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OCT 24

4th-Annual Raible Run to Remember

Pittsburgh, PA
Welcome to Steel City NROTC's 4th-Annual Lieutenant Colonel Christopher "Otis" Raible Run to Remember! The mission of this event is to ensure that LtCol Raible is not forgotten by the community that he gave his life to protect through the promotion of community engagement, health and wellness, and patriotism and that his values of duty, bravery, and sacrifice are forever valued and emphasized.     Exciting Features of This Year's Event: Official event timing by Gingerbread Timing, a high-quality, veteran-owned, timing service located in Western PA with services including: Fully automatic timing leveraging RFID-equipped runners' bibsAn LED-leaderboard at the finish lineLive results posted directly to this webpage   Virtual Participation Participants wishing to support the Mission from afar will receive a private Strava Club invite where they will be able to compete with other participants from anywhere around the globe. We will provide instructions on how to create
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OCT 24

The Swissvale Mile: Race and Family & Dog Walk

Pittsburgh, PA
The Swissvale Mile is a community family-friendly fitness event. Choose from a one mile timed race or a dog-friendly, family fun walk. The Swissvale Mile is a 100% volunteer organized event funded by registrations, sponsorships, and donations. In addition to supporting our community, this event is a fun way to be active and to get to know the neighbors and neighborhood. ​Your involvement makes a direct positive impact on our community! Since the Mile was founded in 2014, proceeds from the Mile have been used to support many worthwhile causes including the Woodland Hills Chromebook Fund (helped provide Chromebooks to students forced to go virtual in 2020), The Swissvale Orioles Baseball and Softball Association, the Swissvale Community Enrichment Fund, our Swissvale K-9 Officers and the annual Swissvale Juneteenth Celebration! For the 4th year, are partnering with Swissvale Rotary to multiply our local impact and support their work in the community! The Rotary provides annual funding to Carnegie Free Library of Swissvale, the Swissvale Senior Center and Community Days and has donated to the Woodland Hills Foundation Backpacks of Hope, both the Swissvale and Union Baptist Church food pantries, the WH Girls’ Basketball team and the Swissvale/Braddock Football organization. Last year we were able to contribute $3,000.00 to Swissvale Rotary from our proceeds! Thank you for being involved!
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OCT 24

Musicians of Steel 5K Run/Walk

Pittsburgh, PA
Please join us for the 10th Annual Musicians of Steel 5K Run/Walk, a charity race organized by the Musicians of the Pittsburgh Symphony Orchestra! This marks a huge milestone for us and our community. Thank you to everyone who has supported us in the past; we sincerely hope you will join us again this October for our 10th Anniversary Race! All proceeds go to the Musicians Care Fund, an invaluable resource which provides future generations with access to classical music. Read more below. • MUSIC! ♫ You’ll be serenaded at the start line by the world-class musicians of the PSO in addition to local musicians along the course! Virtual participants, never fear! You’ll receive a unique running playlist specially curated by your PSO Musicians to help you cross the virtual finish line! • SWAG! 🎽 Show off your love for music and running around town with our official race T-shirt, free with every registration! • PRIZES! 🏆 As always, our prize packages are awarded to the top three male and female finishers overall and the top finisher in various age categories. Prizes include special items like PSO recordings and gift cards to local Pittsburgh businesses. • COMMUNITY! 💞 Connect with your PSO Musicians! Stay in touch on our Facebook page and tell us how you’re preparing for the race! Most importantly… • SUPPORT AN AMAZING CAUSE! 🎻 Music education should be a cornerstone in every young person’s life. We believe that music education is more important now than ever. We are proud to provide support to local music programs in need by donating 100% of race entry fees directly to the PSO Musicians Care Fund. The money raised for the PSO Musicians Care Fund is used to buy instruments for local students, secure school buses for transportation to and from Heinz Hall for PSO’s “Schooltime” concerts, in addition to other invaluable resources. Race entry fees (not including online processing fees) and any additional contributions to the “PSO Musicians Care Fund” are tax deductible to the fullest extent permitted by law. The “PSO Musicians Care Fund” is a component fund of the Pittsburgh Foundation which is a 501(c)(3) organization.
5K
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OCT 24

