Woodstock’s Quirky History

A timeline of interesting and sometimes wacky Woodstock history:

Turtle Mound
Turtle Mounds

The land that Woodstock now occupies was once the territory of the Illini, Miami, Ho Chunk and Pottawatomie tribes as well as other indigenous people for thousands of years before them. Human made artifacts dating back about 10,000 years have been found in McHenry County and ancient animal shaped mounds have been found within a few miles of Woodstock. A 190 foot long mound shaped like a headless lizard (inexplicably called Turtle Mound) was discovered in Rockford and many smaller mounds dot the area. A thousand years ago the city of Cahokia in current day Illinois was larger than the cities of London or Paris at the time.

Route 14 was built over an old Indian trace (known as the Kinzie Trail or the Great Chicago-Algonquin-Woodstock Trail) that was used by native people for many years before Europeans arrived. This trail (and the original Rt. 14) passed right through the Square and it is reasonable to assume the cool fresh water spring on the Square was a popular stopping spot for native people traveling along this trail.

Before any European ever settled here, the land that Woodstock is now on was passed around like a hot potato for several hundred years by Europeans that never lived here. Click here for a timeline of who claimed control of the land Woodstock is on from 1492 to 1836.


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Black Hawk in 1832

In his 1833 autobiography, Black Hawk  (whose real name was Ma-ka-tai-me-she-kia-kiak), said that he brought his entire band of about 1500 people to the headwaters of the Kishwaukee River to hide during the Black Hawk War after the battle of Stillman’s Run in April 1832. The headwaters of the main branch of the Kishwaukee River are in Woodstock.

After The Black Hawk War, the 1834 Treaty of Chicago  required the native people to cede and vacate the land where Woodstock is now by August 1836.

In 1836 McHenry County was formed out of the upper portions of Cook and LaSalle counties. The county (as well as the town of McHenry) was named for Major William McHenry, a member of the Illinois Militia during Tecumseh’s War, a major during the Blackhawk War in 1832, and a member of the Illinois House of Representatives and Senate. William McHenry does not seem to have any obvious relation to James McHenry the namesake of the famous Fort McHenry in Baltimore. Fun Fact: There is another McHenry County in the middle of North Dakota.

Original Courthouse Mchenry
Original 1838 McHenry County Courthouse

The very first McHenry County Courthouse was commissioned to be built in 1838 west of the Fox River where McHenry’s Veterans Memorial Park is now. A two-story 40 x 60 ft frame structure was completed in 1840 on Court Street. This structure was moved to the NW corner of Riverside Drive and Pearl Street in 1844 and is still standing! Fun fact: The original courthouse was converted to a bar and allegedly served alcohol during prohibition.

A trial was held in this first courthouse in which Davis and Taylor Driscoll stood accused of murdering John Campbell on June 27, 1840. At that time, northern Illinois was home to “Banditti of the Prairie,” organized gangs of horse thieves, counterfeiters, and stage coach robbers who gave the settlers so much trouble that they organized themselves into a vigilante band of “Regulators,” led by John Campbell of Lee County. Campbell was shot at his home by the accused and the murder was witnessed by Campbell’s wife and 13-year-old son Martin. During the trial Martin said that he would have shot Driscoll at the time had his gun not misfired and that he would kill him if he ever caught him outside of the court-room. The trial resulted in the accused murderers being set free, however one of them was soon killed by an unknown avenger. On June 29th 1841, four members of the Driscoll gang were captured south of Rockford and tried and executed on the spot by a lynch mob. The firing squad consisted of 56 men!

Illinois 1836

McHenry County originally extended all the way to Lake Michigan with the county seat in the town of McHenry but in 1839 the county was divided into Lake and McHenry Counties. Woodstock was originally called Centerville due to it being in the middle of the new McHenry County. The name Centerville was changed to Woodstock in 1845 after the Vermont birthplace of early settler Joel Johnson.


There was an artesian spring on the Square that bubbled out clean fresh water where the drinking fountain under the Spring House Gazebo is now. This spring was one of the main reasons that the first white settlers built their homes here. Bradford Burbank erected the first log house near the spring in 1843. Alvin Judd erected the first frame dwelling at the NE corner of Benton St. and E Jackson St. (formerly Dietz St.) in 1844.

In 1844 Alvin Judd platted a new town called Centerville. The plat, a central square oriented to the compass points surrounded by rectangular grid, was recorded by George Dean in June, 1844.

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June 14, 1844 plat of Centerville Illinois (photo courtesy of Woodstock Public Library)
Depiction of the 1844 Courthouse – by artist Jim Pearson

In 1844 the county built a 2-story frame courthouse and jail near the spring on the land that is now the Square. The Sheriff’s office, living quarters and jail were on the first floor and the courtroom was on the second floor.

