Play, sight-see, eat, socialize, collect and explore along Maryland’s famous estuary. Use these 25 ideas for things to see and do along the Chesapeake to get you going.
America's Sailing Capital (not to mention Maryland's capital city) is a charming historic town with 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.
2 Smith Island
Smith Island is a cultural treasure, discovered by Captain John Smith and settled about 350 years ago. With the land changing due to erosion, storms, and rising seawaters, 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.
Home port of the schooner Sultana and home to a thriving arts community, this beautiful historic college town is just up the Chester River on the Eastern Shore. 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.
One of the oldest towns in Maryland, Oxford retains its charm as a waterman's port city. Quiet but with a host of waterfront activities, Oxford was once an international shipping powerhouse and retains its Eastern Shore charm. Yachting magazine voted Oxford the “world's best waterfront town” in the first of its annual contests. Stop for dinner at Latitude 38° Bistro & Spirits, then pick up a little dessert at the walk-up window of The Scottish Highland Creamery to nibble on while you walk around this historic town.
5 Deal Island
Deal Island is home to the annual Skipjack Festival held each year on Labor Day. It is a beautiful, small watermen's community where Chesapeake Bay skipjacks and workboats abound, harvesting oysters, crabs and rockfish.
6 Chesapeake City
Chesapeake City sits at the northern end of the Bay, where the Chesapeake and Delaware Canal connects the Bay to points north. The canal is still in use, and ships and tugs still pass through the center of the city on their way to Delaware and New York. Stop in the C&D Canal Museum which pays homage to the history of the waterway.
More about Chesapeake City Historic District
History & Heritage
100 Bohemia Avenue
Chesapeake City, MD 21915
7 Thomas Point Shoal Lighthouse
The only active screw-pile (meaning the pilings are screwed into the sandy bottom) lighthouse left in the Bay, this National Historic Landmark guards the entrance to South River, not far from Annapolis. Limited public tours are available throughout the year, departing by boat from Annapolis.
More about Thomas Point Shoal Lighthouse
History & Heritage
Mouth of the South River
Annapolis, MD 21403
8 Chesapeake Bay Maritime Museum
Skipjacks, log canoes and draketail oyster boats, all native Chesapeake Bay craft, find their retirement at this museum. Check out a working shipyard and explore the waterfront history of the Bay in St. Michaels, a lovely Eastern Shore town.
More about Chesapeake Bay Maritime Museum
213 N. Talbot St
St. Michaels, MD 21663
Settled in 1684, this waterfront town played an important part on the Underground Railroad (Harriet Tubman was born nearby), and is home to shops, restaurants and maritime museums. Come in July to the Taste of Cambridge Crab Cook-Off and Festival for some of the best crabs you’ll ever eat. Take a ride on the skipjack Nathan of Dorchester, and visit J.M. Clayton Company, the world's oldest working crab house.
10 Hart-Miller Island
A convenient boating destination near Baltimore City, this island, along with neighboring Pleasure Island, is one of the most popular anchorages in the Bay. Food boats ply the water in summer as families enjoy the island beaches, or cook out on the mainland at Rocky Point State Park. Camping on the island is first-come, first-served, and fills up quickly in the warmer months, so make your camping plans early!
More about Hart-Miller Island State Park
2813 Jerusalem Rd
Kingsville, MD 21087
11 Dock Bars of the Bay
Whether you approach them by boat or by car, waterfront bars are the best place to spend a summer afternoon watching the water (or a game on TV). From humble tiki bars to ornate oyster houses, this area is dotted with boat-up bars that are a waterfront tradition of Bay life. Try Spinnacker’s in Ridge, then head up the Bay to Abner’s Crab House on Chesapeake Beach and Kentmorr Restaurant in Stevensville.
12 Tilghman Island
Tilghman Island, a traditional waterman's village on the Eastern Shore, is accessible via a drawbridge. The Tilghman Watermen's Museum will give you a feel for the history there, and the seafood restaurants will give you a sense of why it's there. Boat rentals and public water access let you experience it for yourself.
More about Tilghman Island
Scenic Points & Landmarks
US 322 to Rt 33
Tilghman, MD 21671
13 Hooper's Island
Home to the Hooper's Island Lighthouse and several watermen's villages, this island is one of the oldest settled areas of Maryland, and is still home to around 400 people despite threats to the island from erosion and rising water. The people here make a living from the Bay, as they have for hundreds of years.
14 Blackwater National Wildlife Refuge
To see the natural beauty of the bay, take a trip to this refuge covering 25,000 acres of the Eastern Shore. An “estuarine marshland ecosystem,” as well as home to over 250 species of birds, the refuge is also a major stop for migratory birds along the Atlantic Coast. Walking and paddling trails give visitors a chance to explore this unique ecosystem.
