6 events in Pittsburgh, Pennsylvania

Martha's Ride 2026 Benefiting The Martha Fund — Building Playgrounds Across Pittsburgh, Honoring Those Who Serve

Martha's Ride honors FBI Special Agent Martha Dixon, killed in the line of duty on November 22, 1994, and stands in support of the law enforcement community that shares her legacy. Inspired by the Police Unity Tour, this annual ride travels from her name on the National Law Enforcement Officers Memorial Wall in Washington, D.C. to the Martha Dixon FBI Field Office in Pittsburgh — 329 miles along the C&O Canal Towpath and Great Allegheny Passage. Every dollar raised builds playgrounds for Pittsburgh's kids in the communities our officers protect every day.

THREE WAYS TO RIDE

Endurance Ride — Sept 28–Oct 2 329 miles over five days. Depart the National Law Enforcement Officers Memorial Wall in Washington, D.C. on Monday, September 28 and finish at the Martha Dixon FBI Field Office in Pittsburgh on Friday, October 2. Overnight stops in Harper's Ferry, WV (Clarion Inn); Hancock, MD; Cumberland, MD (Fairfield Inn); and Ohiopyle, PA. A SAG vehicle and trailer accompany the full route with limited mechanical support, nutrition, and gear transport. Full-service bike shops are available along the route for serious mechanical issues. Riders arrange their own lodging — recommended accommodations provided at confirmation.

Pittsburgh Day Ride — Oct 3 (10-Mile) Join the finish in Pittsburgh. Start at Southside Riverfront Park under the Birmingham Bridge, ride the 10-mile route, and finish at the Martha Dixon bench near Hot Metal Bridge. A police escort leads the group back down Carson Street to the park for the official finish. Open to all fitness levels — bring the family.

Pittsburgh Day Ride — Oct 3 (30-Mile) Same start and finish as the 10-mile, extended route. Finishes at the Martha Dixon bench with the same police escort back to Southside Riverfront Park.

AFTERPARTY All riders and supporters are invited to the afterparty. More details to follow. Sign up for our updates on the website.

QUESTIONS Visit themarthafund.org or contact Connor Dixon at [email protected].

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.

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.