Chester Trails and Maps

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Find the top rated trails in Chester, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
Surfaces
Type
8 Results
Activities
Length
Surfaces
Type

Ashland Trolley Line

0.5 mi
State: VA
Grass, Gravel

Chester Linear Park

0.68 mi
State: VA
Crushed Stone

High Bridge Trail

32.4 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

22.1 mi
State: VA
Asphalt, Crushed Stone

Victoria Railroad Park

1 mi
State: VA
Asphalt

Virginia Capital Trail

52 mi
State: VA
Asphalt, Boardwalk
Trail Image Trail Name States Length Surface Rating
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...
VA 0.5 mi Grass, Gravel
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 is named is an unforgettable experience, towering 125 feet above the mighty Appomattox River and nearly a half-mile (2,440 feet) across it. The...
VA 32.4 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
The Tobacco Heritage Trail currently runs in a continuous, off-road 17-mile stretch between the southern Virginia communities of Lawrenceville, Brodnax and La Crosse. Along the way, trail-goers can...
VA 22.1 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 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...
VA 52 mi Asphalt, Boardwalk

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Trails by activity

High Bridge Trail

VA - 32.4 miles

The central feature for which the High Bridge Trail is named is an unforgettable experience, towering 125 feet above the mighty Appomattox River and nearly a half-mile (2,440 feet) across it. The...

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...

Ashland Trolley Line

VA - 0.5 miles

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...

Virginia Capital Trail

VA - 52 miles

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...

Accordion

Tobacco Heritage Trail

VA - 22.1 miles

The Tobacco Heritage Trail currently runs in a continuous, off-road 17-mile stretch between the southern Virginia communities of Lawrenceville, Brodnax and La Crosse. Along the way, trail-goers can...

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...

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...

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...

Virginia Capital Trail

VA - 52 miles

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...

High Bridge Trail

VA - 32.4 miles

The central feature for which the High Bridge Trail is named is an unforgettable experience, towering 125 feet above the mighty Appomattox River and nearly a half-mile (2,440 feet) across it. The...

Ashland Trolley Line

VA - 0.5 miles

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...

Tobacco Heritage Trail

VA - 22.1 miles

The Tobacco Heritage Trail currently runs in a continuous, off-road 17-mile stretch between the southern Virginia communities of Lawrenceville, Brodnax and La Crosse. Along the way, trail-goers can...

Accordion

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...

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...

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...

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...

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...

High Bridge Trail

VA - 32.4 miles

The central feature for which the High Bridge Trail is named is an unforgettable experience, towering 125 feet above the mighty Appomattox River and nearly a half-mile (2,440 feet) across it. The...

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...

Accordion

Ashland Trolley Line

VA - 0.5 miles

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...

Virginia Capital Trail

VA - 52 miles

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...

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 - 22.1 miles

The Tobacco Heritage Trail currently runs in a continuous, off-road 17-mile stretch between the southern Virginia communities of Lawrenceville, Brodnax and La Crosse. Along the way, trail-goers can...

Recent Trail Reviews

High Bridge Trail

Water

July, 2017 by afa86baca

Liked the trail but I only found one water fountain on it, which was at Farmville. Also it would be nice if they had a connecting trail from twin lakes state park to the trail.

Virginia Capital Trail

Virginia Capital Trail

May, 2017 by pabradley

On an unseasonably hot and very windy day in early May, 2017, four of us got on our bikes at the parking lot of Jamestowne Settlement for the 52-mile ride to Richmond. The trail is wonderful: a variety of settings from shaded woods to open fields, flat sections and hills. The views in many places are beautiful. Our only criticism is that there are almost no places to refill your water bottle. That was a serious issue on the day we rode with temps near 90 and strong headwinds. The next day was cool when we rode back east so the lack of water was not as serious. Hopefully, as this trail is used more (since it is relatively new) this deficit will be addressed. Right how the trail is in excellent condition and we hope it stays that way. It is a top-notch ride.

High Bridge Trail

It's all about the bridge

April, 2017 by bruceamiller@comcast.net

A friend and I took a break from driving to ride the High Bridge Trail east from Farmville to the bridge. The trail is decent crushed limestone, wide enough to ride 2 abreast. The scenery was the same until you get to the bridge, which is about a half-mile long. Great view from it. Photographing the bridge is a challenge, as hard to get a side view without walking a ways.

