A guide to historic downtown Pendleton’s unique cultural and multisensory offerings

Our team at To The Point Collaborative recently took a roadtrip to Pendleton, Oregon. Known far and wide for its yearly Round Up, the Eastern Oregon town between the Columbia Gorge and the Blue Mountains celebrates Oregon’s history, local craftsmanship, and an entrepreneurial spirit.

Part sight-seeing, part company retreat, we made the 3-hour trip from Portland to work on an upcoming workshop on Event Planning, which we’ll be giving in Pendleton in the spring.

We were lucky enough to get a tour of the city from the manager of the Pendleton Convention Center, Pat Beard, who has worked for Travel Pendleton and is one the town’s most enthusiastic advocates.

With Pat as our guide, we learned that Pendleton is a town of legends, tall tales, and great stories, with at least one of those three waiting for you around every corner.

The sightseeing

We visited too late in the year to see the famous Pendleton Round Up, but there are a ton of other things to see!

We loved walking around Pendleton, discovering the history of the town using the Pendleton Bronze Trail site. It offers a nice tour of the statues all over town, with history behind the people depicted.

Other sights to check out:

  • The Underground Tours — Possibly THE single best way to learn about Pendleton’s rich history, including gambling, bordellos and gold, oh my! It gives you a real feel for Eastern Oregon’s Old West life, and how the area changed over the last 100+ years. The highlight: time capsule-like ‘cozy rooms’.
  • The Pendleton Center for the Arts — Built in 1916 as a Carnegie Library, this building was restored to the lovely art center which has hosted 10+ years of Rock Camps for local teens, and where we got to see a local artist — Jenny Morgan — and her amazing papercut artwork. Executive Director Roberta Lavadour’s passion for the Center and its offerings is contagious.
  • The Pendleton Convention Center hosts events for all ages and interests. From a regular regional robotics competition, to a Leather Trade and Sale Show, Round-Up related activities, high school basketball finals, and lots more.

The food

We couldn’t visit Pendleton without checking out the food. There are too many places to mention — and we sadly didn’t get to try everything — but some of our favorites include:

  • Prodigal Son Brewery — For locally brewed beer and a place that feels like your neighborhood hangout even on the first visit, get to the Prodigal Son. Not only are Tim and Jennifer Guenther welcoming hosts, but their story of taking a historic building and creating a vibrant and inviting brew pub is inspiring. You know what else is inspiring? Their cheese curds with Pendleton Sunshine habanero-orange sauce. Another nice thing about this joint is they are willing to adjust menu items to meet any type of dietary need.
  • Thai Crystal — An excellent Thai restaurant located just opposite the courthouse. It was our first meal in Pendleton upon arrival, and set the standard for every meal after that. Great vegan options!
  • Virgil’s at Cimmiyotti’s — Established in 1959, this is a fun and legendary spot for local diners, business meetings, and prom dates. The red walls, restored with the original wallpaper, immediately makes this place feel special. Lovingly revitalized in 2011, by Jennifer Keeton, this place had a historic, old-timey feel and great steak. If you don’t eat meat, a call to the restaurant a day or two before your visit will result in something delicious for vegan diners.
  • Oregon Grain Growers — Amazing locally distilled whiskeys, gins and vodkas, complemented by one of the best menus in town. We had the posole, a traditional Mexican comfort dish, along with tacos, all excellent.
  • Great Pacific — The traditional watering hole and informal restaurant preferred by the locals. Drop by any evening and meet everyone who’s anyone in town.
  • Hamley Steakhouse — Popular for its generous and delicious steaks, has a killer happy hour that is not to be missed. Old Western environment at its best.
  • Rainbow Cafe — Known as one of America’s most historic restaurants, not only has the Rainbow Cafe been offering up breakfast, lunch, and dinner for over 125 years, but it is filled with Pendleton Roundup history. Annual champion photos line the walls of this popular establishment.
  • The Buckin’ Bean — Though it’s known for their coffee, you have to try their pastry case items — they have THE best homemade scones, and the friendliest staff. It is a comfortable place to sit with your laptop, or a friend. And, they roast their own coffee beans onsite!

This is just a taste of what Pendleton has to offer. In our next post we’ll share where to stay (because there’s so much to do!) and what you absolutely need to take back with you from your trip to Pendleton.




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