5 events in Pittsburgh, Pennsylvania

From big races to Saturday morning group runs—find trail running events and connect with the local endurance sports community.

• Three Rivers Heritage Trail parkrun [parkrun.us]
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  Every Saturday at 9:00 AM

  Description

  parkrun is such a simple concept: turn up every Saturday and volunteer, walk, jog or run 5k.

  5k parkrun Run Trail Walk

  Three Rivers Heritage Trail, 1000 River Ave, Pittsburgh, Pennsylvania, 15219, United States
  OpenStreetMap Google Maps
• Rise Up Hero Trail Runs at Settlers Cabin Park - 50K, 25K, 8miler, 5K - A Last Trail Standing Event [runsignup.com]
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  Sat, May 23, 2026 at 8:30 AM

  Description

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  JOIN OUR FACEBOOK GROUP TO STAY UPDATED ON ALL OF OUR RUNNING EVENTS

  🏃‍♂️ Rise Up Hero Ultra 2026 - An established Ultra on a VERY Well marked course

  Settlers Cabin Park – Robinson, PA | Many great...

  JOIN OUR FACEBOOK GROUP TO STAY UPDATED ON ALL OF OUR RUNNING EVENTS

  🏃‍♂️ Rise Up Hero Ultra 2026 - An established Ultra on a VERY Well marked course

  Settlers Cabin Park – Robinson, PA | Many great hotels & Inns within a mile.

  Rise Up Hero 2026 uses the exact same iconic Last Trail Standing course—just started in the opposite direction. While the trails are familiar, starting them in reverse creates a completely different challenge, with climbs, descents, and technical sections hitting in new ways.

  This loop-based trail race showcases the very best of Settlers Cabin Park, covering nearly every trail in the park and delivering a true test of grit, endurance, and heart.

  🏁 Race Distances

  🔴 50K - 9 hour cutoff (8:30am to 5:30pm)

  🟠 25K (Hikers Welcome)

  🔵 8 Miler (Hikers Welcome)

  🟢 5K (Hikers Welcome • Trained Dogs Welcome)

  🗺️ Course Overview

  • Same route as Last Trail Standing — just started in the opposite direction

  • All race distances start and finish at Algonquin Shelter

  • Gilbert Love Shelter is 7.75 trail miles from Algonquin and serves as the aid station and turnaround point for the 25K and 50K runners. From Gilbert Love, 25K and 50K runners turn around and run the same course in reverse back to Algonquin.

  • ~99% trail through woods, rocks, roots, and rolling terrain

  • A familiar course that feels completely different when started in reverse

  • Very well-marked trails and fully stocked aid stations

  While Algonquin and Gilbert Love are only ~200 yards apart in physical location, the trails connecting them are rugged, technical, and demanding—designed to test the hero you have within. But, being so close makes it very easy and perfect for family and crew to see you at both locations.

  🔁 Course Format

  • 25K: One full loop — Algonquin → Gilbert Love (turnaround) → Algonquin ~2300ft of elevation gain

  • 50K: Two full 15.5-mile loops ~ 4600ft of elevation gain

  • 8 Miler: Runs past the Gilbert Love aid station, then turns and finishes back at Algonquin Shelter

  • 5K: A true 5K loop starting and finishing at Algonquin — 5K runners will not reach Gilbert Love

  🕓 Race Start Times

  • 50K: 8:30 AM

  • 25K: 8:45 AM

  • 8 Miler: 9:00 AM

  • 5K: 9:15 AM

  🧃 Aid, Crew & Drop Bags

  • Two major aid station locations along the course (Start/Finish at Algonquin and halfway at Gilbert Love)

  • Maximum distance between aid stations is under 8 miles

  • 50K Drop Bags: Located at Algonquin (Start Area)

  • 50K runners will access aid multiple times across both loops

  🥾 Hikers & 🐕 Dogs

  • Hikers are welcome in the 25K, 8 Miler, and 5K

  • Trained dogs are welcome in the 5K (must be under control and trail-friendly)

  🦸 Rise Up Hero

  • We all have a hero within us—and we believe it takes doing hard things to find it.

  • The trails of Settlers Cabin will challenge you, push you, and reveal what you’re capable of.

  Be the hero you were meant to be.

  🏅 Additional Notes

  • Professional race timing via Miles of Smiles timing services

  • Finisher medals for all participants with overall placement awards

  • Final race-day instructions will be emailed prior to the event

  A few reasons our runners love Rise Up Hero:

  🦸‍♂️ Be The Hero You Were Meant to Be Bracelet

  Every participant receives a Be The Hero bracelet — a powerful reminder that we all have a hero version inside of us and the people that matter the most want us to find it. Your kids. Your partner. Your parents. Your coworkers. Your friends. You don’t just do hard things for yourself… you do hard things to show others what’s possible.

