HALF (3:30 PM HUDSON) • 10K (4:30 PM ASHLAND) • 5K (ROLLING 4:30–6:30 PM)
An afternoon-into-sunset underground run connecting Hudson and Ashland via rail trail and open backroads—culminating at a secret speakeasy celebration with custom medals and cold celebratory drinks.
In the spirit of bootleggers from every era, this is an unsanctioned, DIY run organized for runners who love raw adventure, good company, and great drinks. No street permits, no barricades — just a scenic route, mutual support, and a party at the end.
Like all our events, this is an Open Course. There are no orange cones or marshals at every corner. Load the provided GPX track to your GPS watch or phone, or print the cue sheet. Run on sidewalks and shoulders, obey all pedestrian signals, and watch for cars.
We use the honor system, not disposable RFID chips. Track your run on Strava, Garmin, or your watch. We'll have an informal finish line logbook and stopwatch to record your bragging rights and dish out rewards.
All three distances share a finish line in Ashland, where we'll try to convince Jon that our experience with bootleg running means we're ready to open the speakeasy upstairs.
Meet the start in Hudson for route briefing and to get a refreshment ticket.
Rollout from start in Hudson onto the Assabet River Rail Trail.
10K runners gather for route briefing at the Ashland finish venue.
10K group rollout through Main Street, Riverwalk, and scenic neighborhood roads.
Flexible rolling start! Arrive and begin your 5K run or walk whenever you wish, with a main wave at 6pm.
Cheer on incoming runners, claim your finisher medal, grab cold drinks and recovery food, and celebrate into the evening in Ashland.
Just because it's an unofficial race doesn't mean you go home empty-handed. We've pooled resources to order custom die-cast medals and speakeasy runner swag for participants who chip in.
A medal almost as cobbled together as the race itself. Perfect token of accomplishment for a group picture.
Post-run gathering at the finish line in Ashland. Redeem your drink ticket if you were awarded one, then enjoy snacks and company.
Stickers sporting the logo of a local running club
Any finisher who wishes can have their time included in our rolling Bootleg Leaderboard. Future events may have perks based on the leaderboard, but the bragging rights are immediate.
You'll be awarded a redeemable ticket in Hudson if you plan to take on the half marathon. Anyone finishing any distance in Ashland will receive a ticket. (Both while supplies last!)
Explore turn-by-turn cue sheets, download GPX files for your GPS watch or phone, and review exact start and finish locations.
Everything you need to know about running an unsanctioned, self-navigated event.
• Half Marathon (13.1M): Starts at 3:30 PM in Hudson, MA (point-to-point to Ashland). • 10K (6.2M): Starts at 4:30 PM in Ashland, MA (loop). • 5K (3.1M): Flexible rolling start any time between 4:30 PM and 6:30 PM in Ashland, MA (loop).
No. This is a completely unofficial, unsanctioned, bootleg run. There are no street closures, no police details, and no official race permits. You are running on public roads and sidewalks at your own risk, though hopefully with friends.
No! All roads are open to normal traffic. You must follow all pedestrian laws: use sidewalks where available, run facing traffic on road shoulders when there is no sidewalk, and stop and look both ways before crossing any street.
The course is NOT marked with cones or arrows. You are responsible for your own navigation. Please download the GPX track to your watch or your smartphone, or print the turn-by-turn cue sheet provided.
Self-timed! Start your watch at the start line and stop it when you arrive at the finish line in Ashland. We will have a casual clipboard to record finish times for folks who want to join the leaderboard.
This inaugural race is self-supported. We recommend carrying a handheld water bottle or hydration vest for the half marathon. We will have some supplies at the start and finish, but on-course you're officially on your own.
The Half Marathon starts at 3:30 PM in Hudson and finishes in Ashland. We recommend coordinating with a friend for a ride, or carpooling beforehand.
This is a non-profit community run. You can join the run for free, or optionally chip in to help cover materials costs.
To help us plan post-run refreshments, medals, and other event logistics, please RSVP below. Participation is completely free.
Share the Bootleg Run
Invite your running crew or post about your Labor Day plans.