Dorchester County, on Maryland’s scenic Eastern Shore, is home to one of the oldest communities in the state. I am, of course, referring to Cambridge—the County Seat and Dorchester’s largest municipality. As the fourth most populous city in that part of the region (just after Salisbury, Elkton, and Easton), this quaint, colonial community, located right along the Choptank River, boasts several classic callouts. From its vast and versatile history to numerous notable attractions and heritage sites, Cambridge boasts many claims to its credit. For this Flashback Friday Feature, I’m sharing the overall story of how Cambridge came to be and its most significant developments through the years.

Early Settlements
The Choptanks (also known as Ababco) were the first to inhabit the area that now comprises the greater Cambridge area and the lower Choptank River basin. This also includes Talbot and Caroline Counties as well as Dorchester. The Choptanks were an Algonquian-speaking Native American people—a subdivision of the Nanticoke and the only indigenous people on the Eastern Shore to be granted a reservation in fee simple by the English colonial government. This occurred after the colonists arrived, of course.

It was in 1684 that the first settlers came here, making this one of the oldest colonial cities in the state. The first permanent settlers were largely of English descent, which explains the city’s adoption of the name “Cambridge.” Cambridge, Maryland, however, wasn’t formally incorporated until 1793, well after the American Revolution and the winning of independence.
During the colonial era, the English colonists who settled here thrived through farming practices that were common along the Eastern Shore. Large plantations emerged, mostly focusing on tobacco originally. Over time, a series of alternate mixed farming practices were added to the mix.

Deep-Rooted Racial Matters
With diversified farming practices came the need for more labor. That led to Cambridge residents relying more and more on enslaved people working the fields and plantations. As a result, Cambridge emerged as a well-known regional trading center.

Interestingly enough, with the institution of slavery being such a big deal here, Cambridge also would go on to be a major stop along the Underground Railroad, with many networks of safe houses established all around the region. The one and only Harriet “Moses” Tubman herself, a native-born Dorchester County resident, would be instrumental in helping fellow freedom-dreaming slaves escape the area via such meticulous methods.

Racial matters would go on to play a key role in the community long after the American Civil War, lasting more than 100 years. Throughout the 1960s, Cambridge was a hub for ongoing riots and social protests surrounding the Civil Rights movement. The atmosphere finally cooled following the formal end to segregation in the nation.

Industry Milestones
Cambridge came to be regarded as an area of commerce throughout the late 1800s. The focus centered around food-processing industries specializing in the canning of oysters, tomatoes, and sweet potatoes. It was through their partnership with the Phillips Packing Company that they shot to fame. Phillips would go on to be the region’s largest employer.

At its peak, as many as 10,000 people were employed by Phillips. The company’s success continued well into the first half of the 20th century, before changing tastes and waning demands led to the Phillips Company ceasing local packing operations in Cambridge.

By the 1960s, mounting unemployment led locals to get creative. Many discovered new niches and reinvented themselves as small business owners. So, out of the ashes came new opportunities that would drive the charming, small-town, idyllic coastal vibes that would eventually define the Cambridge we all know and love today.

A Historical District is Formed
As time passed, folks took notice of the need to preserve Cambridge’s rich architectural heritage and historic landmarks. Small efforts were made throughout the 1980s by a small group of citizens committed to the cause. This eventually resulted in the creation of the Cambridge Historic District, which was then added to the National Register of Historic Places.
The Historic District primarily comprises Downtown Cambridge, extending northwest along the waterfront to include portions of Wards 1, 3, and 4. It encompasses a grand total of 40 city blocks and includes myriad buildings, structures, and homes.

In 2003, Cambridge was officially designated a Maryland Main Street community. Then, in 2013, the community was honored as one of the “Top 10 Best Small Towns in America” by Livability. A year later, Cambridge was declared one of the “12 Places to Visit in Small Town America” by viraltravel.com.

Major Area Attractions and Sites to Explore
You’ll never be bored visiting Cambridge today, with so many area attractions and sites to explore. Both the aforementioned historical callouts and newer endeavors are yours for the taking!
Among the historic sites, these top contenders take the cake on the bucket list: the Brinsfield I Site, Cambridge Historic District, Wards I and III, Christ Episcopal Church and Cemetery, Dale’s Right, Dorchester County Courthouse and Jail, Glasgow, Goldsborough House, LaGrange, Annie Oakley House, Patricia (log canoe), Pine Street Neighborhood Historic District, Rock Methodist Episcopal Church, Stanley Institute, Sycamore Cottage, and Yarmouth. Other must-see stops include the Blackwater National Wildlife Refuge, Choptank River Lighthouse, Harriet Tubman Museum & Education Center, and the Richardson Maritime Museum & Boatworks. And as always, in addition to these, there are plentiful other venues worth exploring.

From its storied past to its promising future, considering a detour to Cambridge will not disappoint. Rather, it will inspire and motivate you immensely—I guarantee. Discover it for yourself, you’ll see what I mean.