Back in Time in Chesapeake Bay

Tour the tiny, coastal villages of Chesapeake Bay for a glimpse of the past and a refreshing respite from the modern metropolis.


There’s nothing like hitting the ocean during the summer, but if you’re on the East Coast and feel like experiencing all the pleasures of the waterfront sans the crowded beaches, consider touring up and down the eastern and western coasts of the Chesapeake Bay.

The largest estuary in the United States is home to bustling cities, like Maryland’s Annapolis, and quieter throwbacks to bygone eras, like Virginia’s Tangier Island. Here are my four favorite stops up and down the Bay:

Chesapeake City, Maryland

Walk down the charming city blocks of Chesapeake City (population: 787) and you’ll see historic plaques dating each wooden house to the 1820s, significant because this is the decade in which construction began to connect the Chesapeake Bay with the Delaware River, creating the C & D Canal. The canal allowed tankers to cut a huge shortcut out to the Atlantic Ocean.

Now only a few pass beneath the town’s hallmark suspension arch bridge per week. These days, much of the traffic and tourism to the city is owed to the yachting set. Their business keeps a busy party atmosphere hopping in a little marina. The small historic downtown can be walked in an hour’s time; gift shops and antique stores line George Street, with cafés, bakeries and inns dotting the way.

Planning Tips

If you like taking hammer to crab, don’t miss the Tap House, where butcher paper covering the tables is the instant solution for catching the heap of shells and crab juice. For dessert, head toward Kilby Cream, a family-run ice cream shop which is popular with the yachting set’s kids. If you’re with small fry, head across the bridge toward the C&D museum, which houses the oldest steam pump and water wheel on its original foundation in the United States.

Smith Island, Maryland

Maryland’s Smith Island is a beautiful day trip. There are three communities located there: Ewell and Rhodes Point, which are connected by a single road through a gorgeous plain of salt marshes, and Tylerton, which is isolated from tourism and reachable only by boat.

There’s really not much to do but walk around, eat a crab cake, listen for the local dialect which to this day contains strokes of Elizabethan intonations and vocabulary (“jumper” is used for sweater, as in England). The Smith Island Center is a lovely small museum whose exhibit nicely lays out the community’s history; much of the chronicling is owed to a Mrs. Frances Kitching who championed the center’s existence and followed it up with a cookbook of her own native recipes. In a nutshell, it’s all about the crabs, and the famous “Smith Island Cake,” a 10-layer-concoction that has become an economic staple for the community.

Eat the cake; it is delicious, but different depending on where you get it. At Ruke’s General Store and Seafood Deck right on the dock, the cake tastes like layers of crêpes stacked with chocolate icing in between each layer. The Smith Island Baking Company, around the corner and down a grassy walking lane, makes a beautiful cake to bring back to shore, but it’s more cakey and slightly dryer.

Be sure to eat the crabcakes at Ruke’s; many say they’re the best they’ve ever had. Order two on a platter and ditch the bun. You can sit on the screened-in deck and view Goat Island, directly across the harbor, which is occupied only by goats and the giant blue herons that roost in the trees.

Golf carts are available for rent, and if you’re there for just the afternoon it’s well worth your while to be able to take the beautiful drive from Ewell to Rhodes Point and back again. Just be sure the teenage boys who rent you the cart check to make sure your battery is loaded enough to return you to your ferry at 4 p.m.

Planning Tips

Ferries leave from Crisfield, Md., or Reedville, Va. Go for a day trip; it’s hard to imagine spending the night unless your desire is to be mellow at best, completely isolated at worst.

Tangier Island, Virginia

Tangier Island, which sits in the Virginia part of the bay, is a place that time forgot, say, 150 years ago—but for the new aluminum siding on most of the old wooden houses, which gives it a strange look of suburbia among the salt marshes. Natives to the island still speak with a very heavy Elizabethan accent; far stronger than residents of its rival Smith Island. The dialect is a strange combination of extreme southern American accent with Cockney spliced in.

Walk around the perimeter down Tangier’s single road and you’ll encounter the island’s children tooling about on their bikes or golf carts. It’s a super-friendly community, but it’s hard to imagine living here. There’s not much to do except gawk at the natural beauty and wind your way through a cemetery or two, marveling all the while at how very few families’ names seem to have made their way onto tombstones.

Planning Tips

Leave from Crisfield, Md., or Onancock, Va. Skip the golf cart rental on this tiny island. The main circle in town can be walked comfortably, at slow speed, in 30 minutes. Visit for more information.

Point Lookout State Park, Maryland (Eastern Shore)

Point Lookout Park boasts as close to 360-degree views of nature as you can get. At its very tip, a fishing pier is home to dozens of daily visitors, many of them Mennonites. Point Lookout is a poignant historical hotbed for Civil War lovers. It served as an overcrowded Prisoner of War (POW) camp for Confederate soldiers, and there are varying reports and opinions about how many soldiers died and under what conditions. Consensus seems to be exposure due to lack of firewood, and starvation.

Planning Tips

If you’re in Point Lookout, you’re there for the Civil War history, fishing, camping and nature. It’s an incredibly serene place, and will certainly be a half-hour drive to a populated place to stay. Solomons Island, about 45 minutes away, could be a nice landing pad after a day at Point Lookout.

Solomons Island, Maryland (Eastern Shore)

If you could take a picture of a quaint village resplendent with a lighthouse, church spires and a marina or two (or three), it would surely be Solomons Island, just one hour south of Washington, D.C., which sits at the mouth of the Patuxent River. An attractive Riverwalk is home to restaurants, gift and antique shops, but the main activity that attracts visitors are sailing and fishing; boating is what it’s all about here.

Planning Tips

Strangely, this town is most famous for the annual opening of the Tiki Bar in late April, which unofficially marks an early opening of the tourism season.

History buffs will find the J.C. Lore and Sons Oyster House, a museum fashioned from formerly the busiest oyster-packing house in Maryland, an interesting stop. There is a boat-building exhibit on the second floor, and the building itself has been designated a National Historic Landmark.

Destinations: Maryland, Virginia

Themes: Historical Vacations

Activities: Fishing, Sightseeing, Boating

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