The Perfect Long Weekend in Central Oregon

Plan your perfect long weekend in Central Oregon with visits to 3 of the 7 “Wonders of Oregon” (and plenty of trips to the brewpubs!).

Want to plan the perfect long weekend in Central Oregon? Look no further!

Our favorite Oregon trip was our perfect long weekend in Central Oregon. 

When most people think of visiting Oregon, their mind goes straight to city of Portland. The good old City of Roses, aka Beervana, home to hippies, craft beer, and people wearing socks with sandals. 

Portland is an amazing city, but I have a serious crush on Central Oregon. 

Once you leave the Willamette Valley behind and drive over the Cascade Mountains, everything is completely different. 

The trees are different, the landscape is different, and you can actually see blue skies more than just three months of the year. 

The air is crisp, the sky is blue, the crowds are absent, and there’s plenty to explore.

Where to Stay

As most people tend to do, we based ourselves in the city of Bend for the weekend.

There are plenty of places to stay in Bend, no matter your budget.


Booking.com

We stayed in a darling little Airbnb just outside the city which boasted its very own hot-tub. There are lots of cute places to stay around town.

Another great option is to stay at the Old St. Francis School, a 1936 Catholic schoolhouse which has been transformed into a hotel. Stay in an old classroom, grab a pint at the pub, catch a movie in the classic theater, or take a dip in the soaking pool. Even if you aren’t staying here, you can still come by for a cozy drink and a self-guided walking tour of the property. 

Smith Rock State Park

Eating & Drinking

A perfect long weekend in Central Oregon wouldn’t be complete with plenty of opportunities to eat, drink, and be merry.

Eats

Best Breakfasts

Hit up McKay Cottage Restaurant for a big breakfast to fuel you up before a big day.

For classic eats, try one of the many local diners like the Black Bear Inn, Jake’s Diner, or Jackson’s Corner.

For a healthy start to your day, head to Mother’s Juice Cafe for smoothies, CBD elixirs, oatmeal bowls, and breakfast sandwiches.

Ready for Lunch?

Looking for classic pub food? Look no further than one of the dozens of brewpubs in the downtown area. People rave about the burgers made from beef fed on spent beer grain at Deschutes Pub, while the wings at Worthy Brewing have their own dedicated fan club.

Offering fusion food and craft cocktails, Spork is becoming a wildly popular lunch spot. Their menu makes me drool!

For something a little different, check out Sintra, a Portuguese restaurant featuring delicious Mediterranean specialties like seafood gazpacho. They also have a lengthy sandwich and salad menu.

Veg(etari)ans will love the entirely plant-based menus at Salud Raw Foods. Mixed group? Head over to Chow to find dishes to suit every dietary preference.

Dinner Time

For the best sunset experience in town, head over to Crux Fermentation for the sundowner special (discounted prices for a half hour before/after sunset). 

For a laid back evening, simply pick a brewpub you didn’t go to for lunch! 

Looking for something a bit more romantic? Try Ariana Restaurant for luscious seafood, the Blacksmith for a classic steakhouse experience, or the Jackalope Grill for delectable cuisine in a white-tablecloth environment. 

For dinner with a river-view, head to Anthony’s at the Old Mill District for Oregon seafood or to Pine Tavern for comfort food in the coziest spot in town.

Drinks

Bend is known for having some amazing breweries, so if you like beer you’ll be in heaven. There’s actually more breweries per capita in Bend than any other city in Oregon (even Portland!). 

Be sure to check out some of my favorites: Deschutes Brewing, Crux Fermentation Project, 10 Barrel Brewing, and Boneyard Brewing

Most of the breweries in Bend do growler fills, so if you’re staying in town for a few days don’t hesitate to pick one up!

This website has a great overview of breweries in Central Oregon, so be sure to check it out if you’re planning a visit.

For the truly dedicated, you can get your commemorative passport stamped on the Bend Ale Trail

Wine and spirit aficionados will also find plenty of places to wet their whistle in Bend.

If you’d rather have someone else handle the planning, Bend Brew Bus will pick you up at your hotel or Airbnb and cart you around on the tour of your choice (beer, cider, wine, spirits, or a mix!).

