Pittsfield, Massachusetts · Saturday, September 12, 2026
The Free to Run Trail Races is a 25k, 50k, running, trail running, and ultra event held on Saturday, September 12, 2026. It is located at 1041 Cascade St in Pittsfield, Massachusetts.
Join us Saturday, 7/11/2026 for our Fifth Annual Smile Like Jack Family Fun Run/Walk. We will have food, beverages (21+ options too), amazing raffles, music, and lots of smiling faces!
Early check-in will be held Friday 7/10/2026, from 4-7 PM at the Knox Trail Inn, for those who wish to get their bibs the evening before.
Day of registration and check-in begins promptly at 7:00 AM, while the race kickoff is at 9 AM.
Prices:
Competitive Race (Chipped Timed) 5k/10k
$40
Family Fun Run/Walk (Not Timed)
$35
We hope to see you there!
Cutoff for T-shirts will be June 1st. This event is rain or shine!
JACK'S STORY
The Smile Like Jack Memorial Fund was established in memory of Jack William O’Brien, a loving son and brother, caring friend, and hard working young man that touched the lives of many with his contagious smile. Jack tragically passed away in a snowmobile accident on March 3rd, 2022. In his 20 short years, he had accomplished many things and leaves behind a legacy that is in a caliber of its own. Jack lived life to the fullest. He was always working exceptionally hard to accomplish his set of goals while also living the outdoorsman lifestyle: fishing, hunting, and riding. Our goal is that the Smile Like Jack Memorial Fund will bring other individuals (with similar passions) the opportunity to live their legacy just as Jack would - working immensely hard in the trades and living life to the fullest in the great outdoors.
For additional information on The Smile Like Jack Memorial Fund, and for live updates, please visit our website: https://smilelikejack.com
Nearly 500 runners and walkers joined us last year, and after three years of tinkering, we finally cracked the code: same course, same start and finish, and the same post-race reward — a cold Common Roots beer. This year, we’re kicking off at 6:30 PM and hoping for clear skies. Thanks to the running clubs, creative teams, and proud wearers of wild shirts and wilder props who make this event what it is. See you at the start line, where good people, great stories, and maybe a few mismatched costumes collide for a cause that runs deep.
BAD BLOOD RUN 2026 RACE DETAILS:
Wed. Aug. 5th @ 6-7:30 PM - Dicks House of Sport, Latham
Thurs. Aug 6th @ 4:30 - 6 PM - Siena Quad
Runners: two loops
Walkers: one loop
Kids Quad Dash $10: starts @ 6:00 pm
USATF Sanctioned, ARE, Running Bib with Chip Timing with ChronoTrack B-Tag.
REGISTRATION FEE SCHEDULE:
$30 until May 31st (Early Bird)
$35 June 1st - August 5th
$45 on race day (4:30 pm-5:30 pm)
FREE STUFF:
Free Shirt - first 200 registrants
Free Common Roots beer with registration (21+)
TOP FINISHER PRIZES - Awards: 7 - 7:15 PM (Quad)
Top Male and Female will receive a $250 GC at High Adventure Ski Shop by Alpin Haus
Top Male and Female finishers, ages 12 and under, 13-19, 20-29, 30-39, 40-49, 50-59, and 60-69. 70+, will receive a $25 GC.
Team Prizes: Best team shirt, Most members, Highest fundraiser receives branded running socks
SWIM: 0.5mi | BIKE: 18mi | RUN: 3mi
Crystal Cove | Old Route 66, Averill Park, NY
The Crystal Lake Triathlon Race is a USAT Sanctioned Sprint Distance Triathlon in Averill Park, NY on Crystal Lake. The race is one of the most scenic races in the area. The race begins at the Crystal Cove beach and features a single loop swim. Transitioning into the bike leg of our race where racers set out on a gorgeous out and back bike course that passes through the beautiful countryside of Rensselaer County. Finally, the racers finish on a mostly flat run course around Crystal Lake.
All participants will be required to either show USAT membership or purchase a one-day license and sign a USAT waiver.
Event Registration Website: cdtriclub.org/index.php/race/
Participation Type:
• Individual (not part of a Team) Adult , Youth
• Join a Team Adult , Youth -
• *Aquabike Adult, Youth
*The Aquabike race covers the same swim & bike courses as the Triathlon but will end when participants enter the Transition Area upon completion of the bike.