In spring 2021, Fox Chapel Borough renamed Squaw Run Road East to Riding Meadow Road and assigned names to many of the unnamed private lanes off of that road. As a result of these changes, Shady Side Academy Middle School and Country Day School both have new street addresses.
The Middle School's street address changed from 500 Squaw Run Road East to 100 Benedum Lane. The previously unnamed private lane the campus sits on was named in honor of the Benedum Family, who have been dedicated supporters of SSA for many years. Generous gifts made to the Academy in 1957 by the Claude Worthington Benedum Foundation and Paul G. Benedum enabled SSA to buy the property that is home to the Middle School.
The private lanes leading to the SSA Country Day School campus were also given names, and the school's address changed from 620 Squaw Run Road East to 400 Christ Church Lane.