Oregon is a treasure trove of charming towns steeped in history and surrounded by breathtaking natural landscapes. In this post, we’ll guide you through ten of our favorite old-world towns in the state, highlighting their rich histories, scenic landscapes, and the unique experiences they offer.

Whether you’re seeking a cultural getaway, a deep dive into history, or a peaceful retreat where you can simply unwind and reflect in a beautiful setting, each of these historical towns has something for you.

Ashland is a delightful small town in the Rogue Valley known for its rich cultural heritage and vibrant arts scene. Its elegant Victorian architecture and quaint downtown area exude will have you feeling like you’ve stepped back in time.

Ashland, marked as one of the top 10 of “The 100 Best Small Art Towns in America”, becomes a magnet for Shakespeare lovers near and far from May through October as they put on their famed annual Shakespeare Festival. If a 5-month display of Shakespearean works amidst the historic buildings of downtown and its surroundings isn’t enough to transport you back in time, we don’t know what is!

For nature lovers, Ashland is home to Lithia Park. This rather massive, scenic park in the town center features pickleball courts, duck ponds, a swimming hole on Ashland Creek, and stunning greenspaces. It’s the perfect place for a picnic. Careful! Locals often try to trick visitors into drinking from Lithia Fountain, a harmless yet extremely sulfurous watering hole.

We highly suggest spending at least a couple of days in Ashland in order to fully absorb its vibrant personality. Book a room at Ashland Springs Downtown. The historic hotel is right downtown, within a stone’s throw of Lithia Park and the famous Cabaret Theatre, a hot spot for theater lovers that radiates old-school jazz-era charm.

Astoria

Where the Columbia River meets the Pacific Ocean, Astoria is another must-visit historic town in Oregon. Known for its maritime past and 19th-century architecture, a visit to Astoria is sure to evoke a sense of nostalgia. As you meander downtown, admire the handsome Victorians and historical buildings that populate the streets, some of whose walls boast colorful old-school murals and vintage advertisements. So fun!

To get a bird’s eye view of the bustling town below, pay a visit to Astoria Column. If you have it in you, climb the 164 steps to the top for breathtaking panoramic views of the town and its surrounding landscape.

Afterward, Astoria Riverwalk is a great spot for a walk or a leisurely bike ride along the water. This scenic pathway follows the Astoria & Columbia River Railroad along the town’s history-laden waterfront. The Riverwalk takes you right past the Columbia River Maritime Museum. Stop there for a peak into the area’s maritime heritage. Other attractions on the walkway path include the Astoria-Megler Bridge and Astoria’s Maritime Memorial.

When it comes to accommodations, the historic Hotel Elliott is our top pick. This beautifully restored boutique hotel in the heart of downtown offers the perfect blend of classic charm, modern comforts, and proximity to local attractions.

Jacksonville

Welcome to Gold Rush country! Jacksonville, Oregon, is an old-time-y Oregon town you can’t miss. Steeped in gold mining history, the quaint streets are lined with Victorian homes and historic storefronts. The community of Jacksonville takes pride in its local arts, foodstuffs, and epicurean way of life. From cute wine and cheese shops to mom-and-pop museums to a range of inviting eateries, it’s all local, local, local!

One of our favorite ways to explore Jacksonville is via trolley tour of the downtown area. Your guide will narrate the town’s gold-boom history and tell you all about the wonderfully unchanged historic architecture. History buffs will also relish a visit to the Beekman Bank Museum and the Beekman House Museum for a glimpse into the life and commerce of the town’s wealthiest pioneer family.

If you find yourself in Jacksonville during the summer months, snag a ticket to the annual Britt Music & Arts Festival. It’s a three-weekend festival that has been going on since 1963! Experience the best of jazz, blues, folk, bluegrass, country music, and more in the gorgeous, naturally-formed outdoor amphitheater in the center of town.

Looking for a place to stay? Book a room at the Jacksonville Inn. This romantic boutique hotel has been serving travelers for over a century, and its in-house wine bar is the perfect place to relax, unwind, and appreciate the beauty of local and regional wines.

