Post Overview: Best Small Towns in Oregon
You know those cheesy Hallmark movies where the career-obsessed city gal returns home for the holidays (inevitably to a charming small town) and runs into a high school sweetheart who shows her the true meaning of Christmas?
Now, I’m not saying Hallmark ruined small towns for me, but I do think some folks have an odd idea of small town living, based on which Reese Witherspoon movie they prefer.
Make no mistake, there’s an undeniable charm to living in a small town. As this list of small towns in Oregon will prove, but I’m just trying to point out the realty seems to surprise some folks and I don’t want that to happen to you.
Some people love city-living because of the access to restaurants, entertainment and seamlessly endless lists of reasons to never be bored. On the other hand, others search for the best small towns in Oregon because they want a slower pace of life.
Different horses for different courses, you know?
You know the drill: there’s pros and cons to everything. Thankfully, you know yourself best. So if you’re searching for the best small towns in Oregon, the list below may be a good starting point. Let’s get to it!
What’s the official definition of a small town?
Before we dive in, let’s cover the official definition of a small town. The US Census Bureau defines a small town as having a population between 25K – 50K residents. As such, this list of the best small Oregon towns will only mention places with a population of less than 50,000 residents.
10 Best Small Towns in Oregon
- Population: 21,600
- Median home price: $600K
- Average age: 45.2 years
Located a mere 15 miles from the California border, Ashland is one of the most famous small towns in Oregon. This is largely thanks to the much beloved Oregon Shakespeare Festival which attracts 400,000 visitors annually to this little town.
Surrounded by mountains and forests, expect access to epic outdoor recreation, kind locals and an overall easy-going vibe. There’s a reason many Oregonians consider this one of the best small towns in Oregon.
But I don’t want to paint a false picture here. Ashland is hot, with average summer temperatures in the high 80 to mid 90s, July through September can be a bear. And that’s not to mention the wildfire smoke that inundates this charming Oregon small town (almost like clockwork) year after year.
Likewise, as with all of the best small towns in Oregon, Ashland’s home prices are on the obnoxious side. Expensive housing is par for the course because the intention is to keep the town small, so new homes aren’t being built. Couple that with the town’s recent spike in popularity and you have yourself one of the most expensive small towns in Oregon.
- Population: 8,350
- Median home price: $820K (ouch!)
- Average age: 36.6 years
Personally speaking, if I were rich (married for love, learn from my mistake), I’d buy a home in Hood River. This is easily one of the best places to live in Oregon and locals know it (especially if home prices are any indication).
The reason is simple, Hood River is one of the most beautiful small towns in Oregon. Mt. Hood serves as a striking backdrop to a charming downtown core where outdoorsy locals buzz around before schlepping off on an outdoor adventure.
The area is ripe for exploration, offering panoramic mountain views and tons of hiking trails, this Oregon small town active folks in hordes. The activity of the hour seems to be wind surfing (Hood River is the wind surfing capital of the world!), but you’re bound to find a new-to-you activity to pick up.
The city doesn’t let locals go thirsty either. Home to a plethora of great breweries and top-notch wineries, there’s always something happening on the weekends.
My favorite part about Hood River are the charming farms. I have a tradition of driving over in the fall (for apples), spring (for blooms) and summer (for wineries). This is definitely one of the most charming small towns in Oregon (by a country mile).
The biggest disadvantage of living in Hood River, in my opinion, are the housing prices. Median home prices of $820K are too close for comfort for yours truly (these numbers are flirting with a million!).
- Population: 3,000
- Median home price: $700K
- Average age: 55 years
Found in the heart of the Southern Oregon’s Wine Region, just a short 10-minute drive from Medford, Jacksonville offers all the charms of small town living while still being connected to amenities like great restaurants, breweries and ample entertainment.
It’s rare you get a mix of both worlds so easily, which is why Jacksonville is one of the best small towns in Oregon. Not only that, but it’s also one of the most charming. How do I know? Well, the entire town is on the National Historic Registry.
The folks that call this Oregon small town home are keen to keep growth to a minimum, so home prices are outlandishly priced and sprawling subdivisions aren’t in the cards (which is part of the appeal).
In terms of climate, Jacksonville leans towards arid and hot. On average, this small town in Oregon gets 199 days of sunshine annually and a mere 4 inches of snow. So heads up, if you’re into moody gray skies and the striking greenery the Pacific Northwest is known for, you won’t find it here (but that sunshine!).
