The Eastern Shore of Maryland, east of the Washington D.C. / Baltimore metropolitan area, is dotted with unique, quaint historic towns offering excellent and varied food, fun events, beautiful architecture, museums and lodging sure to relax one’s mind.
After you cross the tall, four mile long William Preston Lane Jr. Memorial (Bay) Bridge over the expansive Chesapeake Bay, you enter Maryland’s Eastern Shore, and you begin to feel your troubles fade. You soon come upon the lush and vibrant marshes hugging the shore, and the flat but colorful landscape dotted with farms, orchards, forested areas and small quaint towns. It’s where many people in Metro DC and Baltimore escape on weekends and during the summer, leaving the urban bustle behind. Most people continue another two hours east to the ocean resorts such as Ocean City, Rehoboth Beach or Bethany Beach. But there are plenty of places to see along the Eastern Shore of the Chesapeake, and I’ve listed some of my favorite towns, each very unique with their own personality.
Easton
After crossing the Chesapeake and Kent Island, and heading south on Highway 50, you soon enter Easton, the largest town on the Eastern Shore, and the County seat of Talbot County since 1712. It’s been named one of the best small towns in the U.S. by Smithsonian. Compact downtown Easton, centered on N. Washington Street, is a great place to stroll, shop, dine, ride a carriage, go antiquing, visit a museum or observe art in one of the many galleries. Easton harkens back to a small American town of yesteryear – Its treelined streets are filled with Colonial and Victorian architecture, historic cemeteries and granite built, gothic styled churches. Nearby residential areas contain beautiful old homes with large porches, lush beautifully landscaped lawns, and quaint bed and breakfasts.
One may have seen glimpses of Easton from the 2005 film, “Wedding Crashers”, which was filmed at the Ellenborough Estate, currently privately owned. Famous abolitionist, Frederick Douglass was born twelve miles north of Easton, and enslaved at the nearby Wye Plantation, and Harriet Tubman was born south of Easton, in nearby Dorchester County.
There are many options for delicious and fine dining in Easton. On one of our visits, we ate at Scossa Restaurant and Lounge. This upscale restaurant focuses on Northern Italian cuisine such as antipasti, risotto, gnocchi, pastas, and seafood. I had a delicious rigatoni with sausage and tomato sauce.
The Tidewater Inn, located in a historic building in the center of town, is a luxury hotel and tavern with rooms designed in a traditional décor but encompassing modern comforts.
There are numerous scheduled events throughout the year, but one of the more popular is the Waterfowl Festival, held three days in November coinciding with the opening of goose hunting season. Since its founding in 1971, this annual festival attracts thousands of visitors, showcasing wildlife art, food, music, and demonstrations related to waterfowl calling, raptors, retriever dogs, and fly fishing. Proceeds from the Festival go toward environmental, conservation and education projects throughout the Delmarva Peninsula to preserve wildlife, waterfowl, habit, and heritage. Other notable festivals include the Chesapeake Bay Balloon and Wine festival (held in early August), and the Plein Air Event, the largest juried art competition in the U.S., with paintings made in the fresh air.
Saint Michaels
Taking highway 33 about ten miles west of Easton, you will reach the beautiful seaside town of Saint Michaels, located on a peninsula jutting out into Chesapeake Bay. The town center is filled with historic clapboard homes, churches, a town green and several waterfront seafood restaurants along the cozy harbor. Many times, we have taken our sailboat to Saint Michaels, anchored in the harbor, and called up the harbor shuttle (water taxi) to take us into town. Of all of the towns noted, Saint Michaels probably sees the most tourists.
The main commercial district is along Talbot Avenue, lined with shops, galleries, boutiques, and restaurants. There are dozens of good restaurants scattered throughout town, including several upscale ones, such as Ruse, Limoncello Restaurant and Wine Bar, and Theo’s Steak House. One not so upscale place is the Carpenter Street Saloon, a favorite of ours. This very popular local hangout serves a great breakfast, and has live entertainment, karaoke and trivia nights. The Blue Crab coffee house is also a favorite, and is located one block west of Talbot Street, on Fremont Street.
Tourism in Saint Michaels primarily started after the Chesapeake Bay Maritime Museum was opened in 1965. This 18 acre interactive museum is home to a large collection of Chesapeake Bay artifacts, exhibitions and over 100 boats and boat models. The museum contains 35 buildings including the Hooper Strait Lighthouse, a screw-pile style lighthouse built on piles screwed into the sea bottom. The museum has a working boathouse where visitors can learn about the restoration of commercial skipjacks, a type of boat used for oyster dredging.
Saint Michaels has no shortage of lodging opportunities, including a number of Bed and Breakfasts scattered along pretty tree lined streets. Perhaps the most well known hotel is the Inn at Perry Cabin. This luxury resort is located on the north end of town along the waterfront, and is a popular wedding venue. In fact, the reception scene of the 2005 film “Wedding Crashers” was filmed here. The resort features the Spa at Perry Cabin, an infinity pool, fitness center, and several dining options including seafood focused Stars restaurant which offers a three course tasting menu for dinner.
Oxford
Of all of the towns noted, Oxford is the smallest and most tranquil. This sleepy town is located ten miles southwest of Easton via highway 333 at the end of a peninsula formed by the Tred Avon River and Island Creek. The town is primarily residential, and is one of the oldest in Maryland, or the U.S. for that matter. When founded in 1683, it was one of two ports of entry for Maryland, the other being Annapolis. It was considered an international shipping center, and the surrounding tobacco plantations ensured its success. Today, while no longer a thriving place, the town still retains its historic charm.
The tiny commercial area is along Morris Street, and houses a restaurant, the Oxford Museum, the town park, a book store, and convenience store. At the north end of Morris Street is the Robert Morris Inn, located in a building constructed in 1710. The inn has operated since 1800 and is the oldest full service Inn in America, and George Washington was a guest. The inn also features Salter’s Tap Room and Tavern.
Off of Morris Street is the Strand, a street lined with beautiful homes with porches facing the river, the town beach, and access to the harbor.
The Oxford Bellevue Ferry, located at the end of Morris Street, is believed to be the oldest privately owned ferry in the U.S. Service has been continuous since 1836. The ferry traverses across the Tred Avon River, providing a shortcut to Saint Michaels.
Chestertown
Unlike the other three towns, Chestertown is located to the north of the Bay Bridge via highways 301 and 213. This gracious and well preserved town is built along the bank of the Chester River. It was founded in 1706 as a shipping town along the navigable head of the river. In the mid 18th century, it was second to Annapolis as a leading port, resulting in a wealthy merchant class that is visible today by the multitude of beautiful preserved homes. The National Trust for Historic Preservation has called it a ‘treasure hidden in plain sight’.
The quaint downtown is focused along High Street and Cross Street, featuring restaurants, bookstores, art galleries, and boutiques. The two-story red brick commercial buildings line one side of High Street, opposite pretty Fountain Park, where a Saturday Farmer’s market is held. High Street First Friday, an event held the first Friday of each month when shops along High Street put their merchandise on display.
Chestertown houses a reproduction of the Royal Navy schooner HMS Sultana. The ship, located at the Chestertown Marina, was launched in 2001, and is used for both education purposes and for public sailing. This ship is also used during the Chestertown Tea Party Festival, an annual Memorial Day weekend event and parade that celebrates the town’s colonial heritage, as well as a re-enactment of the legendary “tea party.”