  💛 Rilyn’s Way

  Along the course, you’ll pass Rilyn’s Way — a meaningful tribute and reminder to slow down, reflect, and remember what truly matters. It’s a space that represents love, courage, and living fully for the people who mean the most to us. Many runners say it becomes one of the most powerful moments of the entire race.

  👕 Runner-Favorite Shirts

  Our shirts are the ones people actually wear — soft, athletic fit, and designed with purpose. Not the “bottom drawer” race tee. These become trail staples and everyday reminders of the hero you chose to be.

  🏅 Custom Finisher Medals

  Earn it. Every distance. Every mile. Every climb. A medal that represents grit, growth, and the version of you that chose courage over comfort.

  🥇 Age Group Awards

  We celebrate effort at every level. Top finishers in each age group will be recognized — because showing up and pushing your limits deserves to be honored, whether you’re chasing a podium or chasing personal growth. Age group awards are for the 8mile, 25K and 50K distances.

  📣 Great for Spectators

  With our unique course design, family and friends have multiple easy viewing points — especially for the 25K and 50K distances. Your crew won’t just see you at the finish… they’ll be able to cheer you on throughout your journey. And trust us — hearing your name mid-race hits different.

  🌲 Well-Marked Trail Course

  Confidence in the woods. Our course is clearly marked so you can focus on effort, not direction. Just run, climb, dig deep, and discover what you’re made of.

  🍌 Awesome Aid Stations

  Fully stocked. High energy. Smiling volunteers who want to see you win. Fuel up, reset, and get back after it.

  🔥 Established Ultra — With Options for Everyone

  Chase the coveted Axe in the ultra distances… or step into your first big challenge with our 5K or 8 Mile (hikers welcome!). Same powerful atmosphere. Same meaningful experience. Different levels of hero.

  ⏳ Always Sells Out

  This isn’t just another race on the calendar. It’s an experience people come back for year after year. When spots open, they go fast.

  3.1 Miles 5k 8 Miles 15.5 Miles 25k 31 Miles 50k Run Trail Ultra

  608 Ridge Road, Pittsburgh, Pennsylvania, 15205, United States
  OpenStreetMap Google Maps
• Greenfield Glide 5K Run & Walk [greenfieldglide.com] [Register at runsignup.com]
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  Sun, Jun 07, 2026 at 8:30 AM

  Description

  The Greenfield Glide runs through a hilly Schenley Park in Pittsburgh, Pennsylvania. The race begins and ends at the turn-around on Overlook Drive by the Oval Park Shelter, after taking a running tour of the beautiful trails of Schenley Park through the majority of the course. Presented by the City of Pittsburgh Office of Special Events in partnership with the Greenfield Community Association.

  5k Run Trail Walk

  10341 Overlook Drive, Pittsburgh, Pennsylvania, 15213, United States
  OpenStreetMap Google Maps
• Fineview Step Challenge [runsignup.com]
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  Sat, Oct 03, 2026 at 8:30 AM

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  Fineview Citizens Council is hosting its 30th Annual Urban Step & Trail Challenge on Saturday, October 4, 2025.

  Participants will ascend Fineview’s hills, streets, and staircases. Among the steps are...

  Fineview Citizens Council is hosting its 30th Annual Urban Step & Trail Challenge on Saturday, October 4, 2025.

  Participants will ascend Fineview’s hills, streets, and staircases. Among the steps are Pittsburgh’s STEEPEST stair set (371 steps) on Rising Main Avenue, which is the equivalent of a 17-story building!

  The course covers 12 public staircases for a total of over 1,600 steps and provides breathtaking views along the way. All proceeds from the event will benefit our programming related to community beautification, preserving affordability, and events.

  2 Miles 5 Miles Run Trail

  Fineview Overlook On Catoma Street, Pittsburgh, Pennsylvania, 15214, United States
  OpenStreetMap Google Maps
• Last Trail Standing - 50K, 25K, 8 Miler, 5K [runsignup.com]
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  Sat, Nov 14, 2026 at 8:30 AM

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  LAST TRAIL STANDING

  Our Sell-Out Event Is Back!

  Saturday, November 14, 2025

  Settlers Cabin Park – Robinson, PA

  🏃‍♂️ Last Trail Standing is an unforgettable trail running experience that covers every...

  LAST TRAIL STANDING

  Our Sell-Out Event Is Back!

