Hello, I recently moved from Fairfield County and had my horse at a few barns there. Because land is rather expensive, it can be hard to find a barn near good trails. However, there is a great trail system called North Salem Bridal Trails, http://www.nsbta.org. It’s not in Fairfield, but just over the boarder into NY. A barn that I know was good and had direct access to it is River Horse Farm. http://www.riverhorsefarm.com Up in Newtown, CT there is the Newtown Bridal Lands, http://nblact.com. But, I don’t know of any good barn directly off the trails. Sunnybrook Farms in Newtown, has some trails, but not a lot, but they have good care. There is a publication called “Just Horses” that has equine information for CT that might be helpful. http://justhorses.com. Hope this helps a bit.