Oh, lest I forget housing! Median home prices clock in at a steep $700k, so those looking for affordable small towns in Oregon will need to look elsewhere.
Good to Know: Jacksonville is known for hosting the popular Britt Music & Arts Festival, which takes place every summer. Considered one of the best arts festivals in the NW, this event has been attracting high-profile musicians for decades. (Ringo Starr is in the lineup for 2023).
Sisters (one of the most beautiful small towns in Oregon)
- Population: 3,080
- Median home price: $435K
- Average age: 49.5 years
Sisters, Oregon is best know for being the smaller neighbor to the super-popular town of Bend. Offering the same access to breathtaking nature, you’ll be spoiled for choice while living in this mountainous Oregon small town.
For me personally, the incredible landscape is the biggest perk of this small town in Central Oregon. From breathtaking alpine landscapes to the ponderosa pine forests and desert landscapes, the only thing missing is access to the coast (which is 3+ hours away).
While exploring the area, make your way over to Clear Lake, one of the best lakes in Oregon. This is one of the clearest lakes in the state (hence the name) and the lakebed features a forest of petrified trees. It’s chilly, and I can’t tolerate the cold so I don’t normally pop in, but you’ll find me sitting on the beach most weekends in summer.
The little downtown core is charming as can be, it’s also the home of my favorite coffee in Portland (Sisters Coffee). Swing by on a weekend and see why so many locals and visitors congregate on the sunny patio. The coffee is top-notch and the food equally so.
After breakfast, meander the main street and pop into the small local shops full of interesting artwork and craft before making your way to the forest for some fun.
Anyway you slice it, Sisters is one of the best small towns in Oregon for nature lovers and those that want to live life at a slower pace.
Admittidely, the one downside of this charming small Oregon town is how far removed you’ll be. Thankfully the city of Redmond (30-minute drive) has an airport. But it’s a small airport, prepare for inevitable layovers whenever you fly.
- Population: 10,400
- Median home price: $500K
- Average age: 41.5 years
No list of the best small towns in Oregon is complete without mentioning Astoria. This seems to be a statement that divides lifelong locals (myself included), but whether you love it or hate it, there’s no denying that Astoria is one of the best small towns in Oregon near the coast.
Perhaps best known as the filming location for The Goonies, Astoria is not technically a coastal town because it sits at the mouth of the Columbia River, but try convincing me this gem doesn’t ooze coastal vibes. Another clear claim to fame is that Astoria is the oldest city in Oregon!
The town is chock-full of maritime history, so swing by the Columbia River Maritime Museum to get a better appreciation of the importance of the land. Plus, being home to 8 breweries and a plethora of top-notch restaurants doesn’t hurt either.
I’d be remiss if I didn’t mention this downsides of living in this charming small town in Oregon. Mostly it’s the weather and high rates of poverty/crime. I’m all about being honest here, which is why I think these things are important to mention.
Averaging 67 inches of rain per year, this is one of the rainiest small towns in Oregon. The fall and winter months are gloomy and wet. Summers tend to be nicer and have the summer crowds to prove it.
In terms of poverty, 12% of the population lives below the poverty line. As with most Oregon small towns, make sure you have a job lined up before moving, because well-paying gigs are hard to come by in Astoria.
You May Enjoy Reading: 15 Charming Oregon Coast Towns (You Can’t Help But Love)
- Population: 34,600
- Median home price: $450K
- Average age: 38 years
A place where the state’s applauded wine country meets the panoramic views of the Pacific Coast Range mountains, McMinnville is considered one of the best Oregon small towns and it’s not hard to see why.
Being a stone’s throw from award wining wineries will do that! A city for foodies, wine enthusiasts and nature nuts — this small town in Oregon can satiate any palate.
One of my best friends was born and raised in McMinnville, so we often talk about the differences between city vs. small town living in Oregon. He moved to Portland eight years ago but is toying with the idea of buying a home in McMinnville because houses are way more affordable.
I asked him to elaborate on what he loves so much about McMinnville and — without a beat — he dove into the charming small town feel. He believes that locals look out for each other and there’s a sense of community that most major cities lack.
Chock-full of friendly locals, great restaurants and access to the state’s breathtaking wine country, this place is a gem, which is why I consider it one of the best places to live in Oregon.
