If you are looking for races in Roxbury, Connecticut, you have come to the right place. Roxbury has a growing running scene with 10 races listed in our directory, including 7 upcoming events in 2026. Whether you are lacing up for your first 5K or chasing a new personal record, there is something here for every runner.
Upcoming Races in Roxbury, Connecticut
Here is a look at the top upcoming races in Roxbury this year. We update our listings weekly so you always have the most current information.
Roxbury Road Race Series #18
Date: July 11, 2026
Head out for a 3-mile jaunt through the River Road Preserve in Roxbury, CT, where you’ll start at the Land Trust entrance, hit a turnaround cone, and finish near the pond. Read full details →
Roxbury Road Race Series #19
Date: July 18, 2026
Roxbury Painter Hill 10k Active duty military/veterans and active first responders are encouraged to contact the race for a discount. Read full details →
Roxbury Road Race Series #20
Date: August 1, 2026
4.7 Miles- Tierney Falls Active duty military/veterans and active first responders are encouraged to contact the race for a discount. Read full details →
Roxbury Road Race Series #21
Date: August 8, 2026
Get ready for a 6.4-mile adventure through Roxbury, CT that takes you out and back on Falls Road with a loop around Minor Bridge! If you’re serving or have served in the military, or work as a first responder, reach out to the organizers about special pricing options just for… Read full details →
Roxbury Road Race Series #22
Date: August 15, 2026
Head out for a 4.2-mile loop through Roxbury, CT that takes you down South Street, across Wellers Bridge, and features a challenging climb up Hemlock. Read full details →
Roxbury Road Race Series #23
Date: August 22, 2026
7.2 Miles- The Boot. Active duty military/veterans and active first responders are encouraged to contact the race for a discount. Read full details →
Roxbury Road Race Series #24
Date: August 29, 2026
GUESS YOUR PACE RACE! Exact course TBD and will be brand new. All runners will guess their time before the start. Points will be awarded two ways- based on time and based on proximity to each racer's guess. Read full details →
Why Run in Roxbury?
Running events in Roxbury offer a mix of community fun runs, charity 5Ks, and competitive road races throughout the year. The local running community is active and welcoming to runners of all levels — from first-timers to seasoned racers. Many of these events benefit local charities and organizations, making race day about more than just your finish time.
Find More Races in Connecticut
Roxbury is just one part of a thriving Connecticut running scene. If you want to explore more events across the state, check out our full race listings for Connecticut — we track every upcoming running event from 1 mile fun runs to full marathons.
Get Ready to Race
Found a race you want to run? The next step is making sure you are properly trained for it. Whether you are a first-timer aiming to finish or a veteran chasing a PR, having the right training plan makes all the difference.
Take our free 3-question training plan quiz and get matched to the right plan for your fitness level in under a minute. We will send it straight to your inbox so you can start training today.
Good luck out there — see you at the finish line in Roxbury!
