With Valentine’s Day just around the corner, it’s the perfect time to embrace the cozy side of wine country. Oregon’s Willamette Valley, with its intimate tasting rooms, indulgent wine-paired dinners, and truffle-filled adventures, offers plenty of ways to celebrate love during the quieter cellar season. Whether you’re planning a weekend getaway or looking for a special experience closer to home, here are some memorable ways to sip, savor, and celebrate.
Amaterra Wine Paired Dinners during Valentine’s Day
Feb. 13–16: Enjoy a decadent $89 prix fixe Valentine’s Day menu featuring multi-course delights, with optional wine pairings to complement each dish.
Feb. 16: Celebrate big, cozy reds at the 51Weeks Wine Dinner, a luxurious culinary experience where innovative wines are paired with a chef-curated menu at Amaterra’s intimate restaurant perched in Portland’s West Hills.
Tualatin Valley Valentine’s Day Wine Loop & Events
Tualatin Valley’s wineries are joining forces for a weekend of special events, wine tastings, food pairings, and more as part of the Valentine’s Day Wine Loop. From February 14-16, couples can explore the region’s charming vineyards and enjoy exclusive Valentine’s Day themed experiences. Pair your adventure with one of the area’s cozy lodging packages or curated Airbnb stays for a romantic getaway to remember.
Willamette Valley Truffle Tours
Book an exciting day of foraging with First Nature’s “Winter Truffle Forage & Feast.” The day-long experience includes hunting for the culinary delights with a seasoned forager and award-winning Labrador before indulging in a truffle-themed meal and wine pairing.
Inn the Ground Truffle Celebration Dinner
Book a stay at this cozy B&B — situated on a regenerative farm in the heart of wine country — to be your home base for a romantic wine country weekend, or keep the celebration of love going and enjoy an unforgettable evening of culinary artistry at Beaux Frères Winery during their exclusive Truffle Celebration Dinner on March 8. Curated by Humble Spirit and 2025 James Beard Award semi-finalist Sarah Schafer, this decadent multi-course experience showcases truffle-inspired dishes paired with Beaux Frères’ elegant wines.
Cozy Getaways & Wine Tasting in Eugene
Cozy up with your sweetheart at the enchanting Sweet Cheeks Winery in Eugene, where award-winning wines and romantic vineyard views set the perfect mood. Pair this with an elegant stay at the luxurious Inn at the 5th, and elevate your experience with their Celebration Package, complete with thoughtful extras to make your getaway unforgettable.
For a list of other Valentine’s happenings in the Valley:
Valentine’s Day Bistro Dinner at West Hills Vineyards
Valentine’s Bubbles & Truffles Flight at Durant Vineyards
Valentine’s Day Tasting Menu at St. Innocent Winery
Sweetheart’s Dinner at Coria Estate
Saffron Fields Valentine Dinner
Tumwater Valentine’s Day Dinner
Jachter Winery Bespoke Chocolate Pairing
Balsall Creek Valentine’s Wine and Chocolate Pairing
Yamhill Valley Vineyards Wine + Chocolate Flight
