The Bootlegger 5K returns to Montgomery, Indiana on September 5th, bringing runners through the rolling countryside of Daviess County for a spirited morning outing along historic rural roads. Participants will gather at McCracken Curve Distillery early in the day as they prepare for an out-and-back course that winds its way through quaint landscapes and past picturesque cornfields. This event is more than just a race; it’s a celebration of community spirit, local heritage, and casual fitness.
The morning light on September 5th will cast a warm glow over the streets around McCracken Curve Distillery as runners set off for their five-kilometer journey through the heart of Daviess County. The air carries hints of autumn, crisp but not yet chilly, with winds gently guiding leaves across quiet lanes and dirt paths that stretch out before the enthusiastic crowd. As participants meander along these scenic routes, they’ll encounter familiar faces from the community who have come to cheer them on in this annual tradition.
Since its inception several years ago, the Bootlegger 5K has become a beloved fixture of Montgomery’s autumn calendar, drawing runners and walkers alike for an enjoyable day out. Top male and female finishers will receive special prizes to commemorate their achievement, though the event is decidedly low-key with no formal timing or pressure. The race supports local charities through its modest fees, fostering goodwill among participants while encouraging a spirit of fun and camaraderie.
The Bootlegger 5K takes runners on an out-and-back course that utilizes existing rural roads managed by Daviess County’s public works department. Runners will encounter no closed-off streets but must adhere to standard traffic rules throughout their route, which includes distance markers at one-mile intervals along the way. The start and finish lines are both located at McCracken Curve Distillery with bib pickup available from 8:00-8:45 AM Eastern Time (7:00-7:45 AM Central).
On race day in September, runners should expect a mix of clear skies and mild temperatures typical for this time of year. With average high temperatures around 26°C and humidity at 65%, participants will likely experience comfortable conditions throughout their run. The trail surface is expected to be hard and dry underfoot, allowing for smooth passage despite the slight chance of scattered showers during early morning hours.
5K Fun Run/Walk
5K • Start: 09:00:00 • Fee: $35.00
To register for the Bootlegger 5K, visit [https://runsignup.com/Race/IN/Montgomery/McCrackenBootlegger5K](https://runsignup.com/Race/IN/Montgomery/McCrackenBootlegger5K) where you can secure your spot and select between the standard $35 entry (including a t-shirt and finisher medal) or opt for the $30 medal-only option. Race day check-in will take place from 8:00-8:45 AM Eastern Time at McCracken Curve Distillery, where runners must present their confirmation email to collect race packets.
Participants should plan to arrive early on September 5th with plenty of time for bib pickup and pre-race preparations. All registrants are advised that no refunds will be issued once payment is processed unless prior arrangements have been made in advance of the event start date. The Bootlegger 5K welcomes runners from all age groups but requires participants to respect the rules of the road while enjoying their run or walk through Montgomery, Indiana.
The Bootlegger 5K on September 5th offers a unique blend of community engagement and casual competition set against the backdrop of Daviess County’s scenic landscapes. Whether you’re looking for an invigorating morning outing or simply want to join in local festivities, this event promises to be both memorable and meaningful.
