Brick walled Storefronts are part of the view you will see when traveling down Main Street in Brownsville, Oregon, via GarysFRP /

7 of the Quirkiest Towns in Oregon

Oregon, quintessentially a Pacific Northwest state, is renowned not only for its natural wonders but also for the friendliness of its people in both big cities and small towns. From the coastline to the wine country valleys, McMinnville stands out. Here, wine country meets the breathtaking views of the Pacific Coast Range mountains, and the town hosts an annual UFO festival.

Tillamook, deeply entrenched in the aviation and dairy industries, boasts over 800 miles of navigable waterways. "Hitching a ride to Rockaway Beach" is as commonplace as breathing. This town draws millions of visitors each year for swimming, surfing, and traditional beach fun, offering sights like the magical Twin Rocks and mesmerizing sunsets.


Old western style architectural Masonic Lodge building in the rural town of Brownsville, Oregon.
Old western style architectural Masonic Lodge building in the rural town of Brownsville, Oregon.

Just a short journey from Portland, Brownsville, Oregon's third-oldest city, is home to nearly 2,000 people. The residents range from quirky to predominantly outdoorsy characters. A charming blend of history and natural beauty, the Brownsville Historical District is an excellent starting point amidst the timeless ambiance of its 1800s architectural landscape. The Linn County Historical Museum provides a pioneering heritage and insights into Brownsville's initial claim to fame as a historic railroad hub.

Nestled within some of the state's finest inland nature, you might recognize the sights that gained national attention with the release of "Stand by Me." Meanwhile, the Willamette Valley Scenic Bikeway offers a picturesque journey through these landscapes. The unique downtown area beckons with its old-fashioned storefronts and events, alongside modern culinary delights, such as the Caves Bistro and Wine Bar.

Gold Beach

Motel 6 in Gold Beach
Motel 6 in Gold Beach, via Nick Fox /

This idyllic coastal community, located 45 miles north of the California border and at the heart of America’s Wild River Coast, is where the majestic Rogue River meets the beautiful Pacific Coast. Gold Beach, with a population of 2,200—not 22,000—and serving as the county seat, boasts access to both the Pacific Ocean and the beautifully wild Rogue River. This location offers a variety of activities in the western section of the Wild and Scenic River, from navigating exhilarating rapids to taking a jet boat tour with Jerry’s Rogue Jets, complemented by riverside strolls where stunning scenery is a constant backdrop. The fall and spring months appeal to outdoor enthusiasts looking for both adventure and relaxation.

Visitors come for beachcombing along miles of pristine sandy beaches north and south of the town, especially in the summer and fall, which also offer opportunities to taste the bounty of the valley and enjoy some of the best fishing in the bay or up the Rogue. Known as "the staging area," Gold Beach provides a diverse array of attractions, from local craft beer at Arch Rock Brewing Company to mouthwatering barbecue, all enjoyed in a relaxing atmosphere. Thanks to its location in the “banana belt,” Gold Beach enjoys mild, predictable weather, making it a prime spot for whale watching in the winter. The Samuel H. Boardman State Scenic Corridor offers rugged coastline hikes with breathtaking views of towering cliffs and secluded beaches, remaining tranquil even in summer.


Hotel Oregon in McMinnville
Hotel Oregon in McMinnville

Nestled in the heart of Oregon's lush wine country, McMinnville is quirky in every sense, starting with its popular Wacky Willamette Valley Detours offering unique adventures for dreamers, drifters, and misfits, complete with mystery and a dash of the unusual. This deeply historic town allows visitors to experience a blend of old and new downtown, where 64 turn-of-the-century buildings house restaurants, wine bars, art galleries, and wineries.

A stone's throw from award-winning wineries, McMinnville is also a family-friendly destination, boasting attractions like the Evergreen Aviation & Space Museum, an impressive restaurant scene, and natural beauty at every turn where the wine country meets the panoramic views of the Pacific Coast Range mountains. Its annual UFO festival is a hit among global celestial enthusiasts and those who appreciate a mix of the weird, the wine, and the historical.

Pacific City

Pacific City, Oregon, seen from Cape Kiwanda
Pacific City, Oregon, seen from Cape Kiwanda

Situated just north of Lincoln City and neighboring Rockaway Beach further down the coast, this charming small town of around 1,300 residents boasts stunning coastal beauty and easy access to cerulean waters. Whether looking for a weekend getaway or a summer-long retreat, Pacific City focuses on sea-centric activities, scenic dining, and breathtaking sunsets. Popular activities include cruising and deep-sea fishing expeditions with Haystack Fishing, offering memorable excursions that often result in a bountiful catch of salmon or crabs, thanks to the friendly captain and his professional crew.

