Toby's Dream 5K and 1 mile Races

Race, Run, Walk, Wheel in Celebration of Memorial Day, Honor of Veterans, and Rememberence of Toby Pennels

Toby's Dream ProjectToby Pennels was a devoted husband, father, and son, who will be remembered for his commitment to the greater good and his lasting legacy of community service. He personified the spirit of the selfless volunteer, taking on any task and spearheading numerous projects that enriched the lives of those in the community. Toby was a lifelong advocate for education, serving for many years on the Windham School Committee including two terms as Chairman. Perhaps most importantly, Toby was a soldier. In 2011 he retired as a US Army Colonel following a thirty year career that included three tours of duty in the Middle East. During his years of service Toby adopted the mantra “Improve Your Position” a phrase which refers to improving your fighting position/foxhole in a combat situation, but in many respects became his defining philosophy in life.

In 2015, the Toby's Dream Project and 5K was born to support the fundraising efforts for the paving of the Windham Veterans Center drive and parking lot; a project which Toby had intended to complete as the Veterans Center President. In the Fall of 2015 we reached our goal, and were able to finish the project that Toby began.

With the paving project complete Toby's Dream will continue in support and recognition of the military, education, and athletics. The success of the 2015 5k race was a springboard into what we hope to be a growing annual event where our community can gather to celebrate Memorial Day, honor Veterans, and remember our friend and neighbor, Toby.

Race Info

5K and 1 Mile Memorial Race
Saturday, June 23,2018 at 7:45 a.m. Event begins at Windham High School’s canopy entrance to celebrate the life of Toby Pennels

Entry Fee

  • Pre-registration prior to June 22 1 Mile Run - $12.00 plus a $2.75 registration fee at check out.
  • Pre-registration prior to June 22 5K race - $16.00 plus a $2.75 registration fee at check out.
  • Student or Veteran 5K or Mile - $10.00 plus a $2.75 registration fee at check out.
  • Day of race registration 7:00 - 7:30 a.m.- 1 mile $15.00 and 5K $20.00

Race Policy

If race is canceled due to extreme weather conditions, there will be no make-up date and no refunds.


For more information regarding Toby's Dream visit the website.


Make a donation today to support the Toby Pennels Memorial Scholarship fund.