Oregon's 'Friendliest Small Town' Is A Quirky Historic Charmer In The Heart Of Serene Wine Country

Oregon is full of small-town charmers. From comfy, family-friendly cities with scenic nature parks like Wilsonville to underrated coastal towns that offer the best of the Pacific Northwest like Florence, the breathtaking Beaver State's hidden gems sparkle with historic and scenic beauty, welcoming atmospheres, and quirky charm.

Nestled in the heart of the Willamette Valley –– Oregon's premier wine region that is just as scenic as Napa Valley without the crowds –– McMinnville is one such gem. Deemed 'the friendliest small town in Oregon,' the town embraces travelers with its historic downtown district, public art displays, award-winning wineries, and otherworldly events like the annual UFO Festival. Perfect for a weekend retreat from bustling Portland, McMinnville boasts charming lodgings for overnight stays. Nestle into a historic hotel or glamp it up at a retro trailer resort on the outskirts of town, surrounded by idyllic landscapes. An underrated destination in Oregon, McMinnville is a small town with big charms.

Situated about 60 miles south of the Portland International Airport (PDX), whose photo-worthy carpet is so famous it has its own Wikipedia page, McMinnville is a comfortable driving distance from Oregon's largest city. With a population of about 35,000, it's a fraction of its big city neighbor's size, offering a cozier, small-town feel.

The heart of McMinnville is its historic downtown district, which is traversed by Third Street, voted one of "America's Best Main Streets" by Parade for its laid-back atmosphere and picturesque, tree-lined charm. Stroll down the idyllic six-block stretch, where you'll encounter gorgeous buildings dating back to the 1800s, specialty shops, and local eateries. Browse for literary treasures at Third Street Books, and mine for vintage treasures at McMinnville Antiques Mall. When you've worked up an appetite, pop into the Crescent Cafe for a delicious sandwich prepared with locally sourced ingredients, or munch on pub-style bites at the town's beloved watering hole, Blue Moon Lounge.

If you're planning a visit in May, don't miss downtown McMinnville's quirkiest event, the UFO Festival. Inspired by a famous unidentified flying disc sighting on a McMinnville farm in 1950 (with the photographic evidence making the cover of Time), the yearly festival is an extraterrestrial celebration filled with parades, alien costume contests, live music, street vendors, and speaker presentations for a weekend of out-of-this-world fun. All-access passes to the events and speaker presentations can be purchased on their website in advance.

It's impossible to speak of McMinnville without highlighting the beautiful Willamette Valley wine country. Nestled in the McMinnville Foothills, just 10 minutes west of downtown, you'll find a collection of sip-worthy wineries like Youngberg Hill. Situated on a stunning 50-acre estate, the family-owned winery and inn pours award-winning wines alongside picturesque views of rolling hills intertwined with verdant grapevines. To visit the oldest vineyard in the area, head to Yamhill Valley Vineyards, a lush 150-acre estate offering year-round wine tastings with indoor and outdoor seating areas.

After sipping in the flavors of the Willamette Valley, settle in for the night at the historic McMenamins Hotel Oregon in downtown McMinnville. Dating back to 1905, the building once housed an old-fashioned soda fountain, a beauty parlor, and a bus depot. Nowadays, the beautifully restored property holds 38 charmingly appointed guest rooms named after historical figures, an onsite brewpub, and a speakeasy-themed bar adorned with whimsical artwork. For a unique stay with a countryside backdrop, drive 10 minutes east to The Vintages Trailer Resort. A retro paradise complete with pink flamingos and a sparkling pool, the glamping resort features over 30 lovingly-restored vintage trailers, including 1940s Shasta charmers and gleaming 1970s Airstreams.