1846 – The county built a 2-story brick building known as The Rat Hole across from the spring at the SE corner of Benton and E. Jackson (originally called Dietz Street) for the county offices. The Rat Hole got its name in the winter of 1847 when a terrific wind lifted the tin roof off the building and blew it a considerable distance away. The frightened county officers (mostly Democrats) rushed out of the building and were greeted by a shout from merchant Henry Petrie (a Whig) who gleefully exclaimed, “See the damned rats crawl out of their holes.”

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The earliest known picture of The Rat Hole (photo courtesy of Woodstock Public Library)

1846 – School classes are first held in the frame courthouse. The upstairs courtroom was rented at two dollars per month by Mr. Richardson, former teacher of mathematics at Norwich University, Vermont.

1846 – The Illinois Republican Newspaper begins publication in Woodstock.

The first brick school is built in 1847. After 19 years of use as a school the building was converted into a blacksmith’s shop. In the fall of 1849, the new school commissioner, Rev R.K. Todd, organized a teachers institute and trains 150 teachers on the second floor of the old frame courthouse over the course of a week.


In 1851 the Argus Newspaper and 3 other businesses on the south side of the Square are destroyed by a fire.

The town board passes an ordinance in 1853 to regulate “unmuzzled dogs and sluts running at large.” The ordinance permits killing or shooting. The board also passes an ordinance to “prohibit strong beer or porter, sold, given or drank on Sundays.”

While digging a well for a new tannery in 1853, workers unearthed the top of a tamarack tree in the 4’x4′ hole. They continued digging and unearthed a an entire tamarack tree with a trunk 16′ long. This was just east of the Neil Donnelly house…and now for something completely different. The Larch!

In July of 1854 Woodstock established a police force with the following decree: “Whereas, confusion and turmoil seems to be the order of the day, and drinking and dissipation and street fights are practiced by many transient persons…a police force be and is hereby established…whose duty it shall be to suppress intoxication and rioting in the streets or other places, by arresting the parties making loud and unusual noises…”

In 1854 Burtschy’s brewery burns down. His first brewery was near Greenwood in the 1840s but he soon moved it near the Square.

In 1855, an election took place for the removal of the county seat from Woodstock to Crystal Lake. It was voted against 2,095 to 1,049.

In 1855, The Chicago, St. Paul and Fond du Lac Railroad first built the rail line that passed through Woodstock.  Two passenger trains ran daily to and from Chicago (except Sunday). Travel time varied between 2.5 – 4 hours.

depot old
The old Woodstock train depot (photo courtesy of Woodstock Public Library)

Woodstock set fines in 1855 for  “immoderately” driving or riding a horse and for trains going over 10 mph.

The first ice house at Dufield’s Lake was built in 1855 by Haas & Griffing. The ice houses supply over 1,800 tons of ice to local breweries.

In 1855 the town of Woodstock purchased the property on the west side of the Square occupied by Hill’s Tavern, and donated it to the county for the new courthouse. In exchange, the county gave the old frame courthouse and the land including the Square to the town of Woodstock.

The Rat Hole in 1885 (photo courtesy of Woodstock Public Library)

The county sold the Rat Hole in 1855 to Lindsey Joslyn for $723 presumably to move the county offices into the soon to be built brick courthouse. He converted it to a tavern.

1841 Mountain Howitzer
1841 Mountain Howitzer

In November 1856, when the first Republican presidential candidate John C. Fremont won McHenry County, but Democrat James Buchanan won the presidency, a boisterous group of local Democrats used a cannon dubbed “The Woodstock Cannon” to celebrate. The cannon prematurely discharged injuring a man named Orson Bates sufficiently to require the amputation of his right arm, and the left hand above the wrist. He eventually died from the wounds. Four years later the jubilant Republicans fired the cannon at midnight to celebrate the election of Lincoln. The cannon shot was heard in Marengo, Union and Chemung and many windows in Woodstock were shattered by the percussion. In 1867, this same cannon was used to try to recover the body of a seventeen-year-old Woodstock boy named Michael Dwyer who had drowned in Crystal Lake. The second time the cannon was discharged, it exploded and severely injured several men including Michael Dwyer’s father. The Woodstock Cannon was probably similar to the pictured replica of an 1841 Mountain Howitzer on display at the Woodstock Police Station.

Woodstock purchased a new fire engine for $600 in 1856 but found that after testing it, it wouldn’t throw water.

In 1857 the McHenry County Courthouse was built on the west end of the Square. The Courthouse officially opened on October 1, 1857. It was designed by John Mills Van Osdel, the most prolific architect in nineteenth century Chicago who also built the first three Palmer House hotels and the Briggs House Hotel that Abraham Lincoln was in when he learned he had been nominated for president. Van Osdel designed and built the first steamships in Chicago and several of the first opening bridges over the Chicago River. He received the the first US patent ever issued in the city of Chicago for his design of windmill powered pumps for lifting water in the Illinois and Michigan Canal.

