Aerial view of fishing fleet in Yaquina bay harbor marina in Newport, Oregon.

10 Most Charming Cities in Oregon

Oregon is a scenic state with contrasts in nature, from snow-topped mountains like the tallest, Mount Hood, at 11,239 feet, to dramatic cliffs over the wild seas. You will also find deep river canyons, lush valleys, hundreds of state parks, 11 national forests, and fertile plains in between, along with over 6,000 lakes and 112,000 miles of rivers and streams. Needless to say, the state will satisfy your outdoor-starved soul with easy access to nature from its many charming cities. Take the historic Columbia River Highway, the "King of Roads," the Oregon Historic Trail that pioneered the western expansion in the US, or chase after the state's nine historic lighthouses.

Visit "Portlandia," the largest city that inspired artists like Gus Van Sant, Matt Groening, Chuck Palahniuk, Beverly Cleary, and Stephen Malkmus, or Salem, the film setting for "One Flew Over the Cuckoo’s Nest." Enjoy attractions like art scenes, cultural sights, and seafood galore, and head nature side with campsites, countless miles of trails, waterfalls, and wildlife surrounding these charming cities.


People walking to the shops with vehicles parked on the streets, Ashland, Oregon.
Downtown Ashland, Oregon. Image credit Nature's Charm via Shutterstock

    Ashland is a fantastic small city in picturesque southern Oregon, near the border with California. The hub of arts and culture sees thousands flock just for the annual Tony Award-winning Oregon Shakespeare Festival. Stroll around the lively streets every other day, and you will still stumble on a different festival or event like the Ashland Independent Film Festival. Others come for the gateway to Oregon's Rogue Valley with hiking trails and vineyards but linger for Ashland's attractions like vintage shopping and wines.

    Immerse yourself in its European vibe along the scenically winding, hilly streets with terraced cafes, and take a cultural stroll through top-notch art galleries, museums, and flea markets. The inviting city of Ashland is abuzz throughout the year with other top attractions like the linear Lithia Park, the historic downtown district, and wintertime skiing at the nearby Mount Ashland. Thanks to the world-renowned festival, you will never be short of hotels and upmarket restaurants in between charming local places.


    Aerial view of the Old Mill District in Bend, Oregon.
    Old Mill District in Bend, Oregon.

    This charming and thriving city with around 100,000 locals in Central Oregon on the east side of the Cascade Mountains is a popular getaway into Oregon's high desert region and Smith Rock State Park. Enjoy easy access to this natural world, a mecca for rock climbing and hiking under 30 miles north, but first, linger around the charming city with a unique cultural tone. This active community of nature lovers is also a colony of artists, responsible for the beautiful cityscape with attractions and pristine nature. Enjoy eclectic shopping opportunities like boutiques and art strolls through Bend's many galleries.

    The nearby mountains allow for immersive days in the sunny outdoors through plentiful pursuits for any taste. Access the Bend Whitewater Park from the Old Mill District for water fun with tubes, boats, and surfers, or take on the hiking and biking trails along the city's waterway. The naturally charming Deschutes National Forest hugs the city south and west, while its dense forest-covered mountains nearby disclose Newberry National Volcanic Area and Mt. Bachelor Ski Resort, along with Tumalo Falls in the city's backdoor forest.

    Coos Bay

    Charleston Marina in Coos Bay Oregon
    Marina in Coos Bay Oregon.

    Coos Bay, a small city of under 16,000, is unlike any other in Oregon, starting with its unique coastal location amid small towns. Visit this largest seaside city in the state to explore the scenically rugged southern coast with a plethora of nature pursuits and attractions under a close-bounded community feel. Take a stroll along the prettified streets with candy factories, history museums, beautiful public parks, and a charming downtown district. There are many quality local restaurants and the Egyptian Theatre for an entertaining evening.

    Visit this attractive city by the water for its dramatic nature, like the ocean and the stunning Oregon Dunes National Recreation Area just to the north, with picturesque dunes of over 500 feet in height. You can even hike or backpack through the entire stretch all the way to Florence, another charming must-visit city on this itinerary. Coos Bay is a scenic playground for nature lovers and sightseers, including the historic Cape Arago Lighthouse by the ocean, which blends perfectly into the postcard setting. Drive along the Cape Arago Highway, Sunset Bay, and Shore Acres for the best vistas of diverse nature and landscapes.


