From the Madison Public Library clippings file: A time traveler from 1956 wouldn't recognize the place now

July 25, 1956.  

When a stretch of University Avenue was a 3-lane.

Screenshot from 1957 Madison City Directory

Skip's Drive In is located at 3780 University Avenue.

Here's an approximate Google Street View taken during August 2017

Walgreen's (center of pic) is located at 3780 University Avenue.  Hilldale shopping center is off to the right.

More from the Madison Public Library clippings file:
2019
Remembering the hot-rodders of East Wash (1980-1999).  (2/19/2019)
UPDATE,  Eventually, we'll work our way back to the horse and buggy era.  (2/18/2019)
The Battle of Stonefield in Middleton (1986).  (2/18/2019)
An expressway like a dagger through the heart.  (2/7/2019)
Not to worry, folks, Wisconsin public television survived.  (2/5/2019)
Downtown/University area urban renewal, 1971-1981 (1/28/2019)
Madison urban renewal, part 3, the Triangle, 1970-1979.  (1/27/2019)
Madison urban renewal, part 2, the Triangle, 1964-1969 . (1/27/2019)
Madison urban renewal, part 1, 1962-1964.  (1/27/2019) 
Downtown Madison parking ramps, 1956-1971.  (1/22/2019)

2018
History of the Dane County airport.  (12/21/2018)

2017
City's first skywalk opens in 1966.  (10/9/2017)
Typewriter art.  (10/9/2017)
Proudfit and Regent streets widening, 1955.  (9/30/2017)
Northport Connector project, 1960.  (9/30/2017)
Regent Street extension beyond Rosa Road, another bad idea left on the drawing board.  (5/27/2017) 
Drake Street extension, a bad idea left on the drawing board.  (5/26/2017)