Winston Country Roads Sweepstakes May 1 - July 31
Your Sweepstakes Entries 24

Ready for an Adventure?

You could win the ultimate country road trip! Plus, amazing daily prizes. The more you play, the more chances you have to win.

Enter Now Official Sweepstakes Rules
Sweepstakes May 1 - July 31

Ready for an Adventure?

You could win the ultimate country road trip! The more you play, the more chances you have to win.

Play Now
Official Sweepstakes Rules
Your
Sweepstakes
Entries
24

Your dream road trip just came true

There's a whole lotta country out there. Pick the place you'd like to explore with three lucky friends and experience a new kind of country fun!

From dune buggying in Nevada to fishing in the Florida Keys, there's a once-in-a-lifetime road trip for everyone.

Want a chance to win?
Quit waiting and start playing!

Winners Choose
1 of 5
Grand Prize Road Trips

The
Bourbon & BBQ
Road Trip
Explore the Southeast.
  • Take a private limo tour of Louisville, KY’s best whiskey distilleries.
  • Eat at famous BBQ joints.
  • Plus, visit a thoroughbred horse farm and explore Louisville!
The
Go Wild
Road Trip
Explore the Pacific Northwest.
  • Tour Mt. Rainier National Park near Seattle, WA.
  • Go on a breathtaking tree canopy climb.
  • Plus, whitewater rafting and a tour of local breweries!
The
Music Lover's
Road Trip
Explore the South.
  • See a concert at a legendary venue in Nashville, TN.
  • Go on a VIP tour of a historic music site.
  • Plus, a dinner cruise and a Tennessee whiskey tour!
The
Reel 'em in
Road Trip
Explore the Florida Keys.
  • Take the ultimate fishing trip in Key West, FL.
  • Charter a private boat.
  • Plus, sailing, snorkeling, kayaking and more!
The
Daredevils Only
Road Trip
Explore the Desert.
  • Go dune buggying in the desert near Las Vegas, NV.
  • Take a Grand Canyon helicopter tour.
  • Plus, you can hit the Las Vegas strip!

Plus, you could win one of these daily prizes!

How to Play

Let's hit the road.

Play Now

Winston Country Roads Sweepstakes Game

Start your road trip!

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Past Winners

  • January 15 | Rebecca T. | Austin, TX
  • January 15 | Rebecca T. | Austin, TX
  • January 15 | Rebecca T. | Austin, TX
  • January 15 | Rebecca T. | Austin, TX
  • January 15 | Rebecca T. | Austin, TX
  • January 15 | Rebecca T. | Austin, TX