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Plan Your Trip - Trip Ideas & Itineraries in Bend, Oregon

While you are visiting and vacationing in Oregon, you'll find that there is just never enough time to see or do everything in Bend. So, to help you make the most of your time while you are here, we compiled a list of recommended itineraries chock full of fun ideas to help you truly live like a local and get the most out of your Oregon vacation experience.

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Rise and Fish

Fly Fishing the Metolius River

Drive Time: 45 minutes
Directions: Drive West on Hwy 20 through Sisters to Camp Sherman. Inquire at the General Store for the best flies and where the fish are biting.

All over the world fishermen get an early start, and Bend is no different. Your destination is the Pilot Butte Drive-In for a fireside seat and a four-egg omelet. Adequately fortified, your next stop is Fly and Field Outfitters to pick up some local tips on good fly fishing opportunities and spots where the bite is on. Or, just play your luck and go straight to the Metolius, Deschutes or Crooked Rivers for native rainbow and bull trout. Catch or not, life does not get much better than fishing in and around Bend. Head back to town for lunch at Parrilla, where you can either celebrate success or drown your fishing sorrows in their $1 Pabst Blue Ribbon pounders. Or grab a BBQ tri-tip sandwich to-go from Country Catering and fish through lunch (you only need one hand to fish, right?). Play Hemingway and take a nap by the river, or take a walk in the park to while away the afternoon. Either way, you're just passing time until your dinner reservation at 5 Fusion - another great way to enjoy fresh fish. A couple doors down take in a live show at the Tower Theatre. If it's the first Friday of the month, catch the Art Walk at downtown Bend art galleries. Sundays in July and August mean free concert Sundays at the Les Schwab Amphitheater in the Old Mill District. And, of course, you can just wander off and find your own local hot spot. No matter what, you'll hit the sheets tonight dreaming of fish, food, art, and music.


Hit the Trails

Tumalo FallS

Drive Time: 25 minutes
Directions: Drive west on Skyliners Road until the pavements ends, continue another 3 miles down the gravel road to the trailhead. 

Phil's Trailhead

Drive Time: 10 minutes
Directions: Drive west on Skyliners Road, turn left on Forest Service road 4604, (you can't miss the brown sign) follow 1/2 mile to trailhead.

 

Hiking and biking the Bend way are on the menu today, and like most of the locals, you'll want to get out early to beat the rush. Start with breakfast at the little house on Galveston we call The Vic (that's Victorian Cafe to everyone else). Do two things here: arrive before 8 am, and order the eggs benedict. Then load up and get going. Mountain bikers, your destination is Phil's Trail. What started as a bootleg network of local trails in the woods has become the fully Forest Service-blessed stuff of national mountain biking legend and envy. You'll soon find out why - not that it's hard to. Hikers, don't feel left out. You're headed a little further up the road to gorgeous Tumalo Falls. This is a true paradise. Cliffs to the west, forest to the east, and a gigantic waterfall right in front of you spraying a cool mist. Check out the falls' epic 90-foot drop, then hike your choice of routes. Once you've worked off your breakfast it's time to head back to town to spend the rest of the day reliving it at McMenamins Old St. Francis School. This converted Catholic schoolhouse is a great place to stay, with your choice of one private cottage​, guest rooms large enough for a family or converted classrooms. Catch a movie with a beer and a burger, hang by the fire at the scotch and cigar bar, or relax in the Turkish soaking pool. And to punch your locals card, order the Rubinator (Ruby and Terminator Stout mixed). Trust us.


Snow Day

Mt. Bachelor

Drive Time: 35 minutes
Sno-Park Permits are required at Sno-Parks, available at the Bend Visitor Center. Check snow conditions at www.mtbachelor.com.

Today we're hitting the snow, but we need to fill our tanks. On your way to the mountain, hit Longboard Louie's for a gut-busting breakfast burrito. Sufficiently fueled, it's time to head for the slopes. Snowshoers, your destination is Virginia Meissner or Swampy Lakes (at Swampy, we suggest Nordeen Loop, a 4.5 mile trail). Cross country's your game? Head out with the snowshoe gang or to Mt. Bachelor for 56km of groomed track. If you're the planning ahead type, stop by Devore's or Newport Market for a gourmet picnic lunch (live in the moment, too, with a cup of coffee and the best chocolate chip cookies in town from Nancy P's, just next door).

