The 7 Can't-Miss Towns In Oregon
The state of Oregon is packed with endless natural wonders and a mix of can't-miss towns that define its glorious coastal, lakeside, and mountain scenery. The city of Astoria is the oldest in the state and is full of history. Sisters is surrounded by nature. Baker City is full of wonderfully preserved 19th-century architecture. Each community stands out with its own businesses and shops, welcoming people from all over with history and culture that set it apart.
Astoria
The city of Astoria is the oldest community in the state, and boasts Pacific Northwest beauty, cinematic history, and a pleasant riverwalk. An alluring place on the water is the Bowline Hotel, a boutique hotel alongside the Astoria Riverwalk, providing guests with rooms taking in the alluring views of the Columbia River and landscape, relaxing saunas to relieve people from the stress of the week, soaking tubs, and the Knot Bar, a place to gather with friends and family for quality food and refreshing drinks. The hotel also hosts meetings, retreats, weddings, and lively parties for an incredible experience. A nice walk east of the hotel is the Columbia River Maritime Museum, which displays the largest collection of maritime artifacts in the Pacific Northwest, a diverse selection of exhibits, and the Lightship Columbia, which guided ships to safety at the mouth of the river and offers people an opportunity to view where sailors slept, cooked, ate, and worked.
Near the heart of downtown is the Oregon Film Museum. This former jail was converted into a museum honoring movies and TV shows filmed and set in the state, such as The Goonies, as the building was seen in the opening chase scene, Free Willy, Twilight, and Kindergarten Cop. Visitors can also create their own short films in an exhibit featuring small sets and green screens for a fun Hollywood-like experience, without going to Hollywood. On Duane Street is the Buoy Beer Company Taproom, a beer hall and microbrewery serving exhilarating beers like the Czech Pilsner, the Love, Lost at Sea 2024, and the Best Fruit Forward Pale IPA, just to name a few. Buoy Beer Company also hosts events like Oktoberfest in October and has a beer club for people to join to meet new people and make new friends along the way.
Cannon Beach
The coastal city of Cannon Beach is a can't-miss town for its rugged coastline scenery, thriving arts scene, and natural wonders. Cannon Beach is a four-mile stretch of sandy joy in the Pacific Northwest, where beachgoers can enjoy, view Haystack Rock, and observe the tide pools with sealife. The beach is also a wonderful spot to go birdwatching, surfing, and for peaceful walks in the mornings. Just off Spruce Street is the Cannon Beach History Center and Museum, where people can learn more about the community's history, view interactive exhibits featuring artifacts, photographs, and artwork by locals, listen to audio, attend lectures and temporary exhibits, and take educational trips. The museum also hosts events, such as a Summer Jazz Concert in July and Free Community Clothing Swaps in August.
Right near the beach is the Wayfarer Restaurant and Lounge, providing its customers elegant views of the beach and oceanfront, a diverse menu with numerous meals to try, such as the Wayfarer crab bake, filet mignon, the king tide burger, and refreshing drinks to order throughout the day or at the lounge. The Wayfarer can host large parties and provides catering for events off its premises. Just north of the Wayfarer is the Surfsand Resort, a boutique resort hotel that also provides immaculate views of the beach and Pacific Ocean from its gorgeous lobby and comfortable rooms, with some being pet-friendly. Guests get a warm welcome beverage at check-in, pools and hot tubs are available, people can roast hot dogs during the summer, go to the fitness center, and enjoy bonfires outdoors. The hotel is an ideal place to host a beach wedding, family gatherings, a friends' reunion, and corporate events and meetings.
Sisters
Deep in the central region of the state is Sisters, which provides a true Western-town experience for travelers, dramatic views of the Cascade Mountains, and local quirks. In the heart of downtown is the Barn in Sisters, a local bar and taphouse serving burgers, fries, and wood-fired pizza at Boone Dog Pizza, along with craft beers, specialty spirits, and wines from local wineries in a lodge-like setting that also has outdoor seating. The Barn hosts events like the Summer Concerts on Fridays and Saturdays with local artists, bringing the community together, and features paintings, sculptures, gardens, drawings, and craftsmanship by local and regional artists. Across the street from Fir Street Park is the Sisters Museum, where visitors can learn more about the city's past, view educational exhibits displaying documents, artifacts, and photographs, go on walking tours, and attend special events.
On the southern end of town is Creekside Park and the Creekside Campground, where visitors can enjoy the tranquil views and sounds of the Whychus Creek via the footbridge or on the grass, enjoy group picnics on tables, have access to water fountains, and the park can host small events. The campground offers 60 campsites to choose from, including 28 hook-up sites, while each site has its own fire pit and picnic table, and it is a great place to spot wildlife and go birdwatching. Near the campsite is the Peterson Ridge Mountain Bike Trail, a 15.4-mile-long loop trail in the Deschutes National Forest where hikers, bikers, and nature enthusiasts can take in the scenic views of the landscape and the South Sister Volcano, and the alluring sounds of nature.
Ashland
Just off Interstate 5 in the southwestern part of the state is Ashland, a city surrounded by alluring mountains, with a lively arts scene and a thriving culinary and wine scene. The Oregon Shakespeare Festival is a repertory theater that calls the city home, as it's renowned for hosting a wide range of classic and contemporary plays that aren't limited to Shakespeare's plays. The season runs spring through fall, with around ten productions drawing hundreds of thousands of visitors a year. Just next door is Lithia Park, a 100-acre park that is a blissful natural hub in downtown, with the Ashland Creek flowing through it, pickleball/tennis courts to play some games on, the Ashland Japanese Garden calls the park home, where people can view gorgeous Japanese plants, and a few duck ponds for people to listen to the sounds of the ducks quacking around.
