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Kent Narrows Waterfront History Sampler Tour 

Welcome to the Kent Narrows Waterfront. This website hosts walking, cycling tour ideas for those who wish to learn more about this special place. Videos that are linked to the specific thematic experiences that are described in itineraries that describe historic sites and stories associated with the places here in on our waterfront. The tour outlined below is a good one to start with if you are new to the area. The Stories are told by locals who are well versed in our rich history.


Chesapeake Heritage & Visitors Center 

Starting Point and Main Attraction

425 Piney Narrows Road, Chester, Maryland


Ferry Point Nature Park

Main Attraction

Enter Boardwalk Trail behind the Visitors Center and walk to the Chester River


Watermen's Memorial Drawbridge

Landmark and View of the Working Waterfront 

The Drawbridge often opens for boat traffic. Here if you look to the left you will see Harris Seafood, Harris Crab House and Safe Harbor Marina. Look to the right to see Heritage Harbor (The public Marina where many of the fishing and workboats are docked.)


Cross Island Trail 

Continue on the Cross Island Trail and at the base of the bridge cross Rt. 18 (Main Street) to get to the Watermen's Monument.

This leg of the trail joins the Cross County Connector Trail (should you wish to enjoy that you can turn to the left at the bottom of the hill and take the trail towards the Holiday Inn Express. This trail ends at Long Point Park in Grasonville.


Maryland Watermen's Monument

Landmark and Memorial

Kent Narrows Way North and Rt. 18 (Main Street)

Kent Narrows Waterfront History Tour Sampler  


Locations: Piney Narrows Quadrant to Maryland Waterman’s Memorial / Wells Cove Quadrant

Point to Point Walking Time: 40 minutes (may be longer if the drawbridge is opened during your journey or if you chose to spend time on the beach at Ferry Point Park)

Getting here: Exit 41, off Rt.301/50 follow the brown signs to the Chesapeake Heritage and Visitors Center


What you will see and do:


This walking tour takes you to points around the Waterfront Kent Narrows Waterfront that have historic significance.


  • The Chesapeake Heritage and Visitors Center

  • Walk to Ferry Point Park and take in the views of the working waterfront

  • View from shore the Captain John Smith Water Trail (or bring a kayak to paddle along the trail or along other water trails in the area)

  • Pick up the eastern leg of the Cross Island Trail and travel over the Kent Narrows Drawbridge and view of the workboats at the Watermen’s Boat Basin at Heritage Harbor

  • Maryland Watermen’s Monument

Historically, the Kent Narrows is known as a place central to facilitating trade and a key link to the region’s transportation networks. It’s a place where those whose sustenance depended upon the water worked, traveled through and raised their families. Today, the region continues to directly support hundreds of water-related businesses and is rich with maritime heritage. So much has occurred is this place it is hard to condense it all into a few stories. The interpretative signs and places you’ll discover serve as introductions for further exploration.   


A system of water-based, land based and boardwalk trails connects most the points of interest. Some points may be reached by water trails and others by foot or bike. Many land based trails are wheelchair accessible. It’s best to call ahead to determine which trails will be the most accessible since weather conditions may affect our trails and access to them. The interpretative markers and key stops along the way are indicated on the Waterman’s Way Heritage Trail Map. The seven mile Cross Island Trail begins in the Kent Narrows area and links the peninsula to Kent Island.


Starting Point:

Chesapeake Heritage      

 and Visitors Center

425 Piney Narrows Road

Chester, Md, 21619


Climb the towers here for a spectacular view of the Kent Island Narrows, the working waterfront, Ferry Park and the Chester River. Inside is a small museum.


Public Parking and Restrooms Available. (An elevator is available at times when the Visitor’s Center is open. Call 410-604-2100 for hours of operation). 


There are several markers on the property in in front of the visitors center. Next to the flag pole you see a marker that discusses important roles the Harriett Tubman and Frederick Douglass played to abolish slavery in the United States. Many visitors to this area stop here as they prepare to visits the sites along the Harriet Tubman Underground Railroad Byway. For more information about sites along the byway please visit the State of Maryland’s byway pages:


To view Stories of Kent Narrows Videos in advance visit: and click on the Stories icon.


Be sure to pick up the Watermen’s Way Heritage Trail map before you go. The interpretative markers and historic features of the area are listed on the map. If the center is closed maps can be found in the clear plastic box in front of the center.


Boardwalk Trail to Ferry Point Park

Take the boardwalk trail to the Beach at Ferry Point Park. The 40-acre Ferry Point Park lies near the Chesapeake Heritage and Visitors Center on a peninsula bordered by Kent Narrows, the Chester River, and Piney Creek. A 530-foot boardwalk that takes visitors over the marsh onto a trail leading to open space, a wooded area, and a beach overlooking the Chester river.


