Bootlegger's Blitz - road cycling event - in Woolwine, VA - presented by Racing The Woods

Bootlegger's Blitz

Saturday, March 28, 2026I.C. Dehart Park: 2631 Charity Hwy, Woolwine, VA
Event Details

Event Type

Road Race

Location

I.C. Dehart Park: 2631 Charity HwyWoolwine, VirginiaOpen in Maps

Links

Upcoming Dates

Saturday, March 28, 2026Register

Event Location

About This Event
Welcome to the Bootlegger's Blitz, where the racing season kicks off with a dynamic blend of rolling terrain and technical trail sections. Set in the scenic landscape of Woolwine, Virginia, this road race combines fast, open courses ideal for aggressive racing with challenging climbs that separate the field. Whether you're chasing a cash prize or competing for podium positioning, this event delivers the competitive edge you're looking for to start the season strong.
Additional Information

Bootlegger's Blitz - Season Opener Road Race

What to Expect

  • Rolling Hills & Singletrack - A challenging mix of terrain that tests climbing power and technical bike handling
  • Open Course Layout - Plenty of room to execute race strategy and make your move
  • Multiple Race Categories - Competition across Cat 1, Cat 2, Cat 1/2/3, Cat 3, and Junior divisions
  • Cash Prizes Available - Cat 1 racers compete for cash payouts
  • Law Enforcement & Military Discount - Special pricing available for qualifying racers
  • Podium Recognition - Medals and swag for top finishers across most categories

Race Categories & Entry Fees

  • Cat 1 - $50 entry - Cash payout to top finishers
  • Cat 2, Cat 1/2/3, Cat 3 - $40 entry - Medals and race swag
  • Juniors - $25 entry - Medals

Note: Law enforcement and military racers receive a discount. You must select your racing category during registration.

Event Highlights

  • Competitive season opener with aggressive field racing
  • Technical course rewarding both climbing strength and bike handling skills
  • Cash prizes and podium ceremonies for top racers
  • Special pricing for law enforcement and military participants

Bootlegger's Blitz Highlights

 


Frequently Asked Questions

What race categories are available at the Bootlegger's Blitz?

The event features multiple competitive divisions including Cat 1, Cat 2, Cat 1/2/3, Cat 3, and Junior categories. This structure ensures riders compete against equally skilled racers while maintaining the competitive intensity throughout the field.

What kind of terrain will I encounter on the course?

The Bootlegger's Blitz combines rolling hills with technical singletrack sections set in the scenic Woolwine landscape. You'll face challenging climbs that test your power and technical sections that demand sharp bike handling skills - expect a course that truly separates the field.

Are there cash prizes available?

Yes - Cat 1 racers compete for cash payouts at the Bootlegger's Blitz. All top finishers across most categories also earn medals and event swag for their podium positioning.

Is there a discount for law enforcement or military?

Special pricing is available for law enforcement and military racers. Check the event website or contact the organizers for details on how to claim your discount when registering.

What makes the Bootlegger's Blitz a good season opener?

The event combines fast, open course sections perfect for aggressive racing tactics with challenging climbs that test your fitness. The mix of terrain and competitive field sizes make it an ideal way to kick off your racing season with podium positioning and cash prize opportunities on the line.

Will there be spectator areas where fans can watch the race?

The open course layout in Woolwine offers multiple vantage points for spectators to follow the action. Check the event website for specific details on recommended spectating locations and parking options.

Reviews

Reviews

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The first 5 cyclists to review within 72 hours after this event receive a free Starbucks or Dunkin gift card ($10 value).

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