Wine & Food Getaway

Enter for your chance to win.

Explore Oregon Wine Country Sweepstakes

Oregon Wine Month Getaway 2024

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.

Note: Sweepstakes details are subject to change

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

Portland: 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.

Luxury 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.

Transportation: Relax and unwind as you travel in style with transportation provided throughout your adventure, ensuring a seamless and stress-free experience.

Don’t miss your chance to embark on a once-in-a-lifetime wine adventure in Oregon’s breathtaking wine country! Enter now for your chance to win and create unforgettable memories in one of the world’s most renowned wine destinations.

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.