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Chesapeake, Va., is located just across the border from North Carolina. The town is steeped in the Confederate history so predominant in the South, but the area’s waterways made it a pivotal route on the Underground Railroad, providing safe travel and haven to escaped slaves whose stories also infuse Chesapeake’s history with a rally cry to freedom’s resolve. 

The Dismal Swamp’s dense, tangled thorns, muddy terrain, and enormous size enabled hundreds, maybe thousands, of escaped slaves to live here undetected. The Dismal Swamp Canal alternatively offered refugees passage to freer lands. Free African Americans settled several towns in the area, including Cuffeytown, whose origins can be traced as far back as the 1700s. African Americans who fought in the United States Colored Troops during the Civil War later founded a church in Cuffeytown and 13 of them have their final resting place there. 

Many more residents of Chesapeake enlisted and fought with USCT regiments and visitors to the area will find Civil War Trails markers interpreting their stories and those of other African Americans throughout the region. You can also pay homage at the Unknown and Known Afro-Union Civil War Soldiers Memorial, where Sergeant Miles James, a Medal of Honor recipient, is memorialized. According to his medal citation, on September 29,  1864, James distinguished himself at the Battle of Chaffin’s Farm. Members of the Chesapeake-based United States Colored Troops Descendants collected donations and placed the marker there.

E. Curtis Alexander, officer-in-charge of the 139-member group, said at its dedication, “I know this is Confederate territory, but we’re all Americans.”

Honor Roll, 1001 Bells Mill Rd.: The Unknown and Known Afro-Union Civil War Soldiers Memorial pays tribute to colored troops from the Chesapeake area who fought during the Civil War. Thirteen marble and granite grave markers include full names, dates of birth and death, rank, and company, including a marker for Sergeant Miles James, a Medal of Honor recipient. The marker for Sergeant Littleton Owens identifies his years of service in the Virginia House of Delegates. A flag on-site carries the names of the Virginia battles where those memorialized fought, including Wilson’s Wharf, Suffolk, Petersburg, and Chaffin’s Farm. The memorial is on the site of the Sergeant March Corprew Family Memorial Cemetery, which includes a marker and burial headstone for Corprew, who served as a member of Company I, 2nd USCT Cavalry. (Chesapeake Parks, Recreation & Tourism)


Superintendent’s House, 3500 Dismal Swamp Canal Trail: At the 5-mile mark along the Dismal Swamp Canal Trail sits the Superintendent’s House. It’s the only structure still standing on land once owned by the Dismal Swamp Canal Company. The structure is a 19th-century version of prefabricated housing. First constructed elsewhere, pieces of the building had Roman numerals making it easier to put back together. They were placed on a barge that floated on the canal. (Melissa A. Winn)


Historic Cemetery, 2216 Long Ridge Rd.: Thirteen African American veterans of the Civil War are interred in the Cuffeytown Historic Cemetery. They served in the 5th, 10th, and 36th USCT infantry regiments organized in 1863 and 1864. The 5th USCT, organized in Ohio in August 1863, fought in North Carolina as well as in the Virginia battles of the Crater at Petersburg, Chaffin’s Farm, and Fair Oaks. The 10th USCT was organized in Virginia in November 1863 and fought in 1864 at the Battle of Wilson’s Wharf. The 36th USCT, organized from the 2nd North Carolina Colored Infantry in February 1864, fought at the Battle of Chaffin’s Farm, the Appomattox Campaign, and in North Carolina. The 5th USCT was demobilized in North Carolina in September 1865, while the 10th and 36th USCT were ordered to Texas after the war and mustered out there in 1866. (Melissa A. Winn)


Cornland School, 2309 Benefit Rd.: This one-room schoolhouse was built in 1902 as one of the earliest efforts in Virginia to formally educate African American children after the Civil War. The school operated until 1952, and today the Cornland School Foundation is working to preserve and interpret the building and its stories. While the present building dates to 1902, an earlier school building built by freed slaves to educate their children is believed to have stood here or on land nearby as early as 1871. By 1885, official documents begin recording the names of the teachers in the school. (Melissa A. Winn)


A Great Little Battle, 1775 Historic Way: Visitors to the newly opened Great Bridge Battlefield & Waterways Museum can explore three miles worth of trails in the outdoor area of Great Bridge Battlefield Park to learn the story of African American soldiers who fought on both sides during this December 1775 battle. There are a dozen interpretive signs on the trail and a half dozen galleries in this inventive museum explaining this small battle with a big impact. The area’s waterways are also explored, including the importance of the Dismal Swamp for escaped slaves and its future standing during the Civil War. (Melissa A. Winn)


(Melissa A. Winn)


(Melissa A. Winn)