If you had the opportunity to buy on a favorite trail system in the USA, where would that be and why?
I’m beginning to look for a few acres with enough room to share with a housemate or two and their horses.
I’m more partial to the east coast, and will travel in the off season, so north or south isn’t as huge a consideration for me. A good dedicated trail system, budget, culture, and rentability are more important at this time in my life.
Big South Fork National Recreational Area in Jamestown, TN. Tons of trails, horse communities or farms outside the horse communities, and 250 miles of trails. Winters are mild. Tennessee has no state income tax. Real estate and taxes are very low compared to the Northeast.
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We are looking to do the same thing! I’ll be interested in your answers. We are focusing on Southern Ohio, West Virginia, North Carolina. I love the foot hills and weather looks like a good 10 months minimum of riding weather. We are focusing near Pedro Ohio because of the riding at Elkins Creek as well as other locations. We go on a scouting trip next weekend.
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The upside of living on a popular trail system is convenience. The downside is that convenient access for you to the trail is also convenient access to you for others from the trail.
Spend some time with a topographical map, Google Earth, road map, and trail map as you consider different sites. As with any real estate purchase, consider its resale value, remembering that the number of really dedicated trail riders is actually quite small and the odds are you’ll not ultimately sell to another with your view.
None of this means “don’t do it.” It means do it smart!!! 
Good luck in your search.
G.
P.S. The Big South Fork area is a very good idea. The Government management, there, is relatively “equine friendly.” This is NOT the case in MANY other areas, one of them being the Great Smokey Mountains National Park. This means you have to pay some attention to the “politics” of the region. In general, National Parks are quite restrictive and National Forests much less so. Very popular trail systems are often not equine friendly as the hikers and bikers don’t want to share with the horses 'cause they don’t want to get horse manure on their $600 hiking boots. Or $5000 bikes.
I understand from some friends that a major trail system that will allow equines is being developed along the right of way of the old Rock Island Line in MO, KS, and AR. I’ve never looked at it in detail but my friend, a fellow member of the U.S. Cavalry Assn., has lived in the area and followed the development. She is very positive about it. Might be worth a look.
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Guilherme mentioned a good point about living on a public access system. Ideally, I’d rather live near a trail system where
I could ride the horses into the trails nearby rather than have all kinds of strangers have access to my property and pastures and barn and home.
I would worry about strangers coming in from other areas and being so close to my animals and when you’re not home,
how safe is it?
Also an important factor is if the trails are used by motorcycles, 4 wheelers, hikers. Not good. IME.
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I have enjoyed visiting my cousin on the trail system near Tryon. Expensive area, but the perks are great. Lots of horsey stuff, great vet care, three hunts, tack store, lots of rich people spending money, which makes for a thriving area.
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I would buy next to the Greenway Trails in Ocala, in the Santos area. There are lots of people who ride the Florida Greenway trails. The park is huge so there is plenty of room for the hundreds of bicyclists to ride, without interfering with the horses.
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Man, when I went horse shopping in the Kennet Square area of PA, I saw enticing bridle paths everywhere. I didn’t get to ride on any, but it seemed incredible. Oh, and Hitchcock Woods, Aiken where I also did not ride but seemed pretty great. I’m relatively near you and though there are horse trails all through town, connected to conservation land with cross country jumps, and connected to trails in surrounding towns, the ground is so rocky. I always imagine the early Puritans arriving, trying to farm the rocky ground, and accepting it as a penance.
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Thank you for your thoughtful replies. I am spending the winter months on a trail system in northern Florida—private property with access, which sounds ideal. There are many riders wintering here, and i’m excited to be trying it out.
I’ve visited the BSF area and enjoyed trail riding there. What I found lacking was “culture.” It’s a long haul to anything interesting, and the town of Jamestown was a little pitiful. nice people, pretty area, but not interesting as a place to possibly retire from my POV.
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