The following history of the Shire Post was provided by Mayor Will Whitfoot (aka Tom Maringer).
As to Shire Post.... I'll try not to get too verbose here and give the shortest possible version... but I do tend to go on about my favourite topic!
I have long been fascinated by Tolkien's writings, first reading them in the mid 1960s as they began to become popular as paperbacks in the US. I was particularly attracted to the lifestyle of Hobbits... their ability to endure adversity at need, yet thoroughly enjoy prosperity with self-indulgence yet without greed. I have also been both a philatelist (stamp collector) and numismatist (coin collector) since childhood. The origin of Shire Post can be found in this passage from Professor Tokien's masterwork THE HOBBIT:
"... We are plain quiet folk and have no use for adventures. Nasty disturbing uncomfortable things! Make you late for dinner! I can't think what anybody sees in them," said our Mr. Baggins, and stuck one thumb behind his braces, and blew out another even bigger smoke-ring. Then he took out his morning letters, and begin to read, pretending to take no more notice of the old man..."
The key phrase here is "morning letters"! Now many may skim over this phrase, but to a philatelist it has many implications. If there are morning letters then that implies afternoon letters... two mail deliveries per day! This in turn implies a very elaborate postal system, including a convenient means of paying for mail... most likely by stamps. Payment for such an elaborate infrastructure implies a monetary system quite beyond simple barter. So the first questions that popped into my head was "What would the envelope look like? What would the stamps look like? What sort of paper would they use? What kind of printing technology do they posess What about postal markings? What would the postal rates be? In what form would payment be made?" All such questions might escape the notice of all but the philatelically inclined, but to a stamp collector they are central.
Well... be brief, I searched for Shire stamps and found none. Eventually, in 1987, I produced the first indicia of postal payment... a hand-carved wood block print indicating prepayment of 1/4p. But the complexities that followed were nearly daunting. I had determined the basic postal rate to be one quarter of a penny... one farthing... which correstponded in nomenclature with the administrative districts of The Shire as outlined by the professor. So I worked out a postal rate structure... but now had to determine postal routes... which required a detailed map. None existed! The only maps provided in any of the books are either too large or too small in scale, so my early efforts had to be directed towards the production of a suitable map by which postal carrier routes could be devised. Thence followed a complete rate structure, including a monetary system and a system of weights and measures. We also adopted a Shire Calendar based on Takahashi Makoto's excellent work (see http://homepage1.nifty.com/hobbit/english/tolkien/reckon/index.html ) and a Shire Reckoning date that is offset exactly 600 years from the current Gregorian date. (Thus 2001 Gregorian becomes SR1401)
So the original idea of Shire Post was an interdimensional mail delivery service... it worked such that people would adopt a Hobbit name AND be issued an address in the town of their choice. Then by using my service they would be able to write to each other real pen and ink letters, addressed to a Shire name and address, send them to me, and I would apply all the necessary postal indicia and markings just as if the mail had passed through the Shire, then would be sent under separate cover to the recipient via the Real-World postal system. The whole idea of course is to provide a physical object as a "touchstone" to help bring the fantasy world to life. In many ways we try to bring the "Hobbitly Way" into life as well.
Before the advent of the internet the participation was very very small... only ten to fifteen members. In the mid 1990s I acquired the domain name ShirePost dot com and established a website where I invited people to register a Hobbit identity and participate. Since real mail would be delivered we also require a real-world mailing address, which is kept confidential. The membership slowly grew and people began exchanging letters via the system. I some cases long term friendships have been established thereby.
About the year 2000 I began to think again about coinage. It had always been in the back of my mind of course... but it was a task that was technically quite a bit more difficult than making stamps. But eventually I was able to learn enough and acquire the equipment necessary to begin making coins. My idea was to make a bunch of them and then have them in a treasure box so that I could run my fingers through them whilst chortling in piratical glee. There were only sixteen examples made of the very first Shire pennies, because the dies collapsed quickly. I was so proud of these that within an hour I put a picture on the website. Within another hour I had an email offer to purchase one of those pennies! Thus was the coinage aspect of Shire Post born.
In 1401 we began the tradition of having an actual party for Bilbo's Birthday on the saturday nearest the date of September 22. In this way at least some of the membership of Shire Post has been able to actually meet and enjoy each other's company in fact rather than merely in cyber-form.
Currently there are about 500 members... though many of the early memberships are defunct due to people changing addresses and not notifying us. The membership secretary and Addressing Coordinator is Mundee Baggins ( email@example.com or firstname.lastname@example.org ) Currently the participation in the exchange of pen-and-ink is very small... email and online forums have become the dominant mode of contact between members, but the system still exists and post runners are still sent out ever and anon, and the mint is still running to keep up with the demands of merchants for small change.