Rock Hall and Oxford
Two Terrific Tiny Towns on Maryland’s Eastern Shore
Pulling into town in time for dinner, the summer heatwaves are just a memory and out on the water a solitary sailboat cuts a white triangle from the clear blue sky as if in a painting. The trees are on fire with gold, red, and orange fall colors competing with sunsets for your camera's attention. This is just one reason Maryland's Eastern Shore is the place to go for a fall road trip. The twin towns of Rock Hall and Oxford boast stunning bay sunsets, crabbing, sailing, excellent cuisine, and good lodging options for those looking to capture the sights, sounds, and taste of the season.
Rock Hall
Founded in 1707, roots run deep here in this town known for their Pirates and Wenches Weekend, Fourth of July festivities, and more boat slips than houses. A shift began in the 1980s when crabbing, oystering, and fishing could no longer support the town. Recreational boating was outpacing the seafood industry, bringing new visitors and the demand for places to eat and drink, things to do, and places to stay. Today, it’s a gem of the Eastern Shore and a delight for visitors, whether you come by boat or by car!
Eat and Drink
Check out Waterman's Crab House for delicious local seafood on the water, and Osprey Point for homemade breakfast specialties like cranberry-apple crostada, English frittata, and to-die-for peaches and cream French toast. For ice cream, stop at Get the Scoop where they serve locally-made Kilby's ice cream in cones, cups, shakes, and sundaes during spring, summer and fall. Fresh Start is a new grocery store with a focus on local produce, sustainably raised pork, beef, and poultry products. Coffee lovers can get their caffeine fix and delicious homemade baked goods at Java Rock.
Do
Checkout Mainstay in downtown Rock Hall, a non-profit music venue hosting live performances throughout the year. Mainstay's events are tilted towards jazz, thanks to legendary jazz guitarist Charlie Byrd taking a fancy to Rock Hall, but they also welcome bluegrass, folk, and blues bands. Excellent restaurants and cool shops make a visit to downtown a must.
The Blue Crab Crawler Tram is a low-cost way to get around in Rock Hall. The tram runs Memorial Day until the last day of October and charges $2 per person, each way. Charter a sailing trip on the Island Girl at sunset, through Blue Crab Chesapeake Charters, and see the area in style.
And right in town there are some great shops, including Smilin’ Jakes Casual Apparel for all your island wear, and the Hickory Stick boutique for a wonderful selection of gifts for everyone on your list – even if that’s only you!
Stay
The Inn at Huntingfield Creek, built in 1855, draws couples and families to enjoy the dog-friendly 70-acre farm. Both lodge rooms and cottages are available for a night or much longer. Stroll the grounds enjoying flower gardens, a trail to the Chesapeake Bay viewpoint, a dip in the swimming pool, or just unplug and relax. Establishments like the Inn at Osprey Point and the Inn at Haven Harbour also offer first-class accommodations, including private slips onsite for boaters.
Oxford
With a population of less than 700, Oxford scores high marks for hospitality. Founded in 1683, Oxford is on the shortlist of oldest towns in Maryland. Its most famous resident, merchant Robert Morris, Sr., owned the house by the ferry landing, now an Inn named after him. His son, Robert Morris, Jr., is considered a founding father of the United States, signer of the Declaration of Independence, and financier of George Washington’s army during the Revolutionary War. The Robert Morris Inn is said to be one of the oldest inns in the country and is a great place to start your visit.
Eat and Drink
Dinner at the Robert Morris Inn will delight connoisseurs of fine food. Their avocado fries deliver slices of perfectly ripe avocados, first frozen, then breaded and fried. The chipotle aioli completes the appetizer, best paired with a beer or glass of rosé. For entrees, the crab cakes are a must-try, and the dessert menu gives a hint of Chef Mark Salter's British roots with sticky pudding and pavlova. Breakfast, lunch, or dinner is enhanced by dining outdoors on the veranda or terrace in nice weather.
Be sure to save room for one the biggest food attractions in Oxford, the Scottish Highland Creamery. They have over 600 flavors in their creamy arsenal and serve around 20 of these tempting renditions of ice cream any given day. Queue up as early as noon and read the board listing flavors of the day, then proceed to the one of the super scoopers at the order window. I had the waffle cone with a scoop of raspberry coconut truffle topped with a scoop of strawberry. It was so good, I returned the next day for their annual Ice Cream for Breakfast day, starting at 9 am with some servers in pajamas!
Restaurants like Capsize, Doc's Sunset Grille, Latitude 38, and Pope's Tavern are great options for breakfast, lunch, or dinner. For picnic supplies, the Oxford Market has groceries, wine, beer, and Eileen's Deli. Try Eileen's chicken salad sandwiches for lunch in the town park or the town beach.
Do
Oxford is home port to the Oxford-Bellevue Ferry, the oldest privatelyrun ferry in the nation, operating since 1683, and takes you across the Tred Avon River in your car, on a bike, or on foot. Or take some time to unwind and ride the roads along the Chesapeake Bay and Tred Avon River, and paddle boarding, kayaking, fishing, and sailing are all popular water activities in the calm waters off Oxford's shoreline. There are also shops in town, and events happening throughout the season.
Stay
Oxford is known for quiet streets that make bicycling or walking the town appealing. If you stay at the Robert Morris Inn or Sandaway Suites and Beach, bicycles are available onsite. Several elegantly restored county mansions offer bed & breakfast accommodations, including the Combsberry Inn, Nichols House and Oxford Inn.
Note: All reviews are my own, with thanks to the Easton Visitors Bureau and Kent County Office of Tourism for helping to host my visit.
