Wintergreen, VA Hike Trails and Maps

251 Reviews

Looking for the best Hike trails around Wintergreen?

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

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Activities
Length
Surfaces
Type
13 Results
Activities
Length
Surfaces
Type

Blue Ridge Tunnel Trail

2.16 mi
State: VA
Crushed Stone

High Bridge Trail State Park

32.2 mi
State: VA
Crushed Stone

James River Heritage Trail

10.1 mi
State: VA
Asphalt, Dirt, Woodchips

John W. Warner Parkway Trail

1.6 mi
State: VA
Asphalt

Lifecore Trail

3.3 mi
State: VA
Asphalt, Concrete

Saunders-Monticello Trail

2 mi
State: VA
Asphalt, Boardwalk, Concrete, Crushed Stone

South River Greenway Trail

2 mi
State: VA
Asphalt

Virginia Blue Ridge Railway Trail

6.9 mi
State: VA
Crushed Stone, Dirt, Gravel

Chessie Nature Trail

7.13 mi
State: VA
Boardwalk, Dirt, Gravel

Rivanna Trail

21.5 mi
State: VA
Asphalt, Crushed Stone, Dirt, Gravel

Coal Tower Trail

0.5 mi
State: VA
Asphalt

Friendly City Trail

2.2 mi
State: VA
Asphalt

James River Foot Bridge

0.12 mi
State: VA
Boardwalk
Trail Image Trail Name States Length Surface Rating
The Blue Ridge Tunnel Trail is located below Rockfish Gap, with a 2.3 mile crushed-stone trail that leads to the tunnel between the community of Afton on its eastern side and the city of Waynesboro...
VA 2.16 mi Crushed Stone
The central feature for which the High Bridge Trail State Park is named is an unforgettable experience, a bridge that towers 125 feet above the mighty Appomattox River and nearly a half-mile (2,422...
VA 32.2 mi Crushed Stone
Closure Notice: The Point of Honor section of the James River Heritage Trail is closed until 2026. The James River Heritage Trail is one of the premier urban trails in the state, passing through...
VA 10.1 mi Asphalt, Dirt, Woodchips
The enhanced bike-ped trail snakes alongside the John W. Warner Parkway for 1.6 miles, from East Rio Road down to McIntire Park. It mostly lies on the route of the old Southern Railway.  Points of...
VA 1.6 mi Asphalt
Fishersville is a small community located between Staunton and Waynesboro in Augusta County. This pedestrian and cycling path was added as part of Fishersville's road improvements and useful for both...
VA 3.3 mi Asphalt, Concrete
While the Saunders-Monticello trail leads to the home of one the United States most prominent presidents, it is quickly becoming a destination in itself. It’s less than ten minutes’ drive from...
VA 2 mi Asphalt, Boardwalk, Concrete, Crushed Stone
The South River Greenway is a 2-mile multi-use trail along the South River through Waynesboro's Downtown corridor. Views along the way include those of the river, Blue Ridge Mountains, Constitution...
VA 2 mi Asphalt
The 6.9-mile Virginia Blue Ridge Railway Trail offers a quintessential rail trail experience in central Virginia, midway between Lynchburg and Charlottesville (less than an hour’s drive from each)....
VA 6.9 mi Crushed Stone, Dirt, Gravel
The Chessie Nature Trail travels for just over 7 miles through breathtaking rural Virginia countryside, following mile markers left behind by the Chesapeake & Ohio Railroad that ran this route. Trail...
VA 7.13 mi Boardwalk, Dirt, Gravel
Spanning more than 20 miles, the Rivanna Trail surrounds Charlottesville, connecting several parks along the way and providing a recreational outdoor amenity for city dwellers. The trail has a mix of...
VA 21.5 mi Asphalt, Crushed Stone, Dirt, Gravel
The Coal Tower Trail is an 8-10-foot wide path adjacent to Water Street connecting downtown Charlottesville to Carlton Road and the Meade Avenue Trail. The tree-lined path also parallels an active...
VA 0.5 mi Asphalt
The Friendly City Trail runs through Harrisonburg, its namesake city, for 2.2 miles connecting parks, schools, and neighborhoods. The entire path is paved. About the Route This shared-use path...
VA 2.2 mi Asphalt
The James River Foot Bridge carries the Appalachian Trail over the James River in Snowden, Virginia, approximately 20 miles northwest of Lynchburg. About the Route The bridge was built on the...
VA 0.12 mi Boardwalk

Recent Trail Reviews

High Bridge Trail State Park

Great Trail

October, 2025 by qs5xx6zrzd

Love this trail! Nice grades, quiet, not too busy, lots of bathrooms and benches/ picnic tables to stop. High Bridge is lovely with great views. Nice restaurants in Farmville, Charlies is our favorite! Enjoy the serenity and wildlife.

