Dog swimming with man on stand-up paddle board
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25 Can't-Miss Things to Do Along the Chesapeake Bay

By Chris Landers
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Dog swimming with man on stand-up paddle board
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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.

1
Great Chesapeake Bay Loop
Chesapeake Bay Bridge
OTD

Come and engage with Maryland’s Chesapeake Bay, the largest estuary in the United States and a place of serene beauty.  Breathe in her slightly salty air; taste the flavors of her fresh seafood bounty and farms that line her shores; enjoy her waterfront towns; talk to the locals, many of whom still have the accents of their ancestors who settled the area over 300 years ago; and feel the freedom of escaping land and being on her waters.

2
Annapolis
The Annapolis Sailboat Show is the largest and oldest in-water sailboat show on earth.
Annapolis Tourism

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.

3
Smith Island
A slice of the famous Smith Island Cake
Somerset County Tourism

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.

4
Chestertown
Chestertown Town Square Fountain
Town of Chestertown

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.

5
Oxford
Aerial View of Oxford

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.

6
Deal Island
Deal Island Harbor hosts this race each Labor Day Weekend. The event also features a fishing contest and delicious local food.

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. 

7
Chesapeake City
Colorful Houses along Bohemia Avenue in Chesapeake City
https://chesapeakecity.com/

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.

8
Thomas Point Shoal Lighthouse
Accessible only by boat, Thomas Point Shoal Lighthouse is one of only 10 in the country designated a National Historic Landmark.

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.

9
Chesapeake Bay Maritime Museum
Chesapeake Bay Maritime Museum
Courtesy of CBMM

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.

10
Cambridge
Cambridge A&E District
Dave Harp

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 and take a ride on the skipjack Nathan of Dorchester.

11
Hart-Miller Island
Hart-Miller Island State Park
VisitMaryland.org

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!

12
Dock Bars of the Bay
Enjoying crabs
Queen Annes County

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.

13
Tilghman Island
Boat on 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.

14
Hooper's Island
Hooper Island Lighthouse

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. 

15
Baltimore's Inner Harbor
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 Pavilion (Link) (formerly Pier Six Pavilion) 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.

16
Blackwater National Wildlife Refuge
Birds at 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.

17
Chesapeake Ship Graveyard
Mallows Bay Shipwreck

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.

18
Calvert Cliffs
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.

19
Captain John Smith National Historic Trail
Captain John Smith Trail at Piscataway Park
Accokeep Foundation

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.

20
Crisfield
Crab Capital of the World sign - Crisfield

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.
 

21
North East
Beaches, marshlands and wooded bluffs comprise this peninsula at the headwaters of Chesapeake Bay.
Mitch Lebovic

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.

22
North Beach
With such spectacular sunsets on the beach, you may miss that there's plenty to do in this town's history museums and nature parks.
Chris Williamson

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?

23
Havre de Grace
Lighthouse
Adam Rybczynski

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.

24
Watermen Heritage Tours
Waterman on boat
Dave Hawxhurst

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.

25
Fells Point, Baltimore
Baltimore has the foodie experience for you, whether it's local seafood or bombastic burgers and beer.
Visit 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).