A textbook example of everything best about the Bay

Let’s say you are putting together your ideal destination for a weekend getaway. You’ll want easy access by watercraft, whether it’s your own cruiser, paddle craft, or trailer boat. Cambridge easily checks that box, with its site on the Choptank River, its protected basin, and its own deep-water creek. Then, once you get there, you will want to be able to walk to practically everything, from one-of-a-kind restaurants to shops, a farmers’ market, and even special events like skipjack races. Cambridge has all of that. Then you will want this ideal location to be attractive, preferably with tree-lined streets and lovely old homes. Okay, Cambridge has all that too. What about a few museums to add perspective and context? Cambridge, of course. Finally, an ideal destination should have its heroes. You can tell a lot about a place by the people it chooses to honor. Here, Cambridge is at the top of its class. First, it honors watermen, in its murals and with its restaurants, artwork, and even the Richardson Maritime Museum. But there’s more. Harriet Tubman is also very much the hero of Cambridge. Tubman,  who was born and grew up just outside the city, escaped enslavement as a young woman and then risked her life to come back and save dozens and dozens of people. Here she is honored with a museum, stunning murals, and a national historic trail that traces her life and movements in Cambridge and through the neighboring Dorchester countryside. Yes, Cambridge ticks all the boxes.

Cambridge lies 13 miles up the Choptank River, just downstream of the U.S. 50 Choptank River Bridge. Also just downstream of the bridge, short but deep Cambridge Creek divides the town in two. Most of the old town, with its oldish buildings, newish restaurants, Long Wharf, as well as the municipal marina and yacht club, are located on the west side of the creek. Sailwinds Park and Visitor Center, Ruark Boatworks (part of the Richardson Maritime Museum), and plenty more businesses and restaurants can be found within a short walk to the east
of the creek. 

The Choptank waterfront to the west is lined with fine old houses, while the main part of downtown can be found a few blocks inland. If you walk up High Street, which begins at Long Wharf, and then turn left onto Poplar Street—which a block later becomes Race Street—you will find yourself right in the center of things. Gay Street, Muir Street, Muse and Academy streets are all here, and busy with restaurants, shops, the Harriet Tubman museum, murals, pocket parks and history.

 To explore the east side of town, cross the Cambridge Creek by way of the Market Street Bridge, which is off Muse and Academy. To get to the Hyatt Regency Chesapeake Bay and its marina, golf course, and restaurants, continue a mile and a half up the Choptank by boat, or by car take the exit off U.S. 50.

Although Cambridge is one of the earliest English settlements on the Chesapeake, the town—like many towns everywhere—was hit by several devastating fires during its long history. In addition, the African American neighborhood around Pine Street (which was once called Groove City because it attracted top jazz artists like Duke Ellington and Count Basie) was also very nearly destroyed during civil unrest in 1967. The town as a whole took an economic nosedive in the mid-1960s when Phillips Canning Company—by far Cambridge’s biggest employer—closed and thousands of jobs were lost. But during the decades that followed, the citizens of Cambridge worked hard to bring the town back with new businesses, museums, restaurants, and all the other things that attract happy visitors. And believe us, you will be happy when you visit Cambridge!

By boat

If you are coming by boat, all you need to do is to cruise up the Choptank River as far as green 25, the last marker before the U.S. 50 bridge, and then either head for Cambridge’s municipal yacht basin or find the markers 1 and 2 for the entrance channel to Choptank Creek. The other, equally delightful option is to keep going under the bridge (sailboats beware, the vertical clearance is only 50 feet) and dock at the Hyatt Regency’s marina. 

The entrance to the Choptank River is about 23 miles south of the Bay Bridge. It is then about 13 miles upriver to Cambridge. You can cut off a few miles by chancing the Knapps Narrows cut-through from the Bay to the Choptank. However, we strongly recommend that you call Knapp’s Narrows Marina first to get the latest advice on depths and route. Shoaling is a perennial problem, especially on the west side.

