The Maryland Eastern Shore is the peninsula which extends hundreds of miles between Chesapeake Bay and the Atlantic Ocean and offers endless recreational opportunities. The Bay itself is a boating mecca but there are also historic towns, beaches and beautiful natural areas to explore. Of course if you want to step off your boat for a while you can also enjoy activities such as swimming, fishing, bird watching, biking and golf.
Chesapeake City, Maryland
The charming small town located at the northern end of the Eastern Shore, is known for its unique views of ocean-going vessels. The historic area sits just south of the Chesapeake & Delaware Canal, a 14-mile canal that dates back to 1829. Visitors can enjoy art galleries, antique shopping, outdoor concerts, boat tours, horse farm tours and seasonal events. There are several fine restaurants and bed & breakfasts nearby.
Chesapeake City, Maryland
Chestertown, Maryland
The historic town on the banks of the Chester River was an important port of entry for early settlers to Maryland. There are many restored colonial homes, churches, and several interesting shops. The Schooner Sultana provides opportunities for students and adult groups to sail and learn about the history and environment of the Chesapeake Bay.
Don’t miss the Chestertown Tea Party Festival in May, which holds reenactments of the 1774 incident when residents dumped tea in the Chester River as a sign of protest and symbol of solidarity with their Boston brothers.
Chestertown, Maryland
Rock Hall, Maryland
Rock Hall, Maryland
Kent Island, Maryland
Known as “Maryland’s Gateway to the Eastern Shore,” Kent Island sits at the base of the Chesapeake Bay Bridge and is a rapidly growing community because of it’s convenience to the Annapolis/Baltimore-Washington corridor. The area has lots of seafood restaurants, marinas and outlet stores.
Kent Island, Maryland
Easton, Maryland
Located along Route 50 between Annapolis and Ocean City, Easton is a convenient place to stop to dine or take a walk. The historic town is ranked 8th in the book “100 Best Small Towns in America.” Main attractions include antique shops, an art deco performing arts venue – the Avalon Theater and the Pickering Creek Audubon Center.
Easton, Maryland
St. Michaels, Maryland
The quaint historic town is a popular destination for boaters with its small town charm and a variety of gift shops, restaurants, inns and bed and breakfasts.
St Micheals, Maryland
Tilghman Island, Maryland
Located on the Chesapeake Bay and the Choptank River, Tilghman Island is known most for sport fishing and fresh seafood. The island is accessible by drawbridge and has several marinas including a few that offer charter cruises. It is home to the Chesapeake Bay Skipjacks, the only commercial sailing feet in North America.
Tilghman Island, Maryland
Oxford, Maryland
This quiet town is the oldest on the Eastern Shore, having served as a port of entry for British trade vessels during Colonial times. There are several marinas and the Oxford-Bellevue Ferry crosses the Tred Avon River to Bellevue every 25 minutes. (closed Dec – Feb)
Chesapeake Bay Maritime Museum, Oxford, Maryland
Cambridge, Maryland
The main attraction here is the Blackwater National Wildlife Refuge, a 27,000 acre resting and feeding area for migrating waterfowl and home to 250 species of birds, 35 species of reptiles and amphibians, 165 species of threatened and endangered plants, and numerous mammals. The Hyatt Regency Resort, Spa and Marina, one of the region’s most romantic getaway destinations, sits right on the Chesapeake Bay and has its own isolated beach, an 18-hole championship golf course and 150-slip marina.
Cambridge, Maryland
Ocean City, Maryland
With 10 miles of white sand beaches along the Atlantic Ocean, Ocean City, Maryland is the ideal place for swimming, surfing, kite flying, sand castle building, jogging, etc. The Eastern Shore resort is a bustling beach town with amusement parks, arcades, miniature golf courses, shopping malls, an Outlet shopping center, movie theaters, go-kart tracks and the famous three-mile Ocean City Boardwalk.
Ocean City, Maryland
Assateague Island National Seashore
Assateague Island is most known for the more than 300 wild ponies who wander the beaches. Since this is a national park, camping is allowed but you’ll have to drive to nearby Ocean City, Maryland or Chincoteague Island, Virginia to find hotel accommodations. This is a great Eastern Shore destination for bird watching, seashell collecting, clamming, swimming, surf fishing, beach hiking and more.
Assateague Island National Seashore, Maryland
Crisfield, Maryland
Crisfield is located at the southern end of the Maryland Eastern Shore at the mouth of the Little Annemessex River. Crisfield is home to many seafood restaurants, the annual National Hard Crab Derby, and the Somers Cover Marina, one of the largest marinas on the East Coast.
Somers Cove Marina, Crisfield, Maryland
Smith Island, Maryland
Maryland’s only inhabited off-shore island on the Chesapeake Bay is accessible by ferry only, from Point Lookout or Crisfield. With the land changing due to erosion, storms, and rising sea waters, you should visit it while you still can. Ride a passenger-only ferry to the home of the famous Smith Island Cake (the state dessert) and listen to the distinctive Elizabethan accents, remnants of the original English colonial settlers. Take a bike with you to sight-see, rent a golf cart or go bird-watching. It’s a quiet place to visit, a reminder of a time gone by, and represents a way of life that is slowly disappearing.
Smith Island, Maryland
Annapolis, Maryland
No trip to the Chesapeake would be complete without a stopover in Annapolis which is also the capital of Maryland. Annapolis sits on the banks of Chesapeake Bay, where it meets the mouth of the Severn River. It’s known as the “Sailing Capital of the World.” Whether you’re coming here to tie up your own boat on your vacation rental dock, to take sailing lessons at the Annapolis Sailing School, or you just like the view of the boats on the water, Annapolis is a sailor’s heaven. Be sure to take a tour of the U.S. Naval Academy and the many historic 18th-century buildings downtown, and plan to spend a day walking around the City Dock district.
Annapolis has a serious sailing addiction. The city draws thousands every October with sail and power boat shows, and the rest of the year is pretty much an informal boat show down at the city dock. The Wednesday Night Sailboat Races that occur April to September are a fun way to celebrate the mid-week. Grab a refreshing drink and watch the boats go by.
Annapolis is also home to the annual United States Sailboat show: America’s oldest in-water sailboat show. This event happens in October each year. The Sailboat Show features new racing and cruising sailboats from leading U.S. and foreign builders as well as the nation’s largest multihull display. In 2017, for the first time, sailing lessons will be offered for those new to the sport.
US Sailboat Show, Annapolis, Maryland
