Do you want to get away from the crowds and discover the best small towns in Oregon? We are here to help!
Although the big cities have loads to offer, charming small towns are just as much fun. They are a great way to discover a more authentic way of living and relax for the time of a weekend.
Oregon is a beautiful state, filled with natural landmarks and a beautiful coastline.
In this article, you will discover the most charming small towns in Oregon and what to do when you visit them.
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Table of Contents
Let’s start this article with Jacksonville, Oregon.
You probably already know this name as it is one of the biggest cities in Florida but be reassured, we are talking about a small town in Oregon here.
Located in the southern part of the state, Jacksonville was a popular town during the gold rush. The historic buildings in this town possess an undeniable rustic charm.
To appreciate it at its best, take a stroll by the paved sidewalks to enjoy the Victorian-style homes or pop into a local restaurant to sample the cuisine.
Alternatively, you can opt for a segway tour of the town with a local guide. Not only is it a lot of fun but it’s also a great way to learn more about the place. See prices here.
Outdoor lovers can enjoy hiking at the Woodland trails close to the town or they can take a tour of the vineyards (at the Rogue Valley).
The Applegate Valley Wine Trail is also close to the town and it is a popular attraction for visitors seeking to sample wine and special treats.
WHERE TO STAY: Located on the main street, McCully House Inn is one of the cutest inn you can stay at in Oregon. It’s absolutely gorgeous, has a lush garden and breakfast is included. You will also be very close to the restaurants and bars and can park for free. See prices here.
Baker City is a quiet, beautiful town situated on the Oregon Trail. It is bigger than Jacksonville but the population is still under 10,000 people, making it a great destination for a relaxing getaway in Oregon.
From 1865 onwards, the town thrived as a center for commerce, fueled by gold prospects, timber, and the new railroad. Soon, the town would receive the title of the ‘Queen City of Inland Empire’.
As large cities cropped up, the town’s popularity started to wane.
When you visit here today, head over to the Baker Heritage Museum to see the amazing collection of fossils, rocks, and minerals.
Hiking at the nearby Elkhorn Mountains is also a popular activity in Baker City.
At the end of a long day, head to the Geiser Hotel for a delicious meal and refreshment. Geiser is the oldest hotel in the town, having been established in 1889.
WHERE TO STAY: Geiser Grand Hotel is a historic hotel ideally located on the main street of Baker City. The rooms are beautiful and breakfast is included. Bars & restaurants are very close by. See prices here.
Surrounded by the breathtaking Wallowa Mountain ranges, Joseph is a town that promises a unique blend of western culture and modern living and delivers on that promise perfectly.
Hikers have hundreds of hiking trails to explore in the Eagle Cap wilderness.
Each trail offers you scenic and stunning views of the mountain ranges. The Iwetemlaykin, hurricane Creek and BC Falls trails are some of the best trails to explore as a casual hiker in Joseph.
Camping is also allowed in the Eagle Cap Wilderness and with over 360 thousand acres at your disposal, you are only limited by your level of imagination.
Back in the town, you can always catch an event happening almost every week.
Be sure to visit the Joseph Oregon Bronze artwork trail to sample the monumental bronze sculptures that represent common western themes.
WHERE TO STAY: If you want to fully embrace the small town feeling, opt for the Eagle Cap Chalets. This resort offers several cute chalets on the edge of Wallowa Lake. It’s a great place to relax and enjoy your vacation. See prices here.
If you are an avid hiker, windsurfer, or biker, you probably have heard of Hood River town. This town is widely regarded as the Windsurfing capital of the world.
The town is located in the Columbia River Gorge and named after the Hood River. It’s only 1 hour drive from Portland making it the perfect day trip! You can easily get there by car or book a guided tour. See prices.
There are stunning sceneries wherever you look.
Skiers flock to this town in the winter to hold carnivals and festivals as they ski on the breathtaking mountains close to the town.
Kayaking, canoeing, kite surfing, paddle boarding, and other water sports are very popular activities in this town.
But Hood River is not an outdoor-only destination. There is a lot of history to learn and if you are looking for a fun thing to do, you should consider doing a scavenger hunt. You will discover the town and all its secrets while having fun. See prices here.
After a long day, walk into any of the fine eateries in the town to sample local delicacies and sip wine brewed from the vineyards close to the town.
If you are a foodie and are up for some tastings, you can also go wine tasting in some of the local wineries. See prices here.
WHERE TO STAY: Hood River Hotel is a beautiful and historic hotel located on Oak Street. In terms of location, this is as good as it gets! You will be close to everything! The hotel is very well decorated. You will love taking photos there. See prices here.
If you are a mountain biker, you can opt for an adventure vacation in Hood River. Everything is included (accommodation, paddle hire…) and it’s very good fun. It’s organised by locals and such a good way to experience the area. See prices here.
Brownsville is the smallest of the towns we have looked at on this list.
However, what the town lacks in terms of population is quickly counter-balanced with the abundance of natural attractions, making it the perfect destination for outdoor lovers who want to stay away from the crowds.
The town is set at the foothills of the Cascade Mountains, allowing visitors to have uninterrupted access to limitless outdoor opportunities.
If you are not out hiking in the Cascade Mountains, you may take a stroll inside the town to explore some of the historic buildings that still stand today.
There is a beautiful 26-acre park called Pioneer Park that is worth checking out.
