Escape to Maryland's Kent and Queen Anne's Counties

Discover Maryland's Eastern Shore Getaways

Great getaway destinations are hard to find. Fortunately, if you happen to be near Washington, D.C., Philadelphia or Baltimore, you have access to miles and miles of unspoiled countryside, combined with historic towns and waterfront vistas. It's all less than two hours away on Maryland's Eastern Shore.

Queen Anne’s County

As you head east on Route 50 and cross the Bay Bridge, take a break and stop in Queen Anne’s County. The county’s first permanent English settlement, Kent Island, was established in 1631. Europeans who visited the area marveled at the abundant waterfowl and the excellent Chesapeake Bay fishing. Today, Queen Anne’s County is still a sportsman’s paradise.

Begin your visit at the Chesapeake Exploration Center, which combines the best aspects of a tourist information office and local museum. The friendly staff will help you select maps and choose places to visit. Spend some time touring the hands-on exhibits, which explain the area’s history and heritage.

If you’d like to see the Chesapeake Bay at its natural best, stop by the Chesapeake Bay Environmental Center in Grasonville. Bring a picnic lunch and wander along the Center’s trails. You’re bound to see some local birds, as the Center is home to over 200 species. Rent a kayak and explore one of the canoe trails.

As you continue east on Route 50, look for the exit for Route 18. This road is part of the Chesapeake Country National Scenic Byway. Stop in Centreville, the county seat, to see 18th- and 19th- century homes and public buildings. Head north on Route 213 and take a break in Church Hill. Here you can tour Cassinelli Winery and Vineyards if you call ahead to arrange your visit.

Heading northwest on Route 213, you’ll pass through the riverside town of Kingston. Cross the Chester River and get ready to enjoy another historic Maryland county.

Kent County

Chestertown is one of Maryland’s most attractive riverfront communities. The town was an important port long before it incorporated in 1706. Chestertown is also home to one of the oldest American liberal arts colleges. Washington College, founded in 1782, was named for General George Washington, who donated a substantial financial contribution to the college. Today, Chestertown’s gracious historic buildings line the waterfront, and the downtown area is perfect for walking tours, shopping and simply soaking up atmosphere.

To get a taste of life on the Bay, sail on the schooner Sultana. Public sails depart on select Saturdays and Sundays during the summer; be sure to make advance reservations. You’ll be an active member of the crew, helping to hoist the sails and steer the ship.

If you’d like to spend a night or two in Chestertown, you can stay in a motel, bed and breakfast inn or vacation cottage. For upscale luxury, stay at the historic Brampton Inn just west of town on Route 20. The Lauretum Inn, also on Route 20, offers comfortable rooms, bike rentals and a classic front porch, complete with rocking chairs. In Chestertown’s downtown area, try the White Swan Tavern, built in 1733 and lovingly restored to colonial splendor, or the Victorian Imperial Hotel. Many Chestertown inns and motels offer mid-week discounts.

Chestertown’s restaurants can satisfy everyone’s taste and budget. For elegant dining in a historic setting, the Imperial Hotel’s Front Room Restaurant is a popular choice. Chestertown even has excellent, reasonably-priced Mexican food at Plaza Tapatia on Washington Avenue, north of the historic area. Try the pineapple-scented Tacos al Pastor for a different take on Mexican-style pork.

Long famous locally for its marinas and fishing opportunities, Rock Hall is a waterfront town with real character. Tiny beach cottages, popular seafood restaurants and marinas are charmingly jumbled together along the Chesapeake Bay. You can rent kayaks, charter fishing boats or learn to sail in Rock Hall. Traces of the town’s maritime heritage are everywhere, from lighthouse-shaped homes to the tiny Waterman’s Museum.

Once you arrive in Rock Hall, you’ll be torn between relaxing on the water and exploring the many shops and restaurants. Why not linger overnight? You can book a room at a local bed and breakfast or rent a cottage for a longer stay.

If you’re hungry, you have numerous restaurant choices. Although Rock Hall is a very small town, it has enough dining establishments to support its summer population. As you might guess, seafood gets top billing on most restaurant menus, but you’ll be able to find plenty of other dishes if fish isn’t your thing. The Waterman’s Crab House is a popular stop. You can even tie your boat up at one of the restaurant’s slips. Crab cakes and rockfish are Chesapeake Bay traditions; if you’ve never tried these authentic Maryland dishes, now’s the time.

What Rock Hall does best, though, is take visitors back in time to a simpler age, when watermen and farmers harvested the bounty of the Bay and the fields. The town’s old-fashioned shopping area and thriving arts and music scene add to Rock Hall’s appeal. Whether you’d like to explore the shoreline by bicycle, enjoy a good meal at a waterfront restaurant or listen to some of Maryland’s best local music, Rock Hall makes a great daytrip or weekend getaway.