The Run Around the Square is a fixed point on the neighborhood calendar. It has been for more than forty years, and this year's edition, on Saturday, August 22, 2026, will look and sound the way it always does: dogs in scarves at the 1.5 mile start, a 5K field peeling off Milton and dropping into Frick Park, hot dogs and beer waiting in Fern Hollow.
What the race circles, though, is not the same corridor it circled last August. The S. Braddock strip that hosts the finish-line crowd and the pre-race coffee has quietly reset in the last twelve months, and if you have not walked it since roughly this time in 2025, the block reads differently now.
The Saturday itself, in order
The mechanics have not changed, but they reward precision if you are trying to time a school drop-off, a dog walk, or a slot at 61B before the line stretches to the door.
| Time | What is happening | Where |
|---|---|---|
| Friday 5:30–8:00 p.m. | Packet pickup | Wilkins School Community Center, 7604 Charleston Ave., Swissvale |
| Saturday 7:00 a.m. | Race-morning packet pickup opens | Environmental Charter School, Henrietta & Milton |
| 8:15 a.m. | 1.5 Mile Run/Walk starts (leashed dogs allowed with a registered handler) | ECS start line |
| 9:00 a.m. | 5K starts (USATF sanctioned, no dogs, no strollers) | ECS start line |
| ~9:20 a.m. | 5K field crosses the Fern Hollow Bridge on sidewalk | Forbes at Fern Hollow |
| Late morning | Post-race gathering with entertainment, hot dogs, beer | Frick Park, Fern Hollow |
The 1.5 mile Run/Walk starts at 8:15 a.m. at the Environmental Charter School on the corner of Henrietta and Milton, and the 5K starts at the same location. The 5K begins at 9 a.m. The 5K's first mile stays on Regent Square streets before entering Frick Park's cross-country trails, crossing the Fern Hollow Bridge on the sidewalk, and finishing in Fern Hollow. Pre-race packet pickup is Friday, August 21, from 5:30 to 8:00 p.m. at the Wilkins School Community Center at 7604 Charleston Avenue in Swissvale, with online registration closing at midnight Thursday, August 20. Participants and organizers gather in Fern Hollow afterward for entertainment, hot dogs, and beer.
Two details worth internalizing before race day. First, dogs and strollers are only permitted in the 1.5 Mile, because USATF sanctioning policy does not allow animals or strollers in competitions, and the 5K is a USATF sanctioned race. Second, the event is a charity race that has raised more than $350,000 for the Regent Square community over its more than forty year history, and the Regent Square Civic Association is a sponsor and the primary volunteer channel.
What sits at the finish that did not last August
Two openings on S. Braddock have changed the character of the strip most Regent Square residents cross on race morning.
The larger one, in cultural weight, is Confections by Casey Renee, which opened on April 11, 2026 at 1141 S. Braddock. Renee is a two-time James Beard Award semifinalist, and the new location is a material change from the special-order Wilkinsburg operation she had been running since 2020. The new Regent Square spot offers cafe hours for walk-in customers five days a week, with a menu that features French macarons, cookies, truffles, cake by the slice, scones, garlic cheddar biscuits, and a variety of gluten-free and vegan specialties, and the crew remodeled the 1,500-square-foot space starting last September. In practical terms for a neighbor: the block finally has a walk-in pastry counter of consequence, three doors from where the race dumps you out of Frick Park.
The second change is Rockaway Pizzeria, which relocated from White Oak and opened on S. Braddock Avenue at 11:00 a.m. on Friday, May 2, 2025. Owner Josh Sickels used the transition to reset the concept. He spent the interim months on a pizza-focused road trip through New York City, New Jersey, and Connecticut, gathering ideas for the new Regent Square location, and the shop earned an 8.2 from Barstool's One Bite reviews and added a limited selection of hoagies at the new address.
The two openings share a wall of context. Confections neighbors Rockaway Pizzeria and is a short walk from Hemlock House, Frick Park Tavern, El Burro Dos, D's Six Pax and Dogz, and Famous Cafe. That is roughly ninety seconds of sidewalk. Last August, the same walk had one fewer sit-down bakery of pedigree and a different pizzeria in a different zip code.
The ring you already know, briefly
The anchors that make the strip legible on a normal Saturday are still there, and they still do what they do.
- 61B Cafe, 1108 S. Braddock. The neighborhood caffeine hub, where dogs slam on the brakes for a pup cup served out of the walk-up window.
- Hemlock House, S. Braddock. A Pacific Northwest inspired room with a misty mountain mural and a Twin Peaks VHS relic, plus a late-night happy hour from 9 to 11 p.m.
- D's Six Pax & Dogz, 1118 S. Braddock. Regional beers and kid-friendly fare where sidewalk seating fills on any sun-streaked day, with wings, burgers, hoagies, and hot dogs loaded with mac and cheese.
- Frick Park Tavern, S. Braddock. The RSCA Garden Committee meets in front of it for its business-district planter clean-ups.
- Thai Cottage and Istanbul Grille, 1109 and 1103 S. Braddock. Two of the longest tenured kitchens on the block.
- Stay Gold Books. Independent shop; owner Wittig has said the most frequent line she hears is neighbors saying "Welcome to the neighborhood," including from Mister Rogers' son.
- Frick Park Market, 7103 Reynolds St. Different building, same neighborhood gravity; operating since 1941 and closed Sundays.
Friday evening and Sunday morning, as bookends
The race is a Saturday, but the weekend it sits inside has a rhythm.
Friday is packet pickup at Wilkins School Community Center in Swissvale from 5:30 to 8:00 p.m., which is the window most in-town runners use because parking is easier and the line at the ECS on Saturday morning is not. The evening after pickup is one of the busiest of the year for the Braddock corridor. Hemlock House's 9-to-11 happy hour and D's sidewalk seating are the two most reliable places for a table without a wait.
Sunday morning belongs to Famous Cafe and 61B, and to the Frick Park trailheads that are noticeably quieter than they were twenty-four hours earlier. Frick Park Market, closed on Sundays, is a useful reminder that Reynolds Street is not the same district as S. Braddock even if a runner can jog between them in ten minutes.
The block a Regent Square neighbor crosses in August 2026 has one bakery of national reputation, one relocated pizzeria of regional reputation, and one race that has, by the RSCA's own count, moved more than a third of a million dollars back into the neighborhood over four decades. Last August, only two of those three sentences were true.
What the month is telling a resident
Regent Square is small. The City of Pittsburgh portion is roughly 0.192 square miles with an estimated 1,001 residents in the ACS 2018–2022 window, and the four-municipality footprint is only a bit larger. In a corridor that compact, an addition of Confections' size and a relocation of Rockaway's profile are not incremental. They are the year's news.
The Run Around the Square is the moment the neighborhood counts itself. It is also the moment the strip is most visible to residents who normally cross it on autopilot on a Wednesday commute. If you use the race as an annual audit, the 2026 audit is straightforward: the Braddock spine picked up a James Beard-adjacent bakery and a serious pizzeria in the last twelve months, the ring around them held, and the community race that funds the planter beds you walk past is still doing what it has done since the early 1980s.
That is the read a neighbor gets from the finish line. Everything else is a matter of pace.
If you live on one of these streets and are starting to think about what your block looks like from the outside, Black Key Partners works this corridor closely and can walk you through what the last twelve months have done to values, inventory, and timing. Request a Concierge Consultation when you are ready.
