Article Overview: List of the Best Small Towns in Oregon
You know those cheesy Hallmark movies where the career-obsessed city girl returns home for the holidays (to some charming small town) and runs into her 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. And I get it, there’s something endearing about living in a small town.
While some love the amenities of big city-living, like access to restaurants, entertainment and seamlessly endless list of activities. Others seek out the best small towns in Oregon because they want a slower pace of life.
You know the drill: there’s pros and cons to everything. Thankfully, you know yourself best. So, if you’re searching for the most charming Oregon small towns, the list below may be a good starting point. Let’s get to it.
The Most Charming Small Towns in Oregon
(Click here for the table of contents)
Wait, what’s 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.
Ashland
- Population: 21,300
- 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 thanks to the popular Oregon Shakespeare Festival. Since its inception in 1935, the festival has evolved into one of the largest and most prestigious theater events in the country, attracting 400,000 per year on average.
Beyond the festival, the town punches above its weight in charm. Take a lovely stroll through 93-acre Lithia Park before popping over to Mix Bakeshop for some delicious ice cream and afternoon treats.
Afterwards, stroll the downtown streets and admire the Victorian architecture and historic landmarks that pay tribute to the town’s storied past (Ashland served as a hub during the California Gold Rush).
Take in the views around you while you walk around and you’ll instantly see why this is one of the best small towns in Oregon. Surrounded by mountains and forests, locals have unparalleled access to outdoor recreation.
But it’s the rolling hills of vineyards that does it for me personally. In my opinion, this area is home to one of the most underrated wine regions in Oregon.
But I don’t want to paint a false picture though, it’s not all sunshine and rainbows around here. Ashland gets unbearably hot during the summer months. And that’s not to mention the wildfire smoke that inundates this charming Oregon small town (almost like clockwork) year after year.
Hood River
- Population: 8,350
- Median home price: $620K
- Average age: 36.6 years
If I had the means, I’d buy a home in Hood River in a heartbeat. 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 historic downtown where outdoorsy locals park themselves for hours on end at local breweries and cafes.
Renowned as the windsurfing capital of the world, Hood River lures thrill-seekers and water sports enthusiasts with consistent winds and panoramic views of the rugged gorge. But the town’s charm extends beyond its reputation as a mecca for outdoor enthusiasts.
With a history dating back to the mid-19th century, Hood River served as a vital hub for the timber and fruit industries. Today, the area is known for sprawling orchards, farms and (my personal favorite) beautiful wineries. Here’s a roundup of 15 Charming Hood River Wineries (You Won’t Want to Miss).
You Might Enjoy Reading: 12+ Relaxing Things to Do in Hood River, Oregon (Local’s Guide)
Sisters
- Population: 3,000
- Median home price: $835K
- Average age: 49.5 years
Sisters is best know for being the smaller neighbor to the super-popular town of Bend. Offering the same access to great outdoor recreation, you’ll be spoiled for choice while living in this mountainous Oregon small town.
From breathtaking alpine landscapes to the Ponderosa pine forests and sweeping desert landscapes, the only thing missing is access to the coast (which is 3+ hours away). 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 locals congregate on the sunny patio before heading out for a hike. 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 crafts 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. Admittidely, the one downside of Sisters is how remote the town is. Thankfully the city of Redmond (30-minute drive) has an airport. But it’s a small airport, prepare for inevitable layovers whenever you fly.
Joseph
- Population: 1,200
- Median home price: $665K
- Average age: 59.6 years
Located in the northeastern corner of Oregon, Joseph is located amidst the stunning Wallowa Mountains, one of the Seven Wonders of Oregon. With a population barely tipping over a thousand, the area’s natural beauty captivates visitors from across the state (this area reminds me of Switzerland).
Originally inhabited by the Nez Perce Native American tribe, Joseph has rich ties to its indigenous past. The town’s namesake, Chief Joseph, was a revered Nez Perce leader commemorated through various landmarks and tributes.
Wallowa Lake offers ample fishing, boating, and hiking opportunities against the backdrop of majestic peaks. For art aficionados, the town’s vibrant arts scene provides a glimpse into the creative community that calls Joseph home.
As the gateway to the Wallowa Mountains, there’s no denying that this is one of the most beautiful small towns in Oregon. I consider this a must-visit destination for all Oregonians.
Jacksonville
- Population: 3,000
- Median home price: $760K
- Average age: 55 years
Found in the heart of the Southern Oregon’s Wine Region, 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.
Jacksonville locals 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). Those looking for affordable small towns in Oregon will need to look elsewhere.
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 lush green forests, you won’t find it here (but that sunshine!).
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, the event attracts high-profile musicians like Ringo Starr (in 2023).
Astoria
- Population: 10,400
- Median home price: $485K
- Average age: 41.5 years
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 telling locals this gem doesn’t ooze coastal vibes.
Calling Astoria a small town is sure to garner debate, but with a population of 10K, it’s definitely a small town by definition, so it’s making our list. However, it has a ton of big city amenities like hotels, shops and restaurants. Heck, Astoria has the lion’s share of Oregon coast breweries, (there’s more than 5 in town.).
I’d be remiss if I didn’t mention this downsides of living in Astoria. Mostly it’s the weather and high rates of poverty and 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: 10+ Amusing Things to Do in Astoria, Oregon (Helpful Guide)
McMinnville
- Population: 34,600
- Median home price: $475K
- Average age: 38 years
The meeting point of the state’s lauded wine country and the Pacific Coast Range mountains, McMinnville is a sight for sore eyes. A city for foodies, wine enthusiasts and nature nuts alike, 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 in the area.
I asked him to elaborate on what he loves so much about McMinnville. 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, it’s no wonder why McMinnville is considered one of the best places small towns in Oregon to live in.
You May Enjoy Reading: 10 Memorable Wineries in the Willamette Valley
Baker City
- Population: 10,300
- Median home price: $245K
- Average age: 42.6 years
Baker City is a sleepy gem most visitors overlook when considering the best small towns in Oregon. Pity, considering the charm this town oozes and the stunning natural scenery in this part of the state.
Home to a population of about 10,300, Baker City sits near the border of Idaho and is known as the base camp for Eastern Oregon. The historic downtown area is as quaint as can be, with the beautiful 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).
With home prices averaging $245K, Baker City is one of the most affordable small towns in Oregon to grace the list. Hard not to love that.
Lincoln City
- Population: 10,000
- Median home price: $505K
- Average age: 50.8 years
Located along the central coast, Lincoln City is no stranger to gray winters and rainy days, but the scenery of this coastal town can’t be beat. Home to some of the most beautiful spans of beaches in the sate, you’ll seldom want for much.
And that’s mostly who this coastal town attracts, retirees content with watching the formidable Pacific Ocean for days on end. The average age of residents in Lincoln City is 50 years old, making it evident that many locals consider this 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 at the Oregon coast, a dream retirement destination for many Oregonians.
You May Enjoy Reading: 15 Charming Oregon Coast Towns (You Can’t Help But Love)
Cottage Grove
- Population: 10,700
- Median home price: $355K
- Average age: 39 years
Cottage Grove’s vibrant downtown teems with life on sunny weekends in the summer. 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 boaters. 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 cities).
Silverton
- Population: 10,600
- Median home price: $530K
- 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).
Tiny 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!
- Ashland
- Hood River
- Joseph
- Jacksonville
- Sisters
- Astoria
- McMinnville
- Baker City
- Lincoln City
- Cottage Grove
- Silverton
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!