Biking the Chessie Trail Along the Maury River

Biking the Chessie Trail Along the Maury River

Our family loves (like, someone should get us a T-shirt because we’d proudly announce this love) rails-to-trails systems. Lucky for us, Virginia and the Rails-to-Trails Conservancy have invested time and resources into creating many. And the Chessie Trail was another great opportunity for us to get on our bikes and go exploring.

Chessie Trail

The Chessie Trail is a 7-mile long mixed use path that runs alongside the Maury River from Buena Vista to Lexington. Managed by the Virginia Military Institute, the path is generally well-kept and great for families. 

This trail is particularly unique as it enters private property at various points. Entering onto private land, there were gates to open and pass through and then, most fun of all, bike through cow pastures…yes, with cows!!

We were right up and close with these large, doe-eyed animals. The young ones stood in the path, clearly unsure what to make of us, until they realized we were still moving towards them. Then they bolted away. The older cows slowly moved out of our way, not really seeming to care a bit about us.

I got, as I always do when in a close encounter with a behemoth of an animal, a little skittish. But these were tame animals and the kids thought it was great fun.

Chessie Trail

These gates, and the fact that there are quite few, mean that VMI doesn’t think bikes are the best means for navigating the trail. But we thought bikes were great, and saw many other bikers out (as well as casual walkers, runners and those walking their leashed dogs). The gates have been upgraded by the Friends of the Chessie Trail and are really easy to swing open. 

The trail, as most rails-to-trails are, was a sand or gravel mix nearly the entire way. So road bikes likely aren’t the best, but slightly wider tires will handle this just fine. No need for full-out mountain bike, necessarily.

And we loved the way the trail meandered along the Maury River. The water of the Maury is green. I kept wondering why, yet even Google won’t tell me. Regardless, it is so pretty.

Another unique feature of the Maury River is that, while wide and mighty, it is short and completely contained in one county. (This is a fact that I was far more impressed by than my kids.)

Chessie Trail

At the time of our adventure on the Chessie Trail, one of the bridges was being worked on and there was a diversion off the safe trail and onto a back country road.

In 2003, Hurricane Isabel washed out the bridge. Reconstructing this is, as you can imagine, a long-term project. I don’t see any dates of projected completion and it didn’t look that close to done, based on our observations.

The detour was quick, and riders are able to get back on the trail quickly, but being on a road wasn’t ideal. Additionally, there is a steep climb, albeit extremely short, to get up to the detour. I wouldn’t let this imperfection deter you, but do be prepared.

The short, but steep, climb up to the detour:

Chessie Trail

We started at the Buena Vista end of the trail and biked to the Lexington end at Jordan’s Point Park. Neither trailhead is impressive (in fact, the short distance from the Buena Vista lot to the actual trail was so muddy and rutted, we walked our bikes to the maintained stretch), but we didn’t care. We were there for the path itself – and the opportunity to stop along the banks of the Maury and skip rocks.

Chessie Trail (3)

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Even though our family went in the dead-of-winter, we thought this was a really beautiful excursion. As with most rails-to-trails the grade was easy and nothing too demanding from a pedaling point of view.

We took our time doing the 14 miles (because 7 miles out + 7 miles = 14 miles total. This was even a math lesson for the kids!). We had good snacks, lots of water, bike helmets, good seats, and really felt like we got to know how cows live (which seems predictably yet lovingly unexciting).

When done, we all felt happily tired but not over-wrought…just the way a good family outdoor adventure should feel!

“The Chessie Trail was long and fun.”

    – Charlottesville kid “B,” 9-years-old
Chessie Trail

More resources on the Chessie Trail:

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While Raising Charlottesville will share opportunities in the area, everyone must use their own discretion and risk assessment with anything they undertake. Some articles on our site pre-date COVID so we recommend you research new protocols before you go. For questions about operations, safety and modifications, we recommend you contact each business directly.