ONE DAY ONLY Rolling Sturgis To Milwaukee Special Event

One Day. 

One Keyword. 

One Shot at Sturgis.

Saturday, June 27th, Illinois Harley-Davidson^® is your stop for a chance to win the ultimate motorcycle getaway.

For ONE DAY ONLY, we’re giving out an exclusive in-store keyword that enters you for a shot at an unforgettable trip to the legendary Sturgis Motorcycle Rally. Once the day is over, the keyword is gone.

One lucky winner will receive:

• A 3-night trip to Sturgis
• An EagleRider motorcycle rental
• A Meet & Greet with Jesse James Dupree
• A $1,000 shopping spree

No keyword. No entry. No second chance.

Make plans to be here, grab the keyword, and get yourself entered before this one-day event rides off into the sunset.

*NO PURCH/PAYMENT NECESSARY. Enter on 6/27/26 at 9 AM ET until 11:59 PM ET at a local participating dealer. You must be legal US (excl HI) res, 21+. Purchase does not increase odds of winning. One entry per person. Winner selected 6/29/26. Trip Giveaway prize includes three (3)-night stay at the Pappy Hoel Campground’s Full Throttle Saloon during the 2026 Sturgis Motorcycle Rally on August 13, 14, and 15, 2026 (ARV: $1,200); one (1) $1,500 Visa® or American Express® Prepaid Card gift card (ARV: $1,500); one (1) $1,000 USD H-D® Dealership shopping spree (ARV: $1,000) and one (1) branded Jesse James Dupree chainsaw (ARV: $300); one (1) three-day EagleRider motorcycle rental during Sturgis Motorcycle Rally for August 13, 14, and 15, 2026 (ARV $1,584) total ARV: $5,584. Other restrictions & eligibility limitations apply. See full rules (avail at particip H-D® dealers or rollingusa.com) for entry details, odds, alt entry method & other info. Sponsor/Operator: Mighty Loud Enterprises, Inc. Void where prohibited.

©2026 Mighty Loud Enterprises, Inc. and affiliates. ©2026 H-D or its affiliates. H-D, Harley, Harley-Davidson and the Bar & Shield Logo are among the trademarks of Harley-Davidson Motor Company.