Welcome to Bootleg Running. We organize underground point-to-point runs, rail trail sprints, and secret backyard finish-line gatherings across Massachusetts. No corporate $100+ entry fees, no closed roads—just honest miles, mutual support, self-direction, and cold celebratory drinks.
Unsanctioned, not unprincipled. We choose to celebrate life by running together, enjoying fun routes and destinations across Massachusetts.
No orange cones or police details. Load the GPX route onto your GPS watch or carry a printed cue sheet. Obey all pedestrian laws, run on sidewalks and road shoulders, and look both ways before crossing.
No corporate entry fees. Anyone can participate. Many events have community sponsored swag or course support.
Every route concludes somewhere we can gather to celebrate and enjoy post-race refreshment.
RSVP is open and GPX route files are now available for our Labor Day gathering.
An afternoon-into-sunset run connecting Hudson and Ashland via the shaded Assabet River Rail Trail and rolling historic backroads, finishing at a local favorite haunt. Custom die-cast medals, stickers, and cold celebratory drinks available for finishers of any distance.
