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Oxford, MD on the Tred Avon River

First Port of Entry on the Eastern Shore retains the charm of a by-gone era

Boats at peace, with a soothing view across the Tred Avon from within the breakwater at Bachelor Point Marina.
Approaching Oxford from the Chesapeake Bay, ships pass by Sharps Light then enter the mighty Choptank avoiding the shoals off Blackwalnut Point. It is always at this place that my memories of Michener's Chesapeake are most vivid, with images of native Americans watching the birds smash oysters on the shore, thereby getting the idea that there may be tasty morsels inside. The expanse of the Choptank before it turns to starboard toward Cambridge is impressive. Just there, between Benoni Point and Castle Haven, the Tred Avon meanders to the North. Entering the River with its majestic estates and deep water channel is like entering a lovely secret garden.

Oxford is no ordinary place. This is a very special destination indeed. It has an authenthic colonial feel established in 1683 that is unspoiled by globalized commerce. In 1684, only Annapolis and Oxford were recognized as ports of entry for commerce on Chesapeake Bay, so Oxford became a bustling center of trade, with tobacco as the primary export. With the American Revolution, this era ended and was not to resume until the 1800s when commercial oyster fishing entered the scene. It has not changed much since.

Oxford is much smaller and quieter than St. Michael's. By the way, did I mention that it is a sailing destination, with rarely a power vessel in sight?


The two primary marks for the entrance to Tred Avon are the Choptank River Light which is a spider located about 2 nm south of the river entrance and the Tred Avon River #1 light on Benoni Pt. Navigating up the Tred Avon, be sure to give Benoni Point plenty of room passing well to starboard of FL G "1" as the distance can be deceiving and shoaling is common.

To starboard, when the sea walls marking the entrance channel to Bachelor Point Marina are perfectly aligned, the view toward the exquisitely protected secret inner harbor reveals itself and calls out to passing mariners. If you are entering Bachelor's Point, be sure to stay well out from shore in mid-channel before turning in. Do not turn in until you see the channel perfectly aligned.

Sailing past Bachelor Point the town of Oxford reveals itself little by little. First, the beaches along the park on the main street, then the point at the entrance to Town Creek harboring Mears Yacht Haven, Oxford Yacht Club and the ferry landing, open up to display the true nature of the special find.

Stay clear of the ferry which makes regular crossings from Oxford to Bellevue carrying two cars at most. It is believed to be the oldest privately operating ferry in the country. It was founded in 1683, discontinued after the Revolution, then resumed in 1836 and has been in continuous operation since then.

Finding a snug place to put in

The Tred Avon River contains a high percentage of the most popular anchorages on the Choptank River. That said, it also offers some very good choices in marinas.
Oxford from the Tred Avon heading toward Town Creek.

Mears Yacht Haven offers just about the best location in town. The broad water views and secure protected slips provide deep water accomodation for vessels from 20-130 feet in length. This full service marina offers swimming pool, barbeque area, 110V/220V power, cable TV, showers, laundry, fuel, ice and pumpout - everything the cruising yachtsman needs. If you need boat work done, Oxford Boatyard offers deep water slips to 120 feet and a 75 ton Travel Lift plus expert services in every aspect of yacht repair and restoration.

Bachelor Point Yacht Company also boasts a full service yard and marina, but its location, though idyllic and peaceful, is a bit of a hike into town for cruisers with limited time. There are deep water slips, a pool, showers and laundry facilities. If you have bicycles on board, this is the place to be.

Off Oxford there is an open anchorage in the Tred Avon between the #2 buoy and the entrance to Town Creek.  This is acceptable for a late night arrival, but I would not want to stay here during the day.  The constant power boat traffic on the river makes this unbearable.

Anchorages are readily available on the river, but Town Creek itself is tight and busy, has less than perfect holding, and is strewn with debris. For years we anchored off Crockett's Boatyard in Town Creek, which affords a short dinghy ride to get ashore.  It seemed we always dragged anchor in a thunderstorm or found our anchor fouled. 

You can head for the anchorage in Dun Cove off Harris Creek, which is one of the best by far. Enroute you are likely to see the Oxford-Bellevue ferry and dozens of tiny sailboats from the Tred Avon Junior Sailing Camp. Otherwise try Goldsborough Creek or Plaindealing Creek to get away from the crowds in unspoiled settings. Plaindealing Creek with 10' of depth is immediately across the river from Oxford, and due north of the Town Creek entrance.  Further up the river is Trippe Creek which offers a large, but well protected anchorage. 

For a quiet peaceful anchorage away from town along the Choptank, but only if you are feeling adventurous, try Island Creek or La Trappe Creek. The entrances can be tricky and you've got to hug the entrance channel markers to avoid going aground, but once inside, you'll be rewarded with a private deepwater anchorage amidst lovely immaculate landscapes away from the crowds at Oxford. Check in town for local knowledge about shoaling and go in on a rising tide. Remember the Chesapeake Bay sailors' motto, "If you haven't been aground, you are either lying or you haven't been anywhere worth going." (But do be cautious and check the depth relative to your keel! You wouldn't want to be stranded high and dry for too long, even if the bottom is soft mud.)

