Delmarva Peninsula: A Trip Back In Time

Oxford Bellevue Ferry. Delmarva Peninsula
Oxford Bellevue Ferry at the Oxford landing.

Delmarva = Delaware, Maryland, and Virginia = Worth Visiting!

By Kurt Jacobson

Osprey on top of sailboat mast in Whitehaven MD. . Delmarva Peninsula
Osprey on top of sailboat mast in Whitehaven MD.

Golden sand beaches, small towns barely touched by the passing of time–these dot the map on the Delmarva Peninsula. In warm months, modern beach resorts, fishing, and outdoor activities are what attract visitors to the region.

Like many Americans, I had no clue how amazing the Delmarva Peninsula was. Shortly after my wife and I moved to Baltimore, we heard about Ocean City and St Michaels.

Both these popular towns are in Maryland’s Eastern Shore, part of the Delmarva. It took years for us to discover how much more this fabled area of the U.S. had to offer.

A Historical Hot Spot

It would take a whole book to show all the reasons to visit the Delmarva Peninsula. I’ll attempt to cover the best places I’ve found.

The first thing of note, the Delmarva is one of the oldest European-settled parts of the U.S.

In 1608, Thomas Savage landed in Jamestown, Virginia as a youngster of 13 and was sent to live with the Indians. After some years with the Indians, chief Debedeavon gave Thomas around 9,000 acres of land on the Southern Delmarva Peninsula to increase trade with the Indians.

Thomas did well on his acreage, and to this day, some of his descendants still live in the area. Where else are you going to find over 400 years of this kind of history in America?

Kayaking on the Delmarva Peninsula in St. Michaels. Delmarva Peninsula
Kayaking on the Delmarva Peninsula in St. Michaels.

Most travelers arrive by car driving over the massive Chesapeake Bay Bridge. One of the first historical roadside markers is about Kent Island and its status as the oldest town in Maryland.

Settled in 1631 makes this darn near ancient as the history of the white man in America is concerned.

Most of the charm of Kent Island is tarnished by gas stations, condos, and other modern buildings. I recommend driving on.

Victorian Home in Chestertown. Delmarva Peninsula
Victorian Home in Chestertown.

Over The Big Bridge

Once across the Kent Narrows, it’s time to decide on going left or right at the U.S. 50 and US 301 interchange. Take US 301 and chart a course to Chestertown, or stay on U.S. 50 and head towards Easton and St. Michaels.

Chestertown is home to Washington College, a university-funded in part by George Washington himself.

Washington College is said to be one of the country’s oldest colleges and puts Chestertown on the map.

What I love about Chestertown is the Victorian look, but it also has a modern vibe. Drop into Evergrain Bread Company for some of the best baked goods in the entire Mid-Atlantic.

Evergrain Baking Company in Chestertown. Delmarva Peninsula
Evergrain Baking Company in Chestertown.

Pull up a chair and enjoy free WiFi, while you devour buttery croissants almost as good as you’d get in Paris. Walk the town and check out one of the largest collections of grand old homes from the 17th and 18th centuries.

From Chestertown, drive to Rock Hall to get a taste of a true waterman’s town. On the way, look for the historical marker about the Battle of Caulk’s Field, an important site from the War of 1812.

This is one of the most authentic War of 1812 battlefields looking much like it did on August 14th when British troops encountered the Kent County Militia.

In Rock Hall, grab a bite to eat at one of several excellent restaurants. Check out Waterman’s Crab House and watch modern-day oysterman and crabbers come and go.

Waterman's Crab House seafood nachos.. Delmarva Peninsula
Waterman’s Crab House seafood nachos.

If you want to get out on the Chesapeake Bay for an hour or more, take a ride on the Island Girl sailboat owned by Blue Crab Charters. 

If you’re sticking around for the night, don’t miss The Mainstay for live music at a former hangout of legendary jazz musician Charlie Byrd.

Island Girl's Capt. Mark. Delmarva Peninsula
Sailboat Island Girl’s Capt. Mark.

Get Wild

The Eastern Neck National Wildlife Refuge offers hiking on several trails to get close to local wildlife. The butterfly garden was my favorite part of the hike where I saw gobs of butterflies and local birds happily going about their business.

Butterfly at Eastern Neck Wildlife Refuge. Delmarva Peninsula
Butterfly at Eastern Neck Wildlife Refuge.

Head back to Chestertown and chart a course to Chesapeake City to see this historic town on the banks of the Chesapeake and Delaware Canal. On the way, stop off at either Crow Vineyards or Chateau Bu-De for surprisingly good wine.

Crow Vineyards mascot. Delmarva Peninsula
Crow Vineyard’s mascot.

If you headed south at the intersection highway 301 and 50, you’re on your way to Easton. For over eight years, I just blew past Easton on my way to other towns, not knowing what a cool place it is.

