2025's 11 Best Small Towns To Visit In Oregon
When Meriwether Lewis and William Clark concluded their legendary journey across the continent, they arrived at the edge of one of the nation’s last great wildernesses: Oregon. Nicknamed the Beaver State for its once-thriving beaver population, this region has long been defined by its rugged coastlines, snow-draped mountains, and fertile valleys. Today, 2025's best small towns to visit in Oregon embody the nature-vibrant spirit and fortitude of this majestic state. This year, travelers will find welcoming communities amidst the rivers, mountains, and forests that compose this state, each offering its own blend of charm, history, and hospitality. Whether you are exploring windswept shores, hiking through towering evergreens, or simply enjoying the slower pace of life, the best small towns to visit in Oregon will make you feel like an adventurer on their last stop of their epic journey.
Jacksonville
Around five miles from the city of Medford in the magnificent heights of the Siskiyou Mountains, the idyllic small town of Jacksonville has captivated newcomers due to its status as a National Historic Landmark. Back in the 1850s, gold deposits from the nearby mountains have long attracted various settlers and miners before Oregon officially became a state. Nowadays, Jacksonville is famous for annual festivities such as the Britt Music & Arts Festival, which occurs year-round and includes lively musical performances like reggae and classical genres. For a deeper immersion into Jacksonville’s Historic District, you can book the summertime Trolley Tours with 45-minute trips throughout the area’s informative history and architecture.
You might also be interested in touring the well-maintained abode of Cornelius C. Beekman, one of Jacksonville’s founders, in the Beekman House to see the life and activities of this man. Furthermore, to the south of Jacksonville lies the Oregon Caves National Monument and Preserve, an awesome and astonishing subterranean system made of highly complex marble and other mineral structures that have existed for thousands of years.
Silverton
Only about 15 miles from Salem, the splendid and silver-bright town of Silverton is an affable and astonishing destination that many know as Oregon's Garden City. Here, one can traipse and gallivant through the Oregon Garden, an 80-acre Eden of horticultural splendors, with several specialty plots like a Children's Garden and a Pet-Friendly Garden. Furthermore, the Oregon Garden often hosts a handful of events throughout the year, such as the Arts in the Garden from May 24th to September 1st, 2025.
Beyond the blooming blossoms of the Oregon Garden, travelers will enjoy adventuring in the Silver Falls State Park, with over several miles of trails and treks traversable on foot, horseback, or bicycle as you admire ten or so silvered waterfalls around Silverton. Last but not least is the Canterbury Renaissance Faire, a medieval-themed role-playing event in July, where one can fulfill their dreams of knights and chivalry on the battlefield.
Sisters
Sisters is a serene and stellar town that is adjacent to a trinity of volcanic peaks also referred to as the Sisters. Where 1880s facades are painted over with a smorgasbord of modern artworks, Sisters thrives with artistic nuance in the Cascade Mountains in central Oregon. Mostly, it is famous for its proximity to the high-desert terrain of Oregon, specifically Smith Rock State Park, with its arid desert biomes. On the other hand, you can also go walking through the ponderosa pine forests of Deschutes National Forest for more forested adventures in Oregon.
When traversing routes such as the Pacific Crest Trail, you can discover more of Oregon’s fascinating and intriguing biodiversity, especially when venturing into the waterfall-filled wilderness of the Willamette National Forest. Best of all, you can ski and snowboard down the winter-draped slopes at the Mt. Bachelor Ski Resort.
Hood River
Perched at the spot where the Columbia River Gorge meets Mount Hood, Hood River remains a vibrant and verdant destination celebrated as the windsurfing capital of the world, where both novices and pros ride strong, steady gusts in the air from spring through early fall. The Hood River Fruit Loop continues to delight visitors with a scenic 35-mile rural drive dotted with orchards, lavender fields, wineries, and cideries, making Hood River one of Oregon’s most charming farm-to-table experiences.
For further adventures in the outdoors, one can reach Mount Hood and propel themselves into the sky when traversing both the Timberline and Cooper Spur Trails. Additionally, the Columbia Gorge Hotel & Spa, set amid lush gardens along the river, still offers a peaceful, art-deco retreat for travelers seeking relaxation from all their hiking and flying escapades.
Cannon Beach
One will be roaring and booming their way through life once they get a glimpse of the amazing town of Cannon Beach. Just about 90 minutes from Portland, this small town has remained one of the most postcard-perfect destinations to visit. The iconic Haystack Rock still stands tall at 235 feet, accessible at low tide, and continues to enchant newcomers with protections in place to preserve its marine gardens and nesting seabirds.
Just up the coast, Ecola State Park contains a number of tidepools and other amenities, with offering sweeping views of the coastline and access to trails like Clark’s Point of View for a better immersion into Oregon’s coastal habitats. Meanwhile, Hug Point State Recreation Site features a scenic beach, picnic spots, and a touch of local history as a former stagecoach route hugging the cliffs.
