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5 Best Cities To Visit In Oregon

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April 24, 2019

5 Best Cities To Visit In Oregon

Whether you’re a craft beer connoisseur, a nature-loving adventurer or patron of the arts, the best cities to visit in Oregon have it all. A road trip is a perfect way to explore the Beaver State, so load up with your friends or family and prepare for an adventure. From the Redwoods of Southern Oregon to the Coastal dunes near Florence all the way to the mountains of central Oregon and the weird city of Portland, Oregon will blow your mind.

Wondering Where To Visit In Oregon?


Ashland is the first city you will pass once you’ve crossed over the border from California. Home of the Oregon Shakespeare Festival, Southern Oregon University, and a thriving artisan culture, Ashland is known for attracting a diverse blend of people. One simply needs to walk around down by the Plaza for an hour to start to grasp why this city attracts a lot of attention. People are very forward thinking and the vibes are always good, don’t be surprised when people smile and greet you as you pass them on the street.

Dining along the creekside in downtown Ashland
Ashland is home to some amazing restaurants including several right along the creek near the Plaza

When in Ashland be sure to check out:

  • Lithia Park and all of the other beautiful parks in town
  • The Plaza
  • Bars and nightlife
  • Some of the nearly 100 restaurants in town
  • Oregon Shakespeare Festival
  • Emigrant Lake

There’s even a mountain to ski on in the winter that is only a 30-minute drive from downtown, aptly named Mt. Ashland. Explore some of the best places to stay in Ashland here.


If you’re anything like us, then you enjoy straying off the beaten path when you travel. Jacksonville, Oregon is just such a place. Once a gold mining town in the 1950s, this charming little town is just a short drive from Medford and Ashland. The laid back atmosphere and abundance of culture year-round make Jacksonville a great city to visit on any Oregon adventure. While you’re there you can explore a variety of delicious cuisine, boutique, and antique shopping, world-class wine, or simply be one with nature “out in the Applegate” (as the locals say).

People enjoying a concert at Britt Festival in Ashland
Britt Festival In Jacksonville

Here’s some ideas for things to do while you’re in Jacksonville:


Medford lies the heart of Southern Oregon and is a major jumping off point to get anywhere else within the state. Known for being a global wine destination, according to Forbes Magazine, Medford is home to beautiful wineries, an abundant craft beer scene, and is right in the middle of a plethora of fun things to see and do throughout the Rogue Valley. There is an abundance of events year round, a thriving performing arts scene, and outdoor activities to satisfy every adventurer. Medford even has its own airport and you can typically find affordable flights from major hubs around the country.

City of Medford Oregon
View of the Rogue Valley near Roxy Anne Peak.

While you are in Medford be sure to check out:

Explore some of the best places to stay in Medford here.


“There are a million ways to play in Bend”, and this central Oregon city is all about living an outdoor lifestyle. If you look at a Map of Oregon, Bend is basically smack dab in the middle. Nestled between the snow-covered peaks of the cascades and surrounded by an abundance of rivers, lakes, and hot springs to explore. If you’re looking for a healthy vacation alternative filled with outdoor activities, sport, and experiences, then this may just be your favorite city in Oregon.

View of farewell bend park in Oregon
Bend is natures playground with tons of great outdoor activities including floating down the Deschutes River.

Some of our favorite things to do in Bend are:

  • Golfing
  • Mountain biking
  • Hiking
  • Skiing at Mt. Bachelor
  • Camping
  • Soaking in Cougar Hot Spring
  • Rafting down the Deschutes River
  • Drinking craft beer at one of the 22 breweries
  • Driving through the mountains


The Oregon city most people have heard of is our largest, Portland, and for good reason. Known for being a little on the weird side, this city continues to gain popularity and attracts visitors from around the world who come to experience its laid back vibes and peculiar culture.

Perhaps one of the greatest traits of our largest city is the abundance of street food you will find there. Everywhere you look, you will find food carts and trucks lining the streets. And no, these are not your typical hot dog stands and greasily fried food, Portland takes the food truck scene to a whole new level offering up gourmet cuisine from around the world. Check out a few of the mind-blowing food carts you can experience while you’re there.

View of Portland, Oregon at night
Portland is a fun city where you are bound to find something delightful and maybe even a little weird…

Besides eating your way through the city you should also look into:

Are you planning a trip to Oregon? With so much to explore and so many reasons to visit, planning a trip through Oregon can be a difficult task. Let us know what cities you are planning to visit in Oregon in the comments below.

And if you’re looking for more fun things to do while you’re in Oregon, check out the top ten things to do in Southern Oregon.