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If you live anywhere in Pittsburgh's East End, you have probably heard about this race for years without ever running it. This is the one that closes down Regent Square on a Saturday morning in August and ends with most of the neighborhood standing around in Fern Hollow.
Run Around the Square 2026 takes place on Saturday, August 22 in Regent Square. The 1.5 mile Run/Walk starts at 8:15am and the 5K starts at 9:00am, both from the Environmental Charter School at the corner of Henrietta and Milton. Registration is online only and closes at midnight on Thursday, August 20.
Here is what you actually need to know before race morning.
It is a neighborhood charity race that has been running for more than forty years, raising money to maintain and improve the Regent Square community. Across those four decades the event has brought in over $350,000.
That history is part of why it feels different from a corporate road race. The course runs past the porches of the people organizing it. The volunteers are neighbors. It is one of the genuinely good community traditions in this part of Pittsburgh, alongside things like the Frick Park trails themselves.
Roughly the first mile winds through Regent Square streets, then the course crosses the Fern Hollow Bridge before dropping into Frick Park's cross-country trails and finishing in Fern Hollow.
Two things to plan for. First, the trail section is genuinely trail, so this is not a flat road 5K and your usual pace will not hold. Wear shoes with some grip. Second, and this is important, the organizers are not closing a traffic lane on the Fern Hollow Bridge, so runners need to follow course signage and stay on the sidewalk while crossing.
The finish in Fern Hollow is the best part of the morning. Awards begin around 10:00am, with the 1.5 mile awards first and the 5K awards after. If you plan to have a beer in the hollow afterward, bring a photo ID, because the event's insurance requires them to card anyone who looks under 30.
Only to the 1.5 mile Run/Walk. Dogs are prohibited in the 5K because it is a USATF sanctioned event.
If you do bring your dog to the 1.5 mile, it needs to be leashed, and a registered owner or handler has to be signed up with every dog, no exceptions. That is worth reading twice if you were planning to have someone hold the leash who was not planning to register.
One more note on the 1.5 mile: awards go only to participants 13 and under, and USATF rules require them to complete the course on their own. Toddlers in strollers or kids being carried or assisted are not eligible.
Bib and t-shirt pickup is at the Wilkins School Community Center, 7604 Charleston Avenue in Regent Square, on the Friday before the race from 5:30pm to 8:00pm, or on race morning starting at 7:00am until fifteen minutes before your start time. There is no registration at packet pickup, so do not plan to sign up in person.
Parking takes a little strategy. No parking is permitted on the course streets after 5:00am on race day, and none in the Fern Hollow section of Frick Park. The organizers recommend the streets on the east side of S. Braddock Avenue, which puts you in easy walking distance from Edgewood and the Swissvale side.
Getting there early is the move. Neighbors are out, the line for the porta-johns exists, and standing around Regent Square at 7:45am on a summer Saturday is not a bad way to spend twenty minutes.
If you can currently walk comfortably for thirty minutes, yes, and it is fine to walk parts of it.
Do not try to build fitness in the next two weeks. Instead, do two or three easy sessions per week of roughly the distance you plan to cover, one of them on trails or grass so your ankles are not surprised on race day. Take the two days before the race off. That is the whole plan.
The 1.5 mile Run/Walk exists precisely so that "I am not a runner" is not a reason to skip this. Plenty of people walk it with their families and their dogs.
Yes. We will have a booth on race morning and a group of members running both events, which has become one of our favorite Saturdays of the year.
Come say hello whether or not you race. We are based at 210 Thomas St, about ten minutes from the start line on the Wilkinsburg side of the East End, and half of our conversations at that booth every year are with people who were just out walking their dog.
If the race gets you thinking about building something more consistent this fall, we wrote a series on exactly that, starting with Why Do Morning Workouts Stick Better Than Evening Ones?.
Register for Run Around the Square 2026: https://runsignup.com/Race/PA/Pittsburgh/RunAroundtheSquareRegistration closes at midnight on Thursday, August 20, and it is online only.
When is Run Around the Square 2026?Saturday, August 22, 2026 in Regent Square, Pittsburgh. The 1.5 mile Run/Walk starts at 8:15am and the 5K starts at 9:00am, both from the Environmental Charter School at Henrietta and Milton. Awards begin around 10:00am in Fern Hollow.
Can I register on race day?No. Registration is online only through RunSignUp and closes at midnight on the Thursday before the race, which is Thursday, August 20 this year. No registrations are accepted after that, and there is no sign-up available at packet pickup or on race morning.
Are dogs allowed at Run Around the Square?Dogs are allowed in the 1.5 mile Run/Walk only, and they must be leashed with a registered owner or handler signed up for each dog. Dogs are prohibited in the 5K because it is a USATF sanctioned event with different participation rules.
Where do I park for Run Around the Square?Street parking is not permitted on course streets after 5:00am on race day, and the Fern Hollow section of Frick Park is closed to parking. The organizers recommend streets on the east side of S. Braddock Avenue, which is a short walk to the start.
Is the Run Around the Square 5K course hilly or flat?Neither entirely. The first portion covers Regent Square streets, then the course crosses the Fern Hollow Bridge and finishes on Frick Park's cross-country trails. Expect uneven trail footing rather than a fast flat road course, and wear shoes with some grip.
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