​     Morrison writes that in the colonial days of Windham, "letters were rarely written. The people were not a writing people; their business was not such as to demand the frequent use of letters". The writing of letters was saved for the occasion of an important business matter or to, "give tidings of absent and long-separated friends". The first recorded use of a postal system in town was in 1757 when the town, "voted to send a Letter by some fitt[sic] person to Mr. Dunlap & to pay the charge of carrying it from Albany to Cherry Valley ". In May of 1775 a convention met in Exeter, NH to establish post offices in the state. In the early days of the post offices mail was delivered by postmen on horseback. The first rider to deliver mail to Windham was Samuel Bean who routinely delivered mail along the route from Boston to Concord. He rode the route once a week, making stops in, "Andover, Haverhill, Atkinson, Kingston, Exeter, Epping, Nottingham, Deerfield, Pembroke". Although these were his only official stops, he rode through Londonderry and Windham, likely delivering mail to both towns. At the time a, "single letter conveyed by land not exceeding 30 miles", could be mailed for a cost of six cents. 
      In 1805 the first post office was established in town with Andrew Park as the postmaster; he remained at his post until 1814. At this time there were still post-riders, one of which was Horace Park, the son of the postmaster. His route was not limited to Windham; Park started his ride in Windham and made his way through Pelham and onto Billerica, MA. William Morrison was another one of the early post-riders in town; his route was from Windham to Haverhill, MA. One of the best examples of the inefficiencies of mail delivery by horseback can be found in the delivery of news during the War of 1812. When the White House burned during the war it took almost a week for the news to reach Boston; undoubtedly it took maybe even a day or two longer for the news to reach Windham. 

​     In 1883 Morrison wrote that the, "mail facilities at present are good, the mails reaching town on nearly every train, and a through mail is carried by team from Windham Junction to Lowell and return, everyday. By that time there were four post offices in town: Windham Centre, Windham Junction, West Windham, and Golden Brook MIlls. The photographs above and below are two examples of period postmarks in town at the time Morrison wrote his history of the town. 

     The next major event in the postal history of Windham came about in 1905 when free rural mail delivery was established. The first official carrier for this route was Ernest Frost who, according to Rural Oasis, "covered an area of 17 square mills, serving 120 homes, and a population of 450". The entire mail route in town covered about twenty four miles. In the early 1900s the post office at Windham Centre was closed; the West Windham post office remained open, as did the post office at Windham Depot, which became the town's main post office. At the time the salary of the postmaster was $533. The first woman postmaster of Windham was Carolyn Clark who retired after four years of service; it is recorded that when she retired over forty Windham residents, "gathered at the the home of Charles Boyd to give a surprise party for the retiring postmistress". The Exeter News-Letter noted that, "games, refreshments and music helped to make the event a social success". 

     In 1929 "sub-carrier", William Clyde, hired Harvey Wilson to drive him around in his automobile; this was the first time mail was routinely delivered by automobile. As heavy snows and harsh winters are inevitable in New England, there were several times when the early carriers were unable to finish their route. The ingenuity of Windham's early postal carriers is exemplified by an observation recorded in Rural Oasis:
         "Tellis Wells....was frequently seen during the difficult winter months using his own               invented version of the snowmobile. It was a Model T Ford with the front wheels                   removed. In their place were skis and the vehicle was driven by chains placed on the             rear wheels!"
As decades passed there were relatively few, if any, problems with the postal service in town, However, in 1945, "it was discovered by an internal auditor from the postmaster general's office that Windham postmaster, Paul Otis Clyde, had misappropriated postal funds". He was given the chance to replace the missing funds, but failed to do so and was fired shortly after. Charles J Butterfield became the town's postmaster in 1947 and was still at his post when the Windham Depot post office changed it's name to the Windham Post Office. Below is a first day cover that was stamped on the date the name change took effect, October 1, 1956. It was signed by Butterfield and was then sent to Kansas, likely to a collector of first day covers.