The Heart And Soul Of Oregon Is The Small Towns And These 7 Have The Best Downtown Areas
By Sarah McCosham|Updated on September 12, 2022(Originally published September 07, 2022)
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Sarah McCosham
Author
I write like it's my job - because it is! I have a Master's in English and love words: crossword puzzles, Scrabble games, Wordle, and, of course, good, old-fashioned books.
I'm a writer and editor at OnlyInYourState, and a contributing writer at Cincinnati Magazine. I love the Great Outdoors and am endlessly awestruck by this beautiful country of ours. Coffee keeps me going, yoga keeps me sane, my kids keep me grounded, and my writing keeps me inspired.
There are certain places that come to mind when it comes to Oregon towns: Portland, of course, along with Salem, Eugene, Bend, and Oregon City. And while each of these larger locales offers visitors the full PNW experience, Oregon has numerous smaller towns that deserve the spotlight, too. The following are seven of the best downtowns in Oregon. These are charming little locales that capture everything that’s wonderful about the Beaver State — its scenic beauty, amazing restaurants, and unique attractions — plus vibrant downtown districts that are about as charming as it gets.
Jacksonville is best known for its music scene; the town's Britt Music Festival is an incredible annual music festival that draws some of the biggest bands and artists in the industry. But this little locale is so much more than this star-studded event; it has a thriving downtown district that's peak small-town vibes. The Jacksonville Inn Restaurant is a hot spot in town, offering guests a fine-dining experience that's truly unrivaled. If you've never visited the coolest town in the PNW, plan a trip now!
Way over on the eastern edge of the state, Baker City is a total Oregon treasure. With a population of roughly 10,000, Baker City is a one-of-a-kind town that will blow you away. It's been named one of the "Coolest Towns in America," and once you visit, you'll immediately understand why. There's plenty to see and do here, from lounging at cafes and exploring the local shops to visiting historic landmarks and even golfing. The town is also home to the Geiser Grand Hotel, one of the most historic -- and notoriously haunted -- places in Oregon, making it a must-visit for all ghost hunters, historians,
and adventure seekers.
Oh, Florence, Oregon, how we adore you. It really doesn't get any more postcard-perfect than Florence. This sleepy little beach town has amazing waterfront restaurants, charming shops, and some of the best shorelines in all of the state! When you visit, be sure to stay at the Lighthouse Inn, a 75-year-old hotel located in the heart of the town's historic downtown district.
Located about 2.5 hours east of Portland, the tiny town of Condon has a rich history that spans more than 125 years! Its charming Main Street is full of historic buildings that have recently been restored, many of which are also listed on the National Register of Historic Places. If you're into history, a visit to Condon is a must; you can take the experience to the next level by booking a night at Hotel Condon, a landmark hotel that's over a century old!
Ashland is best known for its thriving arts scene and free-spirited community, and it's truly a delightful place to visit. The centerpiece of the town is the Oregon Shakespeare Festival. Founded in 1935, this live theatre venue is straight out of the 1600s, complete with the troupe's iconic outdoor Allen Elizabethan Theatre, which opens in early June and runs through mid-October. If the Bard isn't your thing, that's okay; Ashland's downtown district offers something for everyone, from amazing parks and historical sites to incredible restaurants and local businesses.
The lovely little town of Sisters, Oregon, doesn't often get the spotlight, and that's positively criminal because it really is one of the most delightful places in Oregon! Named for the Three Sisters, a trio of nearby mountains that tower in the west, Sisters is like the kind of place where everyone knows your name. The town of 2,000 residents is also accustomed to visitors, too, as it hosts exciting events and festivals throughout the year. Its downtown is postcard-perfect; full of Wild West nods and old-school restaurants and shops. Whether you come for the outdoor recreation, annual festivals, or downtown charms, you're sure to fall in love with Sisters, Oregon!
Another gem on the Oregon Coast, Yachats is a treasure of a place, offering Oregonians a perfect slice of small-town coastal living. No matter where you are in Yachats, you're sure to have spectacular shoreline views. Take a little coastal retreat in this charming little locale; while you're there, we highly recommend staying at the Drift Inn Hotel and Restaurant, a beloved Yachats establishment. And if you're into seafood (and you live in Oregon, so of course you are!), Luna Sea Fish House in Yachats is a must-visit!
Oregon really is the best place to live in the country. And if it’s small-town vibes you’re seeking, you’ll find it in these amazing little locales in Oregon!
What are your picks for the best Main Streets and downtowns in Oregon? Share them with us in the comments below!
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More to Explore
best downtowns in Oregon
Sarah M.|September 12, 2022
What are some more of the best downtowns in Oregon?
While the above list includes some of the state's smallest towns with the best downtowns in Oregon, Bend is a "little big city" that has one of the most amazing downtowns in the PNW. It’s no secret that we adore Bend and think it’s one of the best all-around towns in Oregon. Not only does this charming locale have a soft spot for the nostalgic (the world's last remaining Blockbuster is in Bend!), but it’s also the ultimate outdoor enthusiast’s playground. Snowshoeing, skiing, hiking, and kayaking … you can do it all in this Central Oregon town. The outdoor recreation here is spectacular any time of the year; the mighty Deschutes flows quite literally through the town itself, providing some of the best kayaking and river floating in Oregon! There are also ample opportunities for waterfront dining in Bend, as well as some top-tier eateries and breweries, some of which have been featured on the Food Network's "Diners, Drive-Ins and Dives" show!
