The Great Woodstock Jail Break

It began with a bedsheet lowered from the jailhouse window. It climaxed with the shooting of a Hartford lawman. It ended with a massive manhunt leading to the recapture of a father and son originally jailed for poaching a deer. 

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That's Woodstock history for you! 


Dustin Shaw, 53, and his son Frank, 31, were jailed in Woodstock in April 1900 on charges of larceny and illegally killing a deer. This came as welcome news to authorities in New York, where Frank had been wanted for three years for cracking the skull of a law officer with a coupling pin. 

Somehow the Shaws learned that New York police were coming for them. The Woodstock jailer, seemingly less concerned about this prospect than the Shaws were, continued to let them roam outside their cells. On the night of the 23rd, father and son bent the iron bars in a second-floor window, lowered a sheet toward the ground -- and descended to freedom.


High Sheriff Romaine Spafford of White River Junction led seven deputies in pursuit. Hunger caught up to the Shaws before the lawmen did. But on Thursday, two days after the breakout, they spent 10 cents on two loaves of bread in Stony Brook -- and that put the posse on their heels. When Spafford and a deputy, Dr. George Hoffman, found them the next day in Stockbridge, the father and son were armed.

"Hold on," Spafford said. "We don't want any shooting."

The father lowered his rifle. The son kept his pointed at Hoffman.

"Drop your gun," Hoffman said, "or I'll bore a hole through you."

The son shot first. "My God he's killed me," the deputy cried, somewhat prematurely.

Spafford and Frank exchanged three shots each, to no avail, before the Shaws turned and fled again.

The victim

Deputy Hoffman was very much an American of his time, having invented himself several times over in his 56 years. At 16 he took a job on the railroad, only to reconsider that occupation the next year after being pinned between two rail cars. He went west and hired on with the government as a telegraph operator in Sioux country, where he met the doomed General Custer.

Tiring of frontier life, he returned to Vermont and found work as a teacher. At 22 he became a dentist, and practiced in White River Junction thereafter. For the last 10 years of his life, he also served as a deputy sheriff and became known for his bravery and daring.

Dr. George Hoffman. (All photos from Inter-State Journal and Advertiser.)

Six doctors -- from Pittsfield, Bethel, White River and Randolph -- gathered to attend Hoffman in the hours after the shooting, but he died before 9 that night. His wife was at his side.

"In this, his last adventure, the attempted capture of escaped prisoners, his courage was not found wanting," said the Inter-State Journal and Advertiser.

The manhunt

For days the Shaws were merely shadows -- a hint in Rochester, a sighting in Ripton -- but their path pointed toward Middlebury, where hundreds joined in the effort to capture them. An unarmed searcher found them asleep in a barn near Three-Mile Bridge and sent for help. Another shootout followed, this one wounding the son and ending with the arrest of both.

Father and son were returned to Woodstock for trial by way of White River Junction. The Journal and Advertiser published two odd photos of Frank, one on Sheriff Spafford's shoulder as he carried the suspect from the train to his office, the other prostrate on the office bench. Exhaustion, the paper said -- but you are left to wonder if the defendant might have suffered at the hands of law officers in transit.

Sheriff Spafford carries Frank Shaw toward justice.

"I don't know what made Frank shoot," the father said while waiting for the train to Woodstock. "I told him not to." 

What can you tell us of his habits? someone asked. The answer was similar, in its way, to worries about video games and their influence on gun violence today.

"Frank has read dime novels ever since he could read anything," his father said. "And I think his head was completely turned by them."


This post is drawn from the May 1900 issue of the Inter-State Journal and Advertiser. The article was packed with great quotes and photographs and ran under the title "Vermont's Sensational Man-Hunt."

The town of Woodstock has a crazy great history -- and you can find a lot of it at the Woodstock History Center. The center opens for the season at the end of May. Woot!


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