THIS POST MAY CONTAIN AFFILIATE LINKS. PLEASE READ MY DISCLOSURE FOR MORE INFO

Chessie Trail


If you’re looking for a shorter trail to run, ride, hike, or bike then Chessie Trail is just what you are looking for. The Chessie Trail is a 7-mile year-round public access walking trail between Lexington and Buena Vista. It’s located along what was the old Chesapeake and Ohio railroad right of way. These days, it is run by the Virginia Military Institute (VMI). It’s a nice place to go when the sun is beating down as it was last week for us.

We rode our bikes along the trail but it could also be a nice place to bring your dog as well. Just remember to keep them leashed. If they like to chase other animals, then they may not be welcome on the farm portion of the trail. But that is toward the end of the trail so it may not be a problem if you turn around at the gate.

Start of Chessie Nature Trail

Things to Remember

The trail is well-maintained. There are a few things you have to be aware of.

  • Depending on when you go there might be lots of cadets from VMI running along the trail.
  • There are lots of different groups in the Lexington community that use the trail. The day we went there we saw lots of young guys out running as well but they didn’t look like cadets.
  • Watch out for the wildlife along the trail if you are biking. We had a rabbit that would not move out of the way. He just kept hopping
    ahead of us along the trail.
  • If you are squeamish about cows or cow pies then you might want to skip this trail. It goes right through a farm. Please make sure that you
    close the gate as you go through so you don’t let the cows out.

The Wildlife

Cows and Cow pies

The cows were really fun to see up close and both my wife and daughter got a thrill to see them just lying in the middle of the path. I was a little worried about how they would react to a group of bicyclists intruding on their turf. They just watched us go by though and did not really pay too much attention to us.

If you are lucky you will see more than cows on your trip. We saw the rabbit that wouldn’t get out of our way. We also ran into a deer and her fawn on the way back. The mother took a few steps towards up and then she scooted her baby off the trail and into the brush when she saw what we were more closely.

A Parasol Made of Leaves

A Parasol of Leaves

One of the great things about this trail is that it is covered most of the way by a thick canopy of leaves that kept out the hot sun. Even though it was very hot and humid the trail itself was not that bad because we were in the shade most of the way. My daughter just reminded me that I should let you know that there are some parts where the trail itself is a little narrow.

Actually the whole trail is about the width of a car most the way but there are some places where there’s only a line where you can see the tires have gone before and it was a little tricky navigating those parts As we reached the end in there was a gate along the trail and only a narrow little space to ride through. Daddy got through fine but my daughter’s fingers took a beating. ( I got the father of the year award for that one.) Just remember to be careful at the Buena Vista end of the trail.

An Easy Ride (For Me)

The trail itself was pretty level the whole way. The only noticeable hill is on the Buena Vista end but it was still not very steep. Unfortunately, for my
wife, her trip was not so easy as she got a flat tire by mile three. She kept wondering why her tire was so slippery. I stopped to take a look at her bike and saw that her back tire was completely flat. Let that be a lesson to you. Always make sure you bring a bike pump and a patch kit to fix any flats with
you. I did not have one that day and my wife had quite a hard time. (Husband of the year award for that one.)

Another nice thing is that the trail is fairly easy to find. There is a bridge going across the Maury River and it is located down a road to the right as you leave Lexington. The parking lot is a little hard to spot as it is located behind a building along that road on the right side of the road. You have to keep your eyes peeled and you can spot it. The parking lot is not that big but it is better than the empty field at the Buena Vista end. If you are going to ride
the whole trail and back, I recommend the Lexington trailhead to start.



Enjoy Lexington

Once you are done with your ride along the trail you can always stop in Lexington for some ice cream at the shop downtown. It’s a quaint little town with lots of unique shops to explore. Stop by Sweet Things which is right on the corner of Route 11 and W Washington Street. Tell them Fox by the Campfire sent you. After you’re done, take a walk along the campuses of Washington and Lee and VMI. They are within walking distance of the ice cream shop. It’s a very historic town filled with lots of Civil War memorabilia and other historic sites.

Enjoy your visit!

Leave a Comment