A Quiet, Nautical Neighbor of St. Michaels
Why You’ll Want to Go
There are few towns on the Eastern Shore with Oxford’s charm. It first appears on maps in 1670, when Oxford and Annapolis (then called Anne Arundel) were the only ports of entry for the entire province of Maryland. Surrounded by prominent tobacco plantations, Oxford was a wealthy seaport with international connections.
Today’s Oxford is a much different place. With a population of less than 800 and a median age of 63 years old, Oxford offers a dramatic slowdown in every facet of life. It’s the type of place for admiring beautiful wooden hulls and thumbing the pages of a used paperback; for sharing gardening tips with strangers and eating a four-star crab cake sandwich wrapped in newspaper; it’s the kind of place where your biggest worry is how quickly your ice cream is melting.
What You Can Expect to Find
Our best recommendation is to let Oxford surprise you. There are more than six miles of peaceful anchorages between Oxford and Easton Point, and when you land in Oxford you’ll be greeted with white picket fences and dinner plate-sized hydrangeas; quiet side streets and secret gardens. Locals are incredibly friendly, and it’s standard to get talking with a shopkeeper, yard worker, or gardener and get lost in the history of this vibrant spot.
Oxford experienced a resurgence in popularity during the 19th century, when steam ships began ferrying the town’s seafood bounty to markets around the Bay. When the railway arrived in 1871, Oxford became popular with tourists from Baltimore and Philadelphia who packed the hotels and guest houses along the riverfront.
Although history has marched on, sometimes cruelly, the Oxford community has made a conscious effort to preserve the quiet, hardworking way of life that made them notable in the first place. You don’t have to be a history buff to enjoy poking around Oxford, but it helps. There are fantastic museums whose staff will educate you on the significance of the town, but there are also businesses preserving a culture of yesteryear in their daily workings.
Getting There
Oxford sits at the mouth of the Tred Avon River, a lengthy northern arm of the Choptank River that extends deep into the shoreline, finally landing in Easton, Md. It’s just roughly seven-and-a-half miles from the mouth of the Choptank, and two good visuals are Choptank River Light, which sits roughly two miles due south of town, and Benoni Point. While Choptank River Light does not need to be honored, it’s wise to leave the lighted green “1” marker off Benoni Point to port when entering the river.
From Benoni Point, the course shifts toward the northwest for just two miles before you see the spit that marks Oxford’s main strip. You can continue exploring the smaller tributaries further upriver, but Oxford deserves a stop. Even if it is just for ice and a crabcake.
Where to Stay
The interior anchorage in Oxford is Town Creek, a busy spot that is one of the most vibrant working waterfronts on the Chesapeake. Anchoring in Town Creek does allow for getting off the boat and exploring by foot, but the bottom is a thin layer of clay and grass over a much more compact surface, and can be less than ideal for lighter anchors, such as a Danforth. Because of this, it’s recommended to head due north out of Town Creek to Plaindealing Creek, which has a better bottom and is more protected in the presence of gales. From Plaindealing Creek, it’s a quick dinghy ride over to the Oxford dinghy dock on Market Street.
Local legend has it that Oxford once had a very thriving Quaker community who lived across the river, and they would bring their wares to the shores of Plaindealing Creek and sell them, hence the area’s name.
There is technically an anchorage off Oxford’s town beach, The Strand, but it’s not recommended if you’re going to spend a significant amount of time on the boat. For many of the same reasons, it’s not easy to secure your anchor, and wakes from other boats will have you spilling your sundowners. However, if you’re just looking for a quick place to drop and take the dinghy ashore, this is a quick option. Just remember to look out for children, who make this the area’s hottest swimming hole.
There are more marinas and boatyards in Oxford than there are churches. Transient slips are available at almost all marinas, and offer quick access to the fun restaurants and cute shops. But remember to call ahead, because depending on the weekend, things can get busy.
If you like to sleep in actual beds when you’re cruising, Oxford has several great options. If you’re bringing over a crew, many of the private cottages will have guestrooms available, or they are available via sites such as AirBnB.com. These go fast, though, and can be more expensive during the prime season.
The Robert Morris Inn is the oldest full-service inn in the United States, and the services it offers are exemplary. Some of the rooms are original to 1710, when the Inn was a boarding house, and the views of the river offer a tranquil lesson in the history of Maryland. If you visit Oxford outside of the heat of summer, it’s practically regulation that you stop in the Inn for some tasty local duck, or a perfectly-seared ribeye. Better yet, stay the night so you can sip your morning coffee around a fireplace at which George Washington once warmed his boots.
If you’re looking to bring a beachy vibe to your weekend, the Sandaway Suites and Beach offers a good mix of surfer chic to their suites. With a private beach overlooking the river, Sandaway is laid-back, friendly, and no-fuss. Rooms are larger and well-appointed (many have screened-in porches), perfect if you plan on staying more than one night.
