August 11, 2023

Road trip around northern Chesapeake Bay via Bay Bridge

Katie and Gene Hamilton

Bring Binocular News

Visiting Annapolis, Baltimore, Harve de Grace, North East, Chesapeake City, Chestertown, Rock Hall and Kent Island via Chesapeake Bay Bridge


To take this trip around the northern Bay you have two choices depending on your starting point. Either route will take you to some wonderful Maryland destinations on the shores of the Chesapeake Bay.

  • West to east: Take the Chesapeake Bay Bridge going north and east from Annapolis on the western shore around the top of the Bay.
  • East to west: Begin the trip loop at Kent Island on the eastern shore going north and then southwest to the western shore.


Our favorite Annapolis restaurant is Chick ‘n Ruths, a diner with a décor unchanged since the 1950s. Black and white photos of old politicians line the yellow and orange walls where at 8:30 a.m. (weekdays) 9:30 a.m. (weekends) everyone from dishwashers to diners stand and say the Pledge of Allegiance.  

The charming waterfront town of Annapolis sits on the shores of the Severn River just south of the Chesapeake Bay Bridge. To many the Maryland capital city is most known as the home of the U.S. Naval Academy. For the past 50 years boaters of all stripes know Annapolis as host to the October Powerboat and Sailboat Shows.  

Century old brick sidewalks line the streets with eclectic (read pricey) retail shops, restaurants and lodging. A sculpture of Kunta Kinte, made famous by Alex Haley’s Roots is centered on the roundabout at the harbor with showoff boats lining Ego Alley and a collection of tour boats.

Our favorite Annapolis restaurant is Chick ‘n Ruths, a diner with a décor unchanged since the 1950s. Black and white photos of old politicians line the yellow and orange walls where at 8:30 a.m. (weekdays) 9:30 a.m. (weekends) everyone from dishwashers to diners stand and say the Pledge of Allegiance.  

The Banneker-Douglass Museum  Banneker-Douglass Museum ( on Franklin Street pays tribute to Black Heritage with an impressive collection showcasing cultural diversity in and around Annapolis.

Just across the Spa Creek bridge Eastport is a small community of sailors and marine services and more good eating options.  A relatively new arrival is Forward, a craft brewery favored by many. Every year residents from Annapolis and the Maritime Republic of Eastport have a just-for-fun Tug of War across the bridge to determine their independence.

Sidetrip: Smithsonian Environmental Research Center

You’ll find 2,800 acres of forest, pastures, cropland, wetlands and tidal marshes just 10 miles from Annapolis in Edgewater on the shores of Rhodes River. Outdoor enthusiasts can download trail maps of the Contee Farm for walking, hiking, biking and birding. To get on the water pick up a canoe/kayak trail guide. Follow this link to learn more about the Smithsonian Environmental Research Center

Annapolis to Baltimore MD, Charm City

It’s about 30 miles going north from Annapolis on Route 50 to Baltimore. It takes you on a string of highways that lead to Charm City, home of sports teams like the Baltimore Ravens (M&T Bank stadium) and the Baltimore Orioles (Camden Yards), both with prominent parks you’ll pass by entering the city. This is a city surrounded by an Inner Harbor, a popular shopping, eating and entertainment center; it’s also a delightful place to walk along the harbor and take in the sights.

Getting around B’more by bus and boat

The best way to get around Baltimore is using their circulator bus called the  Charmcitycirculator. Get on and off at will and avoid traffic and parking. To get an overview of the city and harbor take a ride out to Fort McHenry known for the battle defending Baltimore Harbor against the British Navy in the War of 1812.

The harbor water taxi is another way to see Baltimore and avoid traffic. You’ll find information about the routes and everything you need for a visit at

Begin at the Baltimore Visitor Center in the heart of the Inner Harbor to learn all the places to visit. Two of our favorites are nearby: the American Visionary Art Museum ( and the The Maryland Science Center ( You’re a few blocks from Camden Yard and the National Aquarium.

A short drive from the Inner Harbor is another of our favorites, the B&O Railroad Museum in Mount Clare, a nearby neighborhood. You can park your car and take a walk through an amazing collection of a vintage railroad station, trains and equipment and go aboard the Mile One Express for a ride.

We found an interesting set of self-guided tours at the B&O Museum, one entitled Rail Trails “From Slavery to Civil Rights”. It explained the role of Pullman Company providing meaningful jobs for porters and porterettes while earlier the American railroads, especially in the South, used enslaved people to build them.  

Baltimore to Harve de Grace MD  “Decoys at their finest”

Havre de Grace, some 36 miles north of Baltimore is in Harford County on the shores of the Susquehanna River where the river meets the Bay. The charming historic town is on the far northwestern reaches of the Bay off of Hwy 40. Harve de Grace is known for its connection with decoys created by local artists and carvers of ducks and waterfowl, many who are featured at the Havre de Grace Decoy Museum.

Nearby is the Maritime Museum on Lafayette Street, a familiar name in our early history. Legend says the Marquis de Lafayette gave the town its name when he was leading French Troops there and named the town after the French port city Le Harve. Today the moniker is often shortened to HdG.

