5 running events in Cheshire County, New Hampshire

From big races to Saturday morning group runs—find running events and connect with the local endurance sports community.

• Fitzwilliam to Troy Depot Day Cheshire Rail Trail Fun Run [fitzhistoric.org] [Register at runsignup.com]
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  Sat, Jun 06, 2026 at 10:00 AM

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  ​T​ake a 5 mile run along the ​beautiful Cheshire Rail Trail from the original Fitzwilliam Railroad Depot at 6 Church Street Fitzwilliam, NH to the newly restored Troy Depot on Depot Street in Troy,...

  ​T​ake a 5 mile run along the ​beautiful Cheshire Rail Trail from the original Fitzwilliam Railroad Depot at 6 Church Street Fitzwilliam, NH to the newly restored Troy Depot on Depot Street in Troy, NH.

  The Cheshire Rail Trail starts in Walpole NH going through Fitzwilliam, NH. The original railroad trail started back on May 16 1948, for train uses, they ended in 1960. Eventually, this rail trail became a bicycle/hiking path. The terrain can go from very tall grass areas, to rocky/sandy, or paved and gravel. It is roughly about 43 miles all put together. The Depot Day Fun Run is along a well maintained 5 mile path from Fitzwilliam, NH to Troy, NH. Food & festivities will​ help us celebrate​ at both Depots from 9AM - noon. Adult run begins at 10 AM. Short Children's Loop Run at the Fitzwilliam Depot 11 AM . Fundraiser for the Fitzwilliam & Troy Historical Societies. Please Join us!

  5 Miles Fun Run Gravel Run Trail

  6 Church Street, Cheshire County, New Hampshire, 03447, United States
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• Stag Stampede 5k and Fun Run [dublinchristian.org] [Register at runsignup.com]
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  Sat, Aug 29, 2026 at 9:00 AM

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  Race Date: August 29,2026

  Race Time: 9:30 AM (Fun Run @ 9:00 AM)

  Bib/Shirt Pick Up and Race Day Registration: 8:00-9:15 AM

  For generations, Dublin Christian Academy Stags have been running “the loop"...

  Race Date: August 29,2026

  Race Time: 9:30 AM (Fun Run @ 9:00 AM)

  Bib/Shirt Pick Up and Race Day Registration: 8:00-9:15 AM

  For generations, Dublin Christian Academy Stags have been running “the loop" a legendary training run that has become a rite of passage for our athletes (see course map below). This year, you can test your mettle on the same course that has honed our champions at the inaugural Stag Stampede 5K and Fun Run. Join us to run, walk, or push the kids in the stroller. Stay for post-race refreshments sponsored by DCA Parent Connect. All proceeds from this community 5K will benefit the Dublin Christian Academy athletics programs: DCA Stags soccer, volleyball, and basketball.

  Prices: $25 Early Bird Special thru Jul. 31, 2026

  $30 Aug 1 thru Aug. 27, 2025 (6:00 P.M.) Race Day Registration $35

  Fun Run (.25 mile) FREE (no shirt)

  We look forward to cheering all our runners & walkers on August 29,2026!

  **Race Shirts guaranteed by August 7th.

  Note for 5k Course: Known among DCA athletes as “the loop,” the scenic, single-lap 5K course begins at the playground on the school’s main campus on Page

  Road. The course begins mostly flat and runs south down Page Road, turns east (left) on Craig Road, north (left) on Route 137, west

  (left) on Windmill Hill Road where the elevation gradually rises, and finally, south (left) on Page Road up Alsi’s Hill, west (right) on

  the dirt loop beyond the playground, north (left) back on to Page Road, and ends back at DCA’s playground. This gently rolling, open-road course has a mix of paved road and gravel.

  Note for our Fun Run: We have a beautiful quarter-mile fun run begins at the DCA playground and follows the dirt drive past the shop, then turns south (right) onto

  the dirt drive that leads to the field cottage with a view of Mount Monadnock on the right. The course continues east (left) up Carriage

  Path (grass path between the stone walls) and then turns north (left) at the gate onto Page Road, ending back at the playground

  If you are interested in volunteering or sponsoring this event please contact Tracey Burt - [email protected] for more information.

  3.1 Miles 5k Fun Run Gravel Run Walk

  106 Page Road, Cheshire County, New Hampshire, 03444, United States
  OpenStreetMap Google Maps