I recommend reading Michael Winship’s recent article “Pirates, Shipwrecks, and Comic Almanacs: Charles Ellms Packages Books in Nineteenth-Century America,” in Printing History (N.S. no. 9, January 2011): 3-16. In it, he discusses the earliest almanacs in the United States and the development of the comic almanac specifically. As well as a few pirates.
In graphic arts, we are fortunate to hold the Sinclair Hamilton collection, which includes a photostat of Noadiah Russell (1659-1713), Cambridge Ephemeris. An Almanack of Coelestial Motions, Configurations, &c. for the Year of the Christian Aera, 1684 (Cambridge [Mass.]: Printed by Samuel Green, 1684). Graphic Arts Collection (GAX) Hamilton 5
John Tulley (1638-1701), An Almanack for the Year of Our Lord, MDCXCVI  (Boston, N.E.: Printed by Bartholomew Green, and John Allen, for John Usher, and are to be sold at his shop below the Town-House, 1696 [i.e., 1695?]). Graphic Arts Collection (GAX) Hamilton 6
I prefer American almanacs from the eighteenth century, when the woodcuts become more plentiful, such as seen here with our: John Tobler (1696-1765), The Pennsylvania Town and Country-Man’s Almanack for the Year of our Lord 1756 (Germantown [Pa.]: Printed and sold by C. Sower jun., ). Graphic Arts Collection (GAX) Hamilton 34.
Michael Winship is the Iris Howard Regents Professor of English II at the University of Texas at Austin and editor of the final three volumes of the nine-volume Bibliography of American Literature. He is the author of American Literary Publishing in the Mid-Nineteenth Century: The Business of Ticknor and Fields (1995) and has published widely on the nineteenth-century American book and publishing trades.
Winship’s article is available in paper or (soon) electronically at Princeton University and for others, directly from the American Printing History Association: http://www.printinghistory.org/publications/printing-history.php
See also Charles Ellms, Queer Almanac (1836). GAX Hamilton SS347
Charles Ellms, Shipwrecks and Disasters at Sea, or, Historical Narratives of the Most Noted Calamities…(1836). GAX 2003-1740N