If you think wine tasting is a luxury you can’t afford, think again. Although most Willamette Valley wineries charge $10–15 for tastings, the Eola-Amity Hills AVA, just northwest of Salem, offers an even better value. These verdant hills are home to many of Oregon’s most acclaimed wineries, and though you might have to crack the piggy bank to take the best vintages home, their $5 tastings are a steal.
Although the Hotel Oregon could use some sprucing up, its creaky charm is fine for a couple of nights. Themed for infamous local characters, rooms start at $60 with bathrooms down the hall. Be sure to get a drink at the rooftop bar, which has 360-degree views of Yamhill County. 310 NE Evans St, McMinnville; 503-472-8427; mcmenamins.com
Craving more luxury—or a private bathroom? Opt for the new Inn at Red Hills in Dundee. Conveniently located above the Farm to Fork restaurant, all 20 rooms come with flat-screen TVs and high-thread-count sheets. 1410 N Hwy 99, Dundee; 503-538-7666; farmtoforkdundee.com; queens from $99
If you’re staying at Hotel Oregon, stop off at R. Stuart & Co Wine Bar, a chic boîte where locals linger over wine flights while listening to Django Reinhardt. Rob Stuart, formerly the winemaker at Erath, is known for his pinot noir, pinot gris, and an unusual bubbly made from pinot and chardonnay. 528 NE Third St, McMinnville; 503-472-4477; rstuartandco.com
Nick Peirano opened Nick’s Italian Café in 1977, and 30 years later his daughter Carmen and her husband, Eric Ferguson, took over the kitchen of what had become a Willamette Valley institution. They kept the menu’s old standbys (Dungeness crab lasagna and spinach-and-pork ravioli) while adding inexpensive new items like pizza ($12) and a daily antipasti and pasta menu. The wine list includes more than 100 Oregon labels, plus numerous Italian vintages, too. 521 NE Third St, McMinnville; 503-434-4471; nicksitaliancafe.com