For casual rides, also look at NEATO (New England Arabian Trail Organization) – they have a couple camping weekends a year, mostly in Connecticut and RI. Actually, I think NEATO is now holding a couple of two-day endurance-style rides too. Also check out the Green Mountain Horse Association; they run a couple of LDs, I think, as well as having casual trail riding days (but the trails up and down the hills are no joke. The road rides are lovely, but you get off of the road and into the woods, you are mountain hiking. Get a breast collar. ). There is, or used to be, an LD run out of a barn near Mt. Toby in central Mass; I think it was called the Leverett Ride? I think it was through the American Competitive Trail Association, but not sure. Also, there used to be an endurance ride out of southern Maine — maybe S.M.A.R.T (Southern Maine something something something). New England Equestrian Center of Athol (NEECA) runs a couple of casual camping rides, I think. As others have said, New England Horse and Trail often lists these rides. NEHT probably won’t have much listed now, but give it a couple months and by April, most of the rides start being listed. Many of the rides posted on NEHT will be casual friendly low-key rides of one or two marked loops, short loops of 5-8 miles and long loops of 12 to 18 miles, with lunch served back at the trailers. They can be a really nice way to see new trails. Many people do ride in small groups with their friends, and others are perfectly comfortable riding solo.