This painting! I purchased it from a wonderful seller in Boston, who told me it has come from an estate connected to a traveling carousel somewhere on a lake in Michigan, and that the figure at right was the impresario--but he wasn't sure of exactly where or the the name. Well, a little research led me to the amazing history of the Silver Beach Amusement Park in St. Joseph on Lake Michigan, launched in 1891 and of which a carousel was but a small part, and to Logan Drake, the force behind it, who the man on the right most certainly is! (I've included a photo in the documentation.)
There is a bunch out there, including an extensive section of Southwest Michigan's Business and Tourism website dedicated to the history of the Silver Beach Amusement Park, a mid-western Coney Island of sorts, which, like Coney Island, grew and grew until it didn't, ultimately closing in 1971. I highly recommend giving it a look and a read, here: http://www.swmidirectory.org/History_of_Silver_Beach_Amusement_Park.html.
I don't know who painted the painting or quite why these three together, but I'm really charmed by it. The figure at left, with all seeing eye above her (I think her?), I'm taking for a clairvoyant of some sort, and the Native American chief at center is done very much in the style of an early folk art Cigar Store Indian. On the reverse, in what I believe is pastel, a bucolic landscape which I think quite likely portrays one of what were eventually 80 cottages along the beach built by Drake, who rented them, along with canoes and row boats, to vacationers.
Sold in the frame I found it in, original to it I believe and which cuts it off a bit at the bottom and is a little rickety, but which I think compliments it a kind of a great way. Framed: 25 1/2" x 14 1/2 x 1 1/16. Painting itself, oil on board, measures 20 15/16" x 9 3/4". I believe it likely dates to the very late 19th century or very beginning of the 20th, with some scrapes and scuffs and a few very small holes, as it feels there should be!