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Tobacco Heritage Trail - South Boston

Along this 2.6 mile segment of the Tobacco Heritage Trail in South Boston, history and nature are close at hand. Featured historic sites on the rail-trail include the remains of a cotton mill, the Prizery (once a tobacco warehouse, now a community theatre, museum and events venue), Diamond Hill (a former slave cemetery), and Berry Hill Plantation. Nature enthusiasts enjoy birding, scenic views of the Dan River, and plenty of fresh air.

photo: South Boston Trail Head

Length: 2.60 miles
Loop Trail? No
Type: Equestrian Trail, Fitness Trail, Mountain Bike Trail, Nature Trail, Rail Trail
Agency: Nonprofit
Entry Fee? No
Parking Fee? No

Allowed Uses:

Bicycling (off pavement)
Dogs - On leash
Equestrian - Riding
Heritage and History
Pedestrian - Walking/Hiking/Running
Wildlife Observation


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Location: Railtrail in South Boston, VA
State(s): Virginia
Counties: Halifax
Longitude: -78.91002
Latitude: 36.69716

Driving Directions

From Interstate 85 near South Hill, VA
Head south on I-85 S
Turn left onto US-58 W
Take the ramp on the left onto US-58 W
Turn right onto Main St
Continue onto Broad St
Turn left onto Edmunds St
Turn left onto Railroad Avenue
Parking at Cotton Mill Park


Several historic features of this 2.6 mile segment of the THT make the South Boston section a trail worth visiting! The trailhead is situated at the base of a former cotton mill. All that remains of the mill are two brick towers marking the once thriving cotton industry in South Boston. The Cotton Mill Park situated next to the trailhead makes the location ideal for community events. Recently, the Junior Women’s Club of South Boston hosted its annual Spring Festival here and participants hunted for Easter Eggs along the Tobacco Heritage Trail.

A short 0.4 miles away from the trailhead is the Prizery, which is now a community theatre, museum and venue, but used to be a tobacco warehouse. At one time, the rail system would transport the warehouse’s tobacco along the trail corridor for trade. The Prizery has a rest facility for our trail users complete with showers and lockers.

Other historic features near the trail are an aged sluice gate, which at one time was raised and lowered to adjust the water level, but during a particularly destructive storm it was rendered inoperable. Also, the South Boston section of the Tobacco Heritage Trail provides access to Diamond Hill (a former slave cemetery), and Berry Hill Plantation Resort and Conference Center. As you journey on horse, bicycle or foot down the THT, you will notice the stone wall that separates Berry Hill Plantation from the trail. Each stone was hand placed by slaves who used to work the plantation. Berry Hill welcomes Tobacco Heritage Trail users onto their property to view the graveyard, historic slave quarters and plantation house. Stop in there after your walk or ride and have a bite to eat in “Darby’s Tavern” which is the former kitchen of the mansion.

In addition to the unique historic sights of the new trail section, there are interesting natural features. Approximately two miles down the trail, there is a duck impoundment that birdwatchers and nature enthusiasts can enjoy. The impoundment brings a variety of waterfowl as well as foxes, deer and other wildlife. A natural spring trickles down the side bank at one point of the trail and, at the trail terminus, you may sit at a picnic table. In one direction you can view the scenic Dan River and the opposite direction examine an interesting stone coloration in a rock wall, that locals call, “Tree in the Rock”.

One of our trail advocates reminisced about his days as a boy walking along the old rail road tracks, before it was transformed into the Tobacco Heritage Trail, “The highlight of the trip was ‘tree in the rock’. That was our destination. I reckon to people today, it wouldn't be very much of a destination. It is a geological feature in a wall of stone on the north bank of the railroad where the railroad came within easy sight of the Dan River. It is a unique vein of white quartz that meanders through the stone, and if you used your imagination enough, you might be able to visualize a tree....maybe.”

This newly built section of the Tobacco Heritage Trail is a small taste of what’s to come. This was Phase II of the future 150 mile trail that will eventually loop through Southern Virginia. Until then, both local and out of town visitors enjoy using the trail.

Additional Details

Width: 120 inches.
Primary Surface: Crushed Rock
Secondary Surface: Asphalt

Average Grade: 2%
Maximum Grade: 5%
Elevation Low Point: 326
Elevation High Point: 350
Elevation Gain (cumulative): Not Available

Year Designated:

Contact Information

For more information and current conditions, contact the trail manager (listed below). For questions, suggestions, and corrections to information listed on the website, contact American Trails.

Robin M. Tuck
SPDC Regional Planner - Transportation
Roanoke River Rails to Trails
200 South Mecklenburg Avenue
South Hill, VA 23970
(434) 447-7101
[email protected]



Green Snake by Jeffery Blalock

Green Snake by Jeffery Blalock

Wild Turkey on South Boston Trail, by Robyn Fowler

Wild Turkey on South Boston Trail, by Robyn Fowler


Duck Habitat in memory of Biggie Hunt

Duck Habitat in memory of Biggie Hunt

Historic cotton mill structures at the trailhead

Historic cotton mill structures at the trailhead


Natural rock formations at the end of the trail

Natural rock formations at the end of the trail

An old sluice gate

An old sluice gate


Duck Habitat in memory of Biggie Hunt

Duck Habitat in memory of Biggie Hunt


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