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This is the earliest known picture of the 1857 Courthouse (photo courtesy of Woodstock Public Library)

On July 4 1858 the old frame courthouse and jail located on the Square burned to the ground. As described in the Woodstock Sentinel: “It had been purchased by the bank, which allowed it to remain, the eyesore that it was. The citizens were in favor of having it torn down, but they did nothing. Once before someone tried to burn it, an attempt which had failed. But at this time somebody had hired one of the best fire starters in Chicago to finish it. One night the watchman, was invited away for a few drinks by a “friend.” He returned to find the building flaming. Hurriedly, he caught up a pail of water and threw it on the place. The “water” so conveniently placed was really a very inflammable substance, camphene. The result of these fires was new buildings and a better appearance of the down town district.”

Town of Woodstock had the Square graded and fenced by a Northwestern Railroad civil engineer who suggests that the trees should be planted “promiscuously instead of in rows.” Alvin Judd himself plants and waters the elm trees.

John Bertschy opens a rebuilt brewery in 1858.

In 1859 the town recommends the removal of the cemetery on South Street as “unfit for burials”


In February 1860, a fire destroyed a tin shop, livery stable, saloon, and furniture store on Main Street (formerly known as Wentworth Street). All the horses were saved.

Smallpox was reported at Miles Lyon’s house. Other reported causes of death in 1860 Woodstock are Scarlet fever, consumption, dysentery, typhoid fever, cholera, putrid sore throat, stricture of bowel, bleeding of the lungs and typhus fever.

A party of Pottawatomie Indians, 4 men, 3 squaws, 3 papooses, camp near Dufield’s Lake. They were reportedly on their way home to Wisconsin after a trip to beg pork, flour, etc. to last the winter.

In the winter of 1861 the newly built 150-student Todd School building burned to the ground. A Mr. Cosgrove,  who, when arrested, tried to hang himself but was revived, was convicted of arson and sentenced to 6 years in prison. Reverend Todd presumed that Mr. Cosgrove had been hired to burn the new school by a man that Todd had refused to give “a certificate on the ground of moral character” although this man was never identified or charged.

When The Civil War starts in 1861, Woodstock Light Guards consisting of 78 men and officers join 9 other companies at Camp Scott on the fairgrounds in Freeport but they had no guns. The Woodstock Rifles organize with 51 men and 6 officers.

Civil War 1863
Illinois Company A Fifteenth Volunteer Infantry in winter quarters in Georgia in 1863. Mainly composed of men from McHenry County Illinois. (photo courtesy of Woodstock Public Library)

In 1862 an ordinance was passed to prevent cattle, horses & hogs from running at large during certain hours.

Here is a detailed map of McHenry County in 1862

1863 – Newspapers report that “Scoundrels steal clothes off clotheslines” and “John Steffens, a stranger, pulled a wild parsnip, ate it and died of distemper.” The newspaper also asks farmers that still owe for subscriptions “to pay with a few bushels of corn and oats immediately.”

In March, 1864, Willard Joslyn, was reportedly killed on the farm near Harvard, “while trying to turn a somersault over a pole.”

In April 1865, while celebrating the fall of Richmond, H.G. Otis was killed by an exploding anvil.

The bodies in the South Street graveyard were relocated to the new cemetery in 1865.

In 1867 the South Street Bridge was built. It is a rare Helicoidal Arch bridge (sometimes spelled Heliocoidal and can also be called skew arch or spiral arch). The bridge was built by the Chicago & Northwestern Railroad (formerly The Chicago, St. Paul and Fond du Lac Railroad). It was widened for a second C&NW track in 1897 using the same Helicoidal technique, that’s why the date over the keystone says 1867 on the east side and 1897 on the west side. The bridge is now one of the few remaining examples of Helicoidal construction developed by Scottish architect Peter Nicholson. The only other Helicoidal Arch bridge in Illinois that we know of is near Ingersoll Centennial Park in Rockford and is under part of a railroad bridge structure over the Rock River.

The 1867 Helicoidal Arch bridge at South Street (photo courtesy of Woodstock Public Library)

On May 24 1867 Albert Churchill posts the following ad in the Woodstock Sentinel: “NOTICE – Whereas my wife Anna Churchill, did leave my bed and board, without just cause or provocation, on the 23d of May, 1867, I hereby warn all persons against trusting her on my accounts, as I will not be responsible for any debt contracted by her after that date.”

