Historic Cambridge is located on the Choptank River in Dorchester County, MD. The town is named after the slightly more famous city in England. Cambridge is just a bit off the typical well-traveled path of Chesapeake Cruisers. The trip will take you about 16 miles from the Bay proper, mostly headed east on the Choptank River. Trust us, it is well worth the diversion.

The Choptank River Lighthouse.


Colonists from England settled here beginning in 1684, making it one of the oldest colonial cities in Maryland. These colonists essentially initiated farming on the Eastern Shore—tobacco at first and later a broader mix of crops. The town became a bustling seaport, a nexus for the export of crops and import of goods to build the region.

Over time, the town pier was also a center for slave trading, a history you can learn more about by following the historical markers through the town center. Cambridge became a stop on the Underground Railroad and had an extensive network of safe houses for enslaved people escaping to the north.

Harriet Tubman, born nearby, escaped slavery and became a “conductor” on the Underground Railroad. She led enslaved people to freedom before the Civil War, all while carrying a bounty on her head. She was also a nurse, Union spy, and a women’s suffrage supporter. You should definitely plan to visit the Harriet Tubman Museum and Education Center, a short walk from the marinas.

You should definitely plan to visit the Harriet Tubman Museum and Education Center.

James Michener lived off the Miles River in nearby St. Michaels when he wrote his epic novel, “Chesapeake.” Cambridge was the inspiration for his fictional town of Patamoke, which he placed opposite Cambridge’s actual location.


There are two large marinas behind a shared breakwater as you come upon Cambridge. The always welcoming Cambridge Yacht Club is to starboard as you enter the breakwater. The Cambridge Yacht Basin is to port and includes a fuel dock. Slip reservations for both can be made on Dockwa.

Down at the end of Cambridge Creek is the Generation III Marina. They have a handful of transient slips, but the real attraction is the mechanics and craftsmen on site. Add to that the Yacht Maintenance Company and Mid-Shore Electronics, also on Cambridge Creek, and you can get almost anything old or broken on your boat replaced or fixed. 

And we can’t forget the Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina (see sidebar below for more details).

As you walk from the marinas to town via High Street you will walk past many stately homes.

In Town

From any of these mooring locations, you can easily walk into town. Now the fun begins!    

As you walk from the marinas to town via High Street you will walk past stately homes that were most assuredly initially built by the sea captains who made a home in Cambridge. You can almost hear the celebrations as they return from a long sea journey.

Besides the Tubman Museum, you will find an abundance of historical markers that will deepen your understanding of Cambridge’s place in our local history. The town is also blessed with several murals, all part of the Chesapeake Mural Trail in Dorchester County.

The Richardson Maritime Museum, also along High Street, was founded in memory of Capt. James B. Richardson, a prominent local boatbuilder. The historical record will show that “Mr. Jim’s” boatbuilding skills helped Cambridge transition from seagoing trade to a boatbuilding center. 

Downtown Cambridge has shops of interest and maybe a dozen places to find sustenance, or a beer. 

Sadly, the museum is temporarily closed. A transitional museum display is expected to open to the public in early 2024 and will be worth a look. Check their website for news of the reopening. 

Downtown Cambridge has shops of interest and maybe a dozen places to find sustenance, or a beer. As in any town, some restaurants come and go, the natural order of rejuvenation. If you have not been there recently, there are likely new restaurants to experience.

On our last visit (October 2023), we discovered Thaitalian Infusion Cuisine. As it sounds, the fare is Thai and Italian. The owners and operators are a Thai and Italian couple. We can’t opine as to the level of fusion in the food choices. The folks at our table mostly ordered traditional Thai or Italian favorites. All around the table were happy with their choices!

It is the kids of the owners who are the real fusion. We met a smiling and engaged son and daughter working the tables. Their banter with the diners and each other left it clear that they were having fun working with each other and their mom and dad on a busy Saturday night. 

Historic Cambridge is located on the Choptank River in Dorchester County, MD. 

Ava’s Pizzeria, a branch of the well-known St. Michael’s eatery, has now moved to the former location of the High Spot restaurant. This gives them more room to serve and the opportunity to add a “wine bar” to their name.  

Did I mention ice cream? Since no cruise is truly complete without ice cream, let me assure you that yes, you can find ice cream in Cambridge. Harriet’s Homemade Ice Cream & Cakes and T’s Divine Sweets & More, both on Poplar Street, can make it happen for you.       

For a little take-home taste of the Bay, we suggest you stop at J. M. Clayton Company. They are known for their freshly caught seafood, especially their freshly handpicked jumbo lump crab meat called Epicure. In our opinion their jumbo lump crabmeat is the best on the planet. The Company was founded in 1890 by Captain John Morgan Clayton (known as Captain Johnnie) and has remained in the family for four generations. This is the oldest working crab processing plant in the world.

Cambridge is home to RAR Brewery.

Now, about that beer…  Cambridge is the home of RAR Brewing. Turning left as High Street meets Poplar Street you will find RAR in an 80-year-old former pool hall and bowling alley.  Founded in 2013, RAR brews 10 barrels at a time in this brewery, tasting room, and pub.

We can’t resist a word about craft brewing here. By the end of 2022 there were an amazing 9500 craft breweries in the U.S. Craft brewers had retail sales of $28.4 billion. That accounted for 24.6 percent of the total U.S. beer market. This buildup of craft brewers began in earnest in the early 2000s and RAR was a little ahead of the pack. (For more on Chesapeake Bay microbreweries watch for the August issue of PropTalk.)  

When it comes to Cambridge the expression: “the juice is worth the squeeze” comes to mind. Yes, especially for a slower boat, the trip up the Choptank may be a bit of a reach. But the visitor who makes the trek will be richer for the effort.    

By Mike Pitchford, Sue Mikulski, and Joe Jackins

Hyatt Regency Chesapeake Bay

By Mike Pitchford

The Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina is a destination unto iteself. Photo courtesy of Hyatt

There is a totally different but equally pleasing experience to be had in Cambridge. If you are looking for a relaxing resort, maybe a little golf or a spa visit, the Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina beckons.

The resort is a long walk to downtown, maybe three miles. But why leave? It offers three pools (one indoors), the 18-hole River Marsh Golf Course, and the Sago Spa. There are seven places to get a bite to eat from fine dining to grab-and-go. 

f you are bringing kids with you, they offer a particular advantage. You can drop the kids off for a full-day camp and enjoy a little adult time to take advantage of the golf course or spa.  

You can easily secure the boat in their 150-slip breakwater-protected marina. Stay on the boat or opt for one of their 400 rooms and suites. They book slips via Snag-A-Slip. All boaters who dock their boats overnight at the marina gain access to all of the amenities of the resort, so snag your slip and make the best of their 342 acres of beautiful waterfront on the Choptank River.