Covid-19 Disclaimer: Make sure to check the status of the states, regions, and establishments in which you’re planning to visit prior to travel. Many regions continue to see high infection rates and deaths, while many states and counties remain under varying stay-at-home orders. Those traveling from areas with high rates of Covid-19 should consider avoiding travel for now in order to reduce spread.
Beyond Annapolis, the great Chesapeake Bay Bridge sweeps you across the nation’s largest estuary into the pastoral Eastern Shore. A domain of waterfront villages, corn and soybean fields, meandering rivers, crab shacks, farm stands, and scenic byways perched between the bay and the Atlantic Ocean, this magical realm entwines life between bay and farm. The birthplace of Harriet Tubman, there’s Underground Railroad stories here too, detailing how the legendary abolitionist helped guide enslaved people through the fields and river-laced marshes—much of which remains the same today. And while the region is quiet, an urbane artsy and culinary scene reigns in its towns, notably Easton, Oxford, and St. Michaels. The gateway is the small city of Annapolis, with its historic harbor front, the famous U.S. Naval Academy, and tons of little shops and restaurants in historic buildings.
If you enjoy small-town browsing, blue-crab eating, country-lane biking, bird-watching, and simply breathing in the fresh, bay-scented outdoors, this weekend getaway is for you.
You’ll need a car to explore the Eastern Shore. On the first day, take US 50 east from Washington, D.C., over the Chesapeake Bay Bridge. Kent Island awaits just 5 miles beyond, about an hour from D.C. From here, head to Chestertown via US 301, about 50 minutes; Rock Hall is about 20 minutes beyond Chestertown via Md. 20. Now backtrack, heading south to Easton via US 50, about 50 minutes. On the next day, Cambridge to Annapolis takes about an hour, backtracking the way you came. From there, home awaits less than an hour away (depending on traffic—it can get bad on US 50, especially on Sunday evenings, when everyone is heading back from the beach). Get more info here and here.
Head across the Chesapeake Bay Bridge onto the Eastern Shore. People normally zip across Kent Island, just 5 miles east of the bridge, but this time…slow down! Stop by the Chesapeake Heritage & Visitor Center to see exhibits about the area; it also accesses Ferry Point Park, where a 530-foot marshland boardwalk leads to a sandy beach area. Alternatively, hop aboard a kayak at the Chesapeake Bay Environmental Center in Grasonville to spot bald eagles, ospreys, and herons. Get your first taste of delectable Chesapeake seafood—out-of-this-world crab cakes, fried oyster Caesar salad, sautéed little neck clams, served dockside, of course—at The Narrows Restaurant on Kent Narrows Waterfront.
Continuing on, opt for a quick detour north to the adorable little town of Chestertown on the Chester River, with its red-brick sidewalks, artist studios, and the state’s greatest concentration of 18th- and 19th-century buildings outside Annapolis. The nearby Eastern Neck National Wildlife Refuge is another place to spot birds, including nesting bald eagles; while the adorable little fishing village of Rock Hall has a museum devoted to the region’s watermen.
Now head south to Easton, figuring you’ll arrive in the late afternoon, just in time for a pre-dinner stroll. As storybook as it is with its historic buildings, flowery gardens, and tree-lined streets, this bustling place is considered the mini-metropolis of the region, notable for its world-class theater, internationally acclaimed art galleries, and lauded restaurants. Treat yourself to Bas Rouge, a classic, white-tablecloth French establishment where everything from service to décor is jewel-box exquisite. A three-course prix-fixe menu might feature wagyu tataki, Chesapeake Bay rockfish, and chocolate mousse cake. And there’s no better way to end this glorious day than with a Scotch at the next-door Stewart.
You are in the heart of Maryland’s Eastern Shore here, with the entire day to soak it up. But first things first—linger over a homestyle breakfast at the cozy Breakfast in Easton. If you’re into scrapple (slabs of pork meat scraps boiled with spices and cornmeal), this is the place to try it.
Then, you’re in for a fabulous morning pedaling some of the region’s meandering byways, on the 30-mile Easton/St. Michaels/Oxford loop. (Driving is great too.) From Easton, go south to Oxford, a white-picket-fence, lost-in-time town with front-porched homes, the historic Robert Morris Inn (where James Michener outlined Chesapeake), and handcrafted ice cream at Scottish Highland Creamery. Hop aboard the Oxford-Bellevue Ferry—the nation’s oldest privately-run ferry service, since 1683—across the Tred Avon River, and head up to St. Michaels. Perched on the Miles River, this historic waterfront town has antique shops, boutiques, and (more) homemade ice cream. The Chesapeake Bay Maritime Museum has all-things-Chesapeake, including a lighthouse built in 1879, a small boat shed filled with Chesapeake watercraft (including a Native American fishing and oystering canoe), and a re-created crabber’s shanty. From here, Easton is 10 miles away.
