Chester, VA Trails and Maps

175 Reviews

Looking for the best trails around Chester?

Explore the best rated trails in Chester, VA. Whether you're looking for an easy walking trail or a bike trail like the Ashland Trolley Line and High Bridge Trail State Park. With more than 9 trails covering 117 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.

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Activities
Length
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Type
9 Results
Activities
Length
Surfaces
Type

Ashland Trolley Line

0.85 mi
State: VA
Asphalt, Grass, Gravel

Cannon Creek Greenway

1.9 mi
State: VA
Asphalt

Chester Linear Park

0.68 mi
State: VA
Crushed Stone

High Bridge Trail State Park

31.4 mi
State: VA
Crushed Stone

Newport News Park Bikeway

5.3 mi
State: VA
Crushed Stone, Dirt

Powhatan Creek Trail

2 mi
State: VA
Asphalt

Tobacco Heritage Trail

22.7 mi
State: VA
Asphalt, Crushed Stone

Victoria Railroad Park

1 mi
State: VA
Asphalt

Virginia Capital Trail

51.7 mi
State: VA
Asphalt, Boardwalk
Trail Image Trail Name States Length Surface Rating
The Ashland Trolley Line Trail 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...
VA 0.85 mi Asphalt, Grass, Gravel
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...
VA 1.9 mi Asphalt
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...
VA 0.68 mi Crushed Stone
The central feature for which the High Bridge Trail State Park is named is an unforgettable experience, towering 125 feet above the mighty Appomattox River and nearly a half mile (2,422 feet) across...
VA 31.4 mi Crushed Stone
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...
VA 5.3 mi Crushed Stone, Dirt
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...
VA 2 mi Asphalt
In Southern Virginia, an exciting regional trail project has been taking shape for over a decade. The Tobacco Heritage Trail will one day span 160 miles, connecting the counties of Brunswick,...
VA 22.7 mi Asphalt, Crushed Stone
Victoria Railroad Park is a 21-acre open space located in the central business district of an old railroad town in south-central Virginia. Victoria was the halfway point of a Virginian Railway...
VA 1 mi Asphalt
The Virginia Capital Trail transports visitors through time as it travels nearly 52 miles between the state’s early capital at the Jamestown Settlement and its current capital city of Richmond,...
VA 51.7 mi Asphalt, Boardwalk

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Trails by activity

Victoria Railroad Park

VA - 1 miles

Victoria Railroad Park is a 21-acre open space located in the central business district of an old railroad town in south-central Virginia. Victoria was the halfway point of a Virginian Railway...

Cannon Creek Greenway

VA - 1.9 miles

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...

Ashland Trolley Line

VA - 0.85 miles

The Ashland Trolley Line Trail 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...

Chester Linear Park

VA - 0.68 miles

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...

Accordion

Newport News Park Bikeway

VA - 5.3 miles

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...

Powhatan Creek Trail

VA - 2 miles

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...

Virginia Capital Trail

VA - 51.7 miles

The Virginia Capital Trail transports visitors through time as it travels nearly 52 miles between the state’s early capital at the Jamestown Settlement and its current capital city of Richmond,...

High Bridge Trail State Park

VA - 31.4 miles

The central feature for which the High Bridge Trail State Park is named is an unforgettable experience, towering 125 feet above the mighty Appomattox River and nearly a half mile (2,422 feet) across...

Chester Linear Park

VA - 0.68 miles

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...

Virginia Capital Trail

VA - 51.7 miles

The Virginia Capital Trail transports visitors through time as it travels nearly 52 miles between the state’s early capital at the Jamestown Settlement and its current capital city of Richmond,...

Powhatan Creek Trail

VA - 2 miles

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...

Cannon Creek Greenway

VA - 1.9 miles

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...

Accordion

Ashland Trolley Line

VA - 0.85 miles

The Ashland Trolley Line Trail 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...

High Bridge Trail State Park

VA - 31.4 miles

The central feature for which the High Bridge Trail State Park is named is an unforgettable experience, towering 125 feet above the mighty Appomattox River and nearly a half mile (2,422 feet) across...

Newport News Park Bikeway

VA - 5.3 miles

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...

Victoria Railroad Park

VA - 1 miles

Victoria Railroad Park is a 21-acre open space located in the central business district of an old railroad town in south-central Virginia. Victoria was the halfway point of a Virginian Railway...

Tobacco Heritage Trail

VA - 22.7 miles

In Southern Virginia, an exciting regional trail project has been taking shape for over a decade. The Tobacco Heritage Trail will one day span 160 miles, connecting the counties of Brunswick,...

High Bridge Trail State Park

VA - 31.4 miles

The central feature for which the High Bridge Trail State Park is named is an unforgettable experience, towering 125 feet above the mighty Appomattox River and nearly a half mile (2,422 feet) across...

Ashland Trolley Line

VA - 0.85 miles

The Ashland Trolley Line Trail 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...

Cannon Creek Greenway

VA - 1.9 miles

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...