In 1868 Frederick Arnold Jacob Zimmer & Co. brewery takes over Burtschy’s brewery and operates it until 1884. The brewery produces about 4,500 barrels of beer annually.

The buggy of Reverend R.K. Todd, the founder of the Todd School, was crushed by rail cars backing up on a crossing near the Presbyterian Church because the train failed to ring a warning bell. R.K. Todd and his son escaped injury.


In August 1870, at Woodstock, while moving a building, a timber fell in such a manner, that Bela Darrell was strangled to death.

On October 8th, 1871 The Woodstock Fire of 1871 destroyed nine buildings on the Woodstock Square on Van Buren Street between Dean Street and Johnson Street.  The fire was first discovered in a haystack behind Jas. Lulny’s saloon at the SW corner of The Square. The courthouse was saved by water in two large cisterns at the courthouse. This fire occurred inexplicably on the very same day as the famous Great Chicago Fire as well as the lesser-known but much more deadly Peshtigo, WI fire. The Peshtigo fire killed as many as 2,400 people in Wisconsin and Michigan and was the worst recorded forest fire in North American history. Woodstock had wells dug at the four corners of The Square to help fight fires.

In 1872 a $25 dollar reward was offered for the capture of Charles Randall who escaped from the jail. He had been detained for grand larceny.

All the buildings on the east side of the Square, including 16 businesses, 1 dwelling and 3 barns were destroyed by fire on Aug 27, 1872. Because of this fire Woodstock set plans to buy a fire engine.

1872 fire – View to the South of the East side of the Square. The Rat Hole is visible behind the chimney. (photo courtesy of Woodstock Public Library)

On December 7, 1872, Jacob Hurst, the night watchman at the Woodstock brewery, was killed when a bin of malt above him broke through the floor and buried him in malt.

In 1873 the Spring House was built over the artesian spring on the Square to attract tourists. Six years later an analysis of the water from the Spring House by Chicago’s Rush Medical College reveals recommendation for use in treatment of afflictions of the stomach, bowels, and kidneys; also to treat debility, anemia, etc. It was found to contain “chloride of sodium; sulphate of potassia; sulphate of soda; bicarbonate of soda, lime magnesia and iron; phosphate of iron, alumnina; silica; and sulphurated hydrogen. In addition, it was mildly alkaline.” The town adopts the moniker “Spring City” in honor of the spring.

spring House
1873 Spring House in an undated photo (photo courtesy of Woodstock Public Library)

The Squire Dingee & Co. pickle company is organized in Woodstock in 1873. Cucumbers, cauliflowers and cabbage are pickled.

In 1874 a railroad accident 6 miles north of Woodstock killed 40 people and a child of 10-months drowned by falling head first into a pail of milk.

In October of 1874, while in his cellar sorting potatoes with his wife, George Schneider was struck and killed by lightning.  Mrs. Schneider was frightened but uninjured.

In 1879, 12 men competed in an 8-hour tramp around the Square. The champion walked a total of 40 miles and won $50. A man was arrested for using indecent language in the presence of a lady.


Woodstock Sentinel picture of the blizzard taken on Benton Street, looking north

On March 3, 1880 the railroad between Woodstock and Chicago was blocked by snow and the way remained blocked for a week before trains could get through. Then again on March 14, Woodstock was cut off from all outside communications except by telegraph, by severe weather that continued through the month.

In 1880 an entire block burned. It was suspected that the fire was caused by thieves trying to blow up a safe in the American Express office adjacent to Timothy Dacy’s warehouse.

A pickle growers’ Union was formed with 100 members in 1881.

Woodstock Mayor Merritt Joslyn resigns so he can serve as Second Assistant Secretary of the Interior under President (and facial hair icon) Chester A. Arthur.

In 1885 a man took the bit out of his horse’s mouth so it could get a drink at the Main Street watering trough and the horse ran away with its head down and ran into the hind wheel of a lumber wagon and fell dead.

The first bandstand was built on the square in 1885.

Spring City Band
Spring City Band on the Courthouse steps in 1888 (photo courtesy of Woodstock Public Library)

Here is a detailed Sanborn Fire Insurance map of the Square in 1885.

The German language newspaper Das Volksblatt is established in Woodstock in 1885. The weekly 12-page German language newspaper is published at least until 1901.

On July 16, 1886, James Dacey was hung in the yard of the Courthouse. He was convicted of shooting and killing Chicago Alderman Gaynor in a saloon quarrel. Two trials were held in the Woodstock Courthouse and the hanging was witnessed by 150 people. The gallows were borrowed from Cook County. The body was turned over to Patrick Dacey, a brother, who took it back to Chicago on the 4:52 pm train. Click here for further details.

The Woodstock brewery burned down in August 1886 and was immediately rebuilt.

