Hugo Award Winners from the 1950s
1953 Hugo Winners
Astounding's Hugo
The 1953 Hugos were given out at 11th Worldcon in Philadelphia, PA.
Novel: The Demolished Man by Alfred Bester 
Novelette or Short Story: No Award
Fan Personality: Forrest J Ackerman
Professional Magazine: Galaxy and Astounding (tie)
Cover Painting: Ed Emshwiller and Hannes Bok (tie)
Interior Illustration(s): Virgil Finlay
Fan Magazine: (unclear what won)
Fact Article or Article Series: Willy Ley
New Discovery (Author or Artist): Philip Jose Farmer
Note: This Hugo Award is much smaller than the later awards. The rocket was only about half the size of the current rocket. The categories listed here are as they appeared on the 1953 ballot.
No Hugo Awards Were Given in 1954
Members of the 2004 Worldcon (Noreascon 4) did award RetroHugos for 1954
1955 Hugo Winners
The 1955 Hugos were given out at Clevention in Cleveland, OH.
Novel: They'd Rather Be Right by Mark Clifton and Frank Riley (Currently sold as The Forever Machine)
Novelette: "The Darfsteller" by Walter M. Miller, Jr.
Short Story: "Allamagoosa" by Eric Frank Russell
Magazine: Astounding
Artist: Frank Kelly Freas
Fan Magazine: Fantasy Times (James V. Taurasi, Sr. & Ray Van Houten, eds.)
Special Award: Sam Moskowitz as "Mystery Guest" and for his work on past conventions
1956 Hugo Winners
The 1956 Hugos were given out at NewYorkCon in New York, NY.
Novel: Double Star by Robert A. Heinlein
Novelette: "Exploration Team" by Murray Leinster
Short Story: "The Star" by Arthur C. Clarke
Feature Writer: Willy Ley
Magazine: Astounding
Artist: Frank Kelly Freas
Fanzine: Inside & Science Fiction Advertiser (Ron Smith, ed.)
Most Promising New Author: Robert Silverberg
Book Reviewer: Damon Knight
1957 Hugo Winners
Astounding's Hugo
The 1957 Hugos were given out at Loncon I in London, UK.
American Professional Magazine: Astounding
British Professional Magazine: New Worlds
Fan Magazine: Science Fiction Times (James V. Taurasi, Ray Van Houten, and Frank Prieto, eds.)
This award looks extremely similar to the International Fantasy Award, an award given out during the 1950s.
1958 Hugo Winners
The 1958 Hugos were given out at Solacon in South Gate, CA.
Novel or Novelette: The Big Time by Fritz Leiber
Short Story: "Or All the Seas With Oysters" by Avram Davidson
Outstanding Movie: The Incredible Shrinking Man
Magazine: F&SF
Outstanding Artist: Frank Kelly Freas
Outstanding Actifan: Walter A. Willis
1959 Hugo Winners
The 1959 Hugos were given out at Detention in Detroit, MI.
Novel: A Case of Conscience by James Blish
Novelette: "The Big Front Yard" by Clifford D. Simak
Short Story: "That Hell-Bound Train" by Robert Bloch
SF or Fantasy Movie: No Award
Professional Magazine: F&SF
Professional Artist: Frank Kelly Freas
Amateur Magazine: Fanac (Ron Ellik & Terry Carr, eds.)
New Author: No Award (but Brian W. Aldiss received a plaque as runner-up)
Hugo winners from the 60s.