street view in sisters oregon

9 Cutest Small Towns in Oregon

Oregon is a treasure trove of beautiful destinations hidden in the Western United States. The lively state boasts an array of unique natural parks and formations anyone will adore. Snake River, Crater Lake National Park, and Mount Hood National Forest are just a few ways to experience Oregon’s appeal. Parallel to the sights, Oregon is also filled with history spanning hundreds of years since Spanish settlement. With so much to see and do, Oregon’s small towns offer amazing insight into the state. Their peaceful environment plus cute attractions attract tourists from all over.

Cannon Beach

Cannon Beach on the Oregon coast
Cannon Beach on the Oregon coast

Cannon Beach is a picturesque coastal destination often ranked as one of the country’s most beautiful places. Nestled along the Pacific coast, the town’s beautiful coastline is a sight to behold. Take in the endless views at Cannon Beach, Haystack Rock, and Ecola State Park. Cannon Beach itself is a wonderful beach where one can enjoy white sand and tranquil waves throughout the day. As you walk along the beach, you’re sure to notice the massive Haystack Rock; a 235 ft-tall (72 m) monolith rock. Estimated to be more than 15 million years old, this rock exudes a mysterious vibe attracting tourists. That said, follow the water’s edge and Ecola State Park is a nature lover’s dream. Flora, fauna, and recreation abound, it is great for a family outing. If you’re lucky, you might spot the local puffin colony known for their cute demeanor.

Once you’ve had your fair share of the coast, head into town to take in the adorable towny vibes. Home to a population of 1,700 and always bustling with tourists, there is never a dull moment in Cannon Beach. Whether this involves watching a movie at the historic Coaster Theatre or admiring glasswork at Icefire Glassworks, there is something for everyone.


Street view in Silverton, Oregon, via Laurens Hoddenbagh /
Street view in Silverton, Oregon, via Laurens Hoddenbagh /

Two hours from Cannon Beach, Silverton is a quaint reprieve that exudes small-town charm. Reminiscent of rural farming towns yet still flowing with life, this delightful town is often considered one of Oregon’s hidden gems. Start with a stroll through town and Silver Creek’s tranquil stream will follow you around for some scenic locations. Enjoy the natural vibe? Head over to the Oregon Garden, a botanical garden featuring 80 acres of vibrance and joy. From vibrant pink Heather in the winter to golden leaves during fall, it is a great spot for cute photos.

As you continue touring Silverton, you’re sure to notice the friendly faces and quirky establishments lining the streets. Buzzing with life, one can indulge in this happening environment at spots like The Gordon House and Silver Creek Lanes. Designed by famous architect Frank Lloyd Wright, The Gordon House is a creative masterpiece part of his Usonian series on affordable housing. Built-in 1963, the house still feels like you’ve stepped into the future. That said, if you’re here with family, a fun way to end the day is at the Silver Creek Lanes bowling alley. Featuring great food, fun bowling, and a buzzing atmosphere, everyone can have a blast! So, with its alluring scenery and entertaining activities, Silverton is a charming small town in Oregon.


Cars on the street in downtown Astoria with Astoria-Megler Bridge in the background, via Enrico Powell /
Cars on the street in downtown Astoria with Astoria-Megler Bridge in the background, via Enrico Powell /

Founded in 1811, Astoria is Oregon’s oldest city and the first permanent American settlement west of the Rocky Mountains. Intertwined with interesting tales, the town boasts an air of historic allure. Stroll through Astoria’s delightful downtown area which is embellished with cute architecture and attractions. Oregon Film Museum and Columbia River Maritime Museum are spots that cultural enthusiasts adore. These museums showcase maritime models, film-making techniques, and dozens of artifacts. Or, head over to the coast to witness the immense Astoria-Megler Bridge, a grand structure spanning the Columbia River. Providing breathtaking views since 1966, it is a testament to Astoria’s intricate past. If this isn’t enough, sites like Astoria Column and Flavel House Museum will keep you busy for days!

