Win a 2026 Harley-Davidson Street Glide from O’Toole’s Harley-Davidson with WPDH!

To celebrate our 50th anniversary, WPDH is giving one lucky listener the ride of a lifetime—a 2026 Harley-Davidson Street Glide! If you've been dreaming of hitting the open road on one of Harley-Davidson's most iconic motorcycles, now's your chance. Enter WPDH's Motorcycle Giveaway for multiple opportunities to win this incredible grand prize, courtesy of our friends at O'Toole's Harley-Davidson.

There are plenty of ways to increase your chances of winning throughout the contest. Enter through our sweepstakes below, and don't miss your chance to earn a Golden Key by listening to WPDH each week. We'll announce an Artist of the Day—when you hear a song by that artist, call the studio and you can score a Golden Key, giving you another shot at taking home the brand-new Street Glide. Keep listening and following WPDH so you don't miss a chance to enter.

This incredible giveaway is made possible by two outstanding Hudson Valley businesses. O'Toole's Harley-Davidson in Wurtsboro is your destination for new and pre-owned Harley-Davidson motorcycles, expert service, genuine parts, riding gear, and official Harley-Davidson apparel—all backed by a knowledgeable team committed to keeping you on the road. Whether you're buying your first bike or maintaining your current ride, O'Toole's delivers the service and experience every rider deserves. We're also proud to partner with O'Connor & Partners, a firm dedicated to helping personal injury victims throughout the Hudson Valley get their lives back on track. With experienced trial attorneys and offices in Kingston, Poughkeepsie, and Newburgh, they provide trusted legal representation when it matters most.

Think you've got what it takes to ride away on a brand-new 2026 Harley-Davidson Street Glide? Enter below, and listen every week for your chance to earn a Golden Key. Your next ride could be just one entry away!