Bootlegger 5K 2026 — Montgomery, IN

Date
September 5, 2026
Location
Montgomery, IN
Venue
5757 E. Old US Hwy 50
Start Time
9:00 AM
Entry Fee
$35.00
Events
5K Fun Run/Walk
Includes
T-Shirt
Register NowRegistration OpenOfficial Race Website

The Bootlegger 5K is a running race held in Montgomery, Indiana on September 5, 2026. The event takes place at 5757 E. Old US Highway 50 and features a single 5K distance. The race typically starts at 9:00 AM, giving runners a morning competition time. Entry costs $35.00 per participant. Whether you're targeting a specific time or running for enjoyment, this local race offers a straightforward 5K option. If you're traveling to the Montgomery area for this event, you'll want accommodation within reasonable driving distance of the venue on Highway 50.

From the Race Organizer
Start Time : 9:00AM Eastern Time (8:00AM Central) Location : McCracken Curve Distillery (5757 E. Old US Hwy 50 Montgomery, IN) The Race : The course will be an out and back 5K through the countryside of Daviess County. **Rules of the road will be used! No roads will be closed to traffic so please be careful and adhere to the road rules when running/walking. Cost : $35 includes short sleeve soft cotton t and finisher medal. (deduct $5 for medal only option) **All sales are final, no refunds. Unless prior arrangements are made, no medals/shirts will be saved for after the event. Race Day Check-In : There will be no early pack pick up for this event. Check in & late registration will be from 8:00-8:45AM Eastern (7-7:45AM Central) Awards : Top 3 males and top 3 females will receive a special "prize." Timing : This is a "Fun Run" with no official timing. Weather : The race will go on rain or shine! In the event of severe weather, race will be delayed until severe weather is out of the vicinity.

Hotels Near This Race

Find accommodation close to the start line in Montgomery, IN. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.

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Bootlegger 5K 2026 — Montgomery, IN

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Race Travel Insurance

Don't forget travel insurance for September 5.

You've trained for months and booked a trip to Montgomery, IN. A pre-race injury, a delayed flight, or a family emergency can derail the whole thing. Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it, and may cover medical costs if something goes wrong on the course. Plans typically only run 5-7% of your total trip cost — and running events are covered under standard plans with no additional coverage needed.

  • Trip cancellation up to 100% of prepaid costs
  • Running events covered under standard plans — no add-ons needed
  • Trip interruption up to 150% of non-refundable costs
  • Emergency medical up to $250,000
  • Cancel For Any Reason add-on available
  • 24/7 real-time support
Get a Quote — Faye Travel Insurance

Affiliate links — we may earn a commission at no cost to you. Coverage terms vary by state and plan. Review policy details before purchase.

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Frequently Asked Questions

When is Bootlegger 5K 2026 — Montgomery, IN?

Bootlegger 5K 2026 — Montgomery, IN takes place on September 5, 2026. The race is held in Montgomery, Indiana.

Where is Bootlegger 5K 2026 — Montgomery, IN held?

Bootlegger 5K 2026 — Montgomery, IN is held at 5757 E. Old US Hwy 50 in Montgomery, Indiana.

Where can I find hotels near Bootlegger 5K 2026 — Montgomery, IN?

RaceHotelFinder shows hotels sorted by distance from the race venue in Montgomery. Use the map or list view on this page to compare options and book race weekend accommodation.