Road trip experts, Diane and Jeff Caslow, headed to Talbot County on Maryland’s Eastern Shore for a wonderful winter weekend. If you’re keeping track, this is the fifteenth stop on their two year journey to visit all of Maryland’s counties.


The municipal website for Talbot County, Maryland  provided some wonderful context for our visit: “The county is one of the oldest European settlements. Its history is linked to the water that surrounds it, with the most tidal shoreline of any county in the United States. Native Americans lived in the area well before the first English settlers, who arrived in the 1630s. Talbot County was established by 1661, and life centered on tidewater and tobacco. Oxford was its first town, serving as a port of call for ships from around the world, and traded for English goods with ships which anchored directly off the plantation wharves. Oxford, its first town, was laid out in 1683 and served as a port of call for vessels from all over the world. St. Michaels was a boat building center known for building the Baltimore Clipper ship.

Tilghman Island Country Store, Talbot County, 2017.

Tilghman Island Country Store, Talbot County, 2017.

Tilghman Island

Once in Talbot County, our first stop is Tilghman Island, so named for the family who owned it for over 100 years. There was a booming oyster business as well as boat-building industries for many years and we can see reminders of this rich heritage as we drive around the Island. Looking for morning coffee we head to the Tilghman Island Country Store. What a hidden treasure! The Country Store had everything we needed including good coffee from Rise Up Coffee Roasters and homemade baked goods like infamous chocolate chip cookies. The Store also showcases work from local artists and has a backroom for book clubs and other neighborhood get-togethers.

ST. Michaels

We’ve been to St. Michaels before and highly recommend visiting the Chesapeake Maritime Museum where you can explore the Chesapeake through their exhibits or by renting one of their small crafts made at the Museum and test out your own skippering skills!

On this visit, however, Jeff tracked down the sail maker for the 1978 boat we are rehabbing, Dudley Boycott, and we visited him in his home. Dudley previously lived in Baltimore City but moved to Saint Michaels where be became a volunteer at the Chesapeake Maritime Museum he donated his sail making equipment to the Museum and helps run the sail loft is the Bay History Building.

After hearing wonderful history and stories from Dudley, we walked the main street of Saint Michaels admiring the continued use and adaptive reuse of some of the buildings along the way.  We stopped at Lyon Distilling Company that is housed in an old mill, tasting and buying some of their fine local rums. We also tasted some of the vodka from Gray Wolf Craft Distilling. Now hungry, we were torn between some of fine places in St. Michaels or wander off to Oxford. We chose the latter…

The Oxford-Bellevue Ferry dates to 1683.

The Oxford-Bellevue Ferry dates to 1683.


Oxford is the former colonial port and one of the oldest towns in Maryland dating to somewhere around 1666. We conduct our own driving tour of the area, noting many beautiful examples of historic homes laid out in the original grid pattern from the 17th century. For lunch, we arrive at the ca. 1710 Robert Morris Inn originally the home of Robert Morris, an American merchant who helped finance the American Revolution. The Inn overlooks the Tred Avon River and the Oxford-Bellevue Ferry. This Ferry was started in 1683 and is one of the oldest privately owned operating ferries in the United States! Some town references claim that James Michener wrote his book, Chesapeake, in Oxford; I read it many years ago and have on my list to reread it after our trip.


We backtrack to Easton, so named because of its location east of Saint Michaels. A small sign off a main road into town leads us to the Third Haven Meeting House. The Meeting House was completed in 1684 and is still an active as a house of worship for the Quaker community.  We take a self-guided walking tour of the town, checking out many of the older buildings that have been renovated for a new use, admiring the renovated Avalon Theater, where they are getting ready for a production of A Christmas Carol, and finish up some of our holiday shopping in some of the wonderful downtown stores. We head into the Tidewater Inn for an early dinner and to warm ourselves by the fire…

Another fun county to explore and again, finding interesting people, things to do and see along the way! Next month we head to Montgomery County.