Written by | Derek Carlson

Discover Your Dream Weekend Itinerary in Bend, Oregon

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Bend is known as one of the sunniest places in all of Oregon which makes it the perfect destination for a weekend getaway as you can almost count on the weather cooperating.

The perfect weekend getaway can take on many forms from wandering downtown to take in the underrated dining scene or heading out for a weekend of adventure on the Deschutes River or nearby Cascade Mountains.

Having lived in Bend for more than four years now we feel well qualified to put together the perfect weekend itinerary that combines the best of both worlds!

The cascade mountains near Bend

The Perfect Weekend Getaway in Bend

Day 1 – Arrive in Bend

Arrive in Bend on Friday afternoon. The drive from Portland to Bend is only 3 hours so if you leave mid-afternoon you’ll still have time to head out for a dinner at a local brewpub.

The Redmond airport is only 20 minutes from Bend as well so those arriving from out of state are only a few minutes from Bend once you make your way through our small but efficient airport.

Drop off your bags at a local hotel (we always send family and friends to the Element Hotel) or vacation rental and head out for a quick walk along the Deschutes River.

If you’re staying at The Element you can hop on the newly extended Deschutes River Trail at Pioneer Park for a leisurely stroll through Drake Park and into downtown.

Enjoy the Evening with a Pre Dinner Drink at Bend Brewing

Bend Brewing is one of our favorite afternoon hangout spots in Bend with its expansive lawn looking out over the Deschutes River. Grab a Tropic Pines IPA and enjoy the summer vibes at a picnic table.

If the weather hasn’t quite shifted to patio season then check out The Cellar for a true English-style pint or cozy up with a pour of Jubelale by the fire at Deschutes Brewery.

If you want to sample more of what the Bend beer scene has to offer check out our post on our favorite Bend breweries.

Grab Some Dinner at Yoli

Bend may not be known for its diverse food scene but that is changing fast and one of the restaurants leading the way is Yoli. This top-notch eatery focuses on Korean-inspired dishes and serves up one of our favorite meals we’ve ever eaten in Bend.

Treat yourself to Yoli’s 5-course tasting menu in Bend for a delicious adventure featuring expertly crafted dishes that will leave your taste buds wanting more. It showcases the chef’s creativity and guarantees a memorable dining experience.

It’s best to turn in early as there is plenty in store for tomorrow (but if you’re up for a nightcap it’s tough to go wrong with the creative cocktails and inviting space as San Simón.)

Day 2 – Get Outside

Start off the day with a coffee and a quick bite to eat at Lone Pine Coffee. This cozy coffee shop serves up some of the best lattes in town and their liege waffles make for a perfect bite while heading out to the day’s activities.

Breakfast at Chow in Bend

If a Bend breakfast is more your style then Chow opens early (often 8 am in the off-season and 7 am during the summer although the hours can vary) and serves up some tasty and hearty breakfast dishes.

Drive out the Cascade Lakes Highway for a Hike

Mt. Bachelor from Sparks Lake

Hit up some of Bend’s famous hiking trails by heading up the Cascade Lakes Highway. Located only 30 minutes from downtown you can easily go from sipping coffee and finishing brunch to hitting the trail for some scenic views of the Three Sisters Wilderness.

Plan ahead and grab a Central Cascades Wilderness Permit for the Green Lakes Trail for a challenging yet incredibly rewarding 9-mile hike that takes you up to an alpine lake at the base of South Sister.

Alternatively, head to Sparks Lake and enjoy the unparalleled views of Mt. Bachelor from the Ray Atkinson Trail (2.4 miles).

Head Back into Town and Grab a Bite to Eat

Bend has become a food truck haven so no matter where you are in town there is a food cart pod where you can grab a quick bite to eat.

Check out the Podski near the Box Factory for one of the best burgers in town from Americana or, if you’re looking for some lighter fare, hop across the street to the uber-popular Fix and Repeat Cafe. Their Acai bowl and Bahn Mi Bowls are go-tos in our house!

Lunch at Fix and Repeat in Bend

Float the Deschutes

If you’re visiting during the summer months then floating the Deschutes River is an absolute must-do!

There is an entire system in place that will rent you tubes, shuttle you to the river, and pick you up at the end of the float. All you need to bring is some sunscreen, a bathing suit, a water bottle, and the ability to sit back and relax for a couple of hours.

Just watch out for the rapids at the halfway point! They’re not bad but have caught plenty of folks off-guard and given them an unwelcome swim.

Head to the Tumalo Creek Park-and-Float in the lot off of SW Simpson and SW Columbia to get started.

Take in Dinner with a View

After changing into some more dinner-appropriate attire, or not, no one here really cares much in the summer, head over to Crux for one of the best evening views in town.

Crux has grown to one of the most popular breweries in town both for its amazing beer and equally amazing space which features a brewery built out of an old transmission shop building along with a massive lawn for enjoying those summer Bend evenings.

Crux serves up food from their kitchen along with food trucks serving up pizza, Mexican food, and Americana fare. There are plenty of picnic tables or space to spread out a picnic table and enjoy the sunset over the cascades.

Day 3 – Check Out the Town

After yesterday’s activities, you’ll probably be ready for a break.

Grab Some Brunch

Latte art at Thump Coffee in Bend

Start up the day by grabbing a latte at Thump Coffee followed by a quick walk over to The Lemon Tree for brunch.

This popular brunch spot (get there early or be prepared for a 45-minute – 1-hour wait) serves up international-inspired dishes with a local twist.

This is our favorite brunch spot in town and a must-visit for folks on a weekend getaway in Bend. Try the warm cinnamon roll and crab cake benedict. You won’t be disappointed!

Walk the River

The Deschutes River and Drake park is a must visit destination during a weekend trip to Bend

Enjoy a post-brunch walk along the Deschutes River where you can take in the sights and even do a little shopping at the Old Mill District.

Watching the surfers ride the river wave is always a treat or you can nervously watch the river floaters try to navigate the rapids on their tubes.

The Deschutes River trail continues for miles upstream (you could walk all the way to Sunriver if you were so inclined) so you can make this jaunt as mellow or extreme as you’d like.

Peruse the Local Art in Downtown Bend

Downtown Bend is full of funky shops that feature art from local artists.

Check out Natural Kinships for their slab wood tables and wood and metal art from local artists (you can occasionally find work there from yours truly!)

Lark Mountain Modern is another fun shop (even if I don’t sell any of my work with them) that really captures the spirit of our little mountain town.

Cap off the walk through town by browsing Dudley’s Bookshop. This locally owned bookstore always has an impressively curated selection of books that tell the story of living in the Pacific Northwest.

Grab One Last Lunch at Spork

Before heading out of town hop across the river for lunch at one of our favorite restaurants in town – Spork. I’d say peruse the menu and get whatever looks good but you have to try the Spicy Pork Noodles.

Seriously. This dish is life-changing. I dream about those caramelized fish sauce pork patties and the chile peanut crisp. It is all so so good.

They also serve up some tasty drinks that are best enjoyed in their usually quiet back patio area.

And there you have it – a whirlwind of 48 hours in Bend and just enough of a taste of what this incredible area has to offer that will have you planning your next trip back!

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