The downtown core is full of excellent restaurants, shops, and gorgeous old buildings in great condition.

Lunch at Piazza Italian Market is a must! Check out their hot panini, cold salads, soups, baked goods, and Italian wines.

Emily, the owner, has been to Italy numerous times and provides customers with delicious cheese, meats, pasta, and more for dining on-site, picnics, or taking to a vacation rental.

Three Victorian-era B&Bs offer upscale lodging in Easton or choose from the typical chain hotels out on Highway 50. The Hummingbird Inn is my favorite B&B due to guest service, clean accommodations, and pet-friendly status.

Oxford MD

Oxford Bellevue Ferry. Delmarva Peninsula
Oxford Bellevue Ferry.

From Easton, step back in time by visiting tiny Oxford (founded in 1683). Get out on the water by renting a kayak or hopping aboard the Oxford-Bellevue Ferry.

If you’ve brought or rented a bicycle, the ferry is a great way to get across the Tred-Avon River and ride on over to St. Michaels.

The big difference between St Michaels and Oxford is St Michaels is more developed and has the luxury Inn at Perry Cabin. Both towns are excellent places to spend a weekend or more.

For lodging in Oxford, stay at the Robert Morris Inn (the oldest inn in the U.S.) or Sandaway Suites and Beach, a modern, adults-only getaway. Each offers bike and kayak rentals to enjoy the area.

Robert Morris Inn, Oxford. Delmarva Peninsula
Robert Morris Inn, Oxford.

Follow A Runaway Slave’s Trail

Your next stop should be Cambridge, south of Easton on Highway 50 in Dorchester County. Once a prosperous town due to the region’s thriving veggie market, Cambridge lost its economic engine after the Bay Bridge opened in the 1950s.

What was once known as the “tomato canning capital of the world” succumbed to competition in California and improved transportation.

Nowadays, Cambridge is a good basecamp for exploring the Blackwater Refuge and Harriett Tubman Underground Railroad State Park & Visitor Center.

From Cambridge, head south to one of the hidden gems of the Delmarva. A visit to Whitehaven is like turning the clock back 200 years.

There are virtually no homes newer than the 1880s in this tiny village. Whitehaven was once a thriving town of boat builders, watermen, and a canning factory. If you’re looking for peace and quiet, this is the place.

Sunrise at Whitehaven Hotel. Delmarva Peninsula
Sunrise at Whitehaven Hotel.

Take a ride on the Whitehaven Ferry, (the oldest publicly operated ferry in the country) and head over to Bordeleau Vineyards and Winery.

Stay at the Whitehaven Hotel (circa 1810) and enjoy free breakfast, bikes, and kayaks

Cape Charles

Heading south to the tip of the Delmarva, visit Cape Charles, Virginia. Built in the 1880s as a railroad town, its waterfront location and pristine condition make this a must-stop.

Plan on spending a night or two to take in all the area has to offer.

Cape Charles allows golf carts on the town’s streets, as long as the posted speed limit is 25 mph or less.

Over 300 golf carts are owned by residents and rental shops in town. Reserve lodging and rent a golf cart for a weekend putting around the town.

Golf carts in Cape Charles. Delmarva Peninsula
Golf carts in Cape Charles.

For craft beer fans, check out the Cape Charles Brewing Company.  Hard cider lovers will want to stop at Buskey Cider on the Bay where their tart cherry flavor won me over.

The Shanty or the Oyster Farm are my recommended waterfront dining spots. Both feature local seafood and views of the Chesapeake Bay.

The town’s beach is one of the best on the east side of the Delmarva Peninsula. Cape Charles is dog-friendly and has one of the best ice cream shops in the country.

Brown Dog Ice Cream (open for the summer season) has over 150 flavors of ice cream and offers eight of those each day.

The author's dog being fed Brown Dog Ice Cream. Delmarva Peninsula
The author’s dog being fed Brown Dog Ice Cream.

Check out the Bakery On Mason or Coastal Baking Company for excellent baked goods, picnic fare, and delicious lunch menus. For lodging, I recommend a balcony room at the Hotel Cape Charles, in the center of town.

Magothy Bay 

South of town, check out Kiptopeke State Park where a fleet of ghost ships line the harbor providing a home for marine life and seabirds.

On the opposite side of Highway 13, find Magothy Bay State Natural Area and Preserve. Both parks are good for fishing, boat launching, photography, hiking, and birding.

Oxford fisherman at sunrise.. Delmarva Peninsula
Oxford fisherman at sunrise.

All along the highways and back roads of the Delmarva are historical markers hinting at the deep history of the area. I suggest traveling these roads with time to spare so you can explore what catches your interest.

There are farm markets, historic plantations, resorts, parks, and attractions to see. There’s something for everyone here.

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