A pin on the UE map marks Chesapeake City, Maryland and it’s only a few minutes off the I-95 corridor. Originally consisting of only three buildings, the completion of the Chesapeake & Delaware Canal in 1829 gave rise to opportunities for settlers to service passengers and shippers traveling the canal. By 1839, the town was prospering and officially a spot on the map.  The town grew along both banks of the canal and was a reputable hub for canal traffic until dredging eliminated the need for ships to process through locks. After years of struggling to be sustainable, Chesapeak City is once again a small town catering to boat and historian traffic.

The south bank has been wonderfully preserved and is on the National Register of Historic Places. Several of the buildings have been lovingly restored and capture the character of centuries-gone-by. One building that is a personal favorite is the National Bank of Chesapeake City building, built in 1903 by the John Banks family. The exterior of the building is granite brought in from nearby Port Deposit and inside you can find the original bank vault and tin ceilings. The Dragonfly Gift Shop owned by George and Susan Marin carries American, Canadian, or Fair trade items specializing in glass, pottery, and items for the home. Each time I visit the shop I find a perfect gift! Just browsing and enjoying the historical elements in the building is a great experience.

The old National Bank of Chesapeake Bank building – now the Dragonfly Gift Shop … photograph by H. Kennard

Inside the Dragonfly Gift Shop

The old bank vault of the National Bank of Chesapeake City – photograph by H. Kennard

Just across the street is an award winning Bed & Breakfast, the Blue Max Inn and is listed as one of the Top 15 Inns in the Country! While I have not personally stayed, the building itself is a lure and one cannot help but wonder what it is like to while away a cool summer evening from one of the wonderful and majestic porches. It has received awards for best interior design and from what I can tell by its website, the inside is just as stunning!

The Blue Max Inn Bed & Breakfast – Photograph by H. Kennard

Strolling through the shade along the tree lined streets of Chesapeake City allows you to view the historical markers that are prominently displayed on numerous buildings. They are plentiful. In addition, there are several wonderful boutiques, antique, and gift shops, housed in fabulous historical structures, that can capture your attention for an entire afternoon.

One of many wonderful shops to lose yourself in – photograph by H. Kennard

When you find yourself with an empty tummy, Chesapeake city offers a variety of options to satisfy any palate. The Bayard House Restaurant offers a fabulous waterfront fine dining experience. It’s been years since I’ve eaten there but remember it as romantic and special. Their website offers this description:

“The restaurant’s menu consists of traditional Eastern Shore cuisine with a European flair. Specialties include our award winning Maryland Crab Soup, Maryland Crab Cakes, and Tournedos Baltimore. Prized for an award winning wine list, the Bayard House Restaurant offers elegant dining in a romantic atmosphere.”

The Bayard House Restaurant – photograph by H. Kennard

Just steps away is the Canal Creamery and Sweet Shoppe, infamous for its homemade ice cream! It boasts sixteen flavors ~ including tempting delights such as Kahlua Fudge and Bananas Foster, and also offers milk shakes, sundaes, fresh pie a la mode and light lunch fare (including crabcakes).

The Canal Creamery – photograph by H. Kennard

Another casual option is the much newer Chesapeake Inn & Marina. On holiday weekends, this place is packed! If boating in, a quick call to the dockmaster will get you a slip and boatside service! Every weekend a local band plays on the outdoor deck and can be enjoyed from the marina. This is a favorite of locals and on a warm spring day, it is the first place I think of going to help foster that “summer spirit”! A cold margarita and some Jimmy Buffet tunes does the trick every time!

Chesapeake Inn & Marina – photograph by H. Kennard

These are only some of the highlights that Chesapeake City has to offer. With so much to do, see, and eat… it’s worth the trip whether you are driving to or from somewhere or especially if you  make it the destination! Highly recommended.



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