Brewerey 1886
The Woodstock Brewery rebuilt after the 1886 fire

A jailbreak is thwarted in 1886 when children in a neighboring house notice light through a brick wall in the Courthouse basement jail. Prisoners had made a 2 foot square hole in the wall and were preparing to escape.

Timothy Dacy was struck and killed by a train in 1886 while he was passing out cigars to celebrate the return of Company G from their training exercises in Springfield.

1887 – Construction began on the old Sheriff’s House and Jail building on the Square. The new jail had a capacity of  24 inmates in 12 cells.

1888 –  Construction began on the Woodstock City Hall now known simply as The Woodstock Opera House.  The building served as City hall, public library, reading room, magistrate’s office, police and fire departments. The Opera House was on the second floor and the city calaboose (jail) was located in the basement. Woodstock’s fire engine used to be kept inside under the western archway facing the square.

Woodstock City Hall as pictured from the top of the Courthouse (photo courtesy of Woodstock Public Library)

Geo. F. Mills establishes a Furrier business in Woodstock producing “odorless Russian dog coats and robes.” The business sells $25,000 worth of coats in 1898.


A fire on January 5 1892 that was started by a kerosene lamp at the Waverley House Hotel destroyed businesses on the east side of Main Street including the hotel, 2 saloons, a billiard parlor, a harness shop, a feed store, a boot & shoe store and several residences. Favorable winds limited damage. Citizens held a charity ball and sewing bees to make clothes since there was little insurance coverage.

Aftermath of the 1892 fire. View looking north on the east side of Main Street. (photo courtesy of Woodstock Public Library)

Professor Noble Hill purchases the Todd School in 1892 for $20,000 from Richard Kimball Todd.

In 1892 Antonio Zoia carved the datum on each side the stone steps leading into the Courthouse reading 373’ above Lake Michigan; 954’ above sea level.

An 1893 fire that started in M. Church’s livery barn destroyed the south half of the east side of the Square including the old Rat Hole building. Other buildings destroyed include the German Lutheran Church,  a barber shop, hardware store, milling shop and the hook and ladder company. It was said that the fire finished off the last of the original ramshackle buildings on the Square.

Here is a detailed Sanborn Fire Insurance map of the Square in 1893. Notice the blank space left by the fire at the SW corner of the Square.

In 1895, a Chicago federal court sentenced Eugene V. Debs the former president of the American Railway Union for his participation in the 1894 Pullman labor strike. He was incarcerated at the jail in the Woodstock Sheriff’s House on the Square because of fears that he’d be surrounded with too many sympathetic people in a Chicago prison. It is said that he first encountered the works of Karl Marx and became a socialist while in prison at Woodstock. He was treated well in jail and frequently ate dinner with and even went hunting with Sheriff Eckert. Debs hired a secretary and was allowed to use an adjacent cell for the publication of his Railroad Times news letter. More than 10,000 people reportedly gathered in the Square on the day he was released from prison and he was carried to the train on the shoulders of those in the crowd.  Debs ran for president as a socialist under the newly formed Social Democratic Party in 1904, 1908, 1912, and 1920.

1895 Courthouse
The Courthouse in 1895 (photo courtesy of Woodstock Public Library)

In 1896 city officials donated empty factory buildings to Thomas Oliver and The Oliver Typewriter Company began to produce Oliver Typewriters in Woodstock. Fun fact: Thomas Oliver was born in Woodstock………..in Ontario, Canada.

Oliver Factory
The Oliver Typewriter Co. (photo courtesy of Woodstock Public Library)

The Woodstock Brewing and Bottling Company “received the blue ribbon at the State Fair at Springfield in 1897 for the purity and healthfulness of its beer.”

Here is a detailed Sanborn Fire Insurance map of the Square in 1898.


In 1901 the first automobile arrived to Woodstock. Dr. Windmueller, a surgeon for the Northwestern Road, purchased a Milwaukee Steam Car and drove it all the way from Milwaukee to Woodstock. This steam driven car took some time to get up to steam and it was often necessary to back up and get a longer head start to get up hills but once it was moving Dr. Windmueller frightened citizens by roaring up and down city streets.

1903 Haynes-Apperson calhoun looking wast
We don’t have a picture of Dr. Windmueller’s car but this is a 1903 Haynes-Apperson steam car travelling east on Calhoun St near Dean St. (photo courtesy of Woodstock Public Library)

The Northwestern Rabbitry on East Washington Street expanded in 1901 to become what may have been the largest facility of its kind in the world. Belgian Hares and Flemish Giant breeds were raised for meat and skins. They also bred ferrets, guinea pigs and dogs for pets.

The Woodstock brewery on the NW side of Woodstock was destroyed by a fire again in 1902. The nearest fire hydrant was 3000 feet away and the city only had 2000 feet of hose.