Marinas with Transient Slips
DiMillo’s Marina is located in the heart of the harbor in a space formerly occupied by Hinckley Boats. Their docks are seemingly endless, and they offer a significant number of transient slips. They are a stone’s throw from the Cutts and Case yard. If you’d like to cruise around town on a bicycle, they have plenty to lend you for free.
Campbell’s Boatyards have three locations in Oxford, each offering a full list of amenities for boaters. Each of the marinas acts as a full-service boatyard (two have haul-out capabilities), but for single night stays you can find a pool, bikes, WiFi, and a great picnic area with grills.
What to Do
Cutts and Case
With a shop full of hand tools and a huge shed full of stunningly beautiful custom yachts, Cutts and Case is both a step back in time and the best self-guided museum experience you can ask for. The shop’s workbench alone is possibly one of the most fascinating pieces of Chesapeake Bay history you’ll find anywhere. As a working boatyard, you’ll see the restoration process happening in real time, but staff is incredibly friendly and it’s not unlikely that you’ll get an unofficial tour.
Water’s Edge Museum
Over the last several decades, Talbot County has taken a heightened interest in recognizing the area’s involvement in the trade of enslaved peoples and their work toward freedom. Oxford was a stop on the Middle Passage, with the last ship docking in Oxford in 1772. The Water’s Edge Museum tells the story of Oxford from those Black men and women who were often uncredited in their work toward founding the town. The Museum shares the stories of Oxford’s founding Black families through their beautiful portraiture and engaging stories linking their lives with those throughout the world.
Oxford Bellevue Ferry
In 1673, Talbot County authorized a ferry service leading across the Tred Avon River between Oxford and Bellevue, a small town on the northern shore. A local by the name of Richard Royston was paid 2,500 pounds of tobacco annually to operate the ferry. The ferry has changed significantly since that day almost 350 years ago (and thankfully ferry operators are no longer paid in tobacco). Today you can travel the ferry with your car, RV, and trailer along the same route where so many crossed before you.
Where to Eat
There aren’t too many places to get food in Oxford, but luckily each has phenomenal options and you will not be left wanting.
Oxford Market
You might call this a corner store or a bodega, but its provisions are perfect for anyone stopping in for just a weekend. There’s a great selection of easy foods and snacks, with a few quarts of local produce on the counter. The real gem of this spot is the sandwich counter. You can get a great steak and cheese, but if you don’t take this opportunity to order a crabcake sandwich, you are missing one of the best crabcakes on the Shore. It’s absolute perfection in its un-fussiness, and for the price you won’t find anything even close for hundreds of miles. We’re certain.
Doc’s Sunset Grille
Just south of town near Bachelor’s Point sits Doc’s, a great dock-and-dine destination that is super popular with locals. The restaurant is adjacent to a workboat dock, so the seafood is as fresh as you can get it. If you show up over the weekend, their brunch menu will keep you full until your next port of call. If you just want something simple, grab a seat at the bar and order the “Crabby Grilled Cheese” that is crabcake, sriracha aioli, and cheddar on white toast along with a cold beverage and just watch your entire day improve.
The Scottish Highland Creamery
Roughly 20 years ago, a little ice cream shop opened on the end of Tilghman Street and quickly became a favorite spot for cruisers. Today, the “window” is still serving the best soft serve around, but a second location has opened on Morris St. The new location has the same superior products but with a fun flair: flavors such as “Crushed Strawberry” and “Fourth of July” help your taste buds create core memories, and if you’re feeling fancy, “English Tea Biscuit” and “Ricotta with Candied Orange and Chocolate Chips” will make you feel like royalty … if royalty enjoyed ice cream.
Shopping
Oxford Vintage and Trade
Inside the DiMillo’s office building is, unexpectedly, one of the best antique shops around. Oxford Vintage and Trade stocks shelves with unique pieces that reflect the values of the town: early Americana with exquisite taste. Whether you’re shopping for vintage Limoges china patterns or antique artwork featuring the nautical scenes of the Eastern Shore, this is the best place to find a special piece of Oxford to bring back to your home.
Mystery Loves Company
It’s hard to believe they haven’t made this charming bookshop into its own murder mystery series. There’s a former librarian whose mind is a labyrinth of facts; toward retirement, she turned an old bank into a bookstore, pushing her desk in front of the ancient vault, its door cracked open. And here you’ll find her still, 30 years later, with her encyclopedic knowledge of the murder and thriller genres on full display as soon as you ask for “something good to read.” A wide-ranging section of local authors will have you heading home and writing your own whodunit with this charming town as its focal point.
The Treasure Chest
There is a significant number of artists local to Talbot County, and a favorite place to showcase their designs is The Treasure Chest. There are unique handmade items that reflect the beachy attitude of town, but there are also plenty of antiques dug out of estate sales around the Shore. The owner is a talented furniture restoration specialist and holds clinics on how to turn your old housewares into statement pieces, too.