Brownsville is also a great place to visit if you are into history. The Linn County Historical Museum is an amazing museum and you’ll be surprised to find such a good one in a small town like Brownsville.
Living Rock Studios and Moyer House are also worth a visit. They are both museums with an interesting history.
WHERE TO STAY: Brownsville is one of the cutest small towns in Oregon but it’s not rich in options when it comes to accommodation.
That having been said, there are a couple of beautiful vacation rentals that will make the perfect base.
This loft is an absolutely stunning apartment located just above a wine shop. It’s very well decorated and has such a convivial feel to it with the bricks and everything else. It can sleep up to 4 guests, making it the perfect option for couples, a family or small group of friends. See prices here.
Located 2 hours south of Portland, Cottage Grove is the perfect Oregon small town to visit on a road trip to California or as a day trip from Portland.
Cottage Grove has the highest covered bridges in Oregon, making the town gain the title of the ‘Covered bridge capital of the west’.
There are a total of six covered bridges in Cottage Grove.
Cottage Grove’s charm is in its serene, almost unassuming demeanor.
The best way to explore the town is on foot, taking in the old, historic buildings that make it one of the most attractive towns in Oregon.
If you are a history buff, make sure to visit The Cottage Grove Museum. It contains a lot of information about the town and its inhabitants.
To learn more about the town’s role during the gold mining era, visit the Bohemia gold mining museum.
Finally, Cottage Grove is also a great destination for people who love the outdoors.
Cascading waterfalls, winding rivers, lush valleys, and gorges are some of the things you expect to see if you decide to explore the wilderness in Cottage Grove.
WHERE TO STAY: The Village Green is a resort in Cottage Grove with an outdoor swimming pool. It’s a great place in summer as you can relax, visit the town and cool down in the pool. You will also have access to a hot tub which is a great asset in winter. It’s also worth noting that they are dog-friendly! See prices here.
McMinnville is where you want to go if you love wine. Numerous local vineyards process delicious wines here.
There are over 13 wineries and several breweries in this cute tourist town in Oregon, making it the ideal foodie destination.
If you are willing to drive a bit more (20 miles or so), you will find even more wineries! There are 250 of them in the Willamette Valley. You will be spoilt for choice.
The dining setting in restaurants is something to look forward to when you visit McMinnville. The historical buildings in McMinnville have also been well preserved.
Make sure to visit the space museum and learn more about the town’s history, culture, and national heritage. They hold an annual UFO festival in May so if you are around at this time of the year, that’s well worth a visit.
Finally, McMinnville also is a paradise for shoppers. You will find many cute boutiques and local shops downtown. If you like finding unique pieces of clothing or things to decorate your house, you will be in for a treat!
WHERE TO STAY: McMinnville is only 50 minutes drive from Portland, making it a great day out but it’s also an excellent destination for a getaway.
You can spend a great weekend here!
Opt for a room at the Atticus Hotel. It’s a beautiful hotel, stunningly decorated (you’ll love to take photos here) and very well located. The staff is very friendly and provides impeccable service. It’s one of the best small town hotels in the state! See prices here.
Just a few miles from the Pacific Ocean lies another scenic town called Astoria. This is considered to be the oldest town west of the Rocky Mountains.
It is a great destination for people looking for a coastal town in Oregon, near the border with Washington.
Mountain ranges, waterfalls, rivers, lush forests, and vast landscapes are the characteristics of Astoria.
The Victorian-style homes line up every street, giving the town an old, rustic but charming appeal.
The vast outdoors invite people to engage in all sorts of activities.
Camping, kayaking, and fishing are some of the common activities happening within the borders of the town and beyond. The Astoria-Megler Bridge is the most iconic landmark in the town so make sure to check it out!
While you are downtown, visit the art galleries and eat local cuisine in the fine restaurants inside the town.
If you have some time, the Columbia River Maritime Museum will be a good place to visit and learn more about the town and its historical significance.
Finally, if you are looking for a fun and unique thing to do in Astoria, head to the Oregon Film Museum. It was used as a filming location for the movies The Goonies and is such a fun place to visit.
There you can recreate the scenes of all your favourite movies using the props. This includes The Goonies, Kindergarten Cop, Free Willy and Twilight.
WHERE TO STAY: Astoria Riverwalk Inn is the perfect place to stay in Astoria. This cute Inn is ideally located at the marina. The rooms are beautiful (so is the view) and it includes a delicious continental breakfast. See prices here.
Located on the eastern slopes of Cascade Mountains, Sisters is one of the most charming towns in Oregon.
It was named after the three peaks towering over the town’s streets and buildings.
This is a small farming town where farming, logging, and ranching are the main activities.
There are vast landscapes for outdoor lovers.
The three volcanic peaks offer excellent grounds for rock climbing, camping, and hiking. Other activities include mountain biking, backpacking, skiing, and rafting.
It’s also a great destination for people interested in art. It’s such a vibrant and artsy town, you will love it!
As you roam down Hood Avenue, you will discover cute local boutiques and galleries. Hood Avenue Art is particularly popular.
If you are thinking of visiting in summer, make sure to go during the Sisters Rodeo. It’s nicknamed the Biggest little show and is such good fun.
All in all, Sisters is the perfect small town in Oregon for people who want a relaxing couples’ or family getaway.
WHERE TO STAY: Best Western Ponderosa Lodge is a beautiful and authentic hotel in Sisters. You will have access to the wellness area with a hot tub and get a continental breakfast in the morning. See prices here.