Halloween in Woodstock

By Jennie Shurtleff

When I was growing up, my mother often related to me stories of my grandfather. One of her favorites was of a Halloween prank that my grandfather, as a youngster, and some of his “partners in crime” played on three of the neighboring farmers. All three farmers had cattle with similar markings, although one of the animals was a full-grown cow, one was a heifer, and one was a calf. On Halloween night, the boys swapped around the cow, heifer, and calf so that each farmer had an animal that looked similar to the one he had left the night before, only in a different size.  Apparently the farmers weren’t upset with the prank and, despite some inconvenience in having to swap the animals back to their rightful owners, saw the humor in it.   

A somewhat similar type of prank was perpetrated in Woodstock, according to local resident Dave Farrelly, only instead of three farms, the target was the Railway Depot that was located on Pleasant Street.

In one of his remembrances, David Farrelly wrote: 

I also remember one Halloween night about 1930-1932 when all the various gangs of looking-for-something-to-get-into converged on the Railroad Station. There was a freight car in front of Gillingham’s Warehouse, a coal car at Gilchrist’s coal chute, and one or two others around. We pushed and pulled and moved all these around and left one on the hand-moved turntable between tracks, and one parked in front of the shed where the engine in Woodstock was parked for the night. Satisfied we had really mixed things up we went our way for other mischief. The next morning at school, comparing notes on the Halloween activities, we were greeted by the news from the Depot area kids that the railroad was hardly bothered. The engine came out of its “Roundhouse” shed and had moved the freight cars we had labored on so hard for a couple of hours, into their proper places in 10 minutes!

Woodstock Railway Depot

Given Dave Farrelly’s reference to other mischief, I decided to go back into the old newspapers to see if Woodstock had a lot of mischief on Halloween night. It appears that they sometimes did. While many of the little hamlets in the greater Woodstock area reported, year after year, that they held classic Halloween parties in their little one-room school houses, where the children sang songs, paraded around in costumes, played games, drank sweet cider, and feasted on doughnuts, the reports in Woodstock sometimes included stories of mischief and vandalism intermingled with more appropriate celebrations of the holiday. 

For instance, a letter written by the editor of the Vermont Standard in 1941 refers to the “shenanigans” that took place in Woodstock that year on Halloween night. He notes that “We may be getting gray around the temples but we can still remember the kick we received out of Hallowe’en pranks as a kid. Consequently, we hold no malice toward those youngsters who have fun smearing soap on windows, ringing doorbells and contriving other acts of harmless mischief. But we do object strenuously to the destruction of property, defacement of property and such dangerous practices as last Friday night’s false fire alarms.” 

Another letter to the editor that year reads:

“After the doings of last Hallowe’en it seems to me as a taxpayer in Woodstock that something should be done to stop this vandalism and I mean that of the older boys and girls in this village…

 Three false alarms… what does that cost the taxpayer? Taking the cannon from the school grounds and dumping into the Kedron… funny wasn’t it? Some one has to bring it back…

Ripping and breaking the pickets off the new fence on the Campbell Cross lot… great fun… but expensive for the owner… bad as it looks this destroying the fence doesn’t improve the looks one bit…

Building fires in the street that leads to the rear of the blocks… great fun but dangerous…

If the person or persons are known they should be punished to the limit… the expense incurred last Friday night would go a long ways toward fixing up some of the bad spots in our sidewalks but, could not be done on account of extra expense….”

The following week, the editor of the Vermont Standard followed up his previous editorial with a longer one. In this editorial he noted: “While comments were flying back and forth as to depredations observed in Woodstock Hallowe’en night, other papers over the state carried stories of parades, festivals and frolics which gave everybody a good time – minus most of the undesirable types of pranks.” He goes on to note that on Hallowe’en night in 1941 “a crowd of from 100 to 300 youngsters were gathered in Woodstock’s business section. Underneath it all, there was something pathetic about this gathering. Kids all dressed for an evening’s gay fun – but there wasn’t anything to do. Small wonder, then, that they cheered happily as the fire trucks roared up the street in search of mythical fires…. Next year it will be the same old story – broken fences, false fire alarms, damaged property – unless Woodstock plans something to give the kids a good time.”

The editor goes on to suggest that businesses, clubs, organizations and the school start early to plan a real Halloween festival with a parade, games, food, prizes, dancing, etc. He concluded his remarks by stating “We’ll lay a dollar to a doughnut that the whole affair would cost less than this year’s expenses for dry fire alarms, damaged property and clean up – and there’d be a better taste in everybody’s mouth the next day.” 

It seems that the editor’s suggestions were taken to heart by the community. The following year a big party was planned for the children living in Woodstock Village. It was organized by representatives from the Daughters of the American Revolution, the Rotary Club, the Eastern Star, the League of Women Voters, and high school students. It included such activities as a costume parade (in which children were “urged to use their own ingenuity in planning the costumes, not to use money”), movies in the gymnasium, both square and round dancing, and refreshments. That party turned out to be a “howling” success, such a success that the newspaper noted there were “few disturbances in the village throughout the evening” and apparently a number of townspeople noted the “lack of marking of store windows, the usual street prowling, and the depredation of property.”

By 1953, in the Woodstock area, the featured entertainment appeared to be contests. There was the traditional costume contest where judges Mrs. Paul Bourdon, Mitch Hager, and William James selected the costumes that were the most artistic, funniest, most original, and most horrible.  Later, apparently, as a way to get students to go home instead of prowling the streets, there was a Quiz Game for which 108 students registered. The registered students each got a phone call from either Frank Teagle, Harold Corkum or Frank Riley asking them a question. That year the question was “How many children attended school in the first six grades, Oct 20?” First, second, and third prizes were awarded to both the male and female students whose guesses came the closest to the actual number. The prizes were gift certificates to local stores such as the Men’s Shop, Town & Country, the Woodstock Pharmacy, and the Economy Store.  

When I was a child (many, many years ago), my mother only used to let my siblings and me trick or treat at the houses of a few neighbors. She would drive us to each place and go in with us.  Each stop would take at least 15 or 20 minutes, which limited the number of stops to just four or five for the evening.

I was the youngest child in my family, so one by one, my older siblings stopped trick or treating, until it was just my mom and me going to the neighbors’ houses. By the time I was in eighth grade, going out on a cold October night dressed in a costume in order to get a piece of candy had somewhat lost its appeal for me, so for that year I didn’t trick or treat. My mother got several calls from neighbors the next day asking why I hadn’t come. After that, in future years, a couple of them called my mother the day before Halloween to insure that we would be coming on Halloween to trick or treat. So until I went off to college, every year my mother dug out the shiny, pointed, black plastic witch’s hat that I had gotten when I was in elementary school. She plopped it on my head and told me it was time to go trick or treating, and off we’d go to visit a few of our cherished neighbors to wish them Happy Halloween and maintain the tradition that had started so many years before.

Wishing you all a safe and happy Halloween!