Last Trail Standing - 50K, 25K, 8 Miler, 5K

  • Date Sun 16th November 2025
  • Time 7:15AM EST
  • Location Pittsburgh, Pennsylvania
  • Price $38.35 - $74.39
  • Races 4 races
  • Distances Ultra, 5km

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Event summary

Get ready for an exhilarating day of trail running at the Last Trail Standing event, taking place on Sunday, November 16, 2025, in the scenic Settlers Cabin Park in Pittsburgh, Allegheny! This unique trail running experience invites athletes of all levels to conquer every single trail in the park with four exciting race distances to choose from: 5K, 8-Mile, 25K, and a challenging 50K.

The course features a stunning 7.75-mile point-to-point trail that you'll run in both directions, allowing participants to experience the beauty of the park in a whole new way. With 99% of the course on breathtaking wooded trails, runners will enjoy well-marked paths and top-tier aid stations positioned conveniently for both competitors and spectators. Whether you’re just starting your trail running journey or looking to tackle a grueling ultra, Last Trail Standing is the perfect event for you. Don’t miss this chance to honor the spirit of adventure and exploration on race dayβ€”mark your calendars and get ready to hit the trails!

Organiser's Description

male sign Last Trail Standing November 16, 2025
Settlers Cabin Park Robinson, PA

Join us for Last Trail Standing, an unforgettable trail running experience through the heart of Settlers Cabin Park. Held on Sunday, November 16th, this unique race covers every single trail in the park, offering four exciting distances:

5K
8 Miles
25K
50K


Course Overview
The course is a 7.75-mile point-to-point trail youll run in both directions to complete a full 15.5-mile loop. This clever design gives runners the chance to experience every trail in Settlers Cabin Park, with a route that feels completely different in reverse. The course is 99% trail and absolutely stunning.

25K runners complete one loop (out and back).
50K runners complete two loops (out and back twice).
Aid stations are located at the start/finish (Gilbert Love Shelter) and the turnaround point (Algonquin Shelter), which are just 100 yards apartperfect for spectators!
Elevation gain (50K): ~3,300 ft climb / ~3,100 ft descent
Expect well-marked trails, top-tier aid, and beautiful woods from start to finish.


Race Breakdown
Start Line: Gilbert Love Shelter
Turnaround Point: Algonquin Shelter
5K: A challenging trail version of the classic distancegreat for runners looking to break into trail running.
8-Mile: Run straight through, bypassing the turnaround and finishing at Gilbert Love.
25K: One full loop of the Last Trail Standing route.
50K: Two full loops. Big effort. Big reward.

Timing & Cutoffs
Race Timing: Provided by Miles of Smiles
Registration:

Saturday, November 15th Day-before registration available at Sweat Bar Fitness in Oakdale (just 510 minutes from Settlers Cabin Park)
Race Day Registration: Available onsite before the race
Race Day Details: Final instructions and race day logistics will be emailed 3 days before the race
Shirt Cutoff Date: Register by Saturday, November 8th to receive your race shirt
Finisher Medals: Provided to all runners
Awards: Custom hand-crafted gifts for 1st place male & female in both the 25K and 50K
Cutoff Time: All races must be completed by 4:15 PM

50K runners have a 9-hour time limit

Aid, Crew & Drop Bags
Two major aid stations (Start/Finish & Turnaround), hit multiple times in the 50K
Max distance between aid stations is less than 8 miles
Crew & drop bag support available for 50K runners at the 15.5-mile start/finish checkpoint

Hikers Welcome
We encourage hikers to sign up for the 25K or 8-mile distances! Youll have plenty of time to enjoy the trails and finish strong.


Special Dedication: The Harry J. Shipley Memorial Run
This race is dedicated to Chad's father, Harry J. Shipley, whose birthday falls on race day. The event honors his spirit of curiosity, adventure, and appreciation for the roads less traveled.

My dad loved old country roads. Every time he saw one, hed wonder where it led and often followed it. I did the same while mapping this coursechasing every trail, connecting every dot. This route touches them all. Its the Last Trail Standing, and the only way to conquer it is to join the race.
Chad Shipley

One Last Note
The full course map will not be released in advance. We want the experience to unfold as a true adventure. What we can tell you is this: 99% of the race is on the beautiful wooded trails of Settlers Cabin Park.


Ready to conquer every trail at Settlers?
Well see you at the start line on November 16th.

Races

  • 50k

    Incl. $5.39 Fee & T-Shirt

    Sun 16th November 2025 (7:15AM EST)

    $74.39

  • 25k

    Incl. $4.79 Fee & T-Shirt

    Sun 16th November 2025 (7:30AM EST)

    $63.79

  • 8 Miler

    Incl. $4.79 Fee & T-Shirt

    Sun 16th November 2025 (7:45AM EST)

    $63.79

  • 5k

    Incl. $3.35 Fee & T-Shirt

    Sun 16th November 2025 (8:00AM EST)

    $38.35

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Location

608 Ridge Road, Pittsburgh, 15205, PA, United States

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Nov 16, 2025

$38.35 - $74.39