You May Enjoy Reading: 10 Memorable Wineries in the Willamette Valley
- Population: 10,100
- Median home price: $265K
- Average age: 42.6 years
Baker City is a sleepy gem many people overlook when considering the best small towns in Oregon to live in. Pity, especially considering the charm this town oozes and the stunning natural scenery in this part of the state.
Home to a population of about 10,000 folks, Baker City sits near the border of Idaho and is known as the base camp for Eastern Oregon. The downtown area is quaint and historic, with the Geiser Grand Hotel taking center stage.
The town has a nice selection of restaurants (even a brewery!), handful of pubs and a few local shops to pop into. Swing by the Baker Heritage Museum to learn more about the history behind this small town in Oregon (and see the city’s prized collection of minerals and fossils).
When it comes to activities, there’s never a shortage of outdoor recreational opportunities to choose from, which is why Baker City is considered one of the best small towns in Oregon for nature enthusiasts.
And with home prices averaging $265K, there’s no denying that Baker City is one of the most affordable small towns in Oregon, to boot. Hard not to love that.
- Population: 10,000
- Median home price: $525K
- Average age: 50.8 years
Lincoln City is no stranger to gray winters and rainy days, but that doesn’t stop it from being one of the best small towns in Oregon. Located along the central coast, the scenery of this popular Oregon city can’t be beat.
Home to some of the most beautiful spans of beaches (and one of my favorite recreation areas in the state, Devil’s Lake!), you’ll seldom want for much. And that’s mostly who this coastal town attracts, retirees content with watching the formidable Pacific Ocean without skipping a beat.
The average age of residents in Lincoln City is 50 years old, making it evident that many locals consider the coast as the one of the best small towns in Oregon for retirement. The biggest complaint seems to be lack of access to healthcare (most local hospitals are tiny and severely understaffed).
Other than that, it’s a pretty peaceful, welcoming and scenic small town along Oregon’s breathtaking coastline. No wonder it’s become a dream destination for many Oregonians.
- Population: 10,700
- Median home price: $380K
- Average age: 39 years
The hub of Cottage Grove — one of the best Oregon small towns — is the vibrant downtown core that teems with life on sunny weekend days. Located just 22 miles south of Eugene, you’ll have access to medium-sized city amenities (great restaurants, entertainment, music venues, etc.) while still getting that coveted small town feel.
The city has tons of green spaces, parks and fantastic biking trails (Cottage Grove is known for its strong biking community). Dorena Lake is a huge draw in the summer for swimmers, fishers and baoters. Staying active is a pretty easy ask in this Oregon small town.
Some people liken Cottage Grove to a New England Town, which makes sense because this is the “Covered Bridge Capital of Oregon.” Funny enough, there’s only three covered bridges in the town (but I guess that’s 2-3 more than most Oregon towns and cities).
With all this charm (and stunning display of fall color), is it any wonder why Cottage Grove is considered one of the most charming small towns in Oregon?
- Population: 10,600
- Median home price: $560K
- Average age: 38.6 years
Turns out Cottage Grove isn’t the only Oregon small town with a covered bridge, Silverton has one too!
Wrapping up this list of the best small towns in Oregon is Silverton. No stranger to outdoor enthusiasts, Silverton is a well visited Oregon small town because of its proximity to the popular Trail of Ten Falls (one of the best waterfalls in Oregon).
Small but mighty, Silverton’s shining star is the downtown core. Full of great restaurants, cute local shops and quaint cafes, this is an easy small town in Oregon to fall in love with. If you’re visiting in the spring, pop over the the Wooden Shoe Tulip Festival for an epic display of tulips in April.
Best Small Towns Oregon (Post Overview)
In sum, here’s a quick roundup of the best small towns in Oregon. Hope you enjoyed!
- Hood River
- Baker City
- Lincoln City
- Cottage Grove
You mailed a great article! My favs to visit are McMinnville, Cottage Grove and Silverton, not necessarily in that order. For my husband and I thinking about retirement cities (our town is great – and “small”, but taxes are through the roof!) Our main issye is How close is it to the coast without living AT the coast, and are there good medical facilities. Albany is pretty good, enough to do, right off I-5 to zip to most places easily, but we’re looking for someplace that’s a bit smaller. Dallas is an option too – it’s on the way to the coast!
Thank you again!