Not big into drinking? Never fear, there are plenty of things to do on a long weekend in Central Oregon!

Things to Do

Owners of the Bend Brew Bus, Wanderlust Tours (nice name, right?!), offers local excursions to volcanoes and caves, as well as snowshoeing and canoeing trips.

This is a great option if you’re only in town for a few days and don’t want to bring your own equipment. Canoes are notoriously difficult to fit into the overhead space on an airplane. 

If you have access to a vehicle, my recommendations would be to visit three of 7 Wonders of Oregon that are all reachable as day trips from Bend.

Smith Rock State Park

Smith Rock State Park is a quick 35-minute drive from central Bend. 

It doesn’t look like much from the road…

…but once you get in there you’ll see why it’s a MUST for your perfect long weekend in Central Oregon.

Smith Rock State Park

Do some research ahead of time and pick a trail you’d like to walk.

Monkey Face, Smith Rock State Park

There are beautiful views everywhere in the park!

We did the Misery Ridge Loop (the opposite of the suggested route, the reverse misery ridge loop) and it was epic. 

If you’re not keen to go UP but you still want to look around, there are trails that circumnavigate the big rocks and follow along the river.

You’ll be happy you made the trip!

Crater Lake National Park

The only National Park in the state of Oregon, Crater Lake is a feast for the eyes. 

Crater Lake | A Perfect Long Weekend in Central Oregon

It’s a bit of a drive from Bend (a little under two hours), but it’s absolutely worth it. 

I love to visit here in the winter because there’s hardly anyone around. The pristine snow gives the lake a truly ethereal quality. 

The Painted Hills

The famous Painted Hills can be found about two hours away from Bend, in the opposite direction of Crater Lake. 

I don’t know how I missed out on visiting this spectacular place for more than 30 years! 

We were blown away by the beauty of these hills, especially because we were the only ones there that winter day. 

The hills are one of three parts of the John Day Fossil Beds National Monument, an area made up of layers of fossilized remains from as far back as 45 million years ago.

The three units (Painted Hills, Sheep Rock, and Clarno) are spread out over almost 20,000 acres.

Sheep Rock

There’s a great museum you can visit which will give you an idea of what Oregon looked like way back then.

The museum also doubles as a visitor’s center, so it’s a nice place to start your visit. 

There are no restaurants or gas stations located within the monument, so be sure to plan ahead!

The Painted Hills, John Day Fossil Beds Monument | The Perfect Long Weekend in Central Oregon

While you’re in the area, make the short drive (9 miles) over to Mitchell, Oregon to explore a bona fide ghost town.

Next, head to the Wheeler High School fossil beds where you can  dig for your very own treasures to take home. 

Itinerary: Perfect Long Weekend in Central Oregon

Note: I recommend packing picnic lunches to take with you each day, as restaurants can be difficult to find once you head out of town. Both Market of Choice and Trader Joe’s will have lots of great options!

Friday:

  • Head out early towards the John Day Fossil Beds Monument for a day you won’t soon forget.

Sheep Rock, John Day Fossil Beds Monument | The Perfect Long Weekend in Central Oregon

  • Explore the three units of the monument, dig for fossils at Wheeler High School, and wander the streets of a ghost town. 
  • Watch the sunset beer-in-hand at Crux Fermentation, then get cozy at Pine Tavern for dinner on the river.

Saturday:

  • Spend the morning exploring Crater Lake. Rent some snowshoes before you go, or plan time to take the boat to Wizard Island in the summer months.

  • On your way back to town, stop to visit the High Desert Museum or hike around the Newberry Volcano Caldera (seasonal).
  • Reward yourself with a dip in the soaking pool at the Old St. Francis School, followed by dinner and drinks in the pub.

Sunday:

  • Pack up your things, eat a big breakfast at McKay Cottage Restaurant, and drive to Smith Rock State Park for a day of hiking.

Stunning Smith Rock State Park - A Perfect Long Weekend in Central Oregon

  • Grab a late lunch in Madras (or bring a picnic to Smith Rock!).
  • Bid farewell to your perfect long weekend in Central Oregon and head back to Portland!

March 8, 2019 | Last Updated on June 5, 2021 by Linda

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