There are so many independent letterpress companies these days it's hard to say who's best, but I've found a good handful that make calendars I could love to look at for the next twelve months. My strategy may be to buy several, keep one, and give the rest as gifts. All of these crafty printers can be found on etsy.
Delphine Press, based in Rancho Santa Fe, California
Lizard Press, based in San Francisco, California
Birch and Bristlecone, based in Seattle, Washington
Sycamore Street Press, located in Columbus, Ohio