While Astoria’s history may be its selling point, the town is also a wellspring of outdoor scenery. Nature lovers rejoice at Youngs River Falls, an iconic waterfall set in a secluded forest area. Flowing water coveted by sharp rocks and thick foliage creates a mystical environment rarely found elsewhere. That said, if you don’t want to head out of town to see flowing water, opt for the Astoria Riverwalk instead. Stretching for miles along the waterfront, one can enjoy an evening surrounded by water, restaurants, and stores. All in all, if you’re a fan of history, there’s no place like Astoria in Oregon.

Cottage Grove

Arched sign across East Main Street in Cottage Grove Historic District Oregon, via Ian Dewar Photography /
Arched sign across East Main Street in Cottage Grove Historic District Oregon, via Ian Dewar Photography /

Inland from Astoria, Cottage Grove is a lovely town situated in Lane County, Oregon. Nicknamed the “Covered Bridge Capital of The West,” the town’s pretty bridges draw in people from all over. In total, one can find six covered bridges in town each of which have a unique charm and design. For example, the 1925 Chambers Covered Bridge is an insight into historic construction with a rustic Howe truss design. Similarly, Currin Bridge has a beautiful red and white color scheme that makes it a pretty attraction for tourists in town. To add to the aesthetic, five of the town’s covered bridges are listed on the National Register of Historic Places thanks to their captivating past.

While Quincy’s historical allure is enough to grant it a spot as one of Oregon’s cutest towns, there is still more to see. Tourists can enter Mother Nature’s embrace at the tranquil Row River Trail. Astray from urban hustle and bustle, this 15-mile trail is a slice of solitude where one can appreciate Oregon’s wilderness. After the walk, end the day with one of Saginaw Vineyard's delicious wines and you’ll see cuteness in everything!

Hood River

Beautiful view of Hood River, Oregon
Beautiful view of Hood River, Oregon

Hood River, gracefully set along the Columbia River Gorge, is a wellspring of outdoor experiences. Nicknamed the “Windsurfing Capital of the World,” there are endless ways to take in the cute natural surroundings. Experience the thrill with a session of kiteboarding or windsurfing on the Columbia River. Floating in the air, you’ll feel free of stress as you appreciate the fresh air and soothing environment. If you want to stay on land, Hood River’s many hiking trails are a treat for hikers in Oregon. Cutting through an array of landscapes, one can choose between various routes from the calming Multnomah Falls waterfall to the majestic Mount Hood.

With tourists pouring in, Hood River is infused with a lively aura prevalent no matter where you go. From craft breweries to country stores, there is a harmonious blend of relaxation and entertainment in town. Delve into the adorable vibes with a drive down Fruit Loop, a 35-mile loop centered around miles of pristine orchards. Many small stores along the loop sell fresh berries, apples, apricots, and other produce that you can take home to remember this cute town in Oregon.


A view looking down the main street in downtown, Sisters, via Bob Pool /
A view looking down the main street in downtown, Sisters, via Bob Pool /

If you enjoyed Hood River’s outdoor vibe, then Sisters should be next on your list. Named after a trio of towering peaks near town, Sisters is a home away from home in Oregon. Bustling with vibrant culture coveted by natural allure, the town is a treasure trove of fun activities. For nature enthusiasts, head out to the Cascade Mountains to witness breathtaking sights. With hiking trails such as Misery Ridge Trail Loop open for all, one can reach the mountain summit with panoramic views of Oregon’s countryside. Not into the effort of hiking? There’s no need to fret as you can hop in a car and drive the McKenzie Pass-Santiam Pass Scenic Byway. Spanning 83 miles, grand peaks, lava fields, verdant forests, and waterfalls are just a few of the formations on display.

That said, Sister’s true charm lies in its small-town ambience and adorable aura. Palpable throughout town, tourists often spend their day near Cascade Avenue. Overflowing with Western-themed eateries and quirky stores, the streets have a life of their own. So, grab a local souvenir or check out some art at the Hood Avenue Art District for a fun day out in Sisters!