    Aerial view of the Benton county courthouse in downtown Corvallis, Oregon with the mountains in the background
    The Benton county courthouse in downtown Corvallis, Oregon.

    The bustling college city of Corvallis, in the Willamette Valley of Central Oregon, sits surrounded by charming landscapes and vast views. Check out the acclaimed Oregon State University's sprawling campus, over 150 years old, whose heartbeat thrums through the streets with a youthful ring and plentiful attractions. Join a historical tour around the campus and watch the energetic Beavers compete in athletic events. Visit on the weekend for a spry spirit or through the work week for a tranquil and studious appeal.

    The lush agriculture around Corvallis adds a fresh bite to the food scene, which you must discover at local restaurants across the city with farm-to-table cuisine. Enjoy a classic hike to Mary's Peak and return downtown for a number of fine dining options and handsome pubs. There are plentiful bookshops and cafes to support the culture, as well as student-friendly prices. Visit the upmarket part of town for a riverfront stroll along the Willamette River for lovely views, and drive to the farms with sprawling orchards and wineries with vineyards for tastings and strolls amid easy-on-the-eye scenery.


    The Willamette River flows beside a bike path in Eugene, Oregon.
    Bike path in Eugene, Oregon.

    Eugene, the state's third-most populous city, bursts with charm at the seams, starting with its descriptive slogan, "A great city for the arts and outdoors." Set quaintly along the Willamette Valley amid mountains, Eugene is a growing city of 175,000 locals who enjoy plenty of hiking, biking, rafting, and climbing. The sizable city is often called the best place to live in Oregon, where you can still walk everywhere or paddle without congestion or fumes. The thriving forests are a dreamy place to spend a day of sightseeing strolls and picnicking that feels a world away from civilization.

    Head to the peaks for hiking and rock climbing, and come back in the evening for the lively entertainment scene. The great city with a reputation for the arts is a delight on a stroll, with decorated streets and hotspots like the Symphony, Opera, Ballet, Mozart Players, and Willamette Repertory Theatre. Eugene is also big on academia, with its own University of Oregon that extends into great programs for tourist enjoyment like the Jordan Schnitzer Museum of Art and the Eugene Science Center. Visit the Mount Pisgah Arboretum and the Museum of Natural and Cultural History, and come back in time for the Oregon Bach Festival and The Shedd.


    Beautiful view of Siuslaw River Bridge and the river in historic old town Florence, Oregon.
    Siuslaw River Bridge, Florence, Oregon.

    The enchanting city of Florence, with only about 9,500 residents, will enchant anybody, regardless of age, group, or pursuit. Find everything you need to have the best time and leave with a feeling of nostalgia after its pristine beaches and outdoor scenery. Enjoy plentiful hiking amid the verdant green landscape, fresh air, and sub-tropical climate that will recharge and rejuvenate. Visit the famous Siuslaw River Bridge and the iconic lighthouse, and take a leisurely stroll through the arts and culture-strewn streets with endless attractions like museums and the annual Rhododendron Festival since 1908.

    The popular and diverse city retains a small-town charm thanks to its low population, like the central, soulless commercial strip with eclectic finds and cute eateries, or the secluded Old Town, quaintly painting a whole other portrait of Florence. There is more than enough romance along the picturesque harbor along the Siuslaw River for a delightful stroll with fascinating water views, sunsets, and the nearby Dunes National Recreational Area.


    Aerial view of Medford, Oregon with the mountains in the background
    Oregon's Rogue Valley, Medford, Oregon.

    Medford, a captivating city in the heart of southern Oregon's Rogue Valley, with its 87,000 citizens, overflows with rural charm. It is a tourist destination for the famously grown pears, markets with fruit baskets galore, and a thriving dairy industry with renowned blue cheese. Did you just get an instant picnicking scene in your mind? Medford's easy-going vibe along the streets extends into laid-back activities in the beautiful, natural surroundings, like farm visits and trails. Visit the award-winning Rogue Creamery and stop by Harry & David Country Village for local produce and amazing chocolate truffles, as well as local wineries and breweries along Medford's Bear Creek Wine Trail and Ale Trail.

