help_outline Skip to main content




PV Logo w slogan Hoiz



HomeBlogsRead Blog

Penn's Village Community Blog

The Eastern Shore: Not Far, But a World Away
By Jeanne Sigler
Posted on 11/30/2020 12:34 PM
Great Oak Manor
Great Oak Manor

For the last several years, my husband and I had said to each other, on occasion, “We’ve got to get back to the Eastern Shore.” More ambitious and farther flung travel plans had always taken precedence. But in this season of prolonged pandemic, there was nothing to interrupt. What was so intriguing about the Eastern Shore of Maryland? We recalled that it had a deep colonial history, an abundant natural setting and beauty, a proud abolitionist, and Underground Railroad past, plus a unique religious history encompassing both tribulation and tolerance. Finally, we recalled touches of the gentility and elegance that make for a relaxing respite from the current world.

Thus, on a warm Fall morning, we set out for Chestertown, MD and Great Oak Manor, a former hunting lodge that has served as a graceful 12 room inn with spacious public spaces, wide lawns, and Chesapeake Bay frontage. They offered the promise of quiet, calm, and a lovely contrast to fraught urban life, not to mention pandemic panic and fatigue.  

Route 213, not far below Wilmington, DE is shown on most maps as a scenic byway, so with assistance from a combination of GPS and Rand McNally, we left the I-95 corridor behind and instantly found wide-open spaces and soft harvest colors. Yes!

On an impulse, and with thoughts of lunch, we turned off Route 213 just over the C & D Canal bridge, and found ourselves in charming little Chesapeake City, population 673. As the town lies directly on the Chesapeake and Delaware Canal, it was easy to find a patio and table right on the water at the Bayard House Restaurant. It had a just-right menu and the visual lure of a steady stream of tugboats, barges, oceangoing, and pleasure craft to engage us.

After a satisfying lunch, a walk around the busy marina, together with an exploration of the shops and inns along Bohemia Avenue, convinced us that our impulse to stop here had been a good one. There was more to Chesapeake City than lunch! One large shop, The Mercantile at Back Creek, seemed to have a special flair, together with a feel for the region—nautical, natural, casual, and relaxed.  

An easy mid-afternoon check-in at Great Oak Manor offered us time for a calming outdoor read and cup of tea in the Adirondack chairs facing Chesapeake Bay, as well as a welcoming view of the sunset a bit later.

For dinner, we headed to The Kitchen at the Imperial restaurant on High Street in historic Chestertown, an eight mile and 15-minute drive away. While one cannot go wrong ordering crab soup nearly anywhere on the Eastern Shore, the chef’s preparation here was memorable. The entrees were equally well-prepared and the atmosphere upscale and casual. Although there are other options in Chestertown, we decided to return to the Kitchen at the Imperial the next night and were again pleased.  We were able to enjoy a table in the outdoor courtyard on both visits.

After dinner, we walked around the downtown, which has been the county seat and an active port since 1706. In pre-Revolutionary War days, it was a Royal Port of Entry. Just after the War, Washington College was founded, with the General himself giving his authorization. It was the first institution of higher education founded in the new nation.

The next day was foggy, thus ruling out a visit to the Eastern Neck Wildlife Refuge, a 2,200-acre waterfowl migration site and winter bird refuge on an island at the Mouth of the Chester River. We decided to drive down to Easton, a larger town, equally historic, about an hour’s drive further south.  Again, traveling Route 213, the ride was rural, scenic, and relaxing, with sparse traffic and broad vistas.  

We arrived in Easton just at noon and found a shady parking space downtown on Gay Street with ease.   It happened to be just across from the Tidewater Inn, where a very-attractive and flower-filled restaurant patio was beckoning. There was a short line of socially distanced and masked diners, and the posted menu proved appealing. So, we joined the line and were soon seated for a lunch of quiche and a butter lettuce salad.  

Afterwards, a quick peek at the large lobby, framed by a splendid circular staircase, and a tasteful combination of clean-lined sofas, antique wooden chests, and historic prints suggested that this might be a perfect hotel home on our next trip south.  

That inclination for a second visit was confirmed over the next hour or two as we explored the center of Easton on foot. The deep history of this town of 16,000 was immediately apparent, from the Georgian architecture, to the statue of Frederick Douglass (who was born nearby and spent his early enslaved years here), to the dense array of antique shops full of local maps and memorabilia. 

Vintage Books
Vintage Books


Our favorite stop was at Vintage Books, a bright and lovely setting for used books and fine art. We found all manner of volumes of interest, enhanced by engaging conversation with the proprietors. While we never made it to the large back room, we will definitely return to peruse the enticing collections we missed, including “Fine Books in Scholarly Topics”, “Historic Documents”, and “Historic Newspapers”. It is a unique, well-stocked and welcoming place.

On our trip home the next day, we happened upon the Old Wye Episcopal Church, right on dependable Route 213. Originally St. Luke’s, it was built in 1721 as a ‘chapel of ease’. A feeling of stepping back in time pervades the place. The religious history of the Eastern Shore also includes the first Catholic church and congregation in the colonies, as well as the influence of the Quakers and early African American congregations.  

For those wishing to delve more deeply into African American history, Chestertown and the Historical Society of Kent County offer a brochure for a Driving Tour of the ‘Underground Railroad and the Quest for Freedom’. It details sites where abolitionists, free people of color, and others assisted hundreds of enslaved people in their efforts to escape to the North and freedom.  

Chestertown also has a walking tour which features many 18th and 19th century residences, churches, and public buildings of note, including Sumner Hall, built by African American veterans of the Civil War.  It was placed on the National Register of Historic Places in 2005 and contains a small museum. It is one of only two such sites in the United States.

We returned home satisfied that we had opened a window into an intriguing corner of the Mid-Atlantic on this short but very pleasing three-day trip. While only a 90-minute drive, it was a world away from Philadelphia. If you can imagine yourself gaining fresh perspectives from an earlier and seriously complex era, as well as from the charm of different landscapes and colonial era towns, we recommend this trip for you. 

Leave a Comment
 *