Cottage Grove

Cottage Grove, Oregon, is a picturesque town that transports visitors to another time. Known as the “Covered Bridge Capital of Oregon,” Cottage Grove features stunning covered bridges that date back to the early 20th century. You can walk (or bike!) across these architectural gems and, when you’re done, enjoy a some time meandering through the downtown area with its vintage storefronts and historic buildings.

If you find yourself downtown on a weekend, pop into the Cottage Grove Museum. The museum showcases the town’s rich history, including its role in the Oregon Trail, which brought many a covered wagon loaded with brave pioneers to the West Coast in the mid-1800s.

For an escape into nature, grab a picnic from Urban Kitchen and head to Cottage Grove Lake. There are lots of wonderfuk hiking trails with stunning views of the water and, in warmer months, you can swim and/or water ski in the lake!

Looking for lodging? We suggest renting a cute Airbnb or camping lakeside at Pine Meadows Campground.

Joseph

At the base of Oregon’s picturesque Wallowa Mountains lies the town of Joseph. Steeped in Old Western cowboy culture and the rich heritage of the Nez Perce indigenous people, Joseph’s historic streets and surroundings transport visitors right back to the 1800s.

The historic wooden storefronts that line the downtown area, once a hub for agricultural and timber commerce, have since become a hot spot for artists of all kinds. Admire the life-sized bronze statues on Main Street that tell the town’s history and pop into galleries and shops full of handmade jewelry and native crafts. You could even sign up for an artsy workshop at the Joshephy Center for Arts and Culture!

On your visit, check out the National Historic Oregon Trail Interpretive Center. You will find engaging exhibits and live demonstrations that explore the history of the pioneers who braved the journey West from Missouri.

At the end of the day, settle into a cabin at Wallowa Lake Resort for a relaxing stay with unbeatable views of the nearby river, lake, and mountains. If you have time, enjoy the beautiful lake via hike, swim, or boating excursion at Wallowa Lake State Park.

Florence

With a rich history dating back to the mid-1800s, Florence is a picturesque coastal town you can’t miss. The 19th-century architecture of the Old Town District, now occupied by cute shops, galleries, and seafood restaurants, still bears marks of the region’s fishing and logging history

A visit to Florence wouldn’t be complete without a trip across (or beneath) the Siuslaw River Bridge. This Art Deco steel and concrete bridge was built in 1936 and is absolutely breathtaking. Drive, bike, or walk across it. Alternatively, rent a kayak or a paddleboard for a view from below. Nearby, the Siuslaw Pioneer Museum invites visitors to explore the area’s past, from the time when the indigenous Siuslaw people inhabited the region through its rich Pioneer history and into the present.

When you’re done soaking in the historical significance of this waterfront Oregon gem, indulge in an aimless wander through downtown. Check out the Backstreet Gallery artists co-op, poke your nose into Books ‘n’ Bears (a cute used book shop), and stop into the Krab Kettle (an old-school fish market that dates back to 1962) for some seriously delicious clam chowder.

Staying the night? Book a stay at Edwin K Bed & Breakfast. This 1914 Craftsman-style home turned antique-filled inn offers a cozy stay and a central location in the heart of the Old Town.

Sisters

Sisters, Oregon, is an 1800s logging and agricultural town whose wooden buildings and old-world feel reflect the area’s frontier roots loud and clear. It’s surrounded by the breathtaking beauty of the Cascade Mountains, making it the perfect destination for history buffs and nature lovers alike.

Dive into the town’s rich heritage at Sisters Historical Museum. Here, you’ll learn all about the early pioneers and Native Americans who inhabited the region. Afterwards, roam through the historical streets of downtown and don’t miss a stop into Sisters Coffee Company. Established in 1989, the wooden building that houses this local coffee shop looks like something out of a cowboy western. We love that everything from the baked goods to the long, wooden community table is as local as it can get.