At the Visitors Center on Pennington Avenue pick up a self-guided tour and follow the numbered medallions embedded in the sidewalk. The Lafayette Trail is a 3-mile loop through the streets of HdG’s National Register Historic District, a nice way to explore the architecture of the town. the city now offers a trolley service “The Tide” to get around town. Or take a stroll on The Promenade, a boardwalk along the Susquehanna River passing museums and the Concord Point lighthouse.

Explore Havre de Grace | Official Havre de Grace Tourism Website is a good source of visitor information.

Harve de Grace to North East MD and the Covered Bridge

Heading northeast from Harve de Grace on Route 40, aka Pulaski Highway, you cross the Susquehanna River and parallel Interstate 95, a major connector between Philadelphia and Baltimore. On Route 272 you’ll pass the charming old Gilpin’s Falls covered bridge near I-95 where it sits along the main roadway spanning Northeast Creek. The historic landmark is a 119-foot single-span burr truss bridge, the longest covered bridge in the state of Maryland. The bridge was originally built in the 1860s and over the years has been renovated and cared for by volunteers. 

To reach downtown North East turn off Route 40 on Mechanics Valley Road which splits into a one way Main Street leading into town. We found a walkable downtown with a nice smattering of antique and kitchy shops, restaurants and churches, a popular day trip and for weekenders.

The community park has a waterfront with walking paths, playgrounds and restrooms and the Upper Bay museum about preserving the lifestyle of the waterman and hunter of the Upper Chesapeake Bay. Beyond town is Elk Neck State Park, with the Turkey Point Lighthouse and North East beach area for swimming access to the Susquehanna Flats of the Chesapeake Bay.

North East to Chesapeake City MD, the canal city

From the far north of the western shore of the Chesapeake drive Hwy 40 across the top of the Bay for less than 30 miles, and then turn south to Chesapeake City on the eastern shore. Chesapeake City is currently the only town in Maryland that is situated on a working commercial canal. Most of its interesting 19th-century architecture remains intact, and the area that encompasses it on the south bank has been placed on the National Register of Historic Places. As early as the 17th century, local settlers recognized the possibility of connecting the Chesapeake Bay with the Delaware River. Making a land cut and building a canal would lower the distance substantially.

We’ve anchored or tied up at Chesapeake City many times using the canal so we enjoyed visiting by car to see more of the area. Today the town has the original brick streets and buildings converted to inns, B&Bs, restaurants and retailers with a variety of goods. The canal city has been discovered, especially by weekenders, since it’s an easy getaway from Baltimore and Philadelphia and points east.

A marina sits on the shore across from north Chesapeake City, a short ferry hop  away. You can sit anywhere along the shore and watch ocean freighter traffic and boaters steam across the canal. You can bike, hike, run or walk on the 17-mile Ben Cardin C & D Canal Trail at the foot of North Chesapeake City’s Lock Street, adjacent to the town Ferry Dock.

Chesapeake City to Chestertown MD, a river city with a college

It’s about 30 miles run from Chesapeake City to Chestertown, the home of Washington College. It’s a hip historic town just off Route 50 on the eastern shore not far from Philadelphia (a 2-hour drive) and points east. You find nice shopping opportunities, good restaurants in town and on the riverfront, all with a strong sense of its place in history in a budding United States.

The Visitor Center is on the corner where Route 213 intersects with U.S. 50 and a good stop before entering town. You’ll find information about Chestertown and the surrounding areas at Visitors – Town of Chestertown.

Side trip: Rock Hall MD

Rock Hall, just 12 mile south of Chestertown, on MD 20 is a charming waterman’s town, long a boater’s stopover because it’s just across the Bay from Baltimore.  Marinas, B&Bs and restaurants line the harbor shoreline. fishing minded community with a trailerable boat in many of the homes. Just north of Rock Hall town harbor you’ll find expansive development with waterfront inns, properties with marinas, restaurants and rental homes and cottages on the Bay. There’s a little beach, too. The town website has information on all that Rock Hall has to offer .

Chestertown to Kent Island MD and the Bay Bridge

It’s an easy 45-mile drive south from Chestertown on Route 213 where you’ll pass through bucolic farmlands, busy subdivisions and shopping centers leading to the eastern end of the Bay Bridge at Kent Island where it crosses the Bay to Annapolis on the western shore.

Chesapeake Heritage and Visitor Center on Kent Island (exit 41 from Rt.301/50) is temporarily closed while undergoing renovations.

For birding, walking trails and kayaking in the area go to the Chesapeake Bay Environmental Center in nearby Grasonville. Also go to Terrapin Park by heading west on 301/50 and take the Stevensville Exit for a sandy beach area that overlooks the Chesapeake Bay and Bay Bridge.

​Another good choice is Matapeake State Park which sits on the Chesapeake Bay on the southwest side of Kent Island and has a dog park and swimming beach. ​

To fish from a dock, take the last exit before crossing the Bay Bridge toward the Romancoke Fishing Pier and Kayak Ramp. For printed travel guides and maps of the area you’ll find them at most hotels and restaurants in the Kent Narrows area. 

For a Kent Narrows Travel Guide and map click on line.  

Related Articles

Unpublished Content
April 26, 2024
Unpublished Content
March 1, 2024
Unpublished Content
December 30, 2023
Unpublished Content
December 21, 2023
Unpublished Content
October 16, 2023