1902 Woodstock brewery fire (photo courtesy of Woodstock Public Library)

The rotten bandstand was removed from the park to be burned in 1902.

Lightning from a huge electrical storm in 1904 damaged the flagstaff on the cupola of the Courthouse. 1.21 Gigawatts!

Electric lights were first installed in the city in 1904.

1904 – Burning movie equipment caused dense smoke and damage to the floor of the Opera House. Everyone escaped, some through windows and some jumped onto the roof of an outside balcony.

In 1905 a major addition was built on the Courthouse. A 45’ x 18’ two-story addition was added to the south side of the building that included a larger office and better vault room for the Circuit Clerk.

On December 11, 1905 Jim Russell and Mike Kelehan were charged with torture and robbery of the Forn Brothers. Six saws were smuggled into the County jail in a book, and a lead pipe was acquired. The jail break was thwarted when one of the offenders confessed to the planned escape before it happened.

McHenry County Fair about 1905 (photo courtesy of Woodstock Public Library)

A statue of Abraham Lincoln made of pure McHenry County butter is featured at the 1905 County Fair.

On December 3rd 1907, The Woodstock Pleasure Club presented a program of boxing, wrestling, magic & music at City Hall. Tickets were $1.

The city of Woodstock granted the Western United Gas & Electric Company a franchise to lay gas pipes and supply the city with gas in 1909.

In the early 1900’s Woodstock held an annual 4th of July competition on the square where the object was to climb to the top of a greased pole as fast as possible.

Greased pole
4th of July, 1910 greased pole climb (photo courtesy of Woodstock Public Library)


The Emerson Typewriter Company moved to Woodstock in 1910 and from 1914 through 1950 they produced Woodstock Typewriters at the current site of Emerson Loft condominiums. By the 1920’s half of the world’s typewriters were manufactured in Woodstock. Oliver, Emerson and Woodstock brand typewriters were manufactured here. Fun Fact: A Woodstock brand typewriter was used as evidence to convict State Department official Alger Hiss of being a secret agent for the Soviet Union in the 1930s.

In 1912 the County added space to the jail behind the Sheriff’s House by extending the south wall 10 feet and adding a second story.

The City granted a petition to allow movie screenings on Sundays as long as they were clean pictures depicting historical, educational and biblical topics and only from 7 to 9 pm.

A 1914 fire causes serious damage at City Hall (The Opera House). Two vagrants living in the basement inadvertently set the fire while 600 gentlemen were attending a wrestling match in the theater two stories above. The only casualty is one of the vagrants. 1,906 books were destroyed in the library. While the library was being rebuilt, the remaining undamaged books were stored in the Old Courthouse…in the restroom!

Speed limits are set at 10 mph (and 5 mph around corners) for the Square and business streets.

22 horses were purchased from the Novelty Tie (Tye?) Barn on Throop Street by the British government for use as artillery horses in the war zone.

Woodstock votes to go “Dry.”

In 1916 the City declared that all dogs running on the streets without muzzles will be shot.

Six men were charged in 1917 with bootlegging and illicit liquor traffic.

The Woodstock & Sycamore Traction Company (photo courtesy of Woodstock Public Library)

The Woodstock & Sycamore Gasoline Railroad line ran intermittently from 1910 to 1918. It was one of the least successful interurban railway lines ever. It ran between Sycamore and Marengo and never reached its intended destination of Woodstock. Its headquarters and repair shop were in Genoa, midway on the route.


A Curtis airplane lands on Schuett’s farm just NE of Woodstock in 1920.

In 1920 the newly organized American Legion ejected a man from a dance for doing the “Shimmy”.

Robert Rathbun Wilson attended Woodstock’s Todd school in 1922 and lived with his grandmother who was married to the headmaster Noble Hill. Robert Wilson would go on to work on the Manhattan Project as well as establish Fermilab and become the lab’s first director in 1967.

The Oliver Typewriter Company begins to manufacture motion picture projectors to stay busy after WWI. A scheme to sell typewriters by mail order leaves them with a huge uncollected debt and they manufactured their last typewriter and liquidate all assets in 1926 .

400 people gathered on the square in 1924 to listen to a radio set up by Zenith Corp. to test reception of the newfangled device.

Main Street 1924
Main Street 1924 from the Square looking north (photo courtesy of Woodstock Public Library)

President Calvin Coolidge passed through Woodstock on a train and waved from the observation car.

In 1925 the Sheriff dumped 65 barrels and 25 half barrels of confiscated beer into the sewer behind the Courthouse. The Courthouse and Jail are busy places during Prohibition (1920-1933). At one time 73 federal prisoners were housed in Woodstock.

