There was a time in the not-so-distant past when you could hit the road for a last-minute joyride through Oregon’s wine country, popping in for impromptu wine tastings at your leisure. Then came the pandemic.  

To keep crowds at bay and manage with reduced staffing during the height of Covid, wineries embraced a reservations system, and that has stuck.  For many, mandatory reservations are now the norm.  

But what about those spontaneous trips, where half the fun is just arriving on a whim? For all you non-planners daydreaming about your next trip through wine country, these wineries in the Willamette Valley are welcoming winos who show up unannounced — and that includes Memorial Day weekend festivities galore, from live music, food, and of course, sampling the magic juice. 

Youngberg Hill  

A quick ten-minute drive from downtown McMinnville, Youngberg Hill recently opened a new tasting room deck, just in time for summer sipping. The family-owned winery was established in 1989 ; founder Wayne Bailey has said he is guided by a “holistic, natural approach,” to wine-making. The tasting room is open daily from 10 a.m. to 4 p.m. and welcomes walk-ins to enjoy the views and toss back the good stuff. It’s a smart stop on Memorial Day, when there will be  vertical tastings of the Bailey Family Wine brand, where you can sniff and sip the 2017, 2018 and 2019 pinot noirs, and the 2019 chardonnay.  The goal is to, “offer everyone multiple options to enjoy wine country when and how they want, in a relaxed no reservations way,” says Bailey.  

Cubanisimo Vineyards  

Open daily, you can stroll into Cubanisimo Vineyards any time from 11 a.m. to 5 p.m. to sample some pinot noir and bask in panoramic vistas of the Willamette Valley and the Cascades. Cubanisimo, which means “very Cuban,” takes inspiration from neurosurgeon-turned winery owner Mauricio Collada’s heritage, with Cuban art hanging up in the tasting room, salsa dancing, and even some palm trees planted in the garden for good measure. On weekends there is always some form of entertainment promised, whether it’s a comedy show or live music, which you can book tickets for ahead of time or just buy at the door. And if you happen to stumble there on Memorial Day weekend, you’ll arrive just in time for live Latin music and barbecue bites from El Vaquero.  

Stangeland Vineyards  

Perched in the Eola-Amity Hills, Stangeland Vineyards was founded back in 1978. Owner Larry Miller found potential for grape growing on the vineyard’s south facing slope and has been at it ever since. The winery is named after his grandparents who emigrated from Norway in 1905: Stangeland means strong land. Elegant pinots crafted old-world style though sustainable farming methods are the brief here. You can show up for tastings anytime from 11:30 a.m. to 5:00 p.m. Friday through Saturday with no reservation, otherwise by appointment or “happenstance” on Mondary through Thursday. You might even be greeted on arrival by Bobi, the vineyard’s resident dog, aka Groundskeeper. And if you roll in on Memorial Day weekend, you’ll be treated to food, barrel tastings, and music. 

Day Wines  

Day drinking puns aside, this modern winery in downtown Dundee is as cozy as ever, with a wine tasting courtyard, a warming cedar wall, and a fire pit for those chilly nights. Headed by winemaker Brianne Day, the winery is known for her creative blends, like a pairing of  tannat, malbec, and cabernet franc, for instance. All fruit is sourced from a select group of Oregon growers who practice biodynamic, organic, and sustainable farming. Open daily from 11 a.m. to 5 p.m., walk-ins are welcome — however, groups of six or more are required to make a reservation. Small bites from Olympia Provisions are available for purchase, making this a go-to for a mid-afternoon tasting and snack, (though your best chance of getting seated fast during your last-minute wine country odyssey is if you come during the week.) Check the calendar for weekend events, which just so happens to include a whole slew of Memorial Day weekend festivities, like a woodfired pizza truck, a special wine tasting flight, and live bluegrass music.