It’s Warm and Cozy on Maryland’s Eastern Shore Oxford, Maryland

326 years of history/population 651/3 police officers/zero crime/one market/one shop/one museum/600 miles of tidal shoreline and 700 boat slips!

Are you getting the picture?

Oxford, Maryland is not your typical town. But keep in mind that when I went there I was not looking for the typical getaway. I was looking for a place to truly relax, and I’m happy to tell you I found it in the charm and tempo of this picturesque seaport.

Oxford, one of the oldest towns in Maryland, is listed on the National Registry of Historic Places and marks its official beginning in1693 when it became one of only two ports of entry for the entire province of Maryland. This enabled the town to prosper as an international shipping center of tobacco from surrounding wealthy plantations. Early citizens boasted prominent colonial names, such as Robert Morris, the financier of the American Revolution. But American Independence in 1776 marked an end to Oxford’s glory as the British merchant ships disappeared, and local businesses went bankrupt. The town went into a deep sleep.

The town awakened again with new prosperity after the Civil War with the help of a new railroad and the discovery of improved methods of harvesting and canning the abundance of oysters and crab in the nearby Chesapeake Bay. Business was booming as tourists and boaters came in number. But that too came to an end in the early 20th century when the oyster beds of the Chesapeake were overharvested. Again, Oxford went into a time of slumber except for the “watermen” who continued to work the waters of the nearby Tred Avon River. The Watermen still live here, and so do those who seek the peacefulness that Oxford provides. The town has enjoyed a recent resurgence of tourism based on the promise of quiet charm, leisurely days and a true escape from the fast pace of everyday life.

I found my peaceful oasis at the The Sandaway Bed And Breakfast, a member of the Select Registry of Distinguished Inns of North America. The B&B is a sprawling Victorian mansion that sits hidden at the end of the town’s peninsula and boasts stunning waterfront view rooms with cozy screened in porches. I sat there each morning sipping coffee and noshing on the lite breakfast delivered to my room in a hand-painted basket. After breakfast, I loved to walk the small private beach looking for prized sea glass and then find my favorite Adirondack chair to soak up the sun or lounge in the shade. There, I read my book, took naps, counted the sailboats floating by, sipped wine, and watched the sunsets. It was SO relaxing.

So much activity requires sustenance (lol), and fabulous food is just a short walk away in Oxford, which is only 1 mile long and a 1/2 mile wide. My first night, I was determined to dine on the local culinary treasure Maryland Blue Crab. Doc’s Sunset Grill was the perfect place to crack those red shelled beauties and search for every delicious morsel. With a cold beer in one hand and some Wet Wipes in the other, the meal and sunset could not have been more perfect. My next dining adventure, literally steps from my B&B, was at the historic Robert Morris Inn built in 1710 and owned and operated by Chef Robert Salter. The charm of this historic Inn provided the elegant atmosphere to compliment the chef’s gourmet offerings. I began with a pretzel-encrusted soft-shelled crab and a main course of local rockfish in a beurre blanc sauce that melted in my mouth. But what about dessert, you ask? Just another short walk away is the very popular Scottish Highland Creamery. This unassuming ice cream stand sits opposite the Oxford Boat Yard and always has a line. It is so worth the wait to indulge in the creative flavors of locally sourced frozen goodness.

After lounging for a couple days, I got a little antsy and decided to go exploring. Bike rentals and kayaks were available across the stree,t but I opted to take my car on the oldest operating private ferry in America since 1683, The Oxford-Bellevue Ferry. A $12 fee and a 5-minute ferry across the Tred Avon River landed me a short drive to the lovely town of St. Michael’s. There I found a charming main street to stroll with shopping, antiquing, wine tasting, and a maritime museum. It was the perfect break from the very comfortable pattern of relaxation I had created.

On the way back to my B&B, I spotted quite a few artists with easels propped along the iconic white picket fenced sidewalks of Oxford. I learned they were there as part of the annual Art Competition called “Plein Air Easton’s: Paint Oxford Day.” Over 58 artists from around the world had descended upon this tiny town to paint scenes “en plein air” (outdoors) and try to capture the engaging personality of Oxford on their canvases. I thought about their challenge . . . I’m sure it was hard to choose what to paint because Oxford is truly picture perfect at every angle.

If you go:

Sandaway Beach & Suites

Doc’s Sunset Grill

Robert Morris Inn

Scottish Highland Creamery

Oxford-Bellvue Ferry

Paint Oxford Day

Oxford Tourism info


Kim Adley is the owner and custom tour designer of Passport to Pittsburgh, a custom tour design company for Pittsburgh and beyond ( She is also the sole proprietor of Characters by Kim, a professional storytelling business (