Victoria Railroad Park

VA - 1 miles

Victoria Railroad Park is a 21-acre open space located in the central business district of an old railroad town in south-central Virginia. Victoria was the halfway point of a Virginian Railway...

Accordion

Newport News Park Bikeway

VA - 5.3 miles

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...

Chester Linear Park

VA - 0.68 miles

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...

Powhatan Creek Trail

VA - 2 miles

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...

Tobacco Heritage Trail

VA - 22.7 miles

In Southern Virginia, an exciting regional trail project has been taking shape for over a decade. The Tobacco Heritage Trail will one day span 160 miles, connecting the counties of Brunswick,...

Virginia Capital Trail

VA - 51.7 miles

The Virginia Capital Trail transports visitors through time as it travels nearly 52 miles between the state’s early capital at the Jamestown Settlement and its current capital city of Richmond,...

Recent Trail Reviews

Tobacco Heritage Trail

okay ride

September, 2022 by annab560

It was great as we didn’t see anyone else. We picked up the trail in Laurenceville near New Street. The trail is in fair condition. It is not really crushed rock as grass has grown up in parts. Part of the experience was also seeing a bear. Not anything I wanted to experience though. I’ve done many of the other trail and feel this was a fair rating.

High Bridge Trail State Park

high bridge trail

August, 2022 by aldo_desalvo

I rode over the bridge part And about half the other part of the trail. Trying to get up for a Whole weekend to ride the rest

Newport News Park Bikeway

Great for a Tandem Bike ride¿

July, 2022 by utpaduke

Mel and I rode this beautiful trail on our tandem bike on Mon-Tues. We had planned to ride 2 loops for 10.6M each day. After completing the 1st loop on Monday, we decided to ride the trail in reverse from exit to begin. We found riding in that direction more conducive to the slight ups/downs! Even though it has been hot average 85F, the heat was manageable - 99% shaded¿ Luv it!

Accordion

Victoria Railroad Park

Enjoyed riding the trails on horse back

June, 2022 by horsesnheaven

Very happy that they offer the trails for multi use, we are newer to this area and havnt been able to find horse trails so this was exciting to find. My son and I enjoyed the trails on our horses today. The one side was well groomed while the other direction wasn't as well groomed for the height of horses , But just an observation , no complaints here, it was very quiet and we really enjoyed it and will be back plenty more times with the horses . When you go through the park there are kids on the play ground and it's fun going beside town on the trail , a little exposure for the horses , with out being overwhelming though. Thanks for allowing us to enjoy the trails with you all.

Powhatan Creek Trail

Nice shaded trail starting from the elementary school with bridges going over marshes, and creeks. Not lots of people, but set between some subdivisions. There were a few benches to sit on before getting to the meadow.

June, 2022 by ebenegar_tl

Nice shaded trail starting from the elementary school with bridges going over marshes, and creeks. Not lots of people, but set between some subdivisions. There were a few benches to sit on before getting to the meadow.

High Bridge Trail State Park

The High Bridge is the high point, but otherwise not as appealing as other top VA trails

May, 2022 by jonesandrewd_tl

I rode this trail on 5/11 and 5/12, 2022. I'd divide it into roughly three sections - west, from almost-Pamplin to Tuggle, central, from Tuggle to the eastern cutoff to the Spur Line Trail a bit east of the bridge, and eastern, from that point to the eastern terminus.

The Central section (4.5/5) is by far the most interesting. Tuggle to Farmville is relatively scenic. Farmville to the High Bridge is decently scenic. The High Bridge is impressive; yes, it's "just trees", but you are above them, can see 20 miles, watch the crows and other birds flying above the tree or landing on the bridge, relax with a great view, and see the Appomattox from a great height. In my opinion, the Bridge itself delivered on what was promised online, and at nearly half a mile long, it's probably the longest bridge I've biked across, and quite possibly the longest as well.

Then, you can then lock your bike to one of the racks east of the trail, and take the Camp Paradise and/or Spur Line Trails. If you only have time for one, take the Camp Paradise. Not so much for Camp Paradise itself - a Confederate camp meant to guard the bridge; you can still see the earthworks, but it's not particularly impressive. Instead, take that trail because it takes you below the High Bridge. This gives you another perspective on just how impressive the bridge is, particularly for being originally built in the mid-1850s, lets you see more of its construction, and shows why it was strategically important. Hike back up the southern side of Camp Paradise to get a hint of what it may have been like to move an entire army, carrying packs with supplies as well as rifles, up from crossing the Appomattox without the bridge. It was much easier for the Union to catch the Army of Northern Virginia with the bridge still relatively intact!

The base of the bridge by Camp Paradise also happens to be a butterfly hangout.

The Spur Line Trail is a nice hike through the woods, though the promised overlook is fairly obscured. Still, it's a nice break from the relative visual sameness of most of the trail.

The Rochelle Area mountain bike trails are also in the eastern section; I didn't have enough time to try them out.

