Maryland's Charming Tree-Lined Village Is An Inviting Waterfront Getaway With Cute Shops And Eateries

For a charming Maryland getaway offering Chesapeake Bay views and lots of history, Oxford needs to be on your radar. As one of Maryland's oldest towns, Oxford's colonial-style buildings and brick sidewalks are steeped in historic charm. Time in this quaint town is all about embracing a slow pace — from strolling along the waterfront and its tree-lined streets to watching the sunset — so if you're looking for a relaxing trip, this is it.

The closest airport is Baltimore/Washington International Thurgood Marshall Airport, located just over 70 miles away. From there, the easiest option is to drive the roughly hour-and-a-half journey. Alternatively, you can take two buses to reach Oxford. Ronald Reagan Washington National Airport in Washington, D.C. is another option located just a bit farther at 85 miles. Driving to Oxford will again be the easiest and quickest option, but public transportation is also available. 

In fact, you could even make the drive even more of an experience by traveling along Maryland's "all-American" scenic byway. When in Oxford, you can then plan to explore by foot or by bike — so don't forget comfortable walking shoes and sunscreen!

To dive into Oxford's fascinating past — which included time as a major international shipping center, as a hub for the region's oyster industry, and, today, as a charming tourism destination — visit the Oxford Museum. Here, you can see everything from historic photographs to navigational instruments. The museum is open from mid-April through fall, Fridays to Mondays, and admission is free.

Of course, getting out on the water is non-negotiable as well, and Oxford, which is located on the Tred Avon River, offers many opportunities for just that. Whether it's kayaking, paddleboarding, fishing, or taking a ferry ride, there's plenty to see along the town's scenic waterways and nearby crowd-free vacation towns like St. Michaels, located on the Chesapeake Bay. Just make sure to stay alert, since Maryland's been consistently ranked as one of the most dangerous destinations for boaters in America.

The Oxford-Bellevue Ferry, which operates seasonally, was first established in 1683 — making it one of the country's oldest privately-owned ferries. Be sure to check the schedule in advance and book your spot ahead of time. If you'd rather just relax by the water, head to the Strand, a small public beach right along the river that's perfect for picnicking or watching the sunset.

Oxford's downtown is equal parts charming and picturesque — from its painted picket fences on display during the summer to its numerous shops and dining establishments. Shoppers should pay a visit to Mystery Loves Company, a bookstore specializing in — you guessed it — mysteries, along with books by regional authors. Don't skip The Treasure Chest, either. It's an art gallery and gift shop featuring locally-made artwork and crafts.

No Maryland vacation would be complete without some crab cakes. Unsurprisingly, Oxford is a great spot to enjoy some of the best seafood around. Capsize is a local favorite for casual American cuisine located right on the water, and Doc's Sunset Grille is another great spot for delicious seafood with a view. For dessert, don't miss a stop at the Scottish Highland Creamery — one of the town's most beloved spots for its hand-crafted ice creams. 

Lastly, for a stay filled with the very best of Oxford's charm and history, Robert Morris Inn is a true gem. Once the private residence of Robert Morris, known as the "financier of the American Revolution" and a friend of George Washington, guests can enjoy amenities like a delicious breakfast, waterfront views, and onsite dining at the Financier, which has been open since 1710.