Gangster Hymie Weiss, known as the only man Al Capone feared, was imprisoned in Woodstock. After he was released, he was killed in a shootout in Chicago on October 11, 1926. Bullets from the shootout chipped the cornerstone of Holy Name Cathedral.

Gangster Dapper Dan McCarthy was imprisoned in Woodstock. He was partners with Hymie Weiss in the North Side gang, Al Capone’s bitter rivals.

Orson Welles at the Todd School – (photo courtesy of Woodstock Public Library)

Orson Welles was a student at Woodstock’s Todd School from 1926 – 1931. He performed at the Opera House and made reference to his time in Woodstock and at the Opera house in his 1946 movie “The Stranger.” Click here for more information about Welles’ time in Woodstock. Fun facts: Orson’s older brother, Richard Ives Welles, had attended the school ten years before but was expelled for misbehavior. Orson Welles’ daughter, Christopher Welles Feder, would later become the only girl to attend the Todd School for Boys.

1927 – Movies were shown at the Opera House while the Princess Theater was enlarged and reborn as the Miller Theatre.


On March 16th 1933 at 4:30 a.m. hoodlums blew up 2 large steam shovels and an elevated loader that were parked near Mark Hansen’s farm on Route 47. Pieces of steel go through the farm house and more than 50 windows in the house and barn are smashed along with some dishes.

The original Spring House gazebo was demolished in 1933.

Orson Welles as Svengali in a July 1934 production of Trilby in Woodstock (photo courtesy of Woodstock Public Library)

In 1934 at age 19 Orson Welles shot what may have been his first movie at the the Todd School in Woodstock. The movie was called The Hearts of Age and it is weird. You can see it here. The film stars Welles’ first wife, Virginia Nicolson, and Welles himself. Another cast member, Charles “Blackie” O’Neal became a screenwriter and was the father of actor Ryan O’Neal. The building seen in the film was Wallingford Hall on the Todd school campus. It was torn down in 1964. The bell the woman is sitting on is currently on display at the Woodstock Presbyterian Church, and the gravestone is in Calvary Cemetery on Jackson Street. Although Welles graduated from the Todd School in 1931, he frequently returned to Woodstock since he considered it his home. He staged a drama festival in Woodstock in the summer of 1934 which marked his debut as a professional stage director.

In 1931 only one other county in the entire country has more dairy cows than McHenry County. 85,000 cows!

On July 9, 1934 five prisoners broke free from the jail in Woodstock by spending several nights sawing through the prison bars with hacksaw blades. They used toothpaste, butter and soap mixed with dirt to hide the incomplete cuts during the day. They escaped during the night while no one was on duty and the escape was not noticed until the next morning. The men had been incarcerated for check forgery, bank robbery, auto theft, jewel theft and arson.

Dick Tracy comic strip creator Chester Gould lived in Woodstock from 1936 to his death in 1985. He owned the building “The Double Yolk” is in now and his brother lettered many Dick Tracy comic strips in his office on the second floor. He is buried in Woodstock’s Oakland Cemetery.

In 1939 Woodstock was home to the oldest woman driver in the State. Nellie Galloway lived on Calhoun Street and had been driving since 1904.

A Jailbreak attempt was foiled in 1939. A 14-year-old boy charged with murder, and a 16 and 17 year old that had stolen a police revolver and slugged two men in a robbery stole spoons from their breakfast trays and scraped their way through a plaster ceiling of the jail and into the attic. Only a tin roof stood in their way to freedom. A 16-year-old named Conrad Bremer who was serving time for shooting pheasants out of season informed Sherriff Edinger and young Mr. Bremer was released from jail for his help.

Woodstock holds the first soap box derby in 1939 on the hill on South Street.


In 1941 the Duke & Duchess of Windsor pass by a crowd of 300 as their train passes through Woodstock.

In 1945 the Todd School purchased 90 acres on Route 120 and opened a Class 1 airport where Marion Central High School is now located.

In 1949, actor Paul Newman moved to Woodstock, Illinois, where he signed on with The Woodstock Players theater group and appeared in some 16 plays during the 1949-50 season.


1950 – The fictional town of Hawkins Falls in the NBC Television soap opera called Hawkins Falls, Population 6200 was patterned after the real-life town of Woodstock IL. The show was broadcast from 1950 to 1955 making it the longest running soap opera until The Doctors exceeded it in 1967. Though it was not the first original soap opera on American TV, it was the first to be successful, running for more than five years.

The 1952 Hebron Green Giants basketball team wins IHSA boys State basketball championship which is unprecedented for a school with a total enrollment of 98 students. On the way home from their victory at Huff Gymnasium in Champaign the team visited Woodstock for a parade around the Square.

