Chesapeake: Waterways, Nature and History

On the banks of the Northwest River in southeastern Chesapeake lies Northwest River Park. This 763-acre park offers opportunities for boating, fishing and hiking year-round. If you’d like to combine time on the water with activities on land during your stay, you’ll find several options here in one place.

Nature Trails and Waterways

The Chesapeake Arboretum offers a different focus: a 51-acre “Nature’s Classroom” that promotes awareness of horticulture and the environment through exhibits, education and research. Its trail system covers about 45 acres and is around 3.5 miles long in total. Camellia Cove is also part of the arboretum experience: it is one of three locations in Virginia on the American Camellia Trail. Here, nature trails meet topics related to plants and the environment.

The Dismal Swamp Canal Trail accommodates a variety of activities: it is open to cycling, walking, running and hiking, horseback riding, and boating. Its northern trailhead is at 1246 Dismal Swamp Canal Trail in Chesapeake; from there, the trail runs 8.6 miles south along the Dismal Swamp Canal. By comparison, the arboretum has a trail system of around 3.5 miles. The different trail lengths and permitted activities can help you choose nature experiences that suit your plans.

The Great Dismal Swamp National Wildlife Refuge has a Portsmouth Ditch Entrance at 3457 Martin Johnson Road in Chesapeake. From there, you can access the Black Bear Trail. Check conditions before setting out. If you’d like to find your way around on the water, the free Paddle the Peake Passport can guide paddlers to local paddling waters and share information about their history and ecology. Small boats, kayaks or canoes can be launched at the Ballahack Boat Ramp. Elizabeth River Park, meanwhile, has a 144-foot pier for fishing and crabbing.

History Along the Canal and in Chesapeake

The Dismal Swamp was an important hub for trade, culture and history. The canal itself also has a special historical legacy: it is listed on the National Register of Historic Places and recognized as part of the National Park Service’s Underground Railroad Network to Freedom program. Interpretive signs at Great Bridge Lock Park explain the lock system. These places offer different ways to explore the history of the waterways—from their recognition as cultural heritage to how the locks work.

The Great Bridge Battlefield & Waterways Museum commemorates the site of the first American victory in the Revolutionary War and is open to visitors. Check current visitor information before your visit. The Historical Village’s large gallery includes an exhibit on the Great Dismal Swamp, as well as other exhibits on local and regional history. If you have a particular exhibit in mind, check what is currently on display.

Other notable places and stories reflect the history of African American education and community. The surviving one-room Cornland School was built in 1902. It was one of Virginia’s earliest initiatives for the formal education of African American children shortly after the Civil War. Cuffeytown is a historic community founded by free Black people, with roots dating back to the 18th century. The Cuffeytown Historic Cemetery is the largest cemetery in Virginia for African American Union soldiers of the Civil War among those not maintained by a government or veterans’ organization.

Seasonal Markets

Markets are another way to get to know Chesapeake. The seasonal Waterway Market at Great Bridge Village offers fresh produce, crafts, food trucks and prepared foods. The Chesapeake Farmers’ Market at City Park is also seasonal. Its offerings include farm-grown vegetables, fruit and herbs; plants and cut flowers; honey and eggs; grass-fed beef and pork; free-range chicken; jams, jellies and pickled vegetables. If you plan to visit a market, check the current dates.

When choosing where to stay, your travel priorities can help guide your decision: the arboretum offers trails and insights into horticulture and the environment, while the Dismal Swamp Canal Trail stands out for its length and variety of permitted activities. Museums, historic waterways and the history of African American communities add further topics to the outdoor experience. Chesapeake offers a range of ways to combine time outdoors, cultural history and seasonal markets.

Discover more destinations: Chesapeake, Pulaski County, Clarke County, Russell, Prince Edward County, Henry County, Spotsylvania County, Patrick County

For the overview of the wider region: Virginia.