Along the trail you will see native plants helping to create favorable habitat for wildlife. The interpretative marker at the beginning of the boardwalk trail tells the story of the Kent Narrows waterfront. Another marker looks over the Strait of the Kent Island Narrows and describes how a marshland was turned into the waterway it is today.


After you reach the beach you can imagine what Captain John Smith may have when he sailed past here and further up the Chester River to Chestertown, which is an hour away by car. Sultana projects in Chestertown is involved with managing the Chester River portion of the trail.


Once you arrive at the beach at Ferry Point take the path off to your right. You will be walking through a wooded area and the cove at Ferry Point will be on your right. Continue out to the water. The land mass directly across the river is the Eastern Neck Wildlife Preserve and the landmass to your right is Love Point.  Here you will find the Captain John Smith interpretative marker. Walk further for to see the pathway give way to a stunning view of the area of the place where the Chester River meets the Chesapeake Bay.


The Captain John Smith Chesapeake National Historic Trail travels nearly 3,000 miles across the Chesapeake Bay and it’s rivers. The trail was officially launched as part of the 400th anniversary of the founding of Jamestown, Virginia.


Should you wish to explore by water trail you may launch a kayak from Ferry Point or from the Kent Narrows Public Landing and follow along the same path as Captain John Smith.


The name Ferry Point came from the ferries that once crossed Kent Narrows to link Kent Island with the mainland.

During the late 1800’s steamboat powered ferry boats could be seen traffic traveling along this route.


Follow Walking Path

adjacent to Piney Narrows Road

Here you can see the many boats at Piney Narrows Marina Off to the left you will notice a waterway between Piney Narrows and the Kent Narrows Marine Boatel. During the boating season you may see the large lift at the Boatel in action. At the cross walk continue left along Piney Narrows Road to the next stop sign. (To the right you will see a sign marking the Cross Island Trail path. (Should you wish take a detour from this itinerary, you may venture along this path to see a view of the Piney Creek and the Chester River from the boardwalk trail that leads into woodlands.)


Walk under the US 50/301 Bridge

The bridge was recently dedicated in May of 2018 to R. Clayton Mitchell, III. Former Speaker of the Maryland House of Delegates. The Bridge was built in the early 1990s as part of the US 50/301 upgrades on the Eastern Shore. Turn right at the stop sign on Rt.18 and pick up the pedestrian/

bike path over the Watermen’s Memorial Drawbridge. This path is part of the Cross Island Trail, the American Discovery Trail and the Chesapeake Country Scenic Byway.

Cross the Waterman’s Memorial Drawbridge (Lat / Lon: N 38° 58.230' / W 076° 14.822')

As you walk over the bridge and look to the left you will get a glimpse of Heritage Harbor, Watermen’s Boat Basin. About 80% of the boats berthed here belong to watermen. As you reach the highest part of the bridge, look to the left toward Harris Crab Seafood and catch a glimpse of the Working Waterfront. Here you will often see the workboats delivering their fresh catches to the packing house.


The Waterman’s Memorial Drawbridge also known as the Old Kent Narrows Bridge opened in 1952 and is a well-known landmark. The Kent Narrows Development Foundation dedicated the Bridge as the Watermen’s Memorial Bridge to memorialize the hardworking Watermen that were and continue to be prevalent in the Kent Narrows area. The Bascule Bridge has a vertical clearance of 18 feet. From May 1-October 31 the Bridge opens on the hour and half-hour from 6 a.m. to 9p.m. From November 1-April 30 it opens from 6 a.m. to 6 p.m.


Star Spangled Banner Trail Marker

At the base of the bridge take the crosswalk over Rt.18 and follow the trail. Here you will see the Crossing Point historic marker that explains the significance of the area during the War of 1812. The marker is associated with the Star Spangled Banner National Historic Trail a program of the National Parks Service.


Maryland Watermen’s Monument

Cross over Kent Narrows Way South and to the Maryland Watermen’s Monument. The monument was constructed in 2003. It is dedicated to all watermen in the State of Maryland for their tremendous contribution to the State’s Seafood industry, culture and heritage. It pays homage to their unique way of life and legacy.


End your tour with a meal, a beverage, crab feast or ice cream cone!

Dockside dining is offered at Bridges, The Jetty, The Narrows, Fisherman’s Crab Deck and The Big Owl. Fisherman’s Inn offers traditional Eastern Shore fare. The Garden Grille and Bar is located at the Hilton Garden Inn. The Jetty offers popular bands on evening and on weekends year-round, while other restaurants and dock bars offer a variety of live music during the boating season. You can find ice cream cones and more dockside dining at Harris Crab House and Dessert First should you wish to turn on to Kent Narrows Way North. If you are interested in coffee or specialty beverage to go check out Dessert First.

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