Blue Ridge Tunnel Trail

This was a great short ride for us and our 4 year old. Mostly flat or low grade hill from the east trailhead! Be sure to bring a headlamp or flashlight if walking.

October, 2025 by wkg237

This was a great short ride for us and our 4 year old. Mostly flat or low grade hill from the east trailhead! Be sure to bring a headlamp or flashlight if walking.

Virginia Blue Ridge Railway Trail

Well maintained trail

August, 2025 by jstarkitect96

The trail is in great condition. The combination of shade and open sky made it a pleasant ride in low 80s temps.
Only a few minor repairs need to be made- steps for riders on both sides of the bridges are needed to dismount their horses- a few bridges were missing them. Also, there is a board sticking out into the path on the long bridge at mile marker 4.5. It looks like they tried to repair it, the board needs to be replaced.

Accordion

Virginia Blue Ridge Railway Trail

Love the trail!

July, 2025 by cbertrand35

I love that you are along a river a lot of the time and cross a river multiple times. The trail is mostly shaded. Tons of interesting birds sing in the spring. The bathroom at Rose’s Mill is a plus. They tell you not to drink the water but after I did by mistake I suffered no ill effects. I encounter people on any day of the week, but definitely on the weekends. I highly recommend this trail.

Virginia Blue Ridge Railway Trail

Nice Crushed Rock Trail

July, 2025 by evada

Quiet, flat, maintained, mostly shaded, along the Piney river with benches and the occasional picnic table. Port-a-potty at the Piney River trailhead, running water bathroom at the Roses Mill trailhead .

Virginia Blue Ridge Railway Trail

Lovely trail

May, 2025 by 5y5n8cjb9f

I hiked this trail today and enjoyed it quite a lot. The trail itself is nice and wide, and fairly flat. There’s good tree canopy over most of the route and beautiful views of the rivers and fields. There are benches and picnic tables scattered along the trail as well. Plenty of parking at the Piney River trailhead. Will definitely hike this one again.

Virginia Blue Ridge Railway Trail

Lovely trail

May, 2025 by 5y5n8cjb9f

I hiked this trail today and enjoyed it quite a lot. The trail itself is nice and wide, and fairly flat. There’s good tree canopy over most of the route and beautiful views of the rivers and fields. There are benches and picnic tables scattered along the trail as well. Plenty of parking at the Piney River trailhead. Will definitely hike this one again.

High Bridge Trail State Park

great ride

April, 2025 by dmason511

The trail is in great shape going East from FarmVille. Going West from FarmVille needs some attention. It appears that the area had a storm and a lot of trees fell. Heavy equipment used to remove the trees has left ruts in the trail. We rode for about five miles and decided that it wasn’t going to get better, turned around and went back to FarmVille.

Virginia Blue Ridge Railway Trail

Meh

April, 2025 by tweakhound

Maybe it was the time of year but kinda boring. Well used by horses as there was ample "evidence" lying on the trail. The Nelson County website mentions "restroom facilities" at the trailheads. The Piney River trailheads "restroom facilities" is a single porta potty. The Roses Mill trailhead does have a small bathroom.

High Bridge Trail State Park

High Bridge

April, 2025 by jayneweinhold

We rode two different sections, nice trail. Took the side gravel trail near the bridge to see the underside. At Pamplin, the west end, there’s a small restaurant with excellent burgers, MiPa’s Table. Just past the trails end along the small Main Street.

Blue Ridge Tunnel Trail

Great short trail for families!

April, 2025 by eslone_tl

Amazing tunnel and a fun experience with kids. Be sure to bring your flashlight.

James River Heritage Trail

Great Ride

November, 2024 by haybabiesfarm

Well paved- beautifully kept trail. Had a great morning riding into downtown Lynchburg , where we stopped for a nice lunch. I would definitely ride this trail again.

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