Oxford is just about the prettiest historic town on the Chesapeake Bay.

It’s what children’s books portray as an ideal small town with beautiful Victorians and smaller watermen homes surrounded by white picket fences. The city park looks like a Georges Pierre Seurat painting, and a real Colonial inn sits by the beautiful Tred Avon riverfront.

Oxford was one of the country’s earliest colonial ports, along with Annapolis. But while Annapolis became the state capitol, Oxford focused on commercial trade — shipping tobacco, produce, and seafood.

Now, Oxford is a major port for Chesapeake Bay yachting.

It’s on the end of a peninsula where the Tred Avon River and Town Creek enter the Chesapeake Bay, with the river on the west side and Town Creek on the east side. The creek is more like a river at that point and is home to several marinas.

Oxford is great for a peaceful day trip, walk-about, or weekend getaway. For more active types, there’s no shopping or nightlife to speak of, but there are plenty of outdoor sports such as cycling, kayaking, and fishing.

A warning from locals, follow the speed limit if you’re driving; 25 mph means 25, and no leeway is given.

Downtown Oxford

There is a small downtown section on Morris Street with only a few shops that are usually open on the weekends.

That’s the Oxford Museum (100 S. Morris Street) near the clock, a small building stocked with donated family treasures, including a French-made lighthouse lantern and an Oyster Clock made with shells the size no longer found in the Chesapeake Bay. It’s open on weekends, and some weekdays, from April through November.

Across the street is a large city park facing west across a wide part of the river that is a great picnic spot during the day and offers stadium seating for sunsets. It’s tree-covered nearly to the water and has a playset for kids and benches facing the water for adults.

Picnic tables offer a nice spot for lunch or early dinner, and if you didn’t bring anything, there’s a market across the street with a deli and fresh-baked breads, as well as wine and cheese.

Oxford’s Waterfront

Oxford Custom House

The main road turns at the water, where the ferry is docked. That’s where you’ll find the one-room Oxford Custom House. It’s a replica of the first customs house in the U.S.  A sign on the building says it’s open daily, but don’t count on that.

The Custom House marks the location of where the historic ferry crosses the Tred Avon River to Bellevue. The Oxford-Bellevue Ferry is believed to be the oldest privately-owned ferry in the U.S., making continuous river crossings since 1836.

While it’s been operating that long, the current ferry is modern and carries up to nine cars, in addition to walkers, cyclists, and motorcycles on the ten-minute crossing. Be aware that it closes for the season from December through March.

Strand Beach

Oxford has a public beach.

It’s toward the end of Morris Street, just before the marinas. The beach is wide and has grassy areas covered by shade trees. The parking lot is across the street with a bathhouse and outdoor shower.

Continue down the peninsula and you come across the main marina area. Oxford is a popular stop for boaters, but it’s also home for Chesapeake Bay watermen and boat-repair yards.

Where to Eat & Stay in Oxford

Near the ferry, at the intersection of Morris and Strand streets, is the Robert Morris Inn (314 N Morris Street), built in the early 1700s by ships’ carpenters with wooden pegged paneling, ships’ nails, and hand-hewn beams.

Robert Morris was an English trading company representative in Oxford and the company bought the house for him. His son, Robert Morris, Jr., was known as “The Financier of the American Revolution.” Robert was one of two Founding Fathers to sign the Declaration of Independence, the Articles of Confederation, and the U.S. Constitution.

Because of Robert’s close connection with George Washington and other founders, the Inn maintained its historic structure and decor over the years. The parlors contain 18th Century ‘raised-panel’, pine-paneling and woodwork.

Hanging in the dining room are 140-year-old murals copied from hand-painted wallpaper made in the 1830s. Jackie Kennedy found the original wallpaper murals in another Maryland house and installed them in the White House.

The Inn is now run by British Master Chef Mark Salter. During the slower winter season, he holds cooking demonstrations. The restaurant is closed between meals, but afternoon tea is served 3pm – 5pm. Reservations must be made 24 hours in advance so they know how much to bake.

The Inn’s Salter’s Tap Room and Tavern are casual. They open the outside bar on summer weekends, but the pub is always welcoming.

Latitude 38 (26342 Oxford Road) is at the entrance to Oxford in a historic building. They are not affiliated with Latitude 38 in Annapolis. This American bistro has white linen and candle-lit tables inside for fine dining, and a bar area where “we offer everything but a linen tablecloth.” Reservations are suggested for those linen tables, but not for the bar. They provide transportation to and from Oxford marinas!

Pope’s Tavern at The Oxford Inn (504 South Morris Street) features homemade pasta and Italian cruising. The Inn also has a market that sells Italian wines, meats, cheeses, desserts, and other high-end finger food. Oxford Inn is a victorian mansion with nine bedrooms.

Doc’s Sunset Grill (104 W Pier Street) is where to go for waterside dining and sunsets. They specialize in Chesapeake Bay crabs and other seafood.

Oxford is a popular weekend brunch getaway.

But you don’t want to miss the Scottish Highland Creamery (314 Tilghman Street) if you’re an ice cream fan. It’s in a former crab and oyster business on the water’s edge next to a boat landing.

Because it’s a historic building, the only sign allowed on the building is left over from the former business, Schooner’s. The Highland Creamery sign is on the small ice cream cart. Lines form when the creamery opens and continues through the day.

The creamery is closed during the winter, November through March.

Oxford has a few inns and some B&Bs. The closest hotels/motels are in Easton.

What Else to Know About Oxford

Oxford is also the home of several custom yacht makers. Cutts and Case Shipyard (306 Tilghman Street) specializes in wooden boat designs and has boats on display inside the large picture windows.

Cutts and Case Shipyard is one of two custom boat makers in Oxford.

Cambell’s Custom Yachts is a relative newcomer, starting in 1993.

Several of the marinas rent bicycles, as well as small boats. Dockside Boat Rentals (314 North Morris Street) will drop a rental Zodiac at a dock of your choice. You can also rent bikes at bicycle shops in St. Michaels and do the Oxford cycling loop.

Another beautiful stop just outside Oxford: the Oxford Cemetery. It has an amazing water view. You’ll find it at the end of Oxford Cemetery Road (off Oxford Road/Route 333) on a peninsula in Town Creek.  The older section is on the more protected marshy side.

Lt. Col. Tench Tilghman is buried there. He was George Washington’s Aid de camp, who said of Tilghman, “While living, no man could be more esteemed and since dead, none more lamented than Col. Tilghman.”