The Todd School for Boys closed in 1954

Johnny Stompanato Jr was born in Woodstock on October 10, 1925 and attended Woodstock High School. He was stabbed to death in 1958 by movie star Lana Turner’s daughter. His death was ruled as justifiable homicide because he had been killed in self-defense while attacking Lana Turner with whom he had been romantically involved with. He had been a bodyguard and enforcer for gangster Mickey Cohen and the Cohen crime family. Johnny Stompanato is buried in Woodstock’s Oakland Cemetery.


A tornado in 1967 damaged many of the 110 year old elm trees planted in 1858 in the Square by Alvin Judd, the first mayor of Woodstock. This same tornado first touched down in Belvidere where it killed 24 people including 13 school children. Over the next few years Dutch Elm Disease finishes off the old elm trees on the Square.

In 1969 hippies gather in Woodstock for 3 days of music and love….oh wait… wrong Woodstock.


In 1972, McHenry County Government moves to a new campus on Route 47 and vacates the 1857 Courthouse on the Woodstock Square after 115 years of use.

The Old Courthouse and Sheriff’s House go up for auction and the highest bidder is a group that intends to tear them down to build a parking lot (they wanted to tear down the Opera House as well!). Cliff and Bev Ganschow place a bid that is only $500 higher and thus the Old Courthouse is spared from demolition by a slim $500 margin. Thank you Bev and Cliff!

A 1973 fire at Knoll’s Grain Storage on First Street burns 30,000 bushels of corn over two weeks.

On November 1, 1974, The Old Courthouse and Sheriff’s House as well as the Opera House are recognized by the National Park Service and placed on the National Register of Historic Places.

In 1975 Borden Inc. announces plans to close the Woodstock plant which is one of the worlds largest dairy plants.

In 1976 the Oscar Meyer Company moved their Clausen Pickle plant from Chicago to the former Borden site in Woodstock.

The current day Spring House Gazebo is built in 1976 as a replica of the 1873 original.


In 1982 at 9:11 p.m. on a stormy Friday night in March, an Illinois National Guard K135 tanker jet explodes 13,000 ft over Greenwood during a thunderstorm killing 27 airmen and scattering wreckage and body parts over 4 miles.

In 1982 the entire downtown area including the Square is given landmark designation by the National Register of Historic Places and named the Woodstock Square Historic District.

1984 – Train hits cow. Cow dies.

Several scenes from the 1987 movie Trains Planes and Automobiles starring John Candy and Steve Martin were filmed around the Square in Woodstock.

Before dawn on August 21 1988, Richard Church attacks and kills Raymond and Ruth Anne Ritter and injures Matthew and Colleen Ritter and then escapes. The murder is featured on NBC’s Unsolved Mysteries. After three years on the run, Richard Church was arrested in a fast food restaurant in Salt Lake City. A detective had recognized him from an FBI wanted poster. He was living under the assumed name “Danny Lee Carson”. In July 1992, he pleaded guilty to the murders to avoid the death penalty and was sentenced to life in prison without the possibility of parole.


From 1991 until 2008 the Chester Gould-Dick Tracy Museum operated from the Old Courthouse. The Museum displayed original Dick Tracy comic strips, correspondence, photographs, and memorabilia, including Gould’s drawing board and chair. The museum currently operates online. Check it out here.

In the spring of 1992, the movie Groundhog Day, starring Bill Murray was filmed almost entirely in Woodstock.


2005 – United States Senator Barack Obama held a town hall meeting in the Opera House.


In 2011, ownership of the Old Courthouse and Sheriff’s House is transferred to the City of Woodstock after almost 40 years years of private ownership. The buildings require significant repair and restoration, which the City begins addressing on an annual basis.

-your story here-

This timeline was assembled from a mishmash of sources, some solid and some sort of dubious so we are not guaranteeing the accuracy. We encourage you to research yourself using any resources available including the resources listed below. If you have any corrections or suggestions for additional information to add to this timeline, we’d love to hear from you! Please contact Tom Ellinghausen.

For a more detailed account of Woodstock history you can read “A History of Woodstock 1852-2002 Sesquicentennial Edition” published by The City of Woodstock and edited by Jane Dahm and Joan Mansfield.

Or read Nancy Baker’s Images of America – Woodstock  book published by Arcadia Publishing in 2006.

Or check out the local history section at the Woodstock Public Library or the McHenry County Historical Society. museum in Union IL. The Woodstock Fire Rescue District has a timeline of major fires in Woodstock. The McHenry County Sheriff published a 175th anniversary booklet with some interesting history.

A self-guided walking tour of the Square was put together by the City of Woodstock and the Woodstock Historic Preservation Commission a few years ago. It’s an interesting guide with lots of information about the history of the Square and the buildings around it. You can see it here: Downtown_Walking_Guide