He attended Dickinson College, where he as a member of the Raven"s Claw Society, graduating in 1926, and received a law degree from Dickinson School of Law in 1928.
He was first elected to the State House of Representatives in 1932, and served four terms, until 1941. From 1939-1941, he was Republican Floor Leader. He was then appointed a judge on the Dauphin County Court of Common Pleas, where he served until appointed state Attorney General in 1951.
He was appointed in 1953 to fill a vacancy on the state Superior Court, was elected to a full ten-year term in 1954, and lost his 1964 re-election bid.
In 1962, Woodside had been drafted to run for state Governor. Slot machines were illegal in Pennsylvania, under an 1805 law prohibiting mechanical gambling devices.
Despite this, slot machines were popular at political clubs as fund raisers. In 1951, President Truman signed legislation banning interstate transportation of slot machines when contrary to state law.
Woodside, with Governor Fine"s encouragement, undertook an enforcement campaign against the machines.
He was the first state Attorney General to do so, sending the State Police on thousands of raids when local district attorneys refused to co-operate. Over 700 clubs folded after their slot machines were destroyed. In Erie, the mayor, police chief, and twelve others would be found guilty in 1954 of bribery and conspiracy in regards to the machines.
Woodside was an adjunct professor at Dickinson School of Law (1970-1990).
He was a partner in the law firm Mette, Evans & Woodside. He died in March 1998 while vacationing in Sun City, Arizona.
Senator Hugh Scott strongly opposed Woodside, and ran for governor in opposition, only withdrawing when party leaders backed the then relatively unknown William Scranton.
He served four terms as a member of the State House of Representatives, a term as Attorney General, and a term on the Superior Court.