The Delmarva Peninsula is sort of like the ancient Roman god Janus, who famously faced two ways. But, unlike Janus, who looked to the future and the past, Delmarva has two views of past and present. Delmarva’s eastern side faces the rising sun and the roaring Atlantic Ocean and is fronted by miles of glistening beaches. The western side, a region historically rich in seafood farmed by fishermen in small boats, turns toward the more placid Chesapeake Bay. It boasts a zigzagging shoreline laced with inlets, bays, marshes and pretend rivers whose flow is dictated only by tidal currents.
This upper bay, from Cambridge north, is also rich in history stretching back to the Colonial era. It’s also alive with activities for those who love changing scenery, maritime activities, glimpses into history, outdoor sports, fine and casual dining. and small specialty shops. It’s the perfect place for a getaway weekend—a comfortable drive of about two hours from West Chester or Wilmington.
Easton is a small town but still the largest city in the area. It serves as the region’s living and dining rooms.
Center such a journey in Easton, a small town but still the largest city in the area, which serves as the region’s living and dining rooms. From there, branch out with trips to nearby St. Michaels, Oxford and Tilghman Island. Route 301 is the fastest way to get from here to there. Once past the Chesapeake & Delaware Canal, cross over to Route 219 for a leisurely journey through small-town farm country. This option also allows for a refreshment and shopping stop in historic Chestertown. A great place to have fresh scones and croissants is Evergrain Bread Co. on High Street. Also browse the Queenstown Premium Outlets, a warren of trendy shops near the intersection of Routes 301 and 50.
The area’s primary destination hotel and spa is the Inn at Perry Cabin, overlooking the broad Miles Creek inlet in St. Michaels. If you’re celebrating something or rewarding yourself with a spa visit, definitely book your stay here. It’s also a good place to rent a bike for the duration. Another Eastern Shore destination is the Tidewater Inn in downtown Easton, especially if you enjoy shopping strolls.
There’s much to explore in this section of the Eastern Shore, and it comes in small, digestible bites. This is still farm country, punctuated by wealthy estates. Nature has carved it up into fingers of land stretching out into the bay, interlaced with fingers of water stretching inland. Its many small roads are largely uncrowded, and they lead to a half-dozen or so small towns. All are worth a look.
Just north of Easton, Wye Mills has an old grain mill still in operation that’s open most days to tourists. The mill has a worked-in look with exhibits and a museum store that sells small bags of flour, corn meal and grits milled from local grains, most of them organically grown.
To the southwest on the Tred Avon River is one of the most bucolic towns on the East Coast. Oxford is a Colonial port that dates back to the 1660s. It has one elongated street that stretches out into the water, populated on either side with lovely older homes and a few shops. It ends at the Robert Morris Inn, a good place to have a drink and a bite before leaving town.
There’s also a small ferry in Oxford that connects seasonally across the Tred Avon to Bellevue on the region’s other major peninsula, which is home to St. Michaels and Tilghman Island. St. Michaels is the region’s tourist magnet, reminding one of those summer destination towns along Cape Cod or on Martha’s Vineyard and Nantucket. It has one main business street with lots of places to eat and shop. Don’t miss Chesapeake Bay Outfitters, an upscale, indispensable store that stocks clothes, books, puzzles and accessories.
The town also has a busy harbor that offers boat rentals and sailboat rides. It’s home to the Chesapeake Bay Maritime Museum, with its interesting exhibits inside and several historic boats floating outside. There’s also the St. Michaels Winery, which has a tasting room.
There’s not much to do on Tilghman Island, a quaint little fishing town that’s a 15-minute drive from St. Michaels. You get there along state Route 33, a scenic highway named after Frederick Douglass, the famous writer and abolitionist who was born on a nearby bay plantation, a reminder that much of the region’s original wealth was gained on the backs of enslaved people. There’s also a statue of Douglass at the Talbot County Courthouse.
The region is big enough to support many restaurants to fit all budgets and cravings. Stars at the Inn at Perry Cabin offers an excellent prix-fixe dinner menu and lovely water views. The bustling Hunter’s Tavern at the Tidewater Inn has multiple dining areas and a cozy, busy bar.
A great place for lunch in St. Michaels, Limoncello boasts an imaginative but affordable menu and good wines by the glass. It also has a long bar, should you like to extend your afternoon. A recent highlight was lunch in Easton at the Bas Rouge. The definition of class and elegance, Bas Rouge emphasizes fresh, local ingredients. It’s part of a locally owned group of eateries and drinkeries called Bluepoint Hospitality, which recently opened P. Bordier creperie and patisserie nearby.
At the other end of the spectrum, you must have breakfast, lunch or dinner at the unpretentious Easton Diner on Route 50, with its rows of booths and turquoise leatherette seats. It has good, inexpensive food and a menu with dozens of options.
In addition to the places in St. Michaels, the town center in Easton has several nice shops. Of special note are the jewelry and antique stores. Tom Boyle’s Vintage Books offers one of the best-curated collections of books, maps and historic documents we’ve come across.
Another great thing about the Eastern Shore: Once you’ve had your fill of touring, eating and shopping, you’re only about a two-hour drive from home.