Aerial view of Brookings, Oregon.

9 Of The Most Hospitable Small Towns In Oregon

Oregon's colorful coast, lush forests, heavenly mountains, and verdant valleys have been supporting humans for several thousand years. First, it was the Native Americans, then the Spanish, then the British, and then other Americans on the Oregon Trail. Now, it can be for you to discover Oregon hospitality. Thankfully, you need not risk hypothermia or dysentery like the pioneers. You can see this remarkable state from safe and cozy towns. See where to stop on this Oregon trail.

Cottage Grove

Currin Covered Bridge Near Cottage Grove, Oregon State, US
Currin covered bridge near Cottage Grove, Oregon.

What sounds more idyllic than Cottage Grove? Luckily, its name matches its look. This 10,000ish-person community sits in the Willamette Valley and has cottages, groves, and vibrant businesses like Jack Sprats Restaurant, The Axe and Fiddle, and Cottage Theatre. Moreover, CG is a mix of old-school residents and hip newcomers so you can find your crowd among the cottage dwellers or the bohemian grove protectors. Lastly, what you cannot find in CG you can get in Eugene, which is just about 20 minutes north of town. Take the scenic route over six surrounding covered bridges. Cottage Grove is called the "Covered Bridge Capital of The West."


At the market in Old Town Florence, Oregon.
At the market in Old Town Florence, Oregon.

It may not be Florence in Italy, but Florence, Oregon, is a lovely seaside community with its share of elegance. Walkable beaches and streets, lined with shops like the Purple Pelican Antique Mall and eateries like The Pono Hukilau, are flanked on all sides by woods and lakes that offer many outdoor activities. Florence caters to roughly 9,000 year-round residents, so in addition to quaint and scenic haunts, it has bigbox stores, an airport, and a medical center. Although hospitable to humans, Florence is not very hospitable to whales. The community became infamous in 1970 when authorities used dynamite to blow up a dead beached whale. In 2020, residents commemorated this quirky part of their history by creating Exploding Whale Memorial Park.


City Center in Independence, Oregon
City Center in Independence, Oregon. Image credit: Doug Kerr via

Spend a day - or a life - in Independence. This Willamette River community is home to around 10,000 people from many cultures, translating to fantastic restaurants and heritage sites. Mangiare Italian Restaurant, Cafe Brarlin, Gilgamesh Brewing, San Antonio Mexican Restaurant, Lucky Dragon, Jubilee Champagne and Dessert Bar, and Los Dos Amigos Hacienda are among its diverse eateries, while the Dr. John E. and Mary D. Davidson House, a relic of pioneering days, and the Independence Heritage Museum, which honors the community's large Hispanic population, provide historic importance. Ironically, Independence is attached to Monmouth, a community with a similar population and vibe. It is hard to go wrong with either.


Prineville in Crook County, Oregon
Prineville in Crook County, Oregon. Image credit: Mïk Watson from Ocean Shores via Wikimedia Commons.

Located where the high desert meets pine forest, Prineville is an outdoor adventurer's oasis with a rapidly growing population. It gained more than 3,000 residents between 2000 and 2020, which puts its current population a notch above 10,000. Traditionally a ranching and logging community with personalities to match, Prineville became an unlikely techno haven when Facebook and Apple built data centers on a bluff above town. These attracted tech bros, who were followed by other young professionals taking advantage of cheap rural housing. From the Silicon Valley on a bluff to the actual valley below, Prineville has an environment for everyone.


Cascade Avenue in downtown Sisters, Oregon.
Cascade Avenue in downtown Sisters, Oregon. Image credit: Finetooth via Wikimedia Commons.

Become siblings with Sisters, a tiny community about 35 miles from Prineville. Home to roughly 3,000 people and a similar ecosystem as its sister city (minus data centers), Sisters is a mix of sleepy small-towners and hardcore adventurers. It is perhaps the only place in America where quilters have the same prestige as hikers, bikers, and mountain climbers. Alongside shops such as Stitchin' Post, Sisters hosts a quilt show that is going into its 49th year. Other attractions include Proxy Falls, a 226-foot waterfall in the Willamette National Forest, and the Three Sisters, a triplet of the Cascade mountains for which the community was named.


Downtown Amity, Oregon
Downtown Amity, Oregon. Image credit: M.O. Stevens via Wikimedia Commons.

Situated just north of Independence in the Salem region, Amity might, at first, clench, seem like a place for a bathroom break on the way to larger cities. But your break might last an hour, a day, or a lifetime once you discover the numerous orchards and vineyards in the area. A mini Garden of Eden, Amity claims Green Knoll Orchards, Guerrero Farms, Ruddenklau Farms, Brooks Wine, Coelho Winery, VinTyr, and many other fruitful - and potentially sinful - attractions. Of course, given its proximity to Independence, Salem, and even Portland, Amity is not too far from Earthly goods. You can have the best of both worlds.

Lincoln City

Lincoln City, Oregon
The beautiful coastline of Lincoln City, Oregon.

Another coastal Oregon retreat, Lincoln City boasts beautiful beaches, roughly 10,000 residents, and thousands of tourists during warm months. Despite its periodic congestion, LC, like many Oregon haunts, is surrounded by greenery in which you will not see another person. It is the gateway to the Valley of the Giants, a remote 51-acre preserve of giant geriatric trees and all the nature that they nourish. You can also escape the crowds on the Pacific Ocean or Devils Lake and by strolling through town during the arguably more beautiful off-months. Spring to LC in the spring or fall for LC in the fall.


Main Street in downtown Jacksonville, Oregon
Main Street in downtown Jacksonville, Oregon.

As one of the smallest communities on this list, Jacksonville, a "city" of 3,000 people, can be a relaxing reprieve from a boisterous life. A visitor can stop in for a read at Rebel Heart Books or a glass of wine at Red Lily Vineyards. Yet it can also complement a boisterous life via Bella Union Restaurant, a popular pizzeria and tavern, as well as Forest Park, a 1,080-acre haven for runners, hikers, and mountain bikers. Plus it is a hop, skip, and a jump from Medford, a vibrant city with about 86,000 residents. Although part of the state's "deep south," Jacksonville has purple politics and progressive festivals like Country Queer Summerfest and the Britt Music and Arts Festival.


A fishing boat going out to sea in Brookings, Oregon
A fishing boat going out to sea in Brookings, Oregon.

A quieter coastal community, Brookings has around 6,700 residents and sits in extreme southern Oregon. For some people, it might be even too quiet, especially during the rainy season. For others, it is a miraculous tropical enclave of the Pacific Northwest full of palm trees and sandy beaches. Brookings has its own subtropical climate courtesy of a weather phenomenon dubbed the "Brookings effect." After exploring those natural wonders, visitors can see similarly stunning commercial haunts like Chetco Brewing Company and the Redwood Theater. Postcard-worthy views and deathbed-worthy memories abound in Brookings.

Bold and beautiful Oregon has been attracting vagabonds for millennia. Modern explorers need not suffer like their forefathers, though. They can stay at a number of supremely hospitable towns spread across Oregon's diverse terrain. From Brookings on the coast to Cottage Grove in the valley to Prineville in the desert to Sisters in the mountains, Oregon can cover all bases during a Pacific Northwest adventure.

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