Explore the best rated trails in Highland Springs, VA. Whether you're looking for an easy walking trail or a bike trail like the Ashland Trolley Line and Cannon Creek Greenway. With more than 8 trails covering 79 miles you’re bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
The Ashland Trolley Line runs on a portion of the former Richmond-Ashland Electric Line, which linked the two communities for 31 years until its closure in 1938. During this period, Ashland was a...
The sprawling Virginia Capital Trail snakes along the James River and State Route 5, a Virginia Scenic Byway, for 52 paved miles from the state’s capital of Richmond to the historic capitals of...
While Richmond isn’t necessarily known for its bike-friendliness, the Cannon Creek Greenway is a step in the right direction. The trail is 1.9 miles long, a north-south trail along the east side of...
In western Williamsburg, the Powhatan Creek Trail stretches 2 miles from the historical Jamestown Settlement attraction to Clara Byrd Baker Elementary School. It begins near the one mile marker on the...
Chester Linear Park runs for less than a mile on a former rail corridor in the heart of Chester, Virginia. The path courses through a residential neighborhood, but the enveloping woodlands provide a...
The Newport News Park Bikeway offers a pleasant 5-mile loop through southern Virginia woodlands. The unpaved trail takes you through the 8,000-acre park and offers a connection to Colonial National...
The Railroad Ford Trail is located in beautiful Lake Anna State Park in Spotsylvania County near Richmond, Virginia. The park boasts 2,463 acres with swimming, boating, fishing, horseback riding and...
In western Williamsburg, the Powhatan Creek Trail stretches 2 miles from the historical Jamestown Settlement attraction to Clara Byrd Baker Elementary School. It begins near the one mile marker on the...
While Richmond isn’t necessarily known for its bike-friendliness, the Cannon Creek Greenway is a step in the right direction. The trail is 1.9 miles long, a north-south trail along the east side of...
The sprawling Virginia Capital Trail snakes along the James River and State Route 5, a Virginia Scenic Byway, for 52 paved miles from the state’s capital of Richmond to the historic capitals of...
Chester Linear Park runs for less than a mile on a former rail corridor in the heart of Chester, Virginia. The path courses through a residential neighborhood, but the enveloping woodlands provide a...
The Newport News Park Bikeway offers a pleasant 5-mile loop through southern Virginia woodlands. The unpaved trail takes you through the 8,000-acre park and offers a connection to Colonial National...
The Ashland Trolley Line runs on a portion of the former Richmond-Ashland Electric Line, which linked the two communities for 31 years until its closure in 1938. During this period, Ashland was a...
The Dahlgren Railroad Heritage Trail (DRHT) is currently a private-use trail only, which means a permit is required to use it. Friends of the DRHT are working to create public access to the trail,...
Chester Linear Park runs for less than a mile on a former rail corridor in the heart of Chester, Virginia. The path courses through a residential neighborhood, but the enveloping woodlands provide a...
The sprawling Virginia Capital Trail snakes along the James River and State Route 5, a Virginia Scenic Byway, for 52 paved miles from the state’s capital of Richmond to the historic capitals of...
The Dahlgren Railroad Heritage Trail (DRHT) is currently a private-use trail only, which means a permit is required to use it. Friends of the DRHT are working to create public access to the trail,...
The Railroad Ford Trail is located in beautiful Lake Anna State Park in Spotsylvania County near Richmond, Virginia. The park boasts 2,463 acres with swimming, boating, fishing, horseback riding and...
While Richmond isn’t necessarily known for its bike-friendliness, the Cannon Creek Greenway is a step in the right direction. The trail is 1.9 miles long, a north-south trail along the east side of...
The Newport News Park Bikeway offers a pleasant 5-mile loop through southern Virginia woodlands. The unpaved trail takes you through the 8,000-acre park and offers a connection to Colonial National...
In western Williamsburg, the Powhatan Creek Trail stretches 2 miles from the historical Jamestown Settlement attraction to Clara Byrd Baker Elementary School. It begins near the one mile marker on the...
The Ashland Trolley Line runs on a portion of the former Richmond-Ashland Electric Line, which linked the two communities for 31 years until its closure in 1938. During this period, Ashland was a...
I come here almost every weekend. It gets crowded during summer so make sure u start early to get a parking space.
A challenging ride with lots of rocks, pebbles, and root branches on the trail. Got a great workout going the whole 31 miles. Shotgun blasts by nearby hunters can be disconcerting. I think this trail is more for a mountain bike.
My buddy and I did the round trip this past Sunday, Aug 30. Beautiful day for a long ride.
We started the trail in Jamestown. The trail is well maintained, mostly flat and not too crowded. We rode out to the Sherwood Forest Plantation and turned around. 34 miles round trip. The challenge of the day was the Chickahominy River Bridge. Steep but fun and rewarding view when you get to the top. 100% recommend.
Hi. So, I tried this trail for the first time.. starting from the elementary school.. I loved it!! It was perfect.. the scenery is amazing.. and to get to see some history along the way, it was a great feeling.. There are some hills in the beginning, very doable.. and some turns.. and 2 bridges, that are lovely.. I will say, I did not notice any mile markers, so it was confusing to tell when I approached Greensprings, as I was hoping it would be obvious, so I could turn around and head back.. but I couldn’t tell.. so I just turned around when the watch said 2.4 miles..
Nice 5 mile ride under the trees. Take the turn for the George Washington site about 1/2 way around the loop. From there you can hop on a paved road with many historical markers. If you take the fork that leads to Yorktown you can continue less than 2 more miles to the Yorktown National Cemetery and all the way to Historical Yorktown and the beachfront. Pack a lunch and eat at one of the picnic benches in the grassy area by the water. Public bathrooms available. Total ride was 17 miles round trip with the Yorktown cruise through the historical homes.
A very smooth path that has a couple of road crossings. If you cross Brookland Park Blvd then you can extend your ride. Great if you want a path to calibrate a new bike, power meter, or teach someone.
As much as we have enjoyed the uniqueness of this trail our rides have been diminished by the sound of gun and rifle shots that seem to surround the trail. I would like to feel secure that these shotting ranges or properties are a safe distance away. But the first two miles beginning at the trail head do not feel safe.
This is the perfect short trail for a nice stroll.
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