If you are coming from the Norfolk area, you’ll find the entrance to the Choptank about 100 miles up the Bay. Either Deltaville or Crisfield would make a good stop along the way. From Deltaville, the Choptank is about 65 miles. Alternatively, Mill Creek near the Great Wicomico River would make an easy anchorage.

By car

If you are coming by car, with or without a boat in tow, you will find Cambridge just off of U.S. 50. From the Baltimore area, it’s about an hour-and-a-half drive, using the Chesapeake Bay Bridge. From the Norfolk area, it’s a three-hour drive, taking the Chesapeake Bay Bridge-Tunnel and U.S. 13 to Salisbury, then U.S. 50 the rest of the way. 

There is an excellent launch area with plenty of overnight parking at the Franklin Street Boat Ramp. Here you’ll find two docks, four ramps, and even a breakwater to launch directly into the Choptank. Nearby Trenton Street Boat Ramp is much smaller but will launch you into Cambridge Creek. Neither requires a use permit. North of town, you can launch at the Gerry Boyle Park at Great Marsh boat ramp.

Cambridge Municipal Yacht Basin

If you want to stay at a marina during your visit and be within walking distance of nearly everything in town, your best choice is to take a slip inside the breakwater at the Cambridge Yacht Basin, now managed by Oasis. The farmers market and Long Wharf events, as well as the Choptank River Lighthouse, will be a short walk along Water Street. Plentiful restaurants, shops, and museums will be a little longer walk up High Street.

If the yacht basin happens to be full, you can try the Cambridge Yacht Club, which shares the basin with the city marina and usually has some slips that are open to visitors. 

Cambridge Creek

If you like the idea of anchoring out or tying up to the town’s free dock, follow the channel into Cambridge Creek, one of the Chesapeake’s deepest and a key reason for the town’s long success as a port. On the way in, you’ll pass Yacht Maintenance Company, which can fix anything on any size boat or ocean-going yacht, and then the turning basin. Here you’ll find J.M. Clayton Company Seafood, immediately to the right, and Snappers Waterfront Cafe next door. On the adjoining wall you’ll find the free bulkhead, behind several Dorchester County office buildings. There are plenty of cleats, but you’ll need to be very careful to protect your boat from the long bolts that stick out from the bulkhead in several places. If you prefer to anchor, be sure to allow plenty of room for J.M. Clayton’s crab boats and the boats coming and going from Snappers. If everything here is occupied, and you draft less than five feet, you can also try Generation III Marina, which is located at the head of the creek and sometimes has available space.

River Marsh Marina/Hyatt Regency Chesapeake

If golfing, spas, tennis, swimming, five restaurants, and a bar named Michener’s Library is more your cup of tea, then the marina at the Hyatt Regency (or the Hyatt Regency itself) is for you. Frankly, we’d be tempted to treat this one as a separate destination altogether, though it’s easy enough to get to downtown Cambridge from here.

By boat, simply continue under the U.S. 50 bridge (remember that 50-foot vertical clearance, though, all you sailboats and superyachts) to green 27. From there, point your bow south and you’ll see the marina’s breakwater. Here the entrance faces the downriver side. The marina has all the usual amenities, though they are a bit of a walk, and the added resort fee gives you access to everything the hotel complex has to offer—and that’s saying a lot!


We confess that this category nearly always sends us spinning in circles. Charming up-and-coming destinations like Cambridge naturally have a significant number of charming bed-and-breakfasts to choose from—so many that we can never manage to try them all. So here are just a few that we know we like. Let us know what you discover. 

We can categorically state that the elegant Albanus Phillips Inn in the Cambridge historic district is one of our favorites. This imposing Queen Anne Victorian was owned by one of the Phillips Packing Company scions, and numbers among its past guests both Teddy and Franklin Roosevelt (three decades apart,
of course). 

The circa 1847 Cambridge House Bed & Breakfast is nearby on High Street, not far from Long Wharf. It has six bedrooms, a lovely garden lily pond, and a hot tub. 

