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.

Recent Trail Reviews

Virginia Capital Trail

Virginia capital trial

October, 2023 by aldo_desalvo

I give it 5 stars because it is over the whole way. I rode Williamsburg to Richmond. There are very little roots coming through the pavement which is a positive Shaded for the first 30 plus miles. Plenty of parking in Williamsburg and Richmond. I missed one turn. One nice rest stop about 10 miles from Richmond I live in Chesapeake Virginia and this was very hilly for me. Constant up and down. The negatives are the lack of benches to sit. I counted 3 of them for about 40 plus miles. There was also a lack of stores. Bring you own hydration. The

Virginia Capital Trail

Virginia Capital to Capital Trail, Jamestown, VA

September, 2023 by sebhike13

Wonderful paved trail where I bike and lead rides for our local trail club. Great for all level of bicyclists as its mostly flat on the Jamestown end. Led a group of 10 recently for 36 miles and had lunch at the Jamestown Settlement. It is shaded in the summer. It is one of my favorite paved trail to ride. It is also part of the Trans American Trail for going cross the country.
Sandy

Tobacco Heritage Trail

Biked this section during a trip, nice surface, diamond hill memorial was newly refreshed. Great ride! Recommend if in the area.

July, 2023 by gibsontw

Biked this section during a trip, nice surface, diamond hill memorial was newly refreshed. Great ride! Recommend if in the area.

Accordion

Tobacco Heritage Trail

Biked from la crosse 10 miles east and back in June on a Wednesday, no other bikes seen, first 5 miles paved, second 5 wooded with nice surface, saw one jogger and one walker on the paved end, treasure trail with what appeared as low useage

July, 2023 by gibsontw

Biked from la crosse 10 miles east and back in June on a Wednesday, no other bikes seen, first 5 miles paved, second 5 wooded with nice surface, saw one jogger and one walker on the paved end, treasure trail with what appeared as low useage

Newport News Park Bikeway

First bike trail

July, 2023 by 6cjp4cs74v

This is the first trail I've ever ridden at it was a perfect beginner trail! I'd say 95% of the trail is shaded and I only saw like 3 other people on the trail

High Bridge Trail State Park

high bridge.

May, 2023 by aldo_desalvo

Trail is gravel the whole way. No 2 lane dirt road. There are no service areas at all. Great bike shop that helped me with my flat. The bridge is scenic. The rest is not. Pretty flat and no significant hills. Stayed at an old hotel that had a rooftop bar. Farmington is a cool town.

Tobacco Heritage Trail

Very nice ride

May, 2023 by ericday

I have both biked and walked sections. Very interesting historical markers along the trail. Good surface

High Bridge Trail State Park

Great surface

May, 2023 by ericday

Great surface and nicely maintained

Tobacco Heritage Trail

good trail

May, 2023 by aldo_desalvo

Lots of bathrooms and benches. First part in lawrenceville is probably not used much. Started to see more people near the caboose in lacross There was a down tree that was hard to get through. Abruptly ends at the south hill border. Paved for about 5 miles. A 36 mile round trip.

Newport News Park Bikeway

Older couple enjoying bike ride

November, 2022 by tg7w84nj49

we are older and just started riding, love this trail, beautiful scenery and most roots are marked with blue paint so you can see them easily, there are not that many roots. It was such a nice day, really enjoyed it. When we get better, we plan on taking this trail to Yorktown.

Tobacco Heritage Trail

great ride

October, 2022 by ffsswing

Oct 21 2022. Great colors leaves everywhere. Cool weather. once we hit the gravel -> trail all to myself. Start in the town La Crosse . Where the beginning has pavement and great parking area

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.

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