4 running and walking events in Woodbury, Connecticut

The race is to benefit the Quassapaug Sailing Center, a nonprofit organization designed to provide sailing instruction and encourage and promote good fellowship between persons actively interested in sailing and water sports. Sails to trails summer camp is operated every summer to encourage sailing and outdoor activities for children. Scholarships are offered for children in need.

Race is an out and back road course starting at the Quassapaug Sailing Center. First mile is downhill, then you run back up the hill (no complaining- it’s not that steep!). No Dogs allowed!

Parking is limited- carpooling is encouraged. Race entries will be limited due to space limitations (likely that the race will sell out- sign up early!).

Awards: Overall Male and female finishers & top three in age groups 19 & under, 20-29, 30-39, 40-49, 50-59, 60-69 & 70 & up.

Race day is international Harry Potter day - come with your best costume and try to win an award.

As many of you may already know, a valued member of our Nonnewaug school community, Jon Cheung, was recently diagnosed with Leukemia. Just as he always has done in the classroom, on the sports fields, and in life, Jon is giving his all in this fight and the whole community is behind him. Our chapter of the Math Honor Society, of which Jon is a member want to show support and help raise funds to assist with the medical costs that his recover process involves so that him and his family can focus their attention on his health. To that end, we have planned a charity 5K walk/jog/run on Nonnewaug's campus for the 23rd of May. We hope you will show your support by signing up and enjoying a fun race with music, games, food, and more. If you have any questions, please email [email protected] or text 860-605-3730.

Flanders is excited for its 11th Anniversary Field & Forest 5K Trail Run/Walk on its property in Woodbury, CT. The 5K run/walk is a fun event, which exposes community members to the Flanders Van Vleck Farm & Nature Sanctuary. It promotes health and fitness, capitalizes on the growing interest in trail running/walking, and raises funds to support Flanders' mission to provide opportunities to appreciate nature’s wonders and preserve land, inspiring lifelong learning about our natural world.

Walk/run through the woods and fields of Flanders, officially timed by Fast Track Timing. Celebration after the run includes live music, food trucks, and more!

Register by May 5th to receive a FREE race shirt!

2026 Flanders Field & Forest 5K Trail Course Map

This event is rain or shine; however, Flanders reserves the right to cancel in the event of lightning. We apologize, due to the terrain this event cannot accommodate strollers or pets on the course. Registration fees are non-refundable.

2026 Flanders 5K Race Day Important Information/Instructions