Written by | Derek Carlson

6 Adorable Small Oregon Towns to Visit in 2024

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Oregon is well known for its gorgeous towns and even more gorgeous natural areas. Portland and Bend lead the pack when it comes to must-visit cities, but if you’re looking to get away from the crowds and off the beaten path, there are TONS of charming small towns in Oregon that are a must-visit!

These must-visit towns range from remote and rugged outposts in the far-flung corners of the state to charming spots in the heart of wine country to picturesque coastal getaways.

We have spent years traveling all over Oregon and these are our 6 favorite small towns to visit this year!

Our Favorite Small Towns in Oregon

1. Sisters

sno cap drive in in Sisters, Oregon

Driving into Sisters, Oregon feels like you’re stepping back in time to an old western-style town—the buildings throughout this charming 6-block-long downtown house charming eateries, bookshops, and local boutiques.

This Central Oregon town of 3,000 people serves as a gateway to the nearby Three Sisters Wilderness and world-famous Metolius River.

We love heading up to the Tam McArthur Rim trail for some of the best views around of the Central Oregon Cascades. And of course, no hike would be complete without a stop at Sisters Bakery!

That leads us to our top spots to visit in Sisters! Sisters Bakery (their doughnuts and sourdough bread or some of the best around), Boone Dog Pizza, Sno-Cap Drive-in, and Paulina Springs Books get a visit from us on almost every trip through town.

Places to Stay in Sisters: Sisters, and the surrounding areas, have no shortage of places to stay. These range from modern hotels to rustic or glamorous cabins and lodges. If you want to stay in the heart of Sisters we’d recommend Fivepine Lodge and Spa (our favorite spa in Central Oregon).

Those looking for more rustic and/or remote accommodations can look to the nearby Suttle Lake Lodge or House on Metolius.

2. Joseph

One of our favorite small Oregon towns, Joseph, Oregon with the Blythe Cricket and Wallowa mountains

In our years of living in Oregon, we have only made one trip to Joseph but I can assure you that we will be back many times in the future. This charming town located way out in the Northeastern corner of the state has it all when it comes to a small Oregon town.

Charming downtown – check
Gorgeous scenery – check
Fun eateries and plenty of things to do – check

Joseph is located at the end of Wallowa Lake which is fed by snowmelt by the majestic Wallowa Mountains. These mountains are sometimes called the Alps of North America and for good reason!

Downtown Joseph has a charming mix of touristy type shops, local eateries, and one of the best fly fishing shops you’ll find anywhere in the world (stop by to say hi to the owner and his horse that he rides into work every day!)

Don’t miss the Wallowa Lake Tramway which takes you up to the top of Mt. Howard which offers sweeping views of the mountains and Eastern Oregon plains.

Places to Stay in Joseph: Joseph has a ton of charming places to stay that range from VRBOs to rustic lodges to well-equipped campgrounds. During our stay, we camped at the Wallowa Lake State Park (if you want to camp here book a spot early! This is one of the most popular state parks in all of Oregon.)

Wallowa Lake Lodge or Eagle Cap Chalets offer amazing accommodations at the end of Wallowa Lake and are mere steps from the expansive Eagle Cap Wilderness.

3. Hood River

View of Mt Adams from Packer Orchard outside of Hood River.

Hood River sits in one of the most ideal and picturesque locations in all of Oregon. Add in the sprawling fruit orchards, wineries, breweries, and charming eateries and you have one of the best places to visit in the state!

Hood River is perfect for folks looking to spend a relaxing weekend around town or those looking for an adventure basecamp to the nearby trails in the Columbia River Gorge or Mt. Hood.

We make an annual trip to Hood River in the fall to hike at Tamanawas Falls, pick apples at Mt. View Orchard, and go to the amazing fall festival at Packer Orchards.

Places to Stay in Hood River: Grab a room at the charming Hood River Hotel in the heart of downtown Hood River where you can spend the days walking to nearby bistros and coffee shops or head out to the heart of orchard country at a cozy house rental.

4. Astoria

Throwing a wood glider off the top of the Astoria Column in Astoria, Oregon

Located at the far Northwestern corner of Oregon this maritime-centric town is rich in history and beauty. Located at the mouth of the Columbia River this small Oregon town has served as a maritime center for centuries now and the buildings in the city reflect this unique history.

We loved wandering through downtown taking in the architecture that is so unique for this part of the country. Right beside the historic buildings is the waterfront where you can ride a trolley or walk on an elevated boardwalk by boutique hotels and breweries that call this amazing city home.

Make sure to take a trip up the hill to the Astoria Column where you can take in a very uniquely Astoria activity of flying balsawood planes off the top and watch them glide out of sight on the coastal breeze.

Where to Stay in Astoria: Grab an oceanside room at the newly renovated Bowline Hotel (pronounced bow-lin, not bow-line) or hop across the bay and grab a campsite at Fort Stevens State Park.

5. Pacific City

Pacific City sunset looking out over Haystack Rock

I could do write-ups on virtually every town along the Oregon coast but Pacific City holds a special place in our heart. After spending a week here a few years back it instantly became one of our favorite places to visit in all of Oregon.

This small Oregon town is a bit off the beaten path of Highway 101 so it tends to be a bit slower than some other nearby coastal towns.

We loved the beachfront rental options and the small downtown where you can grab breakfast at a Grateful Dead themed bakery or a microbrew at an oceanfront brewery.

Where to Stay in Pacific City: Book a luxury room at the Headland Coastal Lodge & Spa with its magnificent views of Haystack Rock and Cape Kiwanda Sand Dune or grab an oceanfront cabin (we stayed here and it was AMAZING!)

6. Ashland

Ashland serves as the final outpost in Oregon before you head into the mountains and California. Don’t let that deter you though as this charming town is rich in culture as it serves as the headquarters for the annual Shakespeare Festival which draws hundreds of thousands of visitors to Ashland every year!

As the home of Southern Oregon University the town has no shortage of fun spots to eat and drink (don’t miss the uber popular Case Coffee Roasters located right in the middle of downtown)

The city is also surrounded by trails crisscrossing the local hills so after enjoying a hearty breakfast you can get out and burn off some calories.

Where to Stay in Ashland: Grab a rental at this charming Tudor style home in downtown Ashland or the Shakespeare themed Romeo Inn B&B.

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