Before there could a community, there needed to be a post office. As was so often the case in the prairies, there was often a post office long before there was ever a community and Eastend was no different. It was in the fall of 1899 when 16 families lived in the district that Harry Cross decided to establish a post office. He suggested to the North West Mounted Police that they carry the mail from Maple Creek but the police considered it risky and inconvienant. Cross then attempted to establish a route to an Eastend Post Office from Crane Lake through Skull Creek. This also failed as no one tendered the route. The route was then changed so that it would start in Maple Creek, run through Skibbereen, Skull Creek and arrive at the Eastend area, a total distance of 53 miles.
Once the route was finalized, the Eastend Post Office was born on Nov. 12, 1900, with Harry Cross of course serving as post master. Jules Quesnelle, who came from Fort Walsh, was paid $312 to haul the mail, freight and passengers via stagecoach. Harry Cross was one of the first passengers on the stagecoach which would leave Maple Creek on Friday, stay overnight at the Eastend Post Office and return home the next day.
Harry Cross would remain as post master until 1904 when George Bolingbroke took over. The post office was moved in 1905, then moved back to its original site in 1907.
The hauling of mail from Maple Creek was often a tough affair. Blizzards would strike suddenly on the bench, chinooks would melt the snow and drivers would carry runners that they could bolt to the buggy wheels for snow travel. In the fall, willow branches were placed along the Bench route to guide drivers through the blizzards.
At Ben Rose’ log cabin, people would gather every night to receive their mail, exchange news and dance. The mail would be sorted there and then sent out to the other post offices such as South Fork. In January of 1914, the post office was moved to the Village of Eastend, and J.C. Strong took over as postmaster, which he quit one month later.
J.J. Bird took over as postmaster and remained so until 1917 when Ernie Baker took over. Ralph Blissett followed him in 1919.
In 1915, the mail began arriving in Eastend via the train.
Blissett would stay as postmaster from 1919 until 1950, one of the longest tenures in the entire country. He was followed by Henry Tasche who was postmaster from 1950 to 1975. So, after several postmasters over the course of just 20 years, two postmasters would fill the post for over 50 years.
During the years with those two postmasters, the post office went through several changes. The Post Office was first located south of the McPherson and Younberg store, and then it was in the addition of Blissett’s house and in 1962, it was moved to Main Street.