When you tell an Oregon resident you’re staying at the Allison Inn, the response will always include a deep sigh and a “that place is amazing.” Because it is. About an hour from Portland, the resort sits among picturesque mountains, rolling hillsides and working vineyards. Stay in a grand deluxe king room, with a soaking tub, charming balcony and cozy gas fireplace.
If you’re more of a glamper than a camper, you’re going to want to stay at the Vintages Trailer Resort—a park filled with retro trailers you can rent by the night. Each trailer offers a unique lodging experience with amenities like soaking tubs, luxe terrycloth robes, hotel-quality linens and Caravan Coffee. Grab a cruiser bike and pedal to the nearby town of Dayton for breakfast or dinner.
There is wine tasting, and then there is wine tasting by horseback. Join an Equestrian Wine Tour, where you will hop on a trained Tennessee Walking Horse and trot from winery to winery with striking countryside views.
The Stoller Family Estate boasts a spacious 4,000-square-foot tasting room with floor-to-ceiling glass doors that make you feel like you’re sitting among the vines as you sip. The scenic knoll isn’t just for show; the slope is needed for “gravity flow” wine production. Gravity flow is a gentler style of winemaking, which reduces the need for pumping and conserves energy.
Vista Hills’ tasting room feels like a sophisticated version of your childhood tree house. If you seek unique wines, taste the pinot gris rose “orange wine” while sitting in the light and bright space.
The Willamette Valley is known for its excellent (and endless) pinot noir bottles, and Willamette Valley Vineyards is one of the best places to sip on the varietal. Visit for a tasting with sweeping vineyard views or join the winery chef and winery ambassador for a four-course wine pairing dinner.
In the tiny town of Dayton, there’s a historical white house with a wrap-around porch and tall columns. Inside is the buzzing Joel Palmer House, a sophisticated restaurant featuring Oregon’s seasonal produce and local wines. Headed up by Chef Christopher Czarnecki, the restaurant’s cuisine revolves around wild mushrooms and truffles, paying homage to his father’s original Pennsylvania Restaurant, Joe’s Tavern. Don’t miss the mushroom tart.
Just 30 miles from Portland, the Kitchen at Middleground Farms is a recreational cooking school in a barn space made for a Food Network show. The spacious gourmet kitchen space is decked out with walnut wood farm tables and rustic décor. Chef Jessica Hansen will guide you through a hands-on class providing you with helpful tips along the way to improve your future recipes. After cooking (and eating), tour the farm and meet Jessica’s goats, chickens, and llamas.