Butterfly Friends Foundation 3rd Annual Family Fun Run & Walk

Pittsburgh, PA
Join us for the 3rd Annual Butterfly Friends Foundation Family Fun Run & Walk for a morning of fitness, family, and community while making a meaningful difference in the lives of children with special needs. Whether you're chasing a personal best, enjoying a leisurely walk with family and friends, or cheering from the sidelines, everyone is welcome. This untimed, family-friendly event is open to participants of all ages and abilities. Every registration helps support the Butterfly Friends Foundation's mission of providing financial and logistical assistance to families of children with special needs so they can experience memorable vacations and meaningful adventures together. Event Highlights: Family-friendly run and walk for all ages Beautiful course through Frick Park Music, refreshments, and community activities Opportunity to support an important local cause Register before Oct 13th to get a t-shirt. Registration after Oct 13th is free, however t-shirts will not be provided. Come run, walk, and make a difference—because every step helps create joyful journeys for families who need them most. We can't wait to see you at the starting line!
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OCT 24

4th-Annual Raible Run to Remember

Pittsburgh, PA
Welcome to Steel City NROTC's 4th-Annual Lieutenant Colonel Christopher "Otis" Raible Run to Remember! The mission of this event is to ensure that LtCol Raible is not forgotten by the community that he gave his life to protect through the promotion of community engagement, health and wellness, and patriotism and that his values of duty, bravery, and sacrifice are forever valued and emphasized.     Exciting Features of This Year's Event: Official event timing by Gingerbread Timing, a high-quality, veteran-owned, timing service located in Western PA with services including: Fully automatic timing leveraging RFID-equipped runners' bibsAn LED-leaderboard at the finish lineLive results posted directly to this webpage   Virtual Participation Participants wishing to support the Mission from afar will receive a private Strava Club invite where they will be able to compete with other participants from anywhere around the globe. We will provide instructions on how to create
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OCT 31

Wilkins Township Halloween 5K Run-Walk

Pittsburgh, PA
Welcome to Warm & Wonderful Wilkins! The race starts and finishes at Wilkins Elementary STEAM Academy, and the course takes you through the scenic neighborhood of Penhurst, where you will be rallied on with the local residents support! Come in costume and join in on the fun of this annual fall-time tradition in the Township! No pets allowed. All proceeds to help support our local Volunteer Fire Departments Visit our website at www.wilkinstownship.com
5K
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NOV 1

Friendship Circle 5K and Walk 4 Friendship

Pittsburgh, PA
On November 1st, Friendship Circle is putting 20 years of friendship in motion! Our biggest community event of the year now has two ways to move: the first-ever Friendship 5K, a timed run in the heart of Squirrel Hill, followed by the sixth annual Walk4Friendship, followed by a carnival celebration! One Morning. Two Ways to Move. Registration is open! Form a Walk team and fundraise together, rally your run club, or register solo. Run it. Walk it. Cheer it. However you choose to move, every mile matters and helps build a community where everyone belongs.
5K
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NOV 7

