Run Around the Square Pittsburgh, PA   Aug 23, 2025

Join the annual Run Around the Square 1.5 mile & 5K races! Most of the first mile of the 5K winds through Regent Square streets with plenty of warm, friendly cheers. The remainder of the race is through Frick Park’s cross-country trails, ending in Fern Hollow.

The 1.5 Mile Run/Walk takes place on the charming streets of Regent Square. The family dog can also join in on the fun. Dogs may ONLY participate in the 1.5 Mile Run/Walk. The dog must be leashed and a dog owner/handler must be registered with every dog, no exceptions. USATF sanctioned event policy does not allow for animals to participate in competitions. The 5K is a USATF sanctioned event; therefore, dogs are PROHIBITED in the 5K. Both races start at the Environmental Charter School near the corner of Henrietta and Milton. Join in Frick Park Hollow afterwards for entertainment, hot dogs, and drinks! Run Around The Square is an annual charity event that raises money to maintain, promote and advance the betterment of the Regent Square community. Over the 40+ years, the event has raised over $350,000 thanks to our sponsors and participants.