Accordion

Virginia Capital Trail

2nd time - we've bookended it

March, 2017 by jrutch

rode once here from the southern trail end in jamestown up 12.5 & back ... this time we started at the richmond end and rode 9 to dory park and back -- we'll need to go back and do the middle section one day .... anyhow this section is a little more "citified" than the other end - but great surface - it is hilly here (a little surprising) .... very few road crossings for going through a big city like richmond .. look for the big bike outside the city -- dory park was a good stop .. i wish there was a better trail guide for trying to plan a multi day trip

High Bridge Trail

wow - pretty cool

March, 2017 by jrutch

we started in farmville ... rode to rice ... went over the big bridge ... great surface ... the occasional restroom ... very very very (did i say very) few road crossings ... we want to come back and stay in farmville and do the whole trail eastward one day, westward the other (very doable as it would be about 30 or so each day as farmville is fairly in the middle)

Virginia Capital Trail

Excellent Trail

November, 2016 by mtb_miguel

Today I rode the entire trail both directions. I started in Richmond and rode East to Jamestown, then back to Richmond. The trail is very smooth, constructed of blacktop in good condition. There are several stores and businesses along the route that one can stop and purchase beverages. The trail is fairly flat but has some small undulations with total elevation gain of roughly 1000' in each direction. https://www.strava.com/activities/771724527

Virginia Capital Trail

Smooth Ride

November, 2016 by mkenttodd

Enjoyed a two day adventure from Richmond to Jamestown/Williamsburg and back. This dedicated (bicycles/walkers/runners) trail is relatively flat, smooth, and mostly scenic. The section from Jamestown to Charles City is perfect for beginning cyclist as it is very flat. For the intermediate rider this trail would be a great option for that first century ride.

I rode the trail on a Tuesday and Wednesday in late October, and passed several cycling groups as well as individual runners/cyclist. Based on this experience, I would think that weekend use could be heavy.

Finally, I was surprised that I did not encounter any hostile pets (e.g., dogs) even though the trail crosses through various residential areas.

Many thanks to those responsible for this lovely trail.

Virginia Capital Trail

Enjoyable trail

October, 2016 by lycaeides

We rode this trail from Four Mile Creek Park to Richmond and back this week on Tuesday. It is well maintained and well marked. The other riders/walkers were courteous and friendly. A few days later, we rode from Four Mile Creek Park to Charles City and back which was also very nice. The pavement is good. There are very few crossings where you have to stop. The scenery is farmland until you get to Richmond. Good signage for the wooden bridges and grade changes. Altogether a well done trail and great community builder.

Virginia Capital Trail

October, 2016 by hanni001

Great Trail. Perfect length. Great destinations at both ends. A lot of planning and thought went into design of intersections with side roads. Path crosses side roads further back from stop sign intersections making it a lot safer for trail users and cars. Loved it!

Tobacco Heritage Trail

Definetly a tale of 2 trails

October, 2016 by virginiapaddler

I mountain biked the entire section from Lacrosse to Lawrencville. Great adventure. You have to go west a mile then back to get that little piece out of the way, then go east!
20 miles for the entire section. Great ride, nothing too bad at all. I am new to biking and did it easily with breaks. First 5 or so miles are paved.... almost a blacktop type surface, then it switches to a hard pressed small gravel.
I did see evidence of horses but no damage to trail. Trail was marked well, but there was a time warp near the end when it said I had 5 miles left, then a mile later I was done. Trail ends in Lawrencville with no pomp and circumstance... it just ends.
Many bridges and creeks and you also go over the Meherrin River.
Only bad comment was the litter and trash the last 1 mile or so. They need to get a team in there and clean it up. It ruins the trip to have that be the last thing you see.

Tobacco Heritage Trail

Sept. 24, 2016 La Crosse to Lawrenceville

September, 2016 by river lizard

Had seen the photo of the vines growing over the trail and had to make a trip down from Richmond again. High for today was 84 degree and extremely muggy by noon. Probably not the best biking weather but I managed.
The trail condition was good other than being covered with leaves and of course the over-grown grass on the trail. The grass was mowed down but the crushed stone really needs to be dragged and repacked again to really clean it up again. The section with the foreign vine growth was cleaned up when I went through that area (posted photo).
Didn't see one other biker the whole trip and I only saw 6 walkers.
I did an extra 10 miles because 5 miles into the trail I realized I forgot my cellphone/camera so I had to turn around and pedal back to my vehicle.
My rating of the trail this trip is a 4 star. What would make it a 5? If they'd clean up the actual trail and get the grass out of it. And smooth and pack the crushed stone areas. If they added a few water supply areas, it would definitely be a 6 stars! Nice bathrooms but lacking water supplies along the way.
Overall I love this trail and it's worth my time to drive from Richmond to pedal it. I will continue to visit this trial in the future and look forward to more improvements to it.

Tobacco Heritage Trail

Good ride for the Labor Day weekend

September, 2016 by peter.speller62

Rode the trail today from Lawrenceville to Lacrosse and back. The riding surface was fine for me, riding an old road bike with 25mm tires. Could see where some sections could get churned by horse hooves, but even after yesterdays rain, wasn't an issue. Looking forward to when I can ride all the way to Clarksville!

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