High Street - Cambridge MD
Eastern Shore

#14 Take a Walk Down High Street in Cambridge MD

High Street - Cambridge MD

Everyone who reaches the beach by way of Route 50 drives through Cambridge. It’s the town with the big sail on the building that sits at the base of the Choptank River Bridge. That landmark let’s the vacationer bound for the Atlantic beaches know there’s almost there – just one more hour in the car.

But it’s also a great place to stop for a break, but don’t stop at the fast food joints on the highway. Head into Cambridge’s historic district and take a lovely walk down High Street. It’s a wide brick-paved road lined with big trees and some of the most gorgeous architecture on the Eastern Shore.  It’s only a ten minute walk from Christ Church and the Courthouse to Long Wharf on the Choptank River. Parking on the street is easy and free.  Your little “off-the road” break could last twenty minutes or a few hours depending on what opportunities you take advantage of.  – Scenic walk … picnic by the water … shopping …have a meal in town.

High Street - Cambridge MD

After crossing the Choptank River Bridge, turn right on Maryland Avenue.  Go a until you cross the drawbridge that goes over the creek and then make a right at the light – which will be Academy Street.  Follow that to the next light and you will be at the intersection of Church and High Street.  Park anywhere on High Street and head toward the water (right if you’re facing Christ Church).  You’ll be strolling down one of the most beautiful – and haunted – streets on the Eastern Shore.

Christ Church on High Street, Cambridge, MD
Christ Church on High Street, Cambridge, MD

Cambridge is a Colonial town. In Colonial times when the British laid out a city they often formed a roadway that led straight from the waterfront to the highest point on the land, then called that road High Street. They’d often put the courthouse and the church (and the jail) at the crest of the High Street so they were protected from flooding.  That high spot became the center of town…. a center where one could get judged, punished and redeemed all on the same street corner.

christ church cemetery cambridge MD
Old Graveyard – Christ Church – High Street – Cambridge MD

Cambridge is one of two towns on the Eastern Shore of Maryland that follows this High Street layout.  The other is Chestertown in Kent County. The Town of Oxford also has a High Street, but it’s now a mere alley way.  Oxford never landed the courthouse (another story for another post). Cambridge’s High Street is brick paved and lined with stately old homes including the oldest house in Cambridge – and the oldest house “built” in Cambridge (not the same house as the oldest was built in Annapolis, then dismantled and brought by barge to Cambridge). Another interesting stop on High Street is the graveyard at Christ Episcopal Church.  Dotted with old Yew trees and evergreens, this graveyard is laid out in English style.  The oldest graves date back to the 1700s.  4 Maryland governors are buried there, a few congressman and many interesting inscriptions can be found on these old stones.

Oh … and the yew tree in the center of the front area – the one that has devoured the headstone of Ann Weller (died 1817) is said to to sing when the wind blows.  Very curious vibrations coming from that tree.

Governor Goldsborough's House
Governor Goldsborough’s House – High Street

The homes you see on either side of the street were homes for the elite class in Cambridge.  Some belonged to Maryland Governors, Senators and Representatives.  Others belonged to merchants, attorneys, sea captains and judges.  The sidewalks are shaded by mature Osage Orange and Sycamore trees.  This walk is lovely distraction from the madness of 2 to 3 hours driving on Route 50.

High Street ends at Long Wharf on the Choptank River where there’s an ample waterfront park ideal for walking, picnicking and taking in views of this most scenic river.  Long Wharf is also home to the Choptank River Lighthouse – a replica of an six-sided, screwpile lighthouse that stood near this spot in the early part of the 20th century.

Oldest House in Cambridge
Oldest House in Cambridge haunted by the floating soldier


If you get the sense that you’re “not alone” as you walk past all these gorgeous old homes, then you have a keen sense of the world beyond this one.  High Street is the most haunted street on the Eastern Shore with twelve house that have known associations with the paranormal.  Soldier spirits, ghosts of old sea captains, lawyers, judges, preachers, crazy cat ladies, children, pirates and women who died from broken hearts are all part of the folklore of Cambridge’s High Street.  There are even a few phantom animals that you may see making the walk with you.  If you like to know more about Haunted High Street, register for one of the Cambridge Ghost Walks held the fourth Friday of every month.

After a little respite at Long Wharf, retrace your steps and follow High Street back up to Christ Church.  Then keep on going until you come to Poplar Street.  Here you’re at the cross-roads of Cambridge’s Arts and Entertainment District with shops, galleries and wonderful restaurants.  Have a meal.  Stop in at the Dorchester Center for the Arts.  Visit some of the remarkable shops and chat with the merchants.  They are  all local people very committed to making Cambridge a destination for both locals and visitors.  You’ll feel very much at home.


Cambridge, MD 21613
For more information call City of Cambridge
Christ Church / Courthouse –  38.5720787, -76.0765732
HOURS: Residential – Churchyard open daily from dawn to dusk
ADMISSION: No admission – enjoy your walk

100 Things to Do Between the Bridge and the Beach

Every year millions of people cross a bridge to travel to the Atlantic Beaches on Delmarva. It may be the Chesapeake Bay Bridge, Chesapeake Bay Bridge Tunnel or a bridge over the Delaware Canal. They may be headed to Ocean City, Chincoteague, Rehoboth, Bethany, Dewey or Assateague, but most don’t know about the fabulous sites and attractions they are passing by. This series offers 100 fun things you can do between the Bridge and the Beach encouraging visitors to pull off the highway, take a day trip, and widen your vacation scope of activities – or make the Eastern Shore a destination when you’re not headed for the beach.



Leave a Comment

Your email address will not be published. Required fields are marked *