Oregon Wine Country Adventure Sweepstakes

Enter for your chance to win.

Oregon Wine Country Adventure Sweepstakes

No matter which region you are visiting, we can tell you Oregon wine country will exceed your expectations – and we will – but you’ve got to be here to truly get it. As part of our Oregon Wine Month statewide celebration, enter for a chance to win the ultimate wine lover’s dream adventure – a Choose-Your-Own-Adventure getaway to the picturesque Oregon wine country! Embark on a journey through some of Oregon’s most renowned wine regions, each offering its own unique charm and exceptional wines.

Each Grand Prize for winner and guest includes:

  • Lodging
  • Curated wine and culinary experiences
  • Round trip tickets on Alaska Airlines to a destination of your choosing: Portland, Willamette Valley, Umpqua Valley, or Rogue Valley

Enter for your chance to win. Sweepstakes runs April 1 – May 31, 2024.

GRAND PRIZE: One (1) trip for two to one of the following regions: Portland, Willamette Valley, Umpqua Valley, Rogue Valley. The Grand Prize package includes: two (2) nonrefundable, nontransferable roundtrip tickets on Alaska Airlines from the nearest airport to you that is served by Alaska Airlines to any airport in Oregon served by Alaska Airlines*; one (1) gift certificate for three night’s lodging; two (2) days of wine tasting and culinary experiences for two, ground transportation for two from your accommodation to/from wine tasting destinations within the chosen region. Travel arrangements and winery visits to be arranged directly by the winner. Any expenses not explicitly mentioned above are not included and are the sole responsibility of winner. Estimated prize value is $2,200. Any applicable taxes are the sole responsibility of the winner. Prize is non-transferable. No substitution of prizes or cash will be awarded in lieu of the specified prize.

*One (1) winner of two (2) Alaska Airlines (“Prize Provider”) roundtrip airline vouchers to any Alaska Oregon serviced airport (PDX, EUG, RDM, MFR) from any Alaska serviced airport. Flight must be booked by 09/15/2024 for travel between 6/1/2024 -12/31/2024. Travel times are at the discretion of Prize Provider. Any winner unable to travel between the specific dates may be ruled ineligible to win. Prize Provider will not replace any lost, mutilated, or stolen airline voucher/tickets.

Note: Sweepstakes details are subject to change

Choose Your Own Adventure: Select your preferred destination from the following options:


Delight in the vibrant culinary and wine scene of Portland, where urban sophistication meets Oregon’s renowned wine culture.

Willamette Valley

Experience the heart of Oregon wine country in the Willamette Valley, renowned for its world-class Pinot Noir and scenic vistas.

Umpqua Valley

Immerse yourself in the tranquil landscapes of the Umpqua Valley, where rolling hills and fertile vineyards produce elegant, artisanal wines.

Rogue Valley

Discover the rugged beauty of Southern Oregon’s Rogue Valley, known for its diverse terroir and bold, full-bodied wines.

Your trip will also include the following:

Comfortable Accommodations: Enjoy a luxurious stay at a charming inn, boutique hotel, or vineyard estate, selected to enhance your Oregon wine country experience.

Exclusive Wine Tastings: Savor the flavors of Oregon’s finest wines with exclusive tastings at renowned wineries and hidden gems across your chosen destination.

Culinary Experiences: Indulge in delectable farm-to-table dining experiences, paired with the perfect wines to complement each dish.

Guided Tours: Enhance your wine adventure with guided tours of vineyards, wine cellars, and scenic landmarks, led by knowledgeable local experts.

Cheers to unforgettable adventures in Oregon wine country!

Alaska Airlines logo

Alaska Airlines Mileage Plan™ members may check up to one case of wine for free on any domestic flight from Oregon or Walla Walla, WA. While visiting Oregon’s wine regions, we invite you to enjoy a complimentary tasting when you show your in-bound boarding pass (paper or digital) and proof of your Alaska Airlines Mileage Plan™ membership at any of our more than 300 participating wineries.

How Does it Work?

We know travel remains uncertain for some at this time and our first priority is the safety of all involved. The winner will be provided all the material needed to schedule their trip and will work with a regional concierge to do so. All prize materials are valid until May 31, 2025, some restrictions apply.