On the outskirts of town is the Irvine and Roberts Vineyards, a local family-owned winery in the foothills of the Cascade Mountain Range, serving a diverse selection of wines, from the likes of the 2022 Ascendance Chardonnay, the 2022 Gamay Noir, and the 2025 Rosé of Pinot Noir, just to name a few. The winery and vineyards also have a wine club, host membership events, attend wine tastings, attend culinary events, and enjoy a full-moon dinner at a naturally intimate location. A staple on Main Street is the Ashland Springs Hotel, a luxurious Art Deco boutique hotel with an interior that makes guests feel like they've been transported to a different time period, spacious rooms, and is an ideal place to enjoy weddings and events in the Grand Ballroom, and an elegant dinner at Larks Home Kitchen and its 1920s-style bar.
Baker City
Right on Interstate 84 in the eastern part of the state is Baker City, a city that has a downtown full of 19th-century architecture, acclaimed craft beer, and Pioneer history. Next to Main Street is the Ison House Bed and Brew, situated in a Victorian-style house built in 1887, welcoming guests with its glorious fireplace, the Ison House Pub located downstairs, and four guestrooms that match the theme and era of the exterior. The Ison is also pet-friendly and hosts live music, events, art classes, and paint parties. A great place to grab a bite to eat is Latitude 45 Grille, serving quality meals made with locally sourced ingredients and a diverse drink menu in a friendly and warm, welcoming atmosphere.
Next door to Latitude 45 Grille is the North Seven Brewing Company, welcoming patrons from near and far with incredible IPAs and craft beers, such as the Mow Rider, the Olde Orygun, and the Amber Wave, to name a few. Visitors can pick up merchandise, attend local events, and gather friends, co-workers, and family for some ice-cold drinks after a long day. Near the northern end of town is the Baker Heritage Museum, where the history of the city is preserved through robust exhibits, including a rock and mineral collection, a collection of memorabilia from the town's past, mining history, and Oregon Trail artifacts, including Pioneer wagons.
Pendleton
About 95 to 101 miles north of Baker City is Pendleton, a city that blends Old West history with a diverse museum scene and an appetizing culinary scene. The Flying X Speakeasy Lounge and Restaurant serves delicious Italian cuisine in a mysteriously amazing setting with timeless decor and even better service. The enticing menu items to try include creamy chicken marsala, the gunslinger tenderloin filet, and the underground secret chicken marghereta dinner, to name a few. The Pendleton Underground Tours are a quirky tourist attraction that welcomes visitors to 90-minute historical walk beneath the city. The tour includes viewing the Shamrock Card Room, Hop Sing's (Chinese Laundry), the Empire Ice Cream Parlor, and the "Cozy Rooms," where each of these original stores has well-preserved furniture and artifacts still intact for the masses to enjoy.
Another unique museum to visit is the Pendleton Air Museum, where visitors can learn about the Pendleton Field Corp Air Force Base and its involvement in World War II, view exhibits that change every three or four months, and learn about the pilots and crew who served the country and fought in battles during the war. People can view photographs and artifacts and attend local events held at the museum that bring history enthusiasts and locals together. A warm, welcoming brewery to visit is the Prodigal Son Brewery and Pub, where patrons can enjoy amazing locally crafted beers and IPAs, from the likes of a Beer named Sue, the Wheatstock Hefeweizen, and the Jackalope Jam Session Pale (a seasonal flavor). The Brewery also serves delicious menu options like fish and chips, pub mac and cheese, and beer-battered onion rings, in a modern setting in the eastern part of downtown.
Oregon City
Just 13 to 20 miles south of Portland is Oregon City, a city that blends rich frontier history with modern amenities, an amazing culinary scene, and is near some amazing natural sites, making for a lively place to visit on a weekend trip. Canemah Bluff Nature Park is a tranquil place to enjoy the views and sounds of the Willamette River, explore a network of trails that go through dense forests, and see beautiful landscapes. The park is home to diverse wildlife and is a wonderful place to go fishing, birdwatching, and enjoy nature. On the outskirts of downtown is Canard Oregon City, an elegant restaurant serving classic French cuisine, such as Dungeness Crab Crepes, Foie Gras Dumplings, and Beef Cheek Bourguignon, to name a few. Patrons can also enjoy fresh wine, ice-cold beer, and spirits at a marble-topped bar.
Down on Sixth Street is the Stevens-Crawford House, a local museum allowing visitors to view the home of Mertie Stevens and her preserved family possessions and items from her friends and loved ones. Within the house, people can view well-preserved furniture, old and unique appliances, a sewing room, a toy collection, fine woodwork, and seasonal displays. A unique and quirky landmark to view in town is the Oregon City Municipal Elevator, a 130-foot elevator offering first-rate views of the city and surrounding landscape. The interior features a mural of the city and an observation deck that looks like a flying saucer from a sci-fi movie from the 1950s, and is the continent's only "vertical street" and one of four municipal elevators in the world.
Can't-Miss Excitement Across Oregon
The can't-miss towns scattered throughout the state of Oregon truly blend scenic natural beauty with modern amenities, quirky landmarks, and unique history. Oregon City is a timely place with the Oregon City Municipal Elevator as a landmark attraction. Pendleton is an adventurous eastern town with an incredible Underground Tour. Cannon Beach provides visitors with immaculate beaches and scenic landscapes to enjoy during the summer months. These exciting communities across Oregon stand out during road trips and weekend adventures, leaving visitors with endless stories to share with friends and loved ones for years to come.
