Explore Annapolis, Baltimore, Harve de Grace, Chesapeake City, Chestertown and Kent Island
The Chesapeake Bay Bridge connecting Annapolis on the western shore and Kent Island on the Eastern shore in Maryland is an easy and exciting way to circumnavigate the northern Bay. We first discovered the small harbor towns and big cities on a sailboat in the late 1960s coming from Chicago. It was a long trip through Lakes Michigan, Huron and Ontario to the Welland and Erie Canals to the Hudson River and Atlantic and finally to Delaware Bay to the Chesapeake Bay we had read so much about. Once there we were enchanted by the Chesapeake and later settled on its shores for a lifetime of boating and traveling adventures.
Short Distance to Destinations that are Long on Charm and Maritime History
From wherever you begin and end this road trip, the Bay Bridge is only 4.3 miles across so you can enjoy a magical crossing watching freigthers, tugs, sail and powerboats enjoying the water.
Distance-wise, the destinations we highlight here are less than 40 miles apart.
Annapolis – Baltimore 33 miles
Baltimore – Harve de Grace 37 miles
Harve de Grace – Chesapeake City 22 miles
Chesapeake City – Chestertown 31 miles
Chestertown – Kent Island 39 miles
That’s a total of 162 miles that takes you on major and minor roads, up and down rolling hills, past farmlands and country homes, over rivers and streams and through some fascinating historic sites and towns. We’ve been roaming the roads on bikes, and in cars and RV for years, and invite you to come along for the ride.
Annapolis MD Capital City
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 (maryland.gov) on Franklin Street pays tribute to Black Heritage with an impressive collection of cultural diversity in and around Annapolis. It’s well worth a visit.
Eastport is a small community of sailors and marine services and more good eating options just across the Spa Creek Bridge. You’ll find a nice vibe at Forward, a craft brewery favored by many in the community. Eastport is unique and every year residents of the Maritime Republic of Eastport have a just-for-fun Tug of War across the bridge to determine their independence from Annapolis.
Baltimore MD Charm City
It’s 33 miles going north from Annapolis on Hwy 50 to Baltimore, which takes you on a string of highways that lead to Charm City, home of 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 surrounding the 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
The harbor water taxi is a good way to see Baltimore and avoid car traffic. You’ll find information about the routes and everything you need for a visit at https://www.baltimorewatertaxi.com/.

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 (avam.org) and the Maryland Science Center (mdsci.org). 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 borail.org 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.
Harve de Grace MD “Decoys at their finest”
Havre de Grace, some 37 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 Hwy 40. Harve de Grace is known for its superb connection of 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 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.
Chesapeake City MD Canal City
From Harve de Grace to Chesapeake across the top of the Bay on Hwy 40 it’s 22 miles. We’ve visited the city on the canal many times, by boat and car and watched it evolve. It’s 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 by making a land cut and building a canal to shorten the distance substantially.
You’ll see 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.
Sit anywhere along the canal shore and watch ocean freighter traffic and boaters steam across the waterway. 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.
Chestertown MD River City
The road winds 31 miles from Chesapeake City to Chestertown, a hip historic
Washington College town 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 Visitors – Town of Chestertown. is on the corner where Route 213 intersects with U.S. 50 and a good stop before entering town. Nearby you’ll see students on the grounds of Washington College.
For an easy side trip visit Rock Hall, just 12 mile south of Chestertown, on MD 20 and find a charming waterman’s town, long a boater’s stopover because it’s just across the Bay from Baltimore rockhallmd.com/ .
Kent Island MD East side of the Bay Bridge
It’s an easy 39-mile drive south from Chestertown on Hwy 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.

Kent Narrows, an area with marinas, watersport rentals, motels and seafood restaurants, is home to the Chesapeake Heritage & Visitors Center on Kent Island (exit 41 from Rt.301/50). This busy waterway is at the heart of Kent Narrows and the Visitors Center is a good stop to learn about the area. You can use the six-mile Cross Island Trail, a combination boardwalk and asphalt trail for biking, birding or just enjoying the lush wildlife of the area. You’ll find information to plan your visit at Kent Narrows.
The Hamilton are authors of Chesapeake Bay Road Trip and creators of
- The Drowning Lady in Annapolis Harbor
- Small Harbor Towns on Maryland’s Eastern Shore
- Boating Chesapeake Bay, NJ Shore to New York Harbor
- North Shore of Chesapeake Bay Puzzke
Gene and Katie Hamilton travel the U.S. extensively in search of a favorite place. They are members of the Outdoor Writers Association of America.
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