Rolling Milwaukee

14 May 2024 10:00am - 25 June 2024 12:00pm

As part of the 2024 Rolling USA series, here is your chance to win a 2024 Road Glide® and 1 of 10 trips to the H-D Homecoming® Festival*!

Plus enter to win other great prizes:

  • An Autographed Guitar by Jesse James Dupree
  • Pappy Hoel Campground Wristbands & access to all Full Throttle Saloon concerts during the Sturgis Motorcycle Rally 2024
  • Redemption Certificate for H-D® Museum passes
  • Swag bags containing merchandise from Jesse James Bourbon, Pappy Hoel Campground, the VFW, and more!

National prizes include:

  • A trip to the 2025 H-D® Homecoming Festival through a $1500 Visa or American Express Prepaid Card gift card and H-D® swag
  • 1 lucky winner will receive a 2024 Harley-Davidson® Road-Glide®, a 3-night stay in Milwaukee, AND 2 tickets to the H-d® Homecoming™ Festival

*Sweepstakes entry period from May 14, 2024 at 9 am EDT through June 25, 2024 at 11:59 pm EDT. No purchase is necessary. Purchase does not increase odds of winning. Open to legal residents of U.S. Must be 21 years or older to enter. Void where prohibited. See participating H-D® Dealerships for details or official rules at 

©2024 Mighty Loud Entertainment and affiliates. 

©2024 H-D or its affiliates. H-D, Harley, Harley-Davidson and the Bar & Shield logo are among the trademarks of Harley-Davidson Motor Company.

For more details, visit For sweepstakes rules click here.

Rolling Milwaukee