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7 Must-Visit Cutest Towns in Oregon You Shouldn’t Miss

7 Must-Visit Cutest Towns in Oregon You Shouldn’t Miss

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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, you have to visit these cutest towns in Oregon. This charming place will come as a pleasant surprise.

Oregon is one of the best locations for superb Seattle day trips. The place will give you many reasons to love it with each visit.

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!

Must-Visit Cutest Towns in Oregon

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.

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

And while you’re here in this scenic small town, you can head to Columbia River Gorge, where you can start a beautiful journey and come across different rivers like Columbia River, Hood River, Klickitat River, Deschutes River, and White Salmon River.

Where to Stay in Cannon Beach

2. Joseph

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

Tucked away at the base of the 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 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 the 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!

Florence is one of the cutest towns in Oregon. Be sure to head to Heceta Head Light for a stunning view!
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.

You can capture picture-perfect memories at the local lighthouse or shop till you drop at the many 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 in this beautiful town in Southern Oregon.

Where to Stay in Florence, Oregon

5. Sisters

Ready for a marvelous adventure in Central 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 located just a short drive away from Sisters!

Sisters is one of the cutest towns in Oregon that has scenes like no other! 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 to beachside dining in the summer months.

This is followed up with delectable flavors from local restaurants, 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!

Want to explore more? Head to Baker City and enjoy the historic charms of the place. Visit the Baker Heritage Museum or the Oregon Trail Interpretive Center to learn about the early settlers in the state.

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!

McMinnville is one of the cutest towns in Oregon that looks like scene in a painting. This vineyard will surely take your breath away.
You’ll love all the wine-tasting opportunities!

Dozens of tasting rooms devoted exclusively to sampling delicious local wines grown from vineyards that surround it will spoil wine lovers who visit here.

Once you finish history and wine tasting, you can visit the Evergreen Aviation and Space Museum and marvel 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.

Cottage Grove is one of the cutest towns in Oregon that's definitely worth the drive. This is 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.

If you have more time, you can also visit the Columbia River Maritime Museum in nearby Astoria.

Where to Stay in Cottage Grove, Oregon

Oregon Small Towns Wrap-Up

All these cutest towns in Oregon are amazing locations, whether you’re looking for vacation spots in the Pacific Northwest or romantic getaways.

It’s an enchanting place to be in, and these towns are definitely worthy to be on your bucket list!

Have you visited any of these small towns in Oregon? 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, the most beautiful places in Oregon, Oregon scenic drives, 17 Amazing Places To Visit And Things To Do on Oregon Coast, and unique places to visit in Oregon.

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