There is no railroad operation in New Hampshire that operates cabooses during the winter months. All scenic railroads... Conway Scenic Railroad, Hobo Railroad, Lake Winnipesaukee Railroad, and the Wilton Scenic Railroad (Wilton maybe gone for good), all operate on state owned tracks... So far all state owned tracks operated by scenic railroads close at the end of December and don't open up again till March/April. There is a caboose train that runs during the summer months from Concord to Lincoln but all cabooses are privately owned and its more of a club event that happens once a year.
It takes real skill to choke on air, fall up the stairs and trip over nothing. I have those skills.