You could spend months crisscrossing Central Oregon—hiking the region’s trails, hitting the slopes at local ski resorts, driving scenic backroads, and sipping award-winning ales and lagers at local craft breweries—and still not see all the region has to offer.
So allow us to help with a 3-day vacation getaway that brings together some of the top sites, bites, brews, and attractions around Central Oregon. We couldn’t begin to list every last highlight, but we’re excited to inspire an upcoming vacation.
Here’s how to make the most of your 3-day itinerary:
Keep reading for all of our 3-day vacation ideas—and tips for enjoying your Bend, Oregon, weekend trip.
Day 1: Explore Downtown Bend
Morning
Ease into your 3-day trip with coffee and a light breakfast at one of several cafés in downtown Bend. The Bend-based Thump Coffee pours well-crafted coffees alongside house-made pastries, and the sustainably minded Backporch Coffee Roasters prides itself on ethically sourced, fresh-roasted coffee. Nearby, Looney Bean Roasting Company hosts a cozy nook with a spacious backyard patio that abuts the Deschutes River.
Midday
You’re already in downtown Bend, so explore the heart of the city with a relaxing stroll. Drake Park resides along the Deschutes River at the northern edge of downtown; Cascade peak views, flat walking trails, colorful fall foliage displays, and public art await at the park.
If you’re looking to savor the bustling vibes downtown, head to the city’s brick-lined core—where you’ll find locally owned boutiques, creative souvenir shops, and art galleries that display works from local artists. For other fun ideas, see what to expect when you visit Bend, Oregon.
Afternoon
Keep the fun going downtown with a visit to Deschutes Brewery, which sparked Central Oregon’s craft beer revolution when it launched in a converted law office in 1988; today, the award-winning brewery is a local icon. Sip a Mirror Pond Pale Ale or Black Butte Porter while noshing on upscale pub grub in a spacious restaurant or on the brewpub’s sidewalk patio. If you’d like to further explore Central Oregon’s craft beer scene, pick up a Bend Ale Trail passport to start planning your journey.
Photo credit to @breweryviewsandbrews
Evening
Wrap up a magical day exploring downtown Bend with a night out at one of the area’s acclaimed eateries.
900 Wall dishes hearty American dishes influenced by Italian and French cuisines—including stone oven pizza, pastas, and seafood—typically with fresh, organic, and locally sourced produce. Two blocks away, Zydeco Kitchen brings Southern-inspired flavors to Bend with smoked pork chops, shrimp and crawfish jambalaya, cavatappi pasta with andouille sausage, and other creative dishes. For more ideas, check out our guide to restaurants in Central Oregon.
After dinner, celebrate the start of an exciting weekend by unwinding back at your overnight stay in Bend. You’ll find upscale lodges, resorted hotels, chic motels, luxe resorts, and more. See where to stay in Central Oregon, and find the right accommodation for your visit.
Day 2: Outdoor Adventures
Morning
You’re hitting the ground running for a day of outdoor adventure, so stop by one of the coffee shops you missed out on yesterday for a quick pick-me-up and light bites.
You’ll find sweeping views of Central Oregon farmland, ancient rock formations, high-desert terrain, and the lazy Crooked River at Smith Rock State Park—one of the region’s most popular parks. (Try hitting the trail before 9 a.m. for a bit more solitude.) West of Bend, the Tumalo Falls Day Use Area shows off views of the iconic Tumalo Falls—and provides access to miles of hiking trails that head into the surrounding forest. For a look at the wide-ranging landscapes in and around Bend, hike the South Canyon Reach section of the Deschutes River Trail.
For more ideas, check out our suggestions for fun things to do in Central Oregon.
Midday
Savor a picnic lunch back at the trailhead or at a quiet park, and rest up before a fun afternoon.
