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

location_city Pittsburgh

location_on Pennsylvania

flag United States

calendar_today 16 Nov, 2025

directions_run Running

language Official Website

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About the Event

🏃‍♂️ 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 (Hikers Welcomed)
🔵 8 Miles (Hikers Welcomed)
🟠 25K
🔴 50K

ALL RACES START AND FINISH IN THE SAME PLACE - NO SHUTTLE NEEDED!

DOGS - We love when we can allow dogs to be a part of our event but unfortunately cannot allow them for this one due to runners going in both directions on the course.

 
🗺️ Course Overview
The course is a 7.75-mile point-to-point trail you’ll run in both directions to complete a full 15.5-mile loop. This clever design gives runners the chance to experience a variety of trails in Settlers Cabin Park, with a route that feels completely different in reverse. The course is 99% trail and absolutely stunning. Start/Finish and the aid station at mile 7.5 are within 100 yards apart of each other. All Races Start and Finish at the same spot so no shuttle is needed.

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 apart—perfect 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 distance—great for runners looking to break into trail running.
8-Mile: Run straight through, bypassing the turnaround and finishing at Gilbert Love (Start/Finish).
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 5–10 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 Tuesday, November 4th 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! You’ll have plenty of time to enjoy the trails and finish strong.

 
🕊️ Special Dedication: The Harry J. Shipley Memorial Run
This race is dedicated to  (race director) Chad's father, Harry J. Shipley, whose birthday is on Monday, November 17th. 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, he’d wonder where it led and often followed it. I did the same while mapping out all the trails in Settlers—chasing every trail, connecting every dot. It’s 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?
We’ll see you at the start line on November 16th.

Races Offered

Other

Nov 16, 2025

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Distance — Other

terrain

Type — Trail running

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5K

Nov 16, 2025

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Distance — 5K

terrain

Type — Trail running

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15K

Nov 16, 2025

straighten

Distance — 15K

terrain

Type — Trail running

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Marathon

Nov 16, 2025

straighten

Distance — Marathon

terrain

Type — Trail running

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Weather Overview

These values represent the 3-year monthly averages for November in Pittsburgh.

Temp (°C)
Feels Like (°C)
thermostat 3.9° / 12.4°
wb_sunny 0.0° / 8.8°
Wind (km/h)
Humidity (%)
air 11.8 /
water_drop 70.6%

About Pittsburgh

Scenic view of

The pleasure of Pittsburgh remains a well-kept secret. Though not built up by reputation, the city's unique combination of bridges, steep hills, and broad rivers make it one of the most naturally scenic cities in the country. Cheap food and beer abound in this true sports town and the locals are amazingly friendly. A city of about 303,000 (2021) in Allegheny County, at the center of a metro area of about 2.4 million in southwestern Pennsylvania, Pittsburgh is situated at the confluence of three rivers: the Monongahela and Allegheny Rivers, which meet to form the Ohio River. The city's unique terrain has resulted in an unusual city design and a hodge-podge of unique neighborhood "pockets" with diverse ethnic and architectural heritage. Pittsburgh has a rich history and, for its size, an unusual array of cultural treasures, largely thanks to the wealth that was generated when Pittsburgh was a hub of industry.

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