Things to do

Aerial view of Oxford with Town Creek at center.

The best thing to do in Oxford is relax and act local. There is very little tourist activity. With one market, one general store, one gallery, and two or three gift shops, it takes hardly more than an hour to complete a tour of "the shopping district". Oxford Market and Deli on Morris Street has all the supplies you need, including groceries, liquor, baked goods, video rental, fax service and an ATM machine.

The second best thing is to party at one of the open air pub decks on weekends. Live music, warm breezes, lots of sailors and the town really livens up at night. Try Schooner's and Pier Street to see which one you like best!

The third best thing to do may very well be bicycling. The roads around Oxford are reasonably quiet and flat. The scenery is lovely and unspoiled. The distances easily managed. A circle bike tour from Oxford to Easton and then St Michael's and back is quite realistic at 35 rather flat miles.

If you visit Oxford during the log canoe races, the cardboard boat races or fourth of July, you'll be in for special treats. For the fireworks display and log canoe races, we always liked anchoring in Long Haul Creek. It's a protected deep water anchorage with a perfect view across the river and into town. The dinghy ride into town from here would be a bit iffy with about a mile plus distance across the open river.

The Oxford Inn, built in the late 1800s is a charming Inn and restaurant located at the head of Town Creek. Pope's Tavern has a deep history, including hosting James Michener during his research for the novel "Chesapeake". Make Pope's Tavern a definite stop. But before that, go to The Oxford Mews, the general store in town, and buy a copy of the book Muskrat if they have it. Read it quickly, then go to Pope's to see the mural and display. I won't give it all away, let's just say it's one of the most memorable sailing yarns you'll ever read and involves an unlikely bid for the America's Cup, right here in town. Pope's today is a casual European-style bistro featuring fresh local seafood and produce from the kitchen of chef Lisa MacDougal. Porch dining is available and light fare is served at the bar. They also have a complimentary shuttle from your boat! Just call 410-226-5220 for a pickup!

Places to eat

There are several choices for places to eat. Our personal favorite now is the Pier Street Marina & Restaurant, with fresh seafood (the fried oysters over Caesar salad is to die for!), an open air bar where everyone eventually shows up, and dock space to accomodate the visiting cruiser. It's a spectacular casual setting on the water's edge from which to watch sunsets and people.

Schooner's Landing at the foot of Tilghman Street offers casual waterfront dining and an outdoor deck. They have live music, steamed crabs, and a carryout menu that includes ice and beer. Transient slips are available but check the depth carefully.

If you are looking for something a bit more upscale, try Le Zinc on Mill Street. We have not been there yet but we've heard they serve a nice down-home-country-style French meal, and are open for lunch and dinner.

The Robert Morris Inn is the original centuries-old destination smack at the end of the main street. It is more formal, with dark interiors and full selection of meals for breakfast, lunch and dinner. It is where Michener spent much of his time while writing Chesapeake, and he named theirs the "best crab cakes." The Robert Morris Inn also offers accomodations. Don't forget to order your "crab cakes to go."

Latitude 38 is a casual bistro on the way out of town on the left hand side of Oxford Road just past the fire station. Oxford Spirits next door offers, wine, spirits, and gasoline.


If you have access to a car or are willing to call a cab, you can take a ride into historic Easton, about a 15-minute drive from Oxford. This colonial town is the center of culture and commerce on this section of the Eastern shore. It's a delightful and easily manageable town with plenty of shops, restaurants, and tourist appeal. Easton is home to the Waterfowl Festival which is an amazing gathering of artists, hunters, craftsmen and preservationists, all working together to celebrate the wildlife that abounds on the shores of the Bay and to achieve sustainable populations.

You might also consider a visit to Bellevue on the Oxford-Bellevue ferry.


If you drive into Oxford, by all means observe the speed limits. Hunting speeding tourists is a local sport taken very seriously. There is a spot just before entering town where the limit is drastically reduced. OBSERVE IT! You should also observe great caution in traveling the road out of Oxford after dark. Deer ("hoppy critters") are plentiful and cross the road at the most inopportune times.


It's small wonder that Oxford spawned a yarn the likes of Muskrat with the legendary Oxford Boatyard, Cutts & Case Shipyard, Crocket Brothers, and Campbell's providing the highest quality yacht services. Whatever your boat needs, from rigging adjustments to complete restoration, you are likely to receive TLC in Oxford.

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Some useful links to information about Oxford and environs

Further reading:

Joy of sailingCoastal Boating (Reg. in Ireland No. 443222) is a division of Knowledge Clinic Ltd.
Port Aleria, Rosnakilly, Kilmeena, Westport, Co. Mayo, Ireland - USA: PO Box 726, Mahwah, NJ 07430
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