If you find yourself in Sisters in mid-June, make sure to grab tickets to the Sisters Rodeo, also known as “The Biggest Little Show in the World.” It’s been going on since the early 1940s, and from the bull riding to the barrel racing to evening celebrations downtown, it’s a cultural event you won’t want to miss.

Grab a cozy cottage at The Scout for the night or a campsite at Scott Lake Campground. The sunrises over the lake will take your breath away.

Brownsville

Brownsville is a delightful little town on the Calapooia River brimming with 19th-century nostalgia. The beautiful vintage storefronts and Victorian architecture of downtown transport you back to a time when horse-drawn carriages were the norm, and eager pioneers flocked to create new lives for themselves and their families.

Brownsville was once home to a hand-haul ferry that transported travelers from one side of the Calapooia River to the other. The ferry is no longer there, but it was replaced by a covered bridge in the 1850s. The New Brownsville Covered Bridge still stands today and is well worth a stroll or a bike ride over.

History buffs will want to stop into the Linn County Historical Museum, which does a great job showcasing the town’s agricultural development and early settlement life. Nearby, the Moyer House paints a picture of a day in the life of one of the more influential families in town in the 1880s.

Brownsville also puts on a variety of events that celebrate its rich history. At their Carriage Me Back weekend in early May, guests can hop on a horse-drawn carriage for a tour through town while actors play out various periods of the region’s history.

We’ve found that Airbnb is the best way to go in Brownsville. Rent a cute, cozy cabin, or if you have brought a tent, consider booking a campsite at Pioneer Park.

Oregon City

For another dose of the pioneering spirit of the West, head to Oregon City. Established in 1844, it was the first city incorporated in the Pacific Northwest! Its well-preserved buildings and historical landmarks make it a real treat for those looking for a taste of the past.

Oregon City’s is home to some pretty neat historic dwellings, particularly the McLoughlin House. This 1820s home has been named a National Historic Site and provides insight into early settler life. Nearby is the End of the Oregon Trail Interpretive Center, where you can learn about the challenges faced by pioneers, Dr. McLoughlin included, traveling westward.

The Oregon City Municipal Elevator is another noteworthy attraction. Built in 1915, this engineering marvel connecting the town’s upper and lower “levels” offers panoramic views of the Willamette River. Then, there’s the Oregon City Bridge. This arched bridge was built over a century ago, merging the communities of Oregon City and West Linn, and boasts breathtaking views of Willamette Falls.

Lodging is limited in Oregon City, but there’s a Best Western in town that has some pretty spectacular river views. Otherwise, the thriving metropolis of Portland is just a 30-minute drive north and hosts plenty of cute hotels and vacation rentals.

Lake Oswego

Lake Oswego, Oregon, is a picturesque city that blends natural beauty with a rich historical backdrop. Founded in the mid-1800s, the town originally centered around iron ore mining.

On your visit, you can’t miss a hike along the Iron Heritage Trail. From once bustling furnaces and iron mines to the Oswego Pioneer Cemetery, where nearly 100 hard-working iron workers were buried, this scenic walkway connects a number of historical sites. Journey through the town’s industrial past while enjoying the beauty of the surrounding forests and green spaces.

A trip to Lake Oswego wouldn’t be complete without a visit to the town’s namesake’s peaceful shores. Enjoy a picnic on Oswego Lake’s well-maintained waterfront park, or book a seat on the Oswego Lake Architectural Boat Tour for a new perspective on some of the town’s historic homes.

So far as lodging goes, we love the Lakeshore Inn, which practically sits on top of the lake. Enjoy sunset views from the lakeside pool or your private lake-view patio before strolling into Lakeview Village for a bite to eat.

The Takeaway

And that’s a wrap! Thanks for following along as we explored some of Oregon’s must-visit old-world towns.

Each of these towns takes pride in its deep-rooted history and a commitment to preserving the stories of the past, and each serves as a gateway to Oregon’s rich cultural tapestry.

Whether you’re drawn to the arts, history, or simply the allure of scenic landscapes, Oregon offers ample opportunity to create memorable experiences celebrating the spirit of the Pacific Northwest.

So pack your bags, load up the car, and get to exploring!