Riverwalk in Siuslaw River in Florence, Oregon
Riverwalk in Siuslaw River in Florence, Oregon

Sharing its name with the tourist hub in Italy, Oregon’s Florence is not far behind. Reminiscent of its Italian counterpart, this small town boasts a beautiful coastline, panoramic viewpoints, and miles of sandy beaches. Attracting adventurers from across the country, the possibilities are endless when your surroundings are so enticing. Drop by Heceta Beach and spend the day surfing, swimming, scuba diving, or just sunbathing in the cool autumn sun. Among the many activities, Florence’s Sea Lion watching is one of the most popular. Home to Sea Lion Cave, tourists line up to watch 200 majestic sea lions in their natural habitat. The whole family will enjoy watching these massive creatures jumping into the water and interacting with one another.

If this doesn’t match your definition of a cute small town, you’ll be glad to know that Florence has a lot more to offer. Head into town for a lovely range of attractions such as the historic Heceta Head Lighthouse, the mystical Hobbit Trail, and dozens of adorable shops. So, whether it’s relaxing along the beach or window shopping with friends, Florence has you covered.

Gold Beach

Gold Beach, Oregon, USA - April 22, 2018: The waterfront at sunset, via davidrh /
Gold Beach, Oregon: The waterfront at sunset, via davidrh /

Two and a half hours from Florence, Gold Beach is another fascinating town that lives up to its name. As the Rogue River meets the Pacific Ocean here, one can find miles of sandy beaches full of life. Explore the never-ending coast through a range of pursuits such as hiking, sightseeing, swimming, and boating. Hikers can head out on the famed Cape Sebastian Trail, a short and steep route with a birds-eye view of the endless Pacific coast. If the waters seem enticing, get a firsthand experience with one of Jerry’s Rogue Jets boat tours. With high-speed jet boats cutting through whitewater waves among beautiful greenery, it is any adrenaline seeker’s dream. As the day comes to a close, couples can enjoy a cute evening at the town’s kissing rock, a romantic vantage point to watch the sunset with a loved one. If you’re not on a romantic vacation, Gold Beach’s lovely town vibe and unique eateries are just as fun for the whole family.


People walking to the shops with vehicles parked on the streets. September 30 2018, Ashland, Oregon, via Nature's Charm /
People walking to the shops with vehicles parked on the streets of Ashland, Oregon, via Nature's Charm /

Ashland is more than just a town, it's a reprieve of cultural vibrance in Oregon. Ranked in the top 10 of “The 100 Best Small Art Towns in America,” you are sure to fall in love with Ashland’s vibe. Award-winning theatres, boutiques, theatres, and eateries are all over the map complimented by Ashland’s friendly locals. So, delve into the culture with a visit to the Oregon Cabaret Theatre, a renovated old church now used to show plays and performances. Or, indulge in local art at the Schneider Museum of Art which is jam-packed with rotating exhibits of stunning pieces. With these and other sites such as the Ashland Library and ScienceWorks Hands-On Museum, cultural enthusiasts will find something cute at every turn.

Among the attractions, one that stands out is not a building but instead a world-famous event. Held between February and October, the Oregon Shakespeare Festival is the epitome of Shakespearean plays. Showcasing hundreds of theatre productions by thousands of renowned artists, tourists are drawn by the spectacular artistic allure. After the fest, end the day at Ashland’s peaceful Lithia Park which is a rustic sight during autumn months.

Appreciate all kinds of cute sights, activities, and events in these lovely small towns. Showcasing Oregon’s cultural charm and vibrant appeal, they are filled with loads of fun for everyone. For example, beach lovers will have a blast in Cannon Beach while Shakespeare can watch a show at Ashland’s festival. Moreover, away from the crowd and stress of urban living, these towns are perfect for a trip to Oregon!

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