If you like delightful accommodations with a view of the Choptank River, then we’re pretty sure you’ll love Victoria Gardens Inn on Oakley Street. It’s convenient to everything, and you can wake to the unforgettable and very European scent of boxwoods in their garden.

Explore the waterfront

Before we venture into town, we’re going to start our exploration of Cambridge down along the shores of the Choptank River. After all, like many towns on the Chesapeake, the water dominated the Cambridge economy for several hundred years, both as food production and as transportation. This is where you’ll find the yacht basin, with the municipal marina and Cambridge Yacht Club. And it was here at Long Wharf that tobacco, tomatoes, and yes, agonizingly, enslaved people, arrived and left the town. Cambridge, with its deep-water creek, served as the main port for the surrounding area. 

Today, crab boats continue to pass by Long Wharf on their way into Cambridge Creek to J.M. Clayton Seafood, where some workers pick the crabs and others steam and can them. Clayton’s crabmeat continues to be sold proudly all over the country. 

Here too you can wander the farmer’s market every Thursday afternoon during the growing season and catch a ride on the town’s skipjack, Nathan of Dorchester.

Now walk out the marina dock nearest Cambridge Creek and you’ll find the Choptank River Lighthouse, built as a symbol of the town rather than as a warning of shoals. Step inside and you’ll see artifacts of the Bay’s lighthouse culture and get a good view.

One quirky thing before we leave the waterfront: As you walk through adjacent Long Wharf Park, look for a mysterious steel structure that looks rather like a disembodied smokestack from a small ship. Well, that’s what it
is…or is supposed to be. It is, in fact, a fake smokestack from Franklin Roosevelt’s presidential yacht Potomac. The fake smokestack actually housed the elevator Roosevelt had to use to go below; he was confined to a wheelchair but didn’t want people to know because he felt that would undermine their confidence in him.

Download some things on your phone

Boy, that sounds like fun, doesn’t it? No, seriously, you’ll like this. The Dorchester County Audio Tours app has cool content so you can learn as you explore. 

Take the Cambridge walking tour, for example. Oh, we know…ho hum. Wrong! We’ve flipped through a lot of walking tours in our time, but this one is at the top of the heap. (Besides, you’ll be walking into town anyway, so you might as well get more out of it.) The two tours on the app explain why you’ll find several old buildings only slightly bigger than a Barbie playhouse along the way. And it will make you shiver as you read the fraught history of the Dorchester County Courthouse. You’ll learn where sharpshooter Annie Oakley and her husband took their meals when they briefly retired to Cambridge. And you’ll learn about Groove City, the name given to the Pine Street neighborhood where, as we mentioned, jazz greats like Ella Fitzgerald, Count Basie, and Duke Ellington came to play.

Cambridge is not all cool old buildings and reflections of the past. It’s also where you’ll find some positively mind-bending murals, including the viral mural that depicts Harriet Tubman with her arm outstretched, which is on the Harriet Tubman Museum & Education Center on Race Street. The Dorchester County app has a guide that gives fascinating stories about all the murals on the Chesapeake Mural Trail. (You can save the ones not in Cambridge for other excursions.)Incidentally, inside Jimmie and Sook’s Restaurant on Poplar Street, you’ll find a wonderful mural by Eastern Shore folk artist Danny Doughty. You can find out more about Doughty in the Onancock chapter.

The last download we want to mention is for the Harriet Tubman National Byway driving tour. This app allows you to aim your phone at various stops along the way, such as the Bucktown General Store, and see what it might have looked like around 1850. At other stops the app uses holograms of reenactors to tell real stories of danger and terror. It’s really quite remarkable. Search your app store for Harriet Tubman Byway.