Back in Easton, grab a late lunch at Sunflowers & Greens, a small, charming café offering divine salads, seasonal soups, and gourmet sandwiches, then head south to Cambridge. You have a couple of good options here. To see more wildlife, head for Blackwater National Wildlife Refuge, where the Blackwater River moseys through tidal flats, past tree-clad islands, before joining the Chesapeake Bay. The refuge’s extensive marshes make prime habitat for migratory birds—Canada geese, great cormorants, pied-bill grebes, yellowlegs, and more. Wildlife Drive opens up this natural world to hikers and drivers.
Another option is to explore Harriet Tubman’s history. The legendary abolitionist escaped from slavery on a nearby plantation, returning many times to transport enslaved friends and family to freedom along the Underground Railroad. The Harriet Tubman Underground Railroad Visitor Center’s four state-of-the-art buildings provide insight. From here, you can drive the self-guided Harriet Tubman Byway that connects other related sites, all the way to the Delaware border. For today, stick to the sites around Cambridge, including Bucktown Village Store, where Tubman received a blow to the head when she was 13 or 14 for speaking up against authority to protect another child; the store is now a museum. When you’re ready, make the push back to Annapolis, about an hour north.
Serving as Maryland’s colonial capital, then state capital, its capitol building reigns as the nation’s oldest state capitols in continuous use, since 1772. With that history comes one of the nation’s greatest concentrations of 18th-century buildings. Yes, it’s cute. Very cute.
Okay, you must be tired and hungry by now. Annapolis has more than its fair share of outstanding restaurants, though for something totally Annapolis, try Mike’s Crab House, an authentic, open-air crab shack with butcher paper picnic tables and piles and piles of Old-Bay-doused blue crabs. And, if you haven’t had enough ice cream already today, top it off with a scoop—or three—of homemade ice cream from the Annapolis Ice Cream Company on Main Street.
Start off the day at Iron Rooster, which serves breakfast all day. Hope you’re hungry, because the extensive menu includes the likes of angry pig omelet (several different kinds of pork with chopped jalapeños), crab hash, and chicken and pancakes.
From here, explore the city’s cobbled streets. The main artery, Main Street, is lively with shops and restaurants, ending at City Dock, the heart and soul of Annapolis. Find a spot along the seawall and watch the parade of people and big boats float along Ego Alley.
For a little more social distancing, explore the quaint alleyways that are part and parcel of the baroque street plan laid out in the late 1600s—possessing charms of their own. Chancery Lane, for example, provides photogenic views of the Maryland State House. And Wayman Alley shortcuts to Prince George Street, home of the historic William Paca House and Garden.
From here, head to the U.S. Naval Academy for a tour of the “Yard,” the 300-acre undergraduate college of the U.S. Navy, established in 1845. If you take the full-on tour, which leaves from the Armel-Leftwich Visitor Center, you’ll visit the world’s third-largest dormitory and see the crypt of Revolutionary War-era naval hero John Paul Jones. You can also just wander around on your own. Be sure to stop by the Naval Academy Museum for perspective.
For a late lunch, walk or catch a water taxi from City Dock for a five-minute ride to garden-filled Eastport and head to the Boatyard Bar and Grill, which is known for its crab cakes, raw bar, smoked fish of the day, and, in season, soft-shell crab sandwiches. Nearby, the Annapolis Maritime Museum and Park has permanent exhibits about life on the Chesapeake, plus a refurbished skipjack (a traditional Chesapeake fishing boat) open for tours.
As you wind up the weekend, there’s no need to rush back home. Leaving Annapolis, take a detour to Quiet Waters Park, located between the South River and Harness Creek just outside town. Here, trails wind through forests and grassy fields of a 340-acre oasis, providing one last gulp of fresh bay air.
WHERE TO STAY
Charming, elegant, yet relaxed is how you’ll find most of the accommodations on the Eastern Shore, ranging from stately inns and hotels to charming B&Bs, with many occupying historic buildings. Be aware that many require a minimum of two-night stays on weekends and other busy times. The historic Tidewater Inn, anchoring downtown Easton, is a go-to, with its elegant guest rooms and alfresco lobby. The romantic, seven-room Oxford Inn in Oxford, perched on one of the nation’s oldest streets, occupies a charming 19th-century house overlooking a creek; enjoy a cup of coffee on the breezy porch and you will never want to leave. In downtown Annapolis, the 215-room Graduate Annapolis Hotel mixes bayside style, Navy pomp, and campus lore. History pervades the three properties belonging to the Historic Inns of Annapolis, dating back to the late 1700s: Governor Calvert House, Robert Johnson House, and the Maryland Inn.
WHEN TO GO
The Eastern Shore is a year-round destination, with summer being the busiest. It’s hot and humid, then, cooled by bay breezes. The shoulder seasons are lovely—May and September—when temperatures are comfortable and migrating birds are winging their way through. Winter is pleasant too, when you won’t be partaking in watery activities, but can enjoy plenty of other goings-on, including regional festivals and holiday celebrations.