History & Heritage in Cambridge, MD

Cambridge, Maryland is full of amazing history. We have a number of events and resources to help you learn more about our past.


Downtown Commercial Architecture

Cambridge boasting some of the Eastern Shore’s greatest collection and density of commercial structures. We’ve created this Walking Tour Brochure to help you exploring the businesses and architecture that make up the downtown commercial district.

(PDF) Downtown Walking Tour Brochure


Walking Tours, Skipjack Sails, Heritage Festivals!

What better way to learn about the history and heritage of downtown Cambridge then to take part in a historic walking tour, heritage festival, or a skipjack sail?

Nathan of Dorchester Skipjack sails, cruises, & charters

Choptank River Lighthouse – features self guided tours and special exhibits

Historic High Street Walking Tour – 11am, every Saturday, April – October (Weather Permitting) West Ends Citizen’s Association hosts regular walking tours of our historic High Street. Do you know Napoleon’s involvement in Cambridge? Have you heard about the prominent lady who returned from the dead? Do you know which house was cut in two on High Street? Have you heard of the “Affair of Honor” which involved two High Street gentleman in a duel? Do you know how FDR changed the landscape of Long Wharf? Do you know who was involved in business conducted on the steps of the Dorchester County Courthouse? A tour will answer these questions and more. 1 hour. Call 410-228-1000 for more information.

Cambridge Ghost Walks – Take a walk down Haunted High Street in Historic Cambridge. Notably the most haunted street on the Eastern Shore.  Hear about the ghosts who haunt and strange events that have happened in just a few short blocks.  Soldiers, Governors, jilted women, Oystermen, an eccentric cat lady, a dying daughter, slain war heroes, suicidal bankers, murderous merchants, laughing children and a one-legged sea captain are some of the spirits that hang around High Street.

Local History / Heritage Festivals:


Choptank Heritage Skipjack Race – September each year

Schooner Rendezvous – In October each year

Downtown GrooveFEST – Third Saturday in September each year

Taste of Cambridge – Second Saturday in July each year

Pine Street Businesses and Cambridge’s Civil Rights History:

Spearheaded by the group Eastern Shore Network for Change, Cambridge has begun to highlight the history of the downtown African American business and residential community prior to 1967, and also have a community conversation about the Civil rights era and its legacy today. Here are some reading resources to help you get started learning about our city’s African American heritage:

Dorchester Banner Article – July 2017 – “Revisiting Up Pine Street and Civil War on Race Street”

“Civil War on Race Street” Book by Peter Levy (2003)

Eastern Shore Network for Change – visit their website

Pine Street is also where Cambridge got it’s kick name “Groove City”, when top name acts would visit Cambridge to perform at the height of the local Cambridge canning and preserving economy.

Harriet Tubman & the Underground Railroad:

The history of Harriet Tubman and slavery can be found and explored in downtown Cambridge. To learn more about the role of places like the County Courthouse, Long Wharf and historic High Street, visit the Harriet Tubman Museum (located at 424 Race Street) or the Underground Railroad State Park Visitor Center (located in nearby Church Creek, MD area).

Harriet Tubman Underground Railroad Byway

Byway Driving Guide Booklet (PDF)

Harriet Tubman Museum & Educational Center (Race Street)