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 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...
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 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...
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...
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...
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...
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...
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...
The Dahlgren Railroad Heritage Trail (DRHT) traverses a scenic forested landscape abounding with wildlife in Virginia's Northern Neck. The rail-trail, which was designated as a National Recreation...
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...
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...
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 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...
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) traverses a scenic forested landscape abounding with wildlife in Virginia's Northern Neck. The rail-trail, which was designated as a National Recreation...
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...
We’re full-time RVers staying at the Newport News Park Campsites for a few nights. What a pleasant surprise to find this awesome and easily accessible trail near our campsite. Once we got on the trail so glad we turned off at the George Washington Headquarters sign. We then enjoyed a “Historic Tour” of the Colonial National Historic Park (NPS). Easy, flat loop.
This bike loop is perfect for a morning workout through the picturesque woods. We typically ride the loop twice to extend it.
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.
Great ride. Rode East and had a great time. I recommend grabbing a small trail map early so you know where bathrooms and tool kits are located.
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.
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