Romantic Things to Do in Oxford MD: Prettiest Town on the Chesapeake

WHY GO: With a population of only 651, you might assume that this tiny Chesapeake Bay town doesn’t have much going for it. But there are several romantic things to do in Oxford MD, a “Mayberry RFD” – like village that has been termed “The Prettiest Town in Maryland.” A weekend here can be just the antidote to a frenzied life.

Oxford Maryland is known as a “yachting town.” With seven boatyards, it’s said there are more boats than people there. And even better, the historic ferry that shuttles cars and visitors from Oxford to Bellevue boasts a woman Captain, Judy Bixler, who co-owns the river shuttle service with her husband, Captain Tom Bixler.

There’s a charming old inn named for a Revolutionary War financier, a miniature library that could win awards for adorableness, and one terrific walking tour that ties it all together.

It’s no big surprise that Oxford MD is listed in our Top Romantic Getaways in Maryland!

Romantic Things to Do in Oxford MD

TOUR:  Walking Tour

Use this Oxford Walking Tour or pick up a hard copy from the Oxford Museum to walk achingly beautiful main and residential side streets.

In the 1600’s and 1700’s, Oxford comprised a small section of Lord Baltimore’s vast tobacco plantation. Tobacco equaled cash in the American Colonies, and Oxford was a major port of entry.

By the 1800’s Oxford’s fortunes turned from Tobacco to Oysters. It became a working class Watermen’s town, with twenty crab and oyster-packing plants on the waterfront. Now there are none.

With the smelly shellfish processing plants gone, Oxford became a sought-after town for wealthy retirees seeking a quiet, small town life in homes with backyards that offer sweeping cove views. Real estate there commands some of the highest prices in Maryland.

Other offbeat tidbits about Oxford MD

In 2026, the Oxford Police Department was down to one single cop who apparently does his job well. There is no violent crime here. Zero percent.

There is one market, one shop, one museum – and 700 boat slips in Oxford.

The Nellie Stevens Holly tree was developed here 109 years ago.

Main street is home to one of the Oldest Grapevines in America, still clinging to a 1730 home.

There is no mail delivery in Oxford. Residents must get their mail from the Post Office at the end of Wilson St., making this little side street the busiest in town.

GREAT TALE: Molly Stewart, Postmaster

One of the most entertaining and satisfying stories, however, involves Mary Stewart, who became the United States Postmistress of Oxford in 1877 (at age 20) after her father, the Postmaster, died. She added a small extension onto her cottage, which served as the local Post Office.

At the end of her term, in 1930, the Republican Committee of Talbot County recommended that a Republican man be appointed Postmaster. But two things were in Mary’s favor. One, she got the highest score on the Civil Service exam, while the Republican appointee flunked it. And two, newspapers of the day took her side, with headlines like; “Republicans Try to Kick Little Old Lady Out of Her Job.”

President Hoover reconfirmed Stewart’s appointment in 1931, and she served as Postmistress until 1940. Her cottage, in private hands, is on the Historic Register.

VISIT: Oxford Museum

You’ll find a 4^th Order Fresnel Lens, carved duck decoys, antique pottery shards, and other historic knickknacks in the grassroots Oxford MD Museum.

You’ll also find former tour-guide Leo Nollmeyer, who serves as curator and all around town booster. See website for operating dates and hours.

RIDE: Oxford-Bellevue Ferry

Take a trip through history; it’s only $10 round trip (pedestrian) to ride on the oldest privately owned ferry – the Oxford-Bellevue Ferry – in the USA (opened 1683), which ushers you across the Tred Avon River, from Oxford to Bellevue, MD and back.

Captains Judy and Tom Bixler signed the papers to purchase the Ferry on the fateful day of 9-11-2001 and have been running it ever since. Daily Mid April to Mid November $20 one-way car and driver, $35 round trip. $5 walk ons each way.

VISIT: Oxford Library

“A few ladies” came up with the idea for this private library in 1939. Tiny, warm and welcoming, the Oxford Library remains a most precious place to get lost in a book.

SHOP: Mystery Loves Company Booksellers

Mystery Loves Company! Who can resist an indie book shop with that name? Especially when its in a repurposed bank. And yes, they’re online and deliver!

Best Places to Eat and Stay in Oxford MD

EAT/ICE CREAM: Scottish Highlands Creamery

Fans from near and far come to this humble homemade-ice cream shop, the Scottish Highlands Creamery, owned by Scotsman, Victor Barlow, who has come up with some pretty eccentric flavors (among 600 he’s created, including “Old Bay Ice Cream”).  Some have crowned Highland’s the “Best Ice Cream on the Delmarva Peninsula.”

EAT: Locals Love

Pope’s Tavern at Oxford Inn for great Italian, Doc’s Sunset Grille for seafood and sandwiches on the waterfront, Oxford Social for coffee and baked goods (next to Scottish Highlands Cremery), and Oxford Market and Deli near the marina for picnic and boat provisions.

STAY: Robert Morris Inn

FYI – Robert Morris Inn closed for renovations in late 2025 with opening date TBD.

Facing the waterfront and ferry dock, the Robert Morris Inn is one of the oldest of Oxford’s lodgings. Built as a private home in the early 1700’s, it served as a retreat for soldiers blinded in WWI, then a dance hall, pool hall, and store, before being turned into this classic establishment.

It’s been said that James A. Michener wrote most of his outline for Chesapeake while staying here.  

STAY: Sandaway Suites & Beach

A rambling old inn on the bay, the Sandaway Suite and Beach is the perfect perch for stunning sunsets. An amazing place for a romantic getaway.

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