Experience the Harriet Tubman
Museum and Byway

After a Hollywood movie, Oscar-nominated song, and a new national historic trail, the full story of Harriet Tubman is deservedly and finally well-known. And Cambridge is the center for celebrating her extraordinary life. You can begin at the Harriet Tubman Museum & Education Center on Race Street and then, if you have come by car, follow the Harriet Tubman Underground Railway Byway. Use the app we mentioned above to enhance the experience. You can also download a map and the description of the route. We recommend that you begin your trip at the Harriet Tubman Underground Railway Visitor Center in nearby Church Creek. 

Visit the Richardson Maritime Museum
and Ruark Boatworks

Come here for a celebration of the Eastern Shore’s long and colorful history of boatbuilding. You’ll see the tools used in crafting the Chesapeake’s iconic watercraft, including the skipjack, pungy, and log canoe. The museum, which is housed in an old bank building on High Street, is named for one of the area’s best known boatbuilders, “Mr. Jim” James B. Richardson. Walk to the other side of Cambridge Creek to see today’s boatwrights building and restoring traditional craft at Ruark Boatworks on Hayward Street. 

Go Shopping

All right, now you can relax and go shopping before your brain explodes. Wander through downtown Cambridge to explore its wide variety of shops. We love the Blue Awning on Race Street and Sunnyside Shop on Poplar. Shoot, we love them all. You’ll find your own favorites here.

You’d better plan a long stay, because there are a lot of good choices in Cambridge. As usual, we are going to pick out a few of our favorites, but the rest is up to you.

Breakfast and lunch

Black Water Bakery

We know we should recommend the super-healthy quinoa bowl at the excellent Black Water Bakery on Race Street, but we usually fall victim to the chorizo tacos breakfast, or maybe the Green Giant Omelet, which is all about asparagus, gouda, and bacon. If we get up too late for breakfast, we start the day there with the curry chicken wrap. It doesn’t matter what you choose, it’s good. 

If you have a car, head out to Bay Country Bakery & Café on U.S. 50 for their doughnuts. Oh yes! π

Lunch and dinner

Jimmie and Sook’s Raw Bar & Grill

Jimmie and Sook’s on Poplar Street serves absolutely local seafood, made from absolutely local recipes. It’s delicious, it’s fresh, and it’s friendly. It’s also open for lunch and dinner. But it’s also about barbecue. What? Yes, it’s a husband-and-wife thing. And, honestly, what could be better? Nothing. Don’t miss it.

Bistro Poplar

We love Jimmie and Sook’s, but we confess that as often as not, we save it for lunch. Our dinnertime heart, at least on the weekends, belongs to Bistro Poplar. When we sit at the table, idly tearing apart our baguette and sipping on a crisp white wine while waiting for steak frites or scallops or other freshly prepared Mediterranean-Asian inspired dishes using local ingredients and seafood, we are transported to Aix-en-Provence or Avignon. We can’t help it. It’s lovely to be in Cambridge, but it’s sometimes also lovely to imagine you are in southern France. In brief, Bistro Poplar is a wonderful restaurant, on any continent.

Also terrific

Really, we’ve only scratched the surface here. And we’re not even off Poplar Street. While you’re here, don’t miss RAR Brewing. They make excellent beer (we are partial to the Nanticoke Nectar IPA) and offer a nice selection of food as well. Elsewhere, you’ll recognize Ava’s Pizzeria & Wine Bar and Theo’s Steaks, Sides, & Spirits from St. Michaels, so you know they are good. Try Blue Ruin for cocktails and small plates, and Canvasback Restaurant & irish Pub for food, ambiance and darts. And you can satisfy two urges at once at Docovino Wine Bar & Boutique. 

Finally, we are not going to leave this list until we remind you that the Hyatt Regency Chesapeake offers a choice of restaurants for every occasion. Take the Water’s Edge Grill, where you can get a very nice breakfast, lunch, or dinner. But when we’re at the Hyatt, we gravitate to Michener’s Library for its name, yes, and its books, but most of all for its two-story, all-window view of the Choptank River. And its very fine cocktails. And its billiards. We love billiards. ⚓️