Skip to Content

7 Cutest Towns in Oregon You’ve Got to See

7 Cutest Towns in Oregon You’ve Got to See

Sharing is caring!

Are you planning a trip to the Pacific Northwest and want to explore places in Oregon outside of Portland? Keep scrolling to learn about the cutest towns in Oregon worth a quick stop!

If you love nature, Oregon is the state for you!

From forests to beaches, mountains to farmlands, and volcanoes to deserts – Oregon is known to be among the most diverse in the country.

With three major cities, stunning landscapes and so many natural attractions competing for your attention, something you may not know about Oregon is the fact that it’s also home to a ton of picturesque towns worth adding to your itinerary.

From charming coastal towns to settlements located right next to some of the most sought-after natural destinations in the state, here are the cutest towns in Oregon you absolutely have to visit!

The Cutest Towns in Oregon You’ve Got to See

1. Cannon Beach

From Haystack Rock and Hug Point waterfalls to the charming small-town feel, Cannon Beach offers it all!

Cannon Beach is one of the cutest towns in Oregon. Image of Haystack Rock in Cannon Beach
Haystack Rock at Cannon Beach.

Embark on outdoor adventures among some of Oregon’s most stunning scenery: Ecola State Park’s gorgeous coastline or explore local art galleries, restaurants, and boutiques.

It’s no wonder National Geographic named this gem one of the ‘most beautiful spots on Earth’ in 2013. Come see for yourself why everyone can’t get enough!

Where to Stay in Cannon Beach

2. Joseph

From distilleries to boutiques, the tiny town of Joseph in Oregon has it all.

Tucked away at the base of Wallowa Mountains and possessing a stunning downtown area complete with life-size bronze sculptures crafted by local artists – this place is truly something special!

Joseph is one of the cutest Oregon towns. Image of a red barn on a grassy lawn with Wallowa Mountains in the background
Does it get much cuter than this?

Dubbed ‘Oregon’s Little Switzerland’, you can explore either on foot or take their convenient tram service which offers views that will leave your jaw dropped.

Not only do they have an array of cultured attractions but also make for a great starting point if wanting to visit renowned landmarks such as nearby Eagle Cap Wilderness and Wallowa Lake.

Another highlight of Joseph is its Swiss-Bavarian carnival reminiscent of Oktoberfest, which is hosted every September

So what are you waiting for? Pack your bags – there’s plenty of adventure awaiting in beautiful little Joseph!

Where to Stay in Joseph, Oregon

3. Brownsville

Brownsville, Oregon is a quaint town of 2000 residents that recently entered the public’s eye with its role in Stand by Me.

This pioneer community has managed to preserve much of its charm and architecture from the old days, old-fashioned storefronts and parades included. 

Its charming and unique downtown beckons visitors to explore! Take a stroll down history lane as you admire authentic buildings from the 18th century.

Be sure to stop at Linn County Museum where stories about Calapooia tribe and early settlers are told or take in some local architecture at The Moyer House. This is an impressive Italian-style villa constructed in 1881 by J.M Moyer. He was a pioneer entrepreneur extraordinaire who owned his own sash & door manufacturing plant!

And finally pay homage to nature when visiting The Living Rock Museum whose colorful facade was created using shimmering agates, crystals and quartz natively found nearby.

Where to Stay in Brownsville, Oregon

4. Florence

Take a drive to the charming Oregon coastal town of Florence and be prepared for an adventure!

Heceta Head Light in Florence, Oregon.
Heceta Head Light in Florence, Oregon.

Soak up stunning views along miles of coastline just an hour’s drive from Eugene. You can also explore impressive sand dunes in Oregon Dunes National Recreation Area or discover sea caves that will captivate your senses.

And you can capture picture-perfect memories at the local lighthouse or shop till you drop with tons of boutique stores around town – plus delectable seafood spots.

With so many fun things to do and places to stay (like riverfront hotels or lakeside cabins), extend your escape by spending a few nights here.

Where to Stay in Florence, Oregon

5. Sisters

Ready for a marvelous adventure in Oregon? Look no further than the charming small town of Sisters!

Surrounded by three awe-inspiring snowcapped peaks and engulfed with 1880s facades, you can relish your visit year-round.

McKenzie Pass, Deschutes National Forest, Sahalie, and the Koosah Falls – a mass of foaming white water that plunges down 100 feet over a natural lava dam, are just a few of the natural sights set just a short drive away from Sisters!

Image of Mountains outside of Sisters, Oregon under the clear late afternoon sky
Mountains outside of Sisters, Oregon.

While Suttle Lake invites nature lovers to explore its camping grounds, Hoodoo Ski is ideal for those who seek some powdery slopes fun during wintertime.

Get ready to be wowed at the annual Sister’s Rodeo or treat yourself while beachside dining in summer months.

This is all followed up with delectable flavors from local restaurants as well as artsy finds from boutiques and creamy coffee offered at Sisters Brewing Company.

If you’re in the mood for some self-care, go ahead and pamper yourself in the various spas, including America’s first beer spa!

Come unravel this natural paradise!

Where to Stay in Sisters, Oregon

6. McMinnville

Ready for a little history and wine?

Allow us to introduce you to McMinnville, an idyllic town nestled in the heart of Oregon’s lush wine country. With 64 historic turn-of-the-century buildings reinvented as restaurants, art galleries and more – this charming locale provides eye candy at every corner!

Image of a vineyard in Oregon
You’ll love all the wine-tasting opportunities!

Wine lovers will be spoilt here with dozens of tasting rooms devoted exclusively to sampling delicious local wines grown from vineyards that surround it.

Once you’re done with history and wine-tasting, you can visit the Evergreen Aviation and Space Museum and gawk at the largest propeller-driven seaplane, the Spruce Goose.

Moreover, if you happen to be visiting in May, you can also attend the annual UFO Festival!

And if nature is your thing too – there are plenty of hiking trails winding through these very same vineyards not far away! It truly is one destination worth exploring… Cheers!

Where to Stay in McMinnville, Oregon

7. Cottage Grove

Nestled in the lush landscape of Oregon’s Willamette Valley, Cottage Grove is a charming destination for any traveler.

Centennial Bridge in Cottage Grove, Oregon, a walking bridge over the river
Centennial Bridge in Cottage Grove, Oregon.

Learn about its gold mining history at Bohemia Gold Mining Museum or explore six stunning covered bridges—Cottage Grove earned quite fittingly “the covered bridge capital of the west” moniker!

Don’t miss out on luscious art galleries and boutique stores around town plus cozy coffee shops to keep your energy up while you seek out unique murals hidden throughout this old-world charmer.

Where to Stay in Cottage Grove, Oregon

Oregon Small Towns Wrap Up

Have you visited any of these Oregon small towns? Which one was your favorite? Let me know all about your experience there in the comment section below!

Looking for more Oregon content? Find out the best things to do in Astoria, adorable Oregon Coast towns, the best things to do in Cannon Beach, cool things to do in Seaside, and unique places to visit in Oregon.

This site uses Akismet to reduce spam. Learn how your comment data is processed.

This site uses Akismet to reduce spam. Learn how your comment data is processed.