The expansive sandy beach is dotted with unique attractions, allowing bathers and loungers to watch their surfing companions or try their hand at sandboarding, a popular local sport, especially on the steep dunes at Cape Kiwanda. Pelican Brewing Company offers award-winning beers paired with delicious pub fare against the backdrop of Chief Kiawanda Rock, while Oar House Bar & Grill serves some of the Pacific Northwest's finest seafood, including fresh oysters, succulent crab legs, and rich chowders.


Hotel in Prospect, Oregon
Hotel in Prospect, Oregon, By Finetooth - Own work, CC BY-SA 3.0, Wikimedia Commons

Prospect, a southern Oregon town with just 560 full-time residents, serves as the nearest community and an idyllic base camp for epic scenery and adventures. One of its most breathtaking nearby attractions is Crater Lake National Park, home to America's deepest lake at 1,943 feet, nestled within the sapphire embrace of Crater Lake itself. The Prospect Hotel, a historic inn located just 25 miles from the park and approximately a quarter-mile from the Rogue River, offers stylish and comfortable lodging, providing a perfect starting point for exploring the surrounding natural wonders.

The town of Prospect is an ideal gateway to a range of grand adventures! History enthusiasts and photographers will be delighted by the old Peyton Bridge, while more active visitors can embark on the National Creek Falls Trailhead. Start your morning with delicious homemade pies at the Prospect Cafe and Trophy Room, set in a modest atmosphere. Whether you're taking a leisurely stroll through the scenic Pearsony Falls or hiking through the Avenue of the Boulders, don't miss the stunning Barr Creek Falls before winding down the evening at a cozy bed and breakfast with a welcoming front porch.

Rockaway Beach

Welcome sign to Rockaway Beach, Oregon.
Welcome sign to Rockaway Beach, Oregon.

Rockaway Beach, nestled on the Rockaway Peninsula, dances to its own unique rhythm and attracts visitors with its quirky charm throughout the year. From swimmers to surfers and divers, the phrase "hitch a ride to Rockaway Beach" has become synonymous with heading towards adventure and relaxation, drawing millions of visitors. This community is a favored family destination for traditional beach fun, located directly west of Portland. Start your day with a caffeine boost from R&R Espresso, perfect for energizing yourself as you watch over the kids playing on the beach, all the way up until a mesmerizing sunset over the ocean.

Rockaway Beach is famed for the 'three S's' along its seven miles of soft, sandy shores—a rarity in the state. Adventure-seekers can rent kayaks or paddleboards from the Surf Shop and glide over the waves. The iconic Twin Rocks, two picturesque sea stacks, majestically rise from the ocean, serving as a prime gathering spot for photographers and beachcombers alike, who scour the beach for polished rocks or seashells. The Rockaway Beach Old Growth Cedar Wetlands Preserve offers a tranquil retreat with lush scenery and shaded picnic spots along its trails. For the freshest catch and seafood specialties in the area, Old Oregon Smokehouse is unrivaled, promising a delectable dining experience.


Street view in Tillamook, Oregon
Street view in Tillamook, Oregon. Image credit Christa Boaz via iStock.

Nestled in a fertile river valley along the edge of Tillamook Bay, Tillamook is a delightful year-round destination, celebrated for its abundant natural resources. The town offers a plethora of "fresh from the source" dining options, including ocean-to-table and farm-to-table restaurants, set against a backdrop of beautiful lush landscapes perfect for refreshing strolls and oceanside beaches. Families, in particular, enjoy the calm waters on the bayside. Surrounded by rivers and a picturesque farmscape, there's an abundance of activities including fishing, farm visits, and a thriving dairy industry. This allows for delightful experiences such as enjoying ice cream on a hot summer day, pairing cheeses with wines, and touring the sophisticated Tillamook Creamery.

In Tillamook, everything exudes a local and welcoming vibe, from its WWII aviation history to the public airport that provides easy access and charter flights over the scenic landscape. The town's immense aviation museum, one of its most popular attractions, displays a collection of old airplanes, blimps, and pilot equipment that captivates visitors of all ages. With multiple hiking trails and over 800 miles of navigable waterways, visitors can embark on a riverside hike at Carnahan Park, enjoy kayaking, and engage in ample crabbing and clamming activities to prepare a delicious fire-cooked feast along the shore. Be sure not to miss the popular Tillamook County Pioneer Museum and the Tillamook Cheese Factory, which also doubles as a diner serving delicious meals throughout the day.

Oregon is filled with fascinating history and breathtaking sights, but it's the welcoming locals that truly make it stand out in the Pacific Northwest. Whether you "hitch a ride to Rockaway" or head to McMinnville for a wine-soaked getaway, the state offers an array of attractions. From stunning coastal gems to charming farming villages, Pacific City presents some of the Pacific Northwest's finest seafood, including fresh oysters, succulent crab legs, and rich chowders. Meanwhile, Tillamook delights visitors with its "fresh from the source" dining, ocean-to-table and farm-to-table options, and serene oceanside beaches.

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