REVIEW: Pleasant Hill Railroad Days 2022 [History Tour]

Pleasant Hill Railroad Days is one of the many small town craft festivals that happen in any given year in the late spring / early summer in this area (and I’m sure across America). I am insanely late in posting this, and I went to a great effort to get it done today since I knew that the 2023 one was likely going to happen pretty soon! That was until I saw a post on the organizers’ Facebook Page revealing that the 2023 iteration has been cancelled for some reasons I will link to below. By the sounds of it, the cancellation was justified. To summarize, they cited a lack of volunteers and a logistics problem arising from the untimely death of one of their historical society board members. It’s a shame because this event was actually pretty fun despite some weather issues we had. Early Spring around here is notoriously bi-polar, and we got the worst of high winds and flash flooding on the Friday before we went. Despite this, everyone seemed to be in high spirits and it was pretty crowded for a town of only like 8,000 people.

Pleasant Hill Railroad Days; Downtown Pleasant Hill, MO

The main historic purpose of the town of Pleasant Hill was being a railroad hub, something that is obviously well-regarded to this day considering the theme of the event. Usually, events like this have the same sort of vibe, that of a craft fair with drunks and blaring country music, but I’ll give them kudos for doing something different. Today, Pleasant Hill is best known as the regional home for the National Weather Service Kansas City/Pleasant Hill, Missouri office, “which serves 37 counties in northern and western Missouri and seven counties in extreme east-central Kansas” according to their site.


From the Wikipedia Page, a look at the town’s history:

“Pleasant Hill was platted in 1844 by William Wright and was recorded as the “Original Town of Pleasant Hill.” Wright and Methodist circuit rider William Ferrell operated a mercantile store. The original location was on a ridge near Pleasant Hill Cemetery. The community was named after its “pleasant situation on an elevated prairie”. Wright also operated a 3-story tavern that was marked by a 12-foot high beacon atop a pole. It was an overnight stop for stagecoaches between Lexington, Missouri and Fort Scott, Kansas.

During the American Civil War and the run-up to it in the 1860s, Pleasant Hill was bitterly divided between the factions and was subject to numerous bushwhacking incidents. The most notable incidents involved the congregations of the Christian and Presbyterian churches which were built side by side on High Street. The Presbyterian Church was burnt in the process. In 1863 all residents in the area were forced to move from the community in General Order No. 11 (1863). In 1865 after residents were able to return the city center moved one mile southwest down the hill to the railhead of the Pacific Railroad (the original town site is still within the city limits, however the area is now called “Old Town”). The new city center was lower than the original and adjoins Big Creek.”


Confession time, I have yet to read this book, Elizabeth’s War – Missouri 1863 by D.L. Rogers, but I bought a signed copy from the author at the event, and need to sit down and get into it soon. This book talks a lot about General Order No. 11, which was a wide-sweeping attempt to curb the ongoing “border wars” through a forced deportation of everyone living in the areas on the edge of Western Missouri. As you can imagine, this was one of the more questionable things the Union Army did during the war, and is one of the reasons you still see a lot of Confederate sympathies here in rural areas some 160 years after the fact.

“In a time when raiders, bushwhackers, and Redlegs rode the Cass County, Missouri, countryside bringing fear and destruction with them, Elizabeth Miers and her family barely survived into the next day. When the enemy, in the form of Elizabeth’s neighbors, comes a-calling more than once with mischief on their minds, Elizabeth fights back to keep her children safe against men she once called friends. On August 25, 1863, following the issuance of General Order No. 11 , thousands of women, children, and the elderly were forced to vacate their homes in the brutal summer heat within fifteen days. With determination and a plan, Elizabeth sets out on a sixty-mile trek toward St. Clair County. Carrying enough prepared food and water on a rickety built sled to reach her family, she prays her kin are there to welcome them, uncertain whether they survived the buring of Osceola two years prior, or not. Facing more than just the lack of food and shelter and the unbearable heat, they’re set upon by raiders and foraging soldiers who try to take more than just their meager provisions. Much more. Left with little, Elizabeth and her fellow travelers continue south, facing more indignities before their journey is done. Through Elizabeth and the thousands of other refugees that traveled ahead of and behind her, feel what they felt in the wake of General Order No. 11, an order that took everything and left them destitute and afraid they wouldn’t live to see one more day.”

The Trip:

Pleasant Hill is not too far from Kansas City, and the downtown area thankfully has plenty of parking on weekends. Some other cities (I’m looking at you Lee’s Summit and Independence) do not have good parking solutions for events like this. While at the event, there were many things to do, of which I will outline below:

Note: I guess I didn’t take any pictures of the people selling stuff, but there was something like 50 people selling anything from seamless siding to scented candles and everything in-between!


We were not there for a lot of this, as most happened later at night, but the event promised multiple bands throughout the three days. We managed to catch an ELVIS impersonator as we arrived.

Model Trains:

There was a whole garage packed with model railroads that was a treat for the kids. If I recall correctly, it was next to the Fire Department, which had a ton of kids stuff going on, so it was one of the top destinations for sure.

Real Trains:

Like the above, just bigger!

Live Theater:

One of the local churches did a dramatization of an odd period in United States history, the so-called Orphan Train. Children from the East Coast, including many immigrant children, were often loaded up on train cars and sent to (hopefully) better lives. According to Wikipedia, “The Orphan Train Movement was a supervised welfare program that transported children from crowded Eastern cities of the United States to foster homes located largely in rural areas of the Midwest. The orphan trains operated between 1854 and 1929, relocating about 200,000 children.” This was a play ran by a church and had children in it, so I was not expecting it to be great or anything, but it did get me curious about the topic.


There were a number of historical re-enactors that had camped nearby portraying a Native American camp and some French fur trappers. My son absolutely loved looking at and learning about the items on display and asked this poor many about 10,000 questions! The downtown area also had some statues and war memorials that were cool.

A Museum:

This was run by the Pleasant Hill Historical Society, and was pretty typical of smalltown county museums. As people pass away, a lot of their belongings get donated to the historical society and put on display resulting in a pretty nice look at local history, and in some cases an unbelievable amount of clutter. This one, thankfully, was not too crazy. Although I did take on exhibit personally…


There’s just something about seeing a computer you used in a classroom in elementary school in a museum like some sort of ancient artifact that really reminds a person how old they are!


This was an all-around fine event to attend, however the actual craft and local business tents were either full of stuff we did not really want or in the process of being removed by the time we got there due to the weather being sort of iffy (high winds especially). Luckily, the live entertainment, food, and the local museum kept us busy and the trip was overall something we all enjoyed. I’m sad this won’t be around this year even though I am insanely busy the weekend it usually happens. Truthfully, I likely could not have made time for this myself, but having the option is always nice just in case. Here’s hoping 2024 is better for them, and they can get this rolling once again.

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For more content like this, check out my History Tour page HERE


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