The Eastern part of the High Bridge Trail (4/5) is, as another reviewer mentioned, a "zen trail". If you've had a stressful week and just want to get away from it for a while and pedal, without having to think too much about the scenery, this would be a great option. It doesn't change direction much, sometimes the rail bed is above the surroundings, sometimes below, giving a cozy feeling, but it's always visually pleasing but not in an attention-demanding (or especially memorable) sort of way.

The Western part (3/5) has similar scenery to the eastern part, but parallels Route 460 (the Prince Edward Highway) pretty closely. Route 460 gets a fair amount of traffic, including truck traffic, which spoils the zen aspect of the eastern part. I'd rather ride most of the trails near where I live in Ohio, not just my favorite local ones, above re-riding the western section.

I'd put all the other Virginia trails I've ridden ahead of this one in terms of scenery - Jackson River Scenic, New River, and Virginia Creeper. Those are also all farther west, and if you are in the area, it's worth at least riding the Central section. There's also a bike shop in Farmville, right near the trail, where you can rent bikes, so you don't even have to plan very far ahead to make a trip out to the Bridge.

Virginia Capital Trail

Suggested rides if you have limited time

April, 2022 by gwilliams2013

If you only have a few days/limited ride time - here are my suggestions, based on 2 days of riding and driving the entire trail (yes - it runs RIGHT BESIDE Hwy 5 for most of its length) Which is why I rate it a 4 instead of a 5.
Background: Trail surface is smooth. I was on the bike at sunrise and finished by 10AM or so - both days (weekdays) I saw fewer than 10 bikers my entire ride, even though this was the week of Spring break (April 4th, 2022) for the local schools. Both trail heads I parked at appeared safe - there were no cars there when I started and only a few when I finished. 
Ride 1: Park at Chickahominy Riverfront Park MM 7, ride East to Jamestown. Jamestown Island has a 5+ mile road that is one way, with a low speed limit. Less than 1 mile from the Jamestown TH is the Powhatan Creek Trail - a nice 2+ mile out and back trail (hilly ride, winding, lots of rough pavement from tree roots, but repairs are in the works). You can also ride several miles of unpaved paths off of the Powhatan Creek Trail. And of course, ride over the Chickahominy Creek bridge to finish your ride. I was able to get in 35 miles on this route. This entire ride is safe for all riders. Also - Colonial Parkway from Jamestown to Colonial Williamsburg is a safe ride with no commercial traffic allowed, but it is a rough surface. The bike route separates from Colonial Parkway - best to follow it rather than stay on Colonial where there is a tunnel that prohibits bicycles.
Ride 2:  Park at Four Mile Creek Park MM 40 (a nice drive on a winding Hwy 5 with minimal traffic from Jamestown), ride West to Richmond. The Great Shiplock Park and Canal Walk are interesting. This is a much hillier ride than the Jamestown end, with several traffic light road crossings. Safe - but not ideal for all riders. With a ride through Dorey Park in Varina, I was able to get in 29 miles. 
Overall a nice trail, very smooth surface, with some sections more appealing than others. Jamestown Island was the highlight.

High Bridge Trail State Park

Originally intended to end in Burkeville. Why was it not completed?

April, 2022 by barrynewcomb1961

Originally intended to end in Burkeville. Why was it not completed?

High Bridge Trail State Park

Can anyone explain why high bridge trail was not completed to Burkeville as originally intended?

April, 2022 by barrynewcomb1961

Can anyone explain why high bridge trail was not completed to Burkeville as originally intended?

High Bridge Trail State Park

Can anyone explain why the trail was,not completed to Burkeville ad originally intended?

April, 2022 by barrynewcomb1961

Can anyone explain why the trail was,not completed to Burkeville ad originally intended?

High Bridge Trail State Park

Well-maintained, quiet & pretty, but not that interesting

March, 2022 by bikeridesandbreweries

The trail is what we call a “Zen ride,” which means there’s not a lot of visual variety so it’s great if you just like being in your head while you pedal. We parked right in the center of town on Main Street which bisects the crushed limestone trail almost exactly in the middle. Conveniently at this intersection, there are clean, air-conditioned restrooms, while more rustic ones with “vault toilets” are located along the trail. There are no other amenities along the trail except the trailer that we encountered on our first trip that sold water out of an ice-filled cooler, along with various tourism chotchkes made by local artisans. We don’t think you can count on it being there, though, so fill up your water bottles before you set out.
First we headed west 4.5 miles to see the famous High Bridge, which oddly, was more interesting to read about than to ride over. It looks out on a wide expanse of trees…just trees. For as far as the eye can see. We continued to bike approximately 10.5 miles past the bridge and, having passed only a handful of walkers and bikers, a few deserted intersections and some vault toilets, the trail ended abruptly at a lonely picnic table surrounded by woods. The other half of the trail runs east briefly then due south. While hauntingly familiar (it’s almost identical to the western portion of the trail), brief glimpses of water, overhead bridges and slightly more varied scenery made it more interesting.
A very good brewery abuts the trail close to the midway point.

Virginia Capital Trail

Great trail

February, 2022 by acuenca5

Love this trail can’t wait to go back

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