No matter the weather or time of year, you’ll find plenty of exciting indoor attractions. The renowned indoor-outdoor High Desert Museum hosts attractions that cover regional history, Central Oregon’s first people, and live displays of local wildlife. If you’re with kids, let them loose at Free Spirit, whose main attraction is a “ninja gym” with plenty of fun obstacles and challenges. If you’d like to stay active, grab a day pass and try your hand at the many routes at Bend Rock Gym.
Afternoon
Ready for a bit more outdoor adventure during your 3-day vacation? Wrap up a memorable afternoon under the sun at popular stops around Central Oregon.
In late spring and summer, rent a paddle craft or tube for floating from Tumalo Creek Kayak & Canoe, and get on the Deschutes River in the midst of Bend. Further west, seasonal boat rentals are available at Suttle Lodge on the shores of Suttle Lake. And in Sunriver, the Sunriver Resort Marina provides tube rentals and paddle craft for checking out a quiet stretch of the Deschutes River.
Visiting in winter? You’ll find plenty of seasonal activities around the region. Old-school fun abounds at local outdoor ice rinks—including the Seventh Mountain Ice Rink and The Pavilion in Bend, and The Village at Sunriver in its namesake community. You’ll also find high-octane fun on the slopes at regional ski resorts—including the charming Hoodoo Ski Area near Sisters (home to Central Oregon’s only night skiing) and the expansive Mt. Bachelor near Bend and Sunriver.
Evening
In recent years, food cart pods have taken root around Central Oregon—and many come with indoor seating, cozy fire pits, and on-site taprooms that showcase some of the region’s most outstanding craft beverage producers.
If you’re passing through Sisters on your way back to your overnight stay, see what’s fresh at The Barn—where live music pairs well with local bites and brews on a spacious lawn and in a barn-like taproom. Just south of downtown Bend, meanwhile, The Podski hosts a globetrotting lineup of food carts that serve sushi, pierogies, Thai fare, regional seafood, and more. Not far from Smith Rock, the Redmond Food Park prides itself on delivering a family-friendly, alcohol-free atmosphere—and hosts up to eight carts at any given time.
Day 3: Final Stop
Morning
On the final day of your action-packed weekend in Bend, Oregon, we can’t imagine you’re in any hurry to head home. Put off your departure a little while with breakfast at one of Bend’s lauded cafés. Local favorites include Nancy P’s Bakery & Café (offering savory pastries, quiche, and more), The Lemon Tree (serving classic breakfast dishes with a global twist), and Sintra Restaurant (dishing a Portuguese-inspired brunch menu).
Brunch and breakfast options aren’t limited to Bend. Cottonwood Café takes an upscale approach to brunch classics in Sisters—imbuing omelets with seasonal ingredients and pairing its country-fried steak with caramelized onions and roasted mushrooms. And One Street Down Café sits at the northern edge of downtown Redmond; the restaurant is as popular for its front-porch patio as it is for a filling menu of fresh breakfast staples.
Tips for Planning Your Weekend Trip
Not sure how to start planning your three-day itinerary in Central Oregon? Here are a few tips to make the most of your adventure.
Outdoor recreation: Given our reputation as an outdoor paradise, you may want to time your visit around whichever adventures you’d like to enjoy. The best months for skiing and snowboarding typically come between January and March, while campgrounds, hiking trails, and mountain bike paths are usually snow-free between June and October. Paddling is best enjoyed between June and September.
Booking hotels: The most popular times to visit Central Oregon align with the ability to enjoy certain outdoor activities; most skiers and snowboarders visit between December and March, while the months of June, July, August, and September—buoyed by warm afternoons—bring the most visitors to the region. If your visit falls within those timeframes, consider trying to book your preferred lodging three to six months in advance.
What to pack: No matter the season, you’ll want to dress in layers to stay comfortable and account for changing temperatures. If visiting in summer, pack a light jacket for after the sun goes down—as well as plenty of sunscreen and bug spray.
Looking for getaway ideas and inspiration? Start with our guide to Central Oregon Vacation Planning, and request a travel guide to map out your next favorite getaway.
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