More about Blackwater National Wildlife Refuge
2145 Key Wallace Dr
Cambridge, MD 21613
15 Chesapeake Ship Graveyard
Mallows Bay is a small bay on the Potomac River, with public boat access from Charles County. It is considered to have the largest shipwreck fleet in the Western Hemisphere, with more than 200 hulls of ships resting here. Today, you can spot wildlife taking shelter in the Ghost Fleet of Mallows Bay, with Ospreys and Bald Eagles nesting nearby, and you can also go kayaking among the wrecks.
16 Calvert Cliffs
A scenic beach dominated by its namesake, Calvert Cliffs is famous for its fossils—once covered by a warm shallow sea that receded 10 to 20 million years ago. Fossil hunters stalk the beaches looking for the remains of ancient sharks, whales and birds. The best time to hunt is after a big storm, when new specimens are revealed.
17 Captain John Smith National Historic Trail
This first national water trail follows the famous captain's 17th century journey of exploration throughout the Chesapeake Bay. There are about 3,000 miles of trail, covering Maryland, Virginia, Delaware, and D.C. Maps are available from the National Park Service.
Seafood is still a way of life here in the “Seafood Capital of the World,” and you can witness it first-hand. It is home to the annual Labor Day National Hard Crab Derby, as well as the Somers Cove Marina, a large marina with entertainment for the kids that includes a swimming pool and a playground, and amenities for you and your fishing buddies like great fish cleaning stations.
19 North East
Explore the hidden gem that is North East, located at the head of the Bay. Shop and dine along the town’s Main Street or charter a boat for an unforgettable Bay tour. The Upper Bay Museum preserves the hunting and fishing history of the area, while Elk Neck State Park offers camping and hiking nearby.
20 North Beach
Nicknamed the “Jewel of the Chesapeake Bay," North Beach is hopping with things to do, like the free summer concerts, beach-side movies and Friday Night Farmers’ Market. For things to see, try the Classic Car Cruise-In, Bayside History Museum, or Wetlands Overlook Park. If you’re looking for something active, rent a kayak or paddleboard; take a walk on the seven blocks of waterfront; hook bait at the public fishing pier; or bike on the half-mile-long boardwalk with bike path. Did we mention there’s a beach, too?
21 Havre de Grace
Just a short drive from Baltimore, where the Susquehanna meets the Chesapeake, Havre de Grace is full of history, shopping and things to do. Directly across the street from the Concord Point Lighthouse sits the home of its first keeper, John O’Neill—appointed to this position as a thanks for his brave actions defending Havre de Grace during the War of 1812. Stroll the Promenade boardwalk next to the lighthouse for a lovely view of the water. The area also contains decoy and maritime museums, and a Main Street full of antiques shops and stores.
22 Watermen Heritage Tours
Get a different view of the Bay, from the people who live and work on the water. The Watermen Heritage Tours program was designed to supplement the earnings of watermen in the face of the declining fishing industry. Trained guides will take you out on their vessels for crabbing demonstrations and oyster tonging, or just to show you the Bay as they know it.
More about Watermen Heritage Tours
716 Giddings Ave, Suite 42
Annapolis, MD 21401
23 Fort McHenry
Maryland children are schooled at an early age on the facts of the War of 1812, not just because it was America’s “second war of independence” but because of Baltimore’s pivotal involvement in it. Shortly after the British burned the U.S. Capitol and White House, they marched 4,500 troops into Baltimore and sent their warships to attack Fort McHenry and other harbor locations. For 25 hours, British ships bombed Fort McHenry but its defenders would not surrender. The British fleet left in defeat and we raised our Star-Spangled Banner at the fort. Francis Scott Key, a witness to the events, even wrote a song you may know about it (hint: it’s our National Anthem). Learn more about Baltimore’s part in this historic event with a visit to Fort McHenry, where you can help fold the flag at the end of the evening and look out at the harbor as the brave defenders did.
More about Fort McHenry National Monument & Historic Shrine
2400 E Fort Ave
Baltimore, MD 21230
24 Baltimore's Inner Harbor
Baltimore's crown jewel is best experienced from the water, via charter boat or water taxi. If you bring your own vessel, try to time it when one of the concerts is performing at the MECU Pavillion (formerly Pier Six Pavillion) on the harbor—boats idle outside to catch the performances. Grab a drink at the tiki barge and take a picture of the iconic Domino's Sugar sign, while ships unload their sugar cargo and the wafting aroma of molasses drifts across the water.
25 Fells Point, Baltimore
Fells Point is a hip neighborhood of bars, restaurants and row homes that hosts visiting ships and markets in Broadway Square. Called a “nest of pirates” by the British during the War of 1812, Fells Point was once a shipbuilding powerhouse. Now you can prowl the Belgian block-stone streets and waterfront bars without fear of waking up in a privateer schooner miles from land (mostly).
More about Fell's Point Visitor Center and Gift Shop/The Preservation Society
History & Heritage
1732 Thames St
Baltimore, MD 21231