    This provincial city in southern Oregon is your gateway for fun adventures around the Rogue Valley. Medford's appeal spans all seasons, like the defining Rogue River when city life moves to the banks for the summer. Stroll along the scenic waterway interlaced with history, including the native cultures that still live here, and climb the plateaued monoliths of Lower or Upper Table Rock above the western banks for the best panoramic views. The shimmering blue waters of the inspiring Crater Lake National Park with its infamous caldera are only 90 miles away.


    Fishing fleet in Yaquina bay harbor marina in Newport, Oregon
    Yaquina bay harbor marina in Newport, Oregon. Image credit steve estvanik via Shutterstock

    Newport is a captivating small city of 10,000 along Oregon's central coast, with plentiful family-friendly pursuits and attractions. Make some memories at Oregon State University's Hatfield Marine Science Center, the world-class Oregon Coast Aquarium, and "Ripley's Believe It or Not!" Newport is a fantastic place to live and visit for the ages, that you can easily discover on foot, and has vast natural outdoor ventures nearby. Explore places like the marvelous Yaquina Head Outstanding Natural Area and the equally beautiful Ocean to Bay Trail.

    Do you feel that maritime culture on the streets? Visit its source at the historic bayfront, with a huge fishing fleet calling Newport home and a delightful seafood scene throughout town. Enjoy waterside dining in any style, where you can even sight frolicking sea lions in the bay area. Check out the kitschy shops and cute art galleries on a stroll through the welcoming atmosphere that extends onto the laidback ocean beaches, an idyllic affair for delightful lounging.


    Portland, Oregon Cityscape at Sunset
    Portland at sunset.

    Portland is a polished riverside city, the largest by population in Oregon, and the cultural capital of the Pacific Northwest. The city is an esteemed national destination for its international art scene, striking waterfronts, and charming attractions. Visit the unique nature in this northern part of the state, from rugged shores to open spaces, rose gardens, and the expansive Forest Park near the center with over 5,000 acres to explore. Enjoy quick access to the astounding Columbia River Gorge with a waterfall and the mighty Mount Hood, Oregon's peak, within a two-hour drive.

    Portland is a passionate and creative community, with the unofficial motto "Keep Portland Weird." The bustling and thriving downtown is lined with top-notch local businesses with a focus on quality, like Portland-based and nationally recognized Powell's Books and Voodoo Donuts. With nicknames like Stumptown and the City of Roses, the diverse city will give you what you desire with sights, like the International Test Rose Garden, the Portland Japanese Garden, and sea stacks on the nearby Oregon Coast.


    Aerial view above Salem Oregon in the Fall season
    Salem, Oregon in the fall.

    The enchanting state capital amid the Willamette Valley has a lot going for it that attracts heaps of culture fans, like its easygoing university vibe, a riverside waterfront, and an outdoor paradise along the Willamette River. Salem boasts a distinct character like no other through a unique array of cultural and natural attractions. Enjoy easy access between Portland and Eugene for a memorable first-time experience that will never be the same when you visit again.

    Visit the eye-catching Oregon State Capitol with its tumultuous backstory and the iconic gilded Oregon Pioneer crowning the top. This stately building with stunning grounds houses a beautiful collection of murals that paint a picture of the state's history. Other notable hot spots include an abbey, a captivating sight perched on a hill, as well as the refreshing state park surrounding Salem for outdoor activities and nature walks.

    This state of endless charm has no sales tax and was "born" on Valentine’s Day in 1859. The ninth-largest state with 98,380 square miles is also the 27th most populous, with charming neighbors like Washington, Idaho, Nevada, California, and the Pacific Ocean. Find the nation's only scenic bikeway program in Oregon with 17 scenic bikeways, while Hells Canyon is North America's deepest river-carved gorge at 7,913 feet deep. There are also over 750 vineyards throughout the state, with a wine and ale trail, 72 different varietals of wine grapes, and great access from Ashland, Corvallis, and Medford. Visit Medford, the biggest pear grower of the state's fruit, with charming markets and mean pear cider and brandy. Love Shakespeare? Then you are meant "to be" in Ashland, with its Tony-winning festival in the man's honor.

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