A Rare Bottle. A Richer Story.

The Pair & Pour Sweepstakes has come to a close. Thank you to everyone who entered

for a chance to win a bottle of 20-Year Pappy Van Winkle.

Our sweepstakes administrator will complete the winner selection process.

  • A Rare Bottle. A Richer Story.

    Get a chance to win a 20-year Pappy Van Winkle with every purchase of our Pappy & Co. Special edition.

    SOLD OUT

  • Every Purchased Counted

    Earn 1 entry for every $40 spent

    Entries were capped at 25 per eligible customer.

  • Entries Are Closed

    The free-entry period has ended. Thank you to everyone who participated in the Pair & Pour Sweepstakes.

Questions

  • Who is eligible to enter the Pair & Pour Sweepstakes?

    United States residents aged 21 or older.

  • Do I need to purchase the Collector’s Edition to enter?

    Purchasing the Collector’s Edition will earn 25 entries in the sweepstakes, but it is not the only way to enter. Additional purchases from Shady Rays and Pappy & Company can earn up to 25 entries, or you can fill out this free form. No purchase is necessary.

  • What can I win?

    The grand prize is one bottle of 20-Year Pappy Van Winkle, signed by Julian Van Winkle III.

  • How many entries can I earn through purchases?

    Every $40 spent at Shady Rays and Pappy & Company earns 1 entry. Earn a maximum of 25 entries through additional purchases during the sweepstakes period.

  • When does the sweepstakes start and end?

    The sweepstakes is live from September 29, 2026 through October 20, 2026.

  • How can I earn entries?

    You can earn entries by purchasing the Pappy & Co. Special Reserve sunglasses, redeeming other purchases from Shady Rays and Pappy & Company for entries, or by filling out the free form.

  • How and when will the winner be selected?

    The grand prize winner will be selected by a third party administrator after the sweepstakes ends on October 20th. The winner will be contacted via email and asked to verify their age and address.

  • Where can I find the official rules for the sweepstakes?

    You can find them here: Pair & Pour Sweepstakes Official Rules