4th-Annual Raible Run to Remember

Pittsburgh, PA
Welcome to Steel City NROTC's 4th-Annual Lieutenant Colonel Christopher "Otis" Raible Run to Remember! The mission of this event is to ensure that LtCol Raible is not forgotten by the community that he gave his life to protect through the promotion of community engagement, health and wellness, and patriotism and that his values of duty, bravery, and sacrifice are forever valued and emphasized. Exciting Features of This Year's Event: Official event timing by Gingerbread Timing, a high-quality, veteran-owned, timing service located in Western PA with services including: Fully automatic timing leveraging RFID-equipped runners' bibsAn LED-leaderboard at the finish lineLive results posted directly to this webpage Virtual Participation Participants wishing to support the Mission from afar will receive a private Strava Club invite where they will be able to compete with other participants from anywhere around the globe. We will provide instructions on how to create a Strava account if you do not already have one. If you do not wish to participate via Strava, please email raible5k@gmail.com to receive further instructions after signing up.Participants will be mailed an official event t-shirtVirtual Participants can record their time anywhere, but need to run between November 6th and November 8th to be officially considered for the virtual competitionThe top male and female virtual runners will be recognized and awarded! What's New A brand new event t-shirt design!Race finishers can look forward to a new finisher medal at the finish lineAn expanded lineup of food vendors for this year's eventRegister before Oct 10th to get a t-shirt with registration Competition! During the registration process, participants can make and join their own teams. The team that has the most participants registered by Race Day, November 7th, will win 500$! For ROTC and JROTC Units This year, we’re introducing a new option for unit participation. Instead of individual registrations, units can register collectively for $75 and will receive a Commemorative LtCol Raible 5K paddle in recognition of their support.Unit registration will be submitted as a 75$ registration fee through the race website. Please email raible5k@gmail.com with your unit name and point of contact to confirm your participation.Individuals who wish to receive a t-shirt and finisher medal may still register separately.Additional unit-based prizes may be introduced depending on participation levels. Details to be announced. What Comes with a Registration? Registration includes an event t-shirt unique to this year, access to the participant village, pre- and post-race snacks, and more! The participant village will be filled with games, raffles, and prizes so be sure to show up ready to have fun and support a great cause. After the race, not only will the winners be announced and prizes distributed, but there will also be a ceremony to honor LtCol Raible, so please feel free to stay for the whole time no matter if you win or lose. [NOTE that participants must sign up before October 10th in order to be guaranteed to receive a shirt in their desired size. All participants who sign up after this date are not guaranteed a shirt (or for it to be in their size if they do receive one).]
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NOV 14

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

Pittsburgh, PA
LAST TRAIL STANDING Our Sell-Out Event Is Back! Saturday, November 14, 2026 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 Male & Female 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.
5Ktrail
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NOV 14

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

Pittsburgh, PA
LAST TRAIL STANDINGOur Sell-Out Event Is Back!Saturday, November 14, 2025Settlers 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 DistancesAll races start and finish at the same location — no shuttle required. 🟢 5K (Hikers Welcome)🔵 8 Miles (Hikers Welcome)🟠 25K (Hikers Welcome)🔴 50K  🕓 Start Times & CutoffsStart times: Listed individually for each race aboveFinal cutoff for all races: 5:30 PM50K time limit: 9 hours 🗺️ Course OverviewThe 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: O
5Ktrail
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NOV 14

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

Pittsburgh, PA
LAST TRAIL STANDINGOur Sell-Out Event Is Back!Saturday, November 14, 2025Settlers 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 DistancesAll races start and finish at the same location — no shuttle required. 🟢 5K (Hikers Welcome)🔵 8 Miles (Hikers Welcome)🟠 25K (Hikers Welcome)🔴 50K  🕓 Start Times & CutoffsStart times: Listed individually for each race aboveFinal cutoff for all races: 5:30 PM50K time limit: 9 hours 🗺️ Course OverviewThe 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: O
5Ktrail
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DEC 5

2026 Jingle Bell Run - Pittsburgh, PA

Pittsburgh, PA
Get ready for this year’s Jingle Bell Run, the original festive race for charity brought to you by the Arthritis Foundation. Wear your favorite holiday gear, and let's jingle all the way toward a cure! Whether you're running, walking, or strolling, bring your friends, family, and coworkers along for the ride. Together, we're spreading joy and making strides towards a brighter future — saying "YES" to life, despite arthritis. Don't miss out on this special occasion to make a real difference while celebrating four decades of impact with the Jingle Bell Run. Let's lace up, hit the pavement, and jingle our way toward victory over arthritis!
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DEC 12

