road from Princess Anne to the island.

Expanses of tidal marsh, frequently broken by open water, characterize most of the habitat of Deal Island’s 13,000-acre wildlife habitats that support a large concentration of herons, egrets, ibis and uncommon ducks attractive to waterfowl hunters. Deal Island Beach is known for natural sea glass that washes onto the sand. Arby’s Dockside Bar & Grill, a nearby waterside shack next to Scott’s Cove Marina, serves crabs and cold beer.

Where to Dock: Scott’s Cove Marina


Tangier Island waterman | Steve Droter-Chesapeake Bay Program on Flickr

Tangier Island

Lat/Long: 37.82 -75.99

In the summer of 1608 while searching for fresh water, Capt. John Smith came across a group of islands in the middle of the bay that he called the “Russell Isles.” Today, the group is known as Smith, Tangier and Watts Islands.

When settled by European farmers in the mid-1700s, the island was twice its current size and is now the last inhabited Virginia island in the Chesapeake. When the demand for seafood increased in the 1840s, the residents began harvesting the waters instead of the land. The island’s central waterway is lined with crab shanties, now the source for many coveted soft shell blue crabs.

Currently, this historic watermen’s community is holding tight to its water-oriented roots and way of life while also thriving on tourism. Guesthouses and B&Bs dot the island. Day-trippers can dock at Parks Marina, then tour the island by bicycle or golf cart and dine on seafood caught that morning at one of the seasonal restaurants.

Where to Dock: Parks Marina

Watts Island

Lat/Long: 37.79 -75.89

Pint-size, uninhabited Watts Island can be reached on a day trip from Tangier, which lies just a few miles west. Initially called St. Gabriell’s Island, it was renamed after landowner John Watts in 1670. Despite its diminutive size, the island has a deep, often violent past.

At one time, the island was a base for pirates who sailed out to commandeer ships, plunder shoreline plantations and steal whatever they came across.

During the American Revolution, Watts was a base for Loyalists who operated much like the pirates. The British built a fort on the island during the War of 1812, though Tangier Island was their major base. During the Civil War, Watts remained under Union Navy control, but both Union and Confederate sailors cut all the trees to fuel their steamships.

In 1800, 15 people lived on Watts Island and raised cattle on the marsh grasses. In 1833, the U.S. government pur- chased Little Watts Island and built a lighthouse placing the light fueled by kerosene at the top of a 48-foot-tall tower. Watts Island and Little Watts Island once covered hundreds of acres of land. Little Watts and the government-built lighthouse are now completely gone while Watts Island continues to erode into Pocomoke Sound.

Gwynn Island

Lat/Long: 37.50 -76.28

Originally part of Powhatan lands, Gwynn Island lies at the mouth of the Piankatank River and is roughly three miles long and a mile wide. About 600 residents live in bungalows with private beaches, but no public access.

According to legend, Colonial Hugh Gwynn was exploring the bay when he heard the cries of an Indian girl whose canoe had tipped over. She was Pocahontas, daughter of the Powhatan chief who gifted Gwynn the island for saving her life.

The Hole in the Wall Waterfront Grill sits at the base of the Cricket Hill bridge. Tie up to dine in or call ahead and have food delivered to your boat. Walk over to Gwynn’s Island Museum to see pottery, artifacts and a 1776 map believed to be drawn by Thomas Jefferson. A replica of the Cinmar Blade, the oldest known Paleo-human artifact found in the Americas — dating back 23,000 years — is on display.

The island is a quiet respite with songbirds, ospreys and frolicking bottleneck dolphins except during the lively Gwynn’s Island Festival in June. Graze on a variety of seafood while exploring handmade items — jewelry, wood crafts, leather, paintings and ironworks.

Where to Dock: Morningstar Marinas Gwynn’s Island

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