The second week of September in Pendleton is a crowded one. Thousands of people come from all over the world to participate in the spectacle that is the Pendleton Round-Up.

With all those people in town it’s good to know ahead of time where you and your friends and family are going to head out for a bite to eat or a drink to wet your whistle during the week’s festivities. Yes, the Round-Up Grounds have various food vendors operating out of trucks and trailers, plus several bars and venues. However, if you really want to get a taste for the town during Round-Up, venture into some of the local establishments.

A breakfast fit for a cowboy (or girl)

They say the most important meal of the day is breakfast, so you may as well start with a hearty and filling breakfast at the local’s favorite morning meal joint, The Saddle Restaurant and Lounge.

This place is famous for its chicken-fried steak breakfast and biscuits and gravy, both of which you will find on their consolidated menu during the week of Round-Up.

“Friendly service, they get their food fast and it’s hometown cooking,” The Saddle lead waitress Leslie Cherry said is what people can expect when they come in to eat there.

While the restaurant at 2220 S.E. Court Ave. is a popular place for locals to eat year-round, the establishment gets some special visitors during Round-Up.

“We also get the rodeo courts from all over everywhere on the Saturday of Round-Up, and they come in and have lunch. We’ve been doing that for years,” Cherry said.

Cherry started working at The Saddle 20 years ago the week of Round-Up, making this year’s rodeo her 20th anniversary with the restaurant.

“My favorite day of Round-Up is Thursday, that’s Tough Enough to Wear Pink Day. I had a lot of family members lost to breast cancer and I just think it’s important. I get all dressed up in pink, in fact, you just reminded me I need to order a pink apron,” Cherry said.

Local watering holes and chuck wagons

While the spirit of Round-Up might have you craving a can of beans out on a dusty trail where you sleep fire side with your head on your horse’s saddle, there are better and more delicious options awaiting in you downtown Pendleton.

Open for breakfast, lunch and dinner and slinging drinks from 6 a.m. to 2 a.m. Monday through Saturday and from 6 a.m. to midnight on Sundays, is The Rainbow Cafe. A local fixture, “The ‘bow,” 209 S. Main St., stakes a claim as oldest tavern in Oregon, though there has been some recent debate, having operated in the same spot it is now since perhaps 1883.

“We’re still claiming to be the oldest bar in Oregon, and an Irish cowboy bar to boot. It’s just a great place,” said Chris Zimmerman, co-owner of The Rainbow.

Up until recently The Rainbow was a cash only bar, but under new ownership patrons now can bank and credit cards to pay for drinks and food inside.

“We run three cash tills, but we do keep our point of sale going, so if you got a card you can definitely get there, but it’s the hardest one to get to,” Zimmerman said.

Zimmerman isn’t joking about “hard to get to.” During the evenings of Round-Up, like much of the rest of town, the Rainbow turns into a sea of people packed shoulder to shoulder.

The bar itself is full of not just Pendleton but Round-Up history. Memorabilia and photos cover the walls.

“We’ve got the line-up of the All-Around Cowboys all the way from 1910 lining the walls,” Zimmerman said. This line-up includes the father of famous country singer and actress Reba McEntire, Clark McEntire, who won All-Around Cowboy at the 1947 Round-Up, and still holds the title of youngest to win. He won the title again in 1949.

Down a cool one at The Packard

Right outside the bar on Main Street, the Main Street Cowboys put on live music and other entertainment, adding to the party ambience.

“It’s the closest thing to the old Let ‘Er Buck Room that you’re going to get,” Zimmerman said.

If you are only looking to shoot some pool and grab a beer while in town for Round-Up, look no further than The Packard Tavern. A beer bar with two pool tables in the back and a jukebox, this local spot can become crowded during Round-Up week. However, because The Packard doesn’t serve liquor, you might find this to be a nice spot to break away from some of the busier locations in downtown Pendleton.

Owner Tim Guenther said sometimes they move the pool tables during Round-Up to accommodate having live music in the bar. Though for the past few years they’ve been leaving them, which people have seemed to enjoy.

“It gets pretty packed in there, but you know it’s a beer bar so if you’re looking for whiskey it’s a different crowd here,” Guenther said.

‘God is a lonely place without steak’

Watching all that roping, racing, riding and bucking sure works up an appetite. If you want to eat like Round-Up royalty head to Virgil’s at Cimmiyotti’s Restaurant & Lounge, 137 S. Main St. It helps to make a reservation, but you can go add your name to the list and wait outside for a table. The regionally famous steakhouse does open up their back patio area, allowing them to serve three times their average capacity during Round-Up week.

Virgil’s provide a classic old West feel with its crushed red velvet wallpaper in the dining room and the wait staff and bartenders dressed to the nines in bow ties and sparkly gowns.

“It’s been around since 1959. Paul Cimmiyotti made a name for it and Jennifer Keaton (the current owner) has kept it going,” Virgil’s head bartender Aurora Torres said. “Not just by keeping the interior pretty original but by adding the name Virgil’s to it, after her grandfather. It’s just a really classy establishment. I mean it’s a party in there, a great place to have a steak dinner and some drinks.”

Torres also pointed out many members of the past and current staff have been on the Round-Up Court, and plenty of rodeo professionals come into to eat and drink there.

“I would recommend the ribeye, it’s just classic,” Torres said. “To drink, I would say order either one of my old fashions or the pistol whip, it’s been on the Cimmi’s list forever it’s a Pendleton whisky cocktail.”

Get the full treatment

The Great Pacific, 403 S. Main St., has a chill and cozy vibe and boasts a large menu that includes appetizers, small plates, hot and cold sandwiches, soups, salads and some of the best pizza in town.

“Something that sets us apart is we have our full menu available during Round-Up and no price increases, with a beautiful list of craft cocktails,” said “GP” manager Addison Schulberg.

Schulberg said the restaurant will host live music Wednesday through Saturday of Round-Up week, with guaranteed acts including James Dean Kindle, William Surly and the Barroom Gospel Band, and Dusty Rust.

Round-Up week can be a bit crazy, and the nights, depending on how hard you party, can be long. Meaning you might find yourself not long for this world a little earlier some evenings than you were hoping for. Fortunately for you The Great Pacific has you covered.

“We have our full espresso bar and fresh coffee from open to close,” Schulberg said “We always have coffee.”

• Prodigal Son Brewery & Pub, 230 S.E. Court Ave.
• BackFire Station, 911 S.W. Court Ave. 
• Joe’s Fiesta and Cantina, 322 S. Main St. 
• Hamley’s Steakhouse & Saloon, 8 S.E. Court Ave.