Maryland: Charming Little Oxford

A memorable swingset on the Tred Avon river in Oxford Maryland. Meredith Bower photos.
A memorable swingset on the Tred Avon river in Oxford Maryland. Meredith Bower photos

Oxford, Maryland: Still Charming After All These Years

By Meredith Bower

The Sandaway B&B is cozy and relaxed.
The Sandaway B&B is cozy and relaxed.

Growing up in the ’60s, our family of six didn’t go on vacations we took daytrips. We’d pile into the station wagon, each fighting for the “window seat” and hit the road. No iPods, no videos, no hand-held electronic games and no seatbelts.

Since several of my siblings were prone to carsickness, we’d usually head to the flat eastern shore of Maryland, rather than to the mountainous western part of the state. Most destinations were about an hour or two from Baltimore, enabling us to make the roundtrip in a day, and since it was more efficient (cheaper) we always packed a picnic.

My favorite destination was Oxford, Maryland, a quaint town on the Tred Avon River in Talbot County. The attraction wasn’t shopping, there were only a few shops, including a small old-fashioned grocery with a wooden floor; and although it is situated on the water, you didn’t go to Oxford to swim.

True, it played a big role in the state’s early history, but those milestones are remembered on historic plaques that we could choose to read…or not.

For me, the appeal of Oxford then, as it is now, is the town’s waterfront park and the little ferry shuttling people, their cars and bikes across the river.

Shopping St Michaels.
Shopping St Michaels.

The park, located right on the open river, with picnic tables, large shade trees and a swing set on the water’s edge is ideal. The high-flying swings are as thrilling as any amusement park ride.

It is the perfect place to spend the entire afternoon….which, in the 1970s I don’t think we did, because it was only a five minute ferry ride and a short drive to the town of St. Michaels best known at the time for it’s Maritime Museum. My parents were big on including an educational component to our summer outings.

You’d think a town like Oxford may lose its charm over the years, but the few changes that have been made over the past 40 years have only increased its appeal and that of the surrounding area. I take any opportunity to visit Oxford and the other towns in Maryland’s Talbot County.

Today, the picturesque Eastern Shore county with its more than 602 miles of shoreline and 171,000 acres of farmland has become a destination not only for day trippers, but it is a second home for a number of Baltimore and Washington newsmakers.

Furthermore, sailors recently voted the tiny town of Oxford one of the Top 50 Waterfront towns in World, and people are flocking to the area for the restaurants and the chefs whose ingredients come from local fields, farms and the Chesapeake Bay.


Biking is one of the most pleasant ways to explore the area, especially since there are virtually no hills to conquer. There are a number of routes to choose from with a favorite being the short trip from Oxford to St. Michaels including a quick ferry ride across the Tred Avon River. More ambitious riders may want to consider the 30-mile roundtrip from Oxford including the town of Easton, which is recognized as one of the Top 25 cycling routes in the country.

Sunflowers in oxford
Sunflowers in oxford

Make sure you time your ride to avoid the heat of the day and direct sunlight as you ride beside open fields of soybeans, corn and sunflowers. And, if your co-riders begin to fade, usually the promise of a cool drink and ice cream is enough motivation to keep them peddling.

Whether you bike, boat or travel by car you’ll discover each of Talbot County’s towns has its own distinct flavor. Decide for yourself, which is your favorite.

Oxford Bellevue ferry, a five-minute trip.
Oxford Bellevue ferry, a five-minute trip.


Oxford, one of Maryland’s oldest towns is the smallest of the Talbot County trio. Less than a mile long, and half as wide, Morris Avenue, the main drag, features a bookstore housed in the former bank, several churches, a general store, the one-room Oxford Museum filled with history and artifacts, and quaint homes with picket fences and front porches outfitted with rockers and porch swings.

The waterfront park looks like it did years ago, swing set and all, and if you don’t come with your own picnic, pop into the old fashion Oxford Market, just across the street, for the essential ingredients and enjoy lunch by the water.

Save some room for homemade ice cream from the Scottish Highland Creamery (314 Tilghman Street). Only several blocks from the park, on the opposite side of town it’s off the beat and path, has no sign, is surrounded by working boatyards, but ask anyone and they’ll direct you to the best ice cream in the area. The fresh flavors and friendly service make it a destination by land and water from April through the end of October.

