Oregon, as a state is pretty underrated in my opinion. There are some hidden gems here that get overshadowed by some of the more popular destinations, but these small towns are worth the trip to the Pacific Northwest! I have lived most of my life in this area of the world and with my lifetime of exploring, I have personally chosen the most underrated towns in Oregon that are must-visit places!


Why visit?

Sisters, Oregon is such a cute, small town. With a population of less than 3,000 it certainly has a small town feel. Many of the shops lining the main street are 1880’s old west themed and are fun to pop in and out of as you stroll your way along until you get to a café, lunch spot, spirit tasting or art gallery. Remember to look up as you explore, the surrounding views are breathtaking!

They host so many fun festivals throughout the year including the world’s largest quilt show, folk and other music fests, antique car, arts & craft fairs, rodeo and “Biggest Little Show in the world” that dates back to 1940!

I love Sister’s because it is just as close to the great outdoors, but it gets overshadowed by destination giant, Bend. Okay, Bend is amazing too, it just leaves Sisters in the dark, making it an incredibly underrated town in Oregon.

Things to do:

  1. The unique festivals alone, is reason enough to visit. It’s a crowd and experience like no other.
  2. Roam the shops, restaurants, art galleries and cafes on Main street.
  3. Get out into nature! Sisters is really close to many lakes, Mt Hood, Smith Rock State park and is surrounded by beautiful forest, laden with trails to hike!

Where to stay:

Sisters Bunkhouse is a fantastic location, right on the main street. It keeps the old west feel with the façade on the front, but inside it is nice and clean.

Cannon Beach

This small beach town might find its way into my life when I hit retirement age. It’s such a quaint town with great coffee, easy beach access and is surrounded by hiking trails with incredible views. (Plus wild bunnies roam the side streets, nibbling garden finds <3 ) Check out my complete guide here.

Things to do:

  1. Get in the beach town feel by grabbing a coffee and exploring the shops. Be sure to get a clam chowder in a bread bowl for lunch! (It’s a beach classic.)
  2. Hit the beach! Spend all day watching the tide come and go, explore tiny sea creatures in the tidepools near the rocks, and make a bonfire on the sand when the sun sinks into the sea. You might even splash in the wake a bit, but I will warn you the water is cold. Don’t be expecting to swim.
  3. Head just outside of town and take a hike! There are so many trails near Cannon Beach and it’s just minutes from Ecola State Park.

Where to stay:

Inn at Haystack Rock. This stay is a little more expensive than I typically suggest, but it is like no other. Each room is an individual, updated cabin with shared outdoor space, complete with gardens, a fountain, and firepit. It’s perfect for a romantic getaway or meeting other travelers.  


Astoria, Oregon has been underrated as long as I can remember. It’s an old fishing port town and still holds a bit of that feel. You can buy fish on the docks from the fisherman, or eat at one of the many restaurants with views of the water! If you’re curious what it looks like, watch the 1985 classic, The Goonies. Many of the scenes were filmed here! It also hosts many festivals throughout the year, including a massive Wine & Seafood Fest (what’s not to love about that?!)

Things to do:

  1. Climb 164 steps to the top of the Astoria column for an unbeatable view.
  2. Visit The Goonies filming sites and museum. If you are in town at the right time, you might even be able to catch it playing at the theater.
  3. Meander the main streets, in search of trinkets, antiques, baked goods, and THC.

Where to stay:

Clementine’s Bed & Breakfast. This 1888 Victorian Inn is an experience all in itself! It’s a great location, and offering a multi-course breakfast, free tea & wine, river views, cooking classes, and down comforters.

Hood River

This might actually be my #1 favorite town in Oregon! It has adventure vibes around every corner, adorable book and second hand shops, delicious restaurants and breweries on the river. It’s dog friendly, has coffee shops galore PLUS it’s a year-round nature lover’s haven! Hanging out down by the river is peaceful or heading up to the woods if you’re ready for adventure.

Things to do:

  1. Walk around and window shop, sip organic coffee, & eat at Broder Ost, a delicious Nordic brunch spot!
  2. Head to the woods for any outdoor adventure you long for. Hiking, biking, swimming, waterfall chasing are popular in the summer, but if you visit in the winter rent some snowshoes, snow mobiles, skis or boards from one of the many adventure shops in town.
  3. Sip wine, ciders or brews at one of the many breweries and wineries in town.

Where to stay:

Hood River Hotel is a beautiful historic building. It dates back to 1888, has comfortable beds, wifi, breakfast and views of the river.


Other than the annual Pendleton Rodeo, this town doesn’t get talked about too much. It’s definitely underrated. Pendleton has grabbed on to the cowboy feel and it still holds up today, with woolen, leather and woodworks abounding. It also celebrates the local native culture and has many sites to learn the history of the area.  It even has an interesting underground story that’s worth a tour!

Things to do:

  1.  Visit the Heritage Station museum, air museum or Tamastslikt Cultural Institute to learn a bit about the area and history.
  2. Plan your adventure to line up with the Pendleton Round-Up (mid-September) or the Whisky Music Festival (Early July).
  3. Hit up the farmers market and picnic in Cattle Drive Park.

Where to stay:

Working Girls Hotel. Don’t let the name scare you, it was an operating Bordello until the 1950s, but is now just an old hotel. It has kept a lot of it’s old charm and is in a perfect location for exploring the shops and restaurants in town.

If you are flying into Portland, Oregon to explore these incredible local spots, be sure to check out my Top 10 Things to do in Portland.

There's always more to explore: