Travel Leisure

Cultural Experiences To Have Before Leaving Chesapeake Bay

The Chesapeake Bay is one of the oldest regions in the United States. The Jamestown colony was established in the Chesapeake Bay and it played a major role in pivotal moments throughout the country’s history. 

Today, the Chesapeake Bay includes six states along the eastern American coast. There’s plenty of things to see and do. However, to grasp the full impact the Chesapeake Bay had on history check out these cultural experiences in the region.

Drive The African American Heritage Trail 

Chesapeake Bay
Photo credit: Maizal Najmi

The self-guided African American Heritage Tour is a true cultural gem of the Chesapeake Bay. The tour takes visitors through miles of historic land where enslaved African Americans, abolitionists, and heroes redefined American history. Travelers will drive through sites highlighting moments from the Revolutionary War, the Underground Railroad, the Civil War, and more. Along the drive, you can listen to a companion podcast to follow along with the landmarks as you drive past. 

Tour The Maryland Lighthouses

lighthouses in Maryland
Photo credit: Mustafa Bodur

Along the eastern shore of the Chesapeake Bay, the Maryland lighthouses are interesting and unique. The state has 26 lighthouses in total. About a dozen sit along the Chesapeake Bay and can be accessed by land and sea. 

Many of these lighthouses, like Cove Point and Drum Point, can be found at the Calvert Marine Museum. The Hooper Strait Lighthouse is located at the Chesapeake Bay Maritime Museum and most lighthouses can be toured during certain hours. The Maryland lighthouses provide real insight into the experiences of lighthouse keepers and seamen throughout American history.

Explore The Maritime Museum

view of maritime harbor
Photo credit: mali maeder

The Chesapeake Bay Maritime Museum welcomes almost 100,000 visitors annually. Travelers can dive into the rich history of the Chesapeake Bay and the sea life surrounding the region. The museum spans 18 acres. Travelers will find historic lighthouses as well as exhibits about Maryland crab picking traditions, wildlife along the shore, and oyster harvesting. 

Bay History is on full display at this maritime museum and it’s not the only one. There are over a dozen museums throughout the Chesapeake Bay where travelers can learn about the region’s rich past along the water.

Experience The Art Culture In Chestertown

Travelers can walk the brick sidewalks of Chestertown for an array of arts and entertainment. The town sits on the banks of Chester Bay in East Maryland and has a blooming artist community. Chestertown hosts a few festivals throughout the year. The Chestertown Tea Party Festival happens annually during Memorial Day weekend. Visitors can watch a re-enactment of the Boston Tea Party as well as a massive beerfest. Each summer, the town also hosts a music concert series in the park. 

Grab Some Seafood In Cambridge

plates of shrimp
Phot credit: Oleksandr P

Cambridge has grown in popularity among traveling foodies. The Chesapeake Bay city has some of the freshest seafood on the East Coast making it the perfect destination for a seafood feast. Cambridge is home to delicious crab, oysters, fish, and more that travelers can’t get enough of. 

Beyond the delectable sea cuisine, Cambridge isn’t far from the birthplace of Harriet Tubman and there are many sites dedicated to her legacy. Travelers can visit the Harriet Tubman Underground Railroad Center and the Scenic Byway to learn more about her legacy in the Chesapeake Bay region.

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