If relaxation and good food is your goal, the sleepy town of Oxford is definitely the place to be. Sleepy, however does not mean it is tired. Some of the area’s finest restaurants are located in Oxford and chefs take advantage of the food harvested locally in the fields and waters of the Chesapeake Bay.

Oxford's shopping district.
Oxford’s shopping district.

For a casual meal overlooking the Tred Avon River, try the Masthead at Pier Street Marina. Pier side picnic tables allow for great views, especially at sunset, and refreshing breezes. While the Masthead closes for the winter months, its sister restaurant, Latitude 38 open year round is a favorite of locals and visitors alike. Located on the Oxford Road just before the town, in what was once a gas station, the menu at the cozy bistro changes regularly.

At the other end of town, the historic Robert Morris Inn has withstood the test of time and ever-changing economies in its 300-year history. The Inn features a dining room, perfect for special occasions, and the more casual, Salter’s Tavern with intimate brick alcoves and a cozy fireplace.

Oxford market.
Oxford market.

If your get-away is truly about getting away, consider the Sandaway Bed and Breakfast, located just down the road from the Robert Morris Inn, tucked away at the tip of the peninsula that is Oxford.

The waterfront rooms of the Victorian mansion are an ideal retreat. Private porches offering sweeping views of the Tred Avon, and the shaded lawn, dotted with Adirondack and lounge chairs is the perfect place to soak up the sun, watch breathtaking sunsets, and marvel at the ever-changing views of the river as it laps up on the property’s small, sandy beach.

Oxford to St. Michaels

The quick, scenic and fun way to travel from Oxford to St. Michaels, is to cross the Tred Avon River aboard the Oxford-Bellevue Ferry. The ferry, which began operation in 1683, runs from April through November and can accommodate nine cars as well as those traveling by bike.

The landing, located at the end of Morris Street is easy to find and the wait is usually short as the crossing only takes about five minutes. After reaching the Bellevue side it’s about a seven-mile ride into St. Michaels through country roads and cornfields.

Like Oxford, St. Michaels sits on the water, but unlike its neighbor, the town’s main thoroughfare, Talbot Street is busy with boutiques, gift-shops, restaurants and galleries. The rich maritime history of the region is celebrated at the Chesapeake Bay Maritime Museum and there are numerous opportunities to explore the area by boat from a hands-on adventure on the skipjack Rebecca T. Ruark to a narrated cruise aboard the St. Michaels Patriot.

Robert Morris Inn: Hundreds of years of history.
Robert Morris Inn: Hundreds of years of history.

Easton is the largest and most land-locked of Talbot County’s main towns, and like its neighbors it is appealing in size and scope. Not only does Easton feel like the quintessential small town, it is also offers a surprising helping of arts and culture.

Aboard the five minute ferry from Oxford to Bellevue.
Aboard the five minute ferry from Oxford to Bellevue.

Featuring metropolitan art, sophisticated shopping, and big city dining along the town’s historic streets. A stroll through town will reveal a variety of one-of-a-kind shops, and a dozen art galleries in addition to the Academy Art Museum.

When it comes to dining, Easton offers food-lovers a variety of innovative options prepared by chefs who use local ingredients to create menus that range from fusion to French and upscale to down home.

Restaurants are just as plentiful and the choices varied. Mason’s on South Harrison Street features a menu, which is both comfortable and sophisticated. Located in a sunny yellow clapboard house with a blue wrap-around porch it’s the perfect place to take a break and watch the town pass by.

From the Plen Air in August, a Jazz festival in September and house tour in the Christmas Be sure to check the town’s calendar of events to discover the variety of activities that appeal to every interest. When it comes to festivals, Easton’s Waterfowl Festival, held annually on the second weekend of November, attracts sportsmen and nature lovers alike.

Crisp temperatures, thousands of migrating Canadian Geese and the small town charm provide the perfect backdrop for the Festival that features wildlife art in many different forms, retriever and duck calling contests, Maryland food and wine, in addition to hunting and fishing gadgets and gear. Proceeds from the festival benefit waterfowl and wildlife habitat preservation, conservation, and education.

Meredith Bower, a freelance writer and mother of four, loves to travel and hopes to have instilled that passion in her family.

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