Sidewinder
- Date:
- Sat, Sep 05, 2026 at 8:00 AM – 6:00 PM
- Location:
-
1371 Joe DeNardo Way
Penn Hills, Pennsylvania
15108
United States
OpenStreetMap Google Maps - Links:
- runsignup.com
- Tags:
- 13.1 Miles 20 Miles 50k Run Trail Walk
Are you ready to launch your running to the next level in 2026? Join us for the first ever Sidewinder in Montour Woods Conservation Area, with proceeds benefiting the Hollow Oak Land Trust*. Choose your distance: Half Marathon (hikers welcome), 20 Mile (hikers welcome), or the full 50K and expect a well-marked route, solid aid, and a welcoming first-year vibe.
Interested in volunteering at the race? Please fill out this form.
About the Course:
Typical Western PA trail conditions: twisty dirt singletrack with plenty of roots, windy switchbacks, and rocky sections that keep you on your toes. The course will consist of three parts: Liftoff, Orbit, and Final Approach.
Liftoff
Starting at Clearview Shelter in Moon Park, Liftoff is a 1.36 mile segment that will connect you from Moon Park to Montour Woods. Expect a nice flowy, downhill section connecting to a wooden boardwalk to start your race and ensure that all systems are go.
Orbit
Time to start into Orbit, consisting of a 9 mile loop around the Montour Woods Conservation Area. Orbit will take you through all the must-see sites in Montour Woods. You’ll cruise through the reclaimed concrete clearing of the old Nike missile site, pop out under the powerline, wind up and down and around the mountain, settle into a scenic stretch beside Meeks Run (with a waterfall spilling over rock ledges and a cave feature that feels like a hidden trail secret), and pass an old oil well tucked along the trail. Aid stations will be available approximately every 3-4 miles along the loop. One Orbit loop for the half marathon, two for the 20 milers, and three for those completing the 50K.
Final Approach
50K and Half Marathon: As the end of your journey draws near, you will climb into your Final Approach, a 2.87 mile, mostly double track loop around Moon Park. The loop gives you that perfect ending, knowing your journey is coming to a close and you're about to achieve your goal.
20 Mile: As the end of your journey draws near, you will climb back to the finish line, the same 1.36 segment as Liftoff but in reverse. An uphill push to the end, you'll be digging deep to finish strong and achieve your goal.
Vertical Gain per Distance:
50K: ~4500 ft
20 Mile: ~3200 ft
Half Marathon: ~1900 ft
--
*Hollow Oak Land Trust partners with municipalities—including Moon and Robinson Townships, Coraopolis Borough, and the Avonworth Municipal Authority—to create interconnected greenways that link parks, conservation areas, and communities. These greenways serve as both wildlife corridors and trail connectors, expanding access to nature while protecting habitat and improving environmental resilience.
Swag
T-shirts are only guaranteed if you sign up by July 5, 2026.
Awards will be given to the top male and female finishers of each distance.
Frequently Asked Questions:
What is the timing cut-off for the race? All three distances will have a cutoff of 10 hours.
Will the race be timed by a timing company? Yes, Miles of Smiles will be timing the event.
Are there nearby hotels? Yes, there are plenty of nearby hotels in both Robinson Township and Moon Township.
When will packet pick-up take place? We will provide more details on this later, but are anticipating packet pickup to be available the night before the race and the morning of.