Oxford, MD, visitors must follow one rule: if you drive into town, slow your car down to 25 miles or less, as the sign says. If you drive 26 mph, you will get a ticket. This is the only thing that happens quickly in Oxford. Take the overarching lesson to heart and slow down. This quiet hamlet on the Chesapeake's Tred Avon River is made for sauntering or cycling along tree-lined streets and stopping for lunch or ice cream.
Founded in 1683, Oxford became one of only two ports of entry to Maryland; the other being Anne Arundel, now called Annapolis. Through the American Revolution the seaport thrived as an international shipping center surrounded by tobacco plantations.
Another long wave of prosperity came to Oxford after the Civil War, when improved canning and packing methods opened national markets for Chesapeake oysters. Once the oyster beds dried up and the packing houses closed, Oxford became a sleepy watermen’s town. It is still such a town today as well as a relaxing destination for weekend visitors and boaters.
Visitors coming from St. Michaels on weekends should consider a ride on the Oxford-Bellevue Ferry, which has been crossing the Tred Avon River for 342 years. This short trip across the river will cost you between $2.50 and $20, depending on whether you walk onboard or drive your car, ride your bike, or take your motorcycle across with you. The ride across will reveal pretty homes along the shoreline upriver and downriver and the mouth of the Tred Avon, leading to the wide Choptank River.
The ferry lands at “the Strand,” the main drag along the Oxford waterfront, where you look right to see the Tred Avon Yacht Club (TAYC), one of the most well-situated clubs on the Chesapeake when it comes to views and breeze. From the ferry landing you may walk to a handful of shops, such as a bookstore and antiques shop; the Oxford Museum; and a couple of restaurants, including Capsize on Town Creek (reopening April 16 for the season) and Doc’s Sunset Grille.
TAYC hosts many sailing events over the summer, with the Oxford Regatta being a signature family-friendly regatta. Even if you’re not a sailor, you will enjoy joining the large spectator fleet of powerboats who watch the graceful Chesapeake Bay log canoes race on the river. Each of the dozen log canoes competing has its own power-driven “chase boat,” some festooned with palm trees, lounge chairs, and festive revelers.
Boaters who arrive in their own vessels may anchor off the Strand free of charge or find a slip at one of the marinas on Town Creek, such as Safe Harbor Oxford, or one of Campbell’s Boatyards’ transient slips on Bachelor’s Point (with a pool) or Jack’s Point.
Do not leave Oxford without eating an ice cream cone! This is as important as driving the speed limit. The Scottish Highland Creamery on South Morris Street makes memorable, award-winning homemade ice cream that’s so good, you will return to Oxford for more.
~M.W.
Upcoming Events:
Oxford Day 2025
Bring the whole family to Oxford Day on April 26. Activities will include a parade, flower sale, family hour of fun activities for children of all ages, a blessing of the animals, dog walk and show, library book sale, opening day of the Oxford Museum, and free walk-on ferry rides on the Oxford-Bellevue Ferry.
There will be designated parking areas in addition to regular street parking; parking is limited. Consider bringing bikes and parking out of town at the Conservation Park, which is a short pedal along wide shoulders.
The event will be held rain or shine. Learn more at oxfordday.org.
Nautical Flea Market
Campbell’s Boatyards is sponsoring a Nautical Flea Market on May 31 for customers and vendors. Unload gear or stock up for the 2025 boating season! To set up a table, please contact [email protected] for more information. This event runs from 8 a.m. to noon rain or shine at Campbell’s Bachelor Pt. location (26106A Bachelor Harbor Dr.).
Fourth of July Fireworks
Don’t let the town’s sleepy reputation stop you from going there for the Fourth of July. Oxford hosts a dazzling fireworks display right off the Strand. Stay tuned to the PropTalk calendar for the exact date for fireworks
Romantic Getaways:
Less than a minute’s walk from the Strand, the 300-year-old Robert Morris Inn is undergoing some renovations but is still open for business. Spend the weekend at this quaint retreat (with no televisions in the rooms). Whether or not you are a guest at the hotel, you may dine at the newly refurbished Financier Restaurant, featuring locally harvested ingredients from farm-fresh produce to the day’s catch from trusted watermen.
Another option is the adults-only Sandaway Suites and Beach boutique hotel. The centerpiece of the two-and-a-half-acre waterfront paradise is the charming Victorian lodge, complemented by thoughtfully designed duplex suites, a cozy cottage, and spacious suites with full kitchens. Most accommodations feature private screened porches and breathtaking river views. The hotel also boasts a private beach and expansive waterfront lawn. Stroll along the shoreline, unwind in the lounge chairs as you take in a sunset over the Tred Avon River, enjoy alfresco dining at one of the picnic tables, or fire up the barbecue grills for a memorable meal with a view.
Find more lodging options in or near Oxford at tourtalbot.org/oxford.