Baker City
Set amid the rolling Blue Mountains, Baker City remains Eastern Oregon’s inviting “basecamp” for travelers exploring Oregon’s history and its wilderness. The Baker Heritage Museum, housed in a historic 1920 Natatorium, presents immersive exhibits on timber, mining, agriculture, Chinese settler life, and even a renowned rock and fossil collection that is open daily from March to October.
Outside the town’s bounds, the Farewell Bend State Park preserves the ruts left behind from wheel wagons on the Oregon Trail, in addition to offering rustic camping in covered wagons or teepees. For even more adventures in the wildernesses of Oregon, you can brave the humungous heights of both the Elkhorn and Wallowa Mountains to reach the summits of these majestic landmarks.
Joseph
Tucked into the foothills of the Wallowa Mountains, the small town of Joseph—often called the "Little Switzerland of America"—thrives as a gateway to alpine sceneries and some of Oregon’s best cultural celebrations. Each July, the town hosts the Tamkaliks Celebration, a vibrant festival featuring drumming, dancing, and feasting in honor of the Nez Perce heritage. Meanwhile, the Wallowa County Museum opens from Memorial Day through September, offering insightful exhibits and year-round tours by appointment on the cultures, traditions, and past stories that compose this town, so named after Chief Joseph of the Nez Perce.
Nearby, the towering depths of Hells Canyon beckon adventurous souls to one of the deepest canyons in North America. Last but not least, the much-anticipated Mule Days in neighboring Enterprise will enliven the region in September.
Yachats
Yachats is a tranquil and meditative coastal town poised where forested slopes meet the restless Pacific Ocean. For years, it has captivated travelers with its unique natural displays and scenic tranquility, and one of its most defining highlights is Thor’s Well, a dramatic coastal sinkhole best seen at high tide or approaching storms.
For sweeping views and a journey through arboreal coastal terrain, the Amanda Trail ascends to the soaring Cape Perpetua Overlook, rewarding hikers with awe-inspiring panoramas and interpretive storytelling along the way. From the Cape Perpetua Visitor Center, the easy Captain Cook Trail loop leads to other natural landmarks such as Cook’s Chasm, Spouting Horn, and rich tidepools filled with life at low tide.
Ashland
Where Southern Oregon’s rolling hills thrive and shine, the small town of Ashland pulses with artistic energy and ambiance, especially during the Oregon Shakespeare Festival, transpiring from the month of March all the way to October. Each season of the festival presents thrilling productions of not just William Shakespeare’s plays but also other reimagined classics and musicals like Into the Woods.
For more still and stationary masterpieces, you can wander through the Schneider Museum of Art to admire the magnificent artworks therein. Similarly, you can browse creative pieces at galleries like Ashland Art Works. When it comes to the outdoors, Lithia Park offers peaceful green paths and a bridge into the natural calm of the Siskiyou Mountains and Rogue River Valley.
The Dalles
Resting at the eastern gateway of the Columbia River Gorge, The Dalles radiates deep history and striking landscapes, making it one of the best towns to visit in Oregon. The Fort Dalles Museum and Anderson Homestead highlight the early pioneer livelihoods of Oregon’s citizens from the mid-1800s to the early 20th century.
To the east of town lies the Deschutes River State Recreation Area, where the Deschutes River is connected to the much larger Columbia River, which delineates the state border separating Oregon from Washington. Most important of all is the Dalles Dam Visitor Center, which provides a comprehensive tour of the dam and the sights that regulate the flow of the Columbia River.
Astoria
Long after the classic film The Goonies was filmed in this coastal small town, Astoria continues to charm newcomers with its maritime history, riverside ambiance, and exquisite setting that reminds one of home. The Columbia River Maritime Museum continues to impress visitors with its exhibits on Coast Guard operations, the perils of the Columbia Bar, and even the floating Lightship Columbia, a floating lighthouse that marked the mouth of the Columbia River from 1951 to 1979.
One can ascend the spiraled staircase of the Astoria Column, a 125-foot-tall monument that, similar to Trajan’s Column in Rome, offers artistic sights and spectacles to be mesmerized by. History continues to be relevant in places like Fort Clatsop, where the Lewis and Clark Expedition in 1805-06 encamped in the winter.
2025’s best small towns to visit in Oregon compose a vibrant tapestry of natural wonders, cultural richness, and invigorating hospitality that will instill memories and merriment in you. From Cannon Beach’s iconic coastlines to Yachats’s churning wells, each of these destinations embodies Oregon’s diverse ingenuity and its beautiful wilderness sceneries for locals and outsiders to all enjoy. Between Baker City’s pioneer fables and Ashland’s theatrical grandeur, these amicable and amazing small towns promise moments of discovery and heartwarming welcomes that, in 2025, will allow you to see Oregon’s quieter corners, where adventure, history, and beloved festivities are in abundance.