  Saturday, November 14, 2025

  Settlers Cabin Park – Robinson, PA

  🏃‍♂️ Last Trail Standing is an unforgettable trail running experience that covers every single trail in Settlers Cabin Park. This race is equal parts adventure, challenge, and meaning — designed for runners and hikers alike.

  Registration refunds available through October 1, 2026.

  🏁 Race Distances

  All races start and finish at the same location — no shuttle required.

  🟢 5K (Hikers Welcome)

  🔵 8 Miles (Hikers Welcome)

  🟠 25K (Hikers Welcome)

  🔴 50K

  🕓 Start Times & Cutoffs

  Start times: Listed individually for each race above

  Final cutoff for all races: 5:30 PM

  50K time limit: 9 hours

  🗺️ Course Overview

  The Last Trail Standing course is a 7.75-mile point-to-point trail, run in both directions to create a 15.5-mile loop. Running the course in reverse gives an entirely different feel, making each loop a unique experience.

  25K: One full loop (out & back)

  50K: Two full loops (out & back twice)

  99% trail, deep in the woods

  Elevation (50K): ~3,300 ft climb / ~3,100 ft descent

  📍 Start/Finish: Gilbert Love Shelter

  📍 Turnaround: Algonquin Shelter

  ➡️ These two locations are within 100 yards of each other, making it ideal for spectators and crew.

  Expect well-marked trails, top-tier aid, and nonstop scenic beauty.

  🏃 Race Breakdown

  5K: A challenging trail take on the classic distance — perfect for new trail runners

  8-Mile: Out-and-back route finishing at the Start/Finish

  25K: One complete Last Trail Standing loop

  50K: Two full loops — big effort, big reward

  ⏱️ Timing, Awards & Registration

  Race Timing: Provided by Miles of Smiles

  Registration Options

  Day-Before Registration:

  Friday, November 13 at Sweat Bar Fitness (Oakdale — 5–10 minutes from the park)

  Race-Day Registration: Available onsite

  📧 Final race details will be emailed 3 days before the event

  👕 Shirt cutoff: Register by Monday, November 2, 2026

  🏅 Finisher medals: Provided to all participants

  Awards

  Top 3 Male & Female Medals — all distances

  Additional Top 3 awards: 8-Mile, 25K, and 50K

  Age-Group Awards: 8-Mile, 25K, and 50K

  🧃 Aid Stations, Crew & Drop Bags

  Two major aid stations: Start/Finish & Turnaround

  Less than 1/2 mile between aid stations for easy spectator viewing/crewing

  50K runners: Crew access & drop bags available at the 15.5-mile Start/Finish checkpoint

  🥾 Hikers Welcome

  Hikers are encouraged to join the 5K, 8-Mile or 25K distances. You’ll have ample time to enjoy the trails and finish strong.

  🪑 The Empty Chair (Dads Chair) & 💙 Rilyn’s Way

  The Empty Chair along the course symbolizes those we’ve lost — a reminder that they’re always with us on the trail.

  💙 Remembering Rilyn — “Rilyn’s Way”

  Rilyn Nicole Hughes was a beautiful 7-year-old girl who lived just a few miles from the race course. After a courageous five-and-a-half-year battle with Neuroblastoma, Rilyn passed away surrounded by those who loved her dearly.

  Before she passed, we committed to honoring her by naming the final half-mile of every race:

  “Rilyn’s Way”

  You’ll see a sign at the ½-mile-to-go mark. Pause if you’d like. Take a photo. Draw strength from Rilyn’s spirit as you finish your race.

  🕊️ Special Dedication

  The Harry J. Shipley Memorial Run

  Last Trail Standing is dedicated to Harry J. Shipley, father of race director Chad Shipley, whose birthday is November 17.

  Harry loved old country roads — always wondering where they led. That same curiosity guided the creation of this race: chasing every trail, connecting every path, and seeing where it all goes.

  “The Last Trail Standing isn’t about speed — it’s about exploration. And the only way to conquer it is to show up and run.”

  — Chad Shipley

  🌲 One Last Note

  The full course map will not be released in advance (same course as 2025). This is intentional. We want the experience to unfold as a true adventure.

  What we can promise:

  99% wooded trails

  Every trail in Settlers Cabin Park

  An experience you won’t forget

  Ready to conquer every trail at Settlers?

  We’ll see you at the start line on November 14.

  3.1 Miles 5k 8 Miles 15.5 Miles 25k 31 Miles 50k Run Trail

  608 Ridge Road, Pittsburgh, Pennsylvania, 15205, United States
  OpenStreetMap Google Maps

Local Clubs & Organizations