It doesn’t get more perfect: Fleetwood Community Center Trail Ride is a must-do


History, horses and a community of trail riders came together at the base of the Blue Ridge Mountains near Massie’s Mill, Nelson County, Virginia, in the middle of October for the fall version of a  twice-a-year ride that is nothing short of spectacular.

Held each spring and fall in April and October, the Fleetwood Community Center Trail Ride, benefits an old school that was built in the 1930s and now functions as the heart of a community. Adjoining landowners give permission for their beautiful lands to be used for the ride. For three days, riders transverse about 5 different trail options, marked by ribbons. The rides are self-guided: Meaning there’s no trail boss at the head of a long string of horses like on many organized trail rides. Riders can move along at their own pace and in the peace of the woods.


Friday’s ride: 8 – 10 miles

Saturday: Short ride: 15 – 18 miles; Long ride: 22 – 25 miles (may include steep grades)

Sunday: 8 – 12 miles

Driving up to the school, the view is the first thing to greet participants. Purple-tinged mountains loom in the background, filled with promise of a great ride to come as you drive up Route 56, just less than a 2-hour haul from Roanoke. Be ready to meet new friends. Everyone was very friendly and eager to say hello, chat, and wish you well on your ride.

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Because the ride relies on agreements with neighboring landowners, it is very important that participants follow the trails as marked and the rules of the ride. Rides are capped at 150 riders and preregistration is required. The ride is often full well before the ride’s weekend, so don’t wait to register if you are sure you want to participate. This year’s fall ride included about 140 riders.

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While the ride is a nice relaxing day in the woods, it isn’t for beginners. For one reason, you’re going to be in the saddle for awhile. Rides run from 10-25 miles depending if you choose the short or long ride. Expect to spend your day riding. Even lunch is served out on the trail. There are water crossings. Most have very easy entrances and exits, including crossing of the Tye River. Others require more careful maneuvering. After 100 horses go across, some of the crossings turned to deep, sloppy mud that an inexperienced horse may struggle with making a smooth crossing. Just like the riders, horses should have some conditioning. There are long, steep climbs and descents, and it’s a long day. Shoes are recommended for the horses. Some of the trails are rocky.

Waiting in line for breakfast in the former school’s gym.

Meals are included in the $80/rider fee to ride. At this year’s fall ride, Friday night’s dinner was BBQ, Saturday’s lunch on the trail was burgers and hot dogs, and Saturday’s dinner was fried chicken. Breakfast included eggs, sausage, bacon and fantastic biscuits with gravy. And a large selection of desserts was available as well. You won’t be hungry at this ride. You may want to have something ready to snack on after Sunday’s ride. After you return in the afternoon, no lunch is served.

The fall ride also included an art show with art by local artists available for purchase. Plus a professional photographer, Anthony Antscapephoto Demarco, is along the trail is capture a keepsake of you and your horse along the trail. The photos can be viewed/purchased by clicking here.

Trailers are parked in the mowed field around the school. There are no stalls; horses are kept in portable corrals brought or put up by riders. There are no electric or water hookups for trailers and generators must be turned off after 10 p.m. So warm clothes, blankets and maybe a propane heater are great ideas. The fields are wide, open and flat. There’s a new wash stall built to spray off sweaty horses after the ride.

If you like to trail ride, the Fleetwood Community Center Trail Ride should be on your bucket list. The views are spectacular and you are sure to make new friends along the trail.

A photo taken by Antscape Photo of Juliet and I crossing the Tye River.





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