I've been in the region since 1994, with a brief leave from 1998-2000, though I've come back to stay with my growing family...and my horses!
Our region has become more and more diverse and I believe that is partially due to the wonderful Cheshire Horse Tack Shop in Keene, NH. They sell everything you need for your pets, not just for horses. Their staff is very knowlegable, and can help you with most all of your equine questions related to feeding, care, and riding.
Miracles in Motion is a therapeutic horseback riding facility, also located in Keene. Though they don't have a website, they provide horseback riding lessons for individuals with disabilities. They need volunteers to help with horse handling, leading and sidewalking.
This photo was taken at Southmowing. Southmowing Stables, though not in Cheshire County but over the border, is a great facility for boarding, lessons and training. They have wonderful trails in the woods with jumps for every level rider. They also hold horse shows for all levels of riders competing in 2 and 3 phase eventing.
Swanzey Stables is located off Homestead Hwy in Swanzey (Rte. 32). Emily and Marty Goodell operate this large facility where there is ample turnout, great stall sizes and a nice, newer indoor riding arena.
One of the best trainers for the aspiring eventer that I know around the region is Jess Systo. She is at a barn in Hinsdale with a brand new 100x200 indoor arena and also has great turnout, some new stalls, and excellent horse care.
If you're a beginner rider (english or western) or a western rider looking for a place near Richmond, Lisa Leclaire owns a boarding, lessons and training business approximately 20 minutes from Keene. She is excellent for beginner riders and takes them to horse shows at the Cheshire Fairgrounds every year. Her stables are a casual place, and she lives on the premises. It's a very comfortable place to ride and there are trails all around her property.
Reiners, a great place is to go to Tory Hill on Glebe Road in Westmoreland. Cheryl Fletcher lives on the property and offers training, lessons and boarding with beautiful pastures or individual turn out, as well as an indoor or outdoor arena.
If you would like to add to this list or if you would like to contact any of these people, please email me at firstname.lastname@example.org or cal 603-283-1948 and I will connect you with other horse people in the region, including farriers, vets, a natural hoof trimmer, or other local facilities.