Lost Souls - The Race That Finds You

Pittsburgh, PA
Lost Souls - The Race That Finds You Saturday, December 12th, 2026 As many loops as you can in 8 hours Background: Last Trail Standing (November) and Rise Up Hero (May) are awesome sister races along the trails of Settlers Cabin Park that both offer various race distances up to 50K. BUT... I've been wanting to create a different kind of race. One that would truly test people mentally, physically, and emotionally. So...I went searching for the most challenging small loop at Settlers Cabin Park and…I think I found it. A brutal ~5K (unpublished and partly made up) trail loop that climbs roughly 550 feet of elevation every loop. Here's how the race works: You can sign up for the 5K Loopy Loop if you simply want to experience the course and enjoy the challenge. You run 1 loop for the honor of saying you ran the 5K loop from hell. Or… You can sign up for the ENDURE challenge and you do as many loops as you can possibly endure in 8 hours. Unlike backyard ultra formats, you DO NOT have to start each loop on the hour. You start when you think you're ready to take on another soul shattering journey. Runners will work to complete the maximum race distance of 10 loops or as many loops as they can within 8 hours. Each loop brings you back to the start, where you must decide: Do you continue to endure…or do you ring the bell and proudly take your wood chip and loop count with you. The maximum is 10 loops, making it a 50K ultra with ~5,500 feet of elevation gain. Awards will be given to the 1st, 2nd, and 3rd overall male and female runners who complete all 10 loops. This race isn't just for ultra runners wanting an incredibly hard 50K challenge. It's also for the people who want to dig deep and see how far they can go. The spirit of the race is to endure for as long as you can. And once you're ready to tap, you ring the bell and you receive a unique keep sake—a reminder of the moment you faced the course, the struggle, and what you discovered about yourself along the way. Lost Souls isn’t just about finishing. It’s about finding out how much you can endure and what you learn about yourself along the way. It's when we're most challenged, that we see our truest self. If it breaks you, it builds you. If it strips you, if finds you. Welcome to LOST SOULS ULTRA & TRAIL RUNS
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DEC 24

The Christmas Eve 5k

Pittsburgh, PA
Join Us at this Special Holiday Event! The Christmas Eve 5k is back! All event participants will receive a Christmas themed finisher medal and a long sleeve race shirt! There will be hot chocolate, cookies, and more post-race refreshments for all! Start your celebration for the best holiday of the year with this family fun event! Runners & walkers welcome. Strollers are permitted. Age based pricing available during checkout. Don't miss out on this Christmas celebration! Location: North Shore by Acrisure Stadium Start Time: 10:00 AM Awards: Awards will be given to the Top 3 Overall Male & Female Finishers plus the top 3 finishers in each of the following categories: 10 & Under, 11-14, 15-19, 20-29, 30-39, 40-49, 50-59, 60-69, and 70 & Over. Only In-Person racers will be eligible for awards. Packet Pickup: Early Packet Pickup from 12/19 to 12/23 at Public Lands (1000 Cranberry Square Dr Ste D, Cranberry Twp, PA 16066). There will be limited race day packet pickup available from 8:00 AM to 9:45 AM by the start/finish area on the North Shore by PNC Park. We recommend you pick up your packet early to avoid long lines on race day. Virtual race packets will be mailed and will not be available at in person packet pickup.
5K
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FEB 13

Cupid's Chase 5K Pittsburgh

Pittsburgh, PA
Check-in begins at 8:00 AM and the race starts at 10:00 AM.The event is fully accessible and pet-friendly, but all pets must remain leashed at all times.This is a certified 5K with professional timing. All results will be posted immediately after the race.To guarantee your Cupid's Chase shirt, please register by January 1, 2027; after that date, shirts will be available while supplies last.Giveaways include a Cupid's Chase finisher medal and drawstring bag, available while supplies last.Trophies will be awarded to the top 3 overall male and female finishers.Age group medals will be awarded to the overall male and female finishers in each of the following 14 age groups: 12 & under, 13–15, 16–19, 20–24, 25–29, 30–34, 35–39, 40–44, 45–49, 50–54, 55–59, 60–64, 65–69 and 70 & over.This is a rain or shine event. All registration fees are non-refundable.
5K
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APR 18

Rise Up Hero Trail Runs at Settlers Cabin Park - 50K, 25K, 8miler, 5K - A Last Trail Standing Event

Pittsburgh, PA
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 courseSettlers 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 directionAll race distances
5Ktrail
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