2 running events in Woburn, Massachusetts

Connolly's Kick in for Kids is a 5K road race and health walk to benefit James L. McKeown Boys & Girls Club of Woburn! The road race is professionally timed using chip timing. Fun for the whole family includes a post event party with a DJ, live band, food, cold refreshments, raffles and awards. 100% of race proceeds support health and wellness programs for kids and teens in Woburn and the surrounding communities. Join us!

The second annual Live Free Fun Run and Festival will be hosted on May 31st, 2026 at Ice House Park (Sturgis Street) at Horn Pond, Woburn MA 01801. The event is focused on promoting awareness and empowerment surrounding mental health and substance use. The scenic 2.5 mile off-road run (or walk!) brings participants around Horn Pond, and will start and end at the Live Free Festival. At the festival, you will find food trucks, raffles, a DJ, yard games, kids' activities and more! There will also be over 25 local mental health and substance use providers hosting tables to spread awareness about their mission and services. Join use for a day of empowerment, community and fun!