Then find a quiet spot mid-mountain with a killer view for feasting and fueling. Nordic skiers, take your picnic and find a hut along the trail at Virginia Meissner, stoke the fire and settle in. We guarantee you'll be torn whether to keep going or stay put. Skiers and snowboarders, if it's a powder day, there's only one place to go: hike the cinder cone at Mt. Bachelor and catch that fresh pow pow all the way down. Play hard, then reward yourself back in town at Deschutes Brewery (locals night and cheap beers, Monday), Bend Brewing Company (locals night, Tuesday) or Cascade Lakes (locals night, Wednesday). You'll get your chance to recap the day's epic runs and pick up some tips from the locals. Don't forget to stop by Visit Bend in downtown to email your pals and drum up some serious jealousy back home. Go to bed, and try to keep yourself from placing this card right back on top of the stack for tomorrow.


Cooling Off

Deschutes River

You'll find several points of access to the Deschutes. If you need to rent gear, go to Tumalo Creek Kayak & Canoe off Colorado on Industrial Way, near the Old Mill District. Sun Country Tours has a kiosk at Riverbend Park that rents float tubes and standup paddle boards, ​along with loaning free PFD devices to children 12 and under.

In Bend, there are at least two ways to beat the breakfast rush. One way is to sleep in, which you've definitely earned. Or two, take a morning walk or run along the beautiful Deschutes River Trail. Choosing number two? A local favorite is the 3-mile loop trail from Farewell Bend Park to the footbridge 1.5 miles upstream, which runs along both sides of the river. Then go fuel up on a late breakfast downtown at ​Cafe Sintra.

Then spend a lazy afternoon the way lazy afternoons were designed to be spent: tubing or paddling the river. You can rent kayaks and tubes at Tumalo Creek Canoe & Kayak or Sun Country tours ​kiosk and let the current carry you. Things the locals always remember: bring sunscreen, don't tease the geese, and be aware. Finished floating? The river is just as much fun from shore. Listen to an evening concert at the Les Schwab Amphitheater from the river, or get tickets for the whole show. On Sundays from June through August, it's free music in the amphitheater - bring a picnic or pick up something to go from one of the local vendors inside the amphitheater, and enjoy the show. At the end of the day, go to bed knowing you lived like a local.


Two Views of Bend

Big Sky Balloon Company

Drive Time: 25 minutes
Activity Time: 3 hours
Location: 15 miles north of Bend in Redmond 
Web: www.bigskyballoonco.com
Phone: 541.316.0398

Today you'll see your new favorite town from every angle. Start out with an early morning hot air balloon ride or airplane tour. You'll see this beautiful place in a way most locals haven't. Once you're back on the ground, get down to business and explore the town on foot. Start downtown with a little shopping. Fashion, jewelry, outdoor gear, and more, it's all here. Don't miss Hot Box Betty, Tres Chic and  LuLu's Boutique for some of the best finds around. Wear out your shoes already? Foot Zone is the place for you. Or head to REI in the Old Mill District. While you're at the Old Mill, spend some time browsing just about any store you can think of. Try to catch John Flannery from The Bend Tour Company for one of his signature tours, You'll be informed and entertained all at once with his electric cruiser car, Segway or electric bike. And then there's the Saturday Market across from the library. Don't forget all the parks. Can you stay a few more days?

Dinner tonight is Mexican at La Rosa, try the Red Cactus Margarita (better make that a pitcher). Want to eat outside? Few things in life beat Anthony's in the Old Mill for their river patio, grilled salmon, and halibut. Back downtown is the slightly exotic and delicious Joolz restaurant. After dinner, catch some live music at Silver Moon Brewing or The Domino Room. For a sweet nightcap, head to Goody's Ice Cream Parlor. A local's tip: order the brownie sundae (not on the menu) or find the best mud pie in town at the Pine Tavern. Then head for bed and wonder how you did all of this in one day.


High Desert Culture

Lava River Cave

Drive Time: 15 minutes
Directions: Drive south on Highway 97, turn left 1 mile south of Lava Lands Visitors Center. Bring a sweater and flashlight or headlamp.
Fee: $5 Recreation Pass required, payable on-site

Wake up and stretch as you gaze at your surroundings. You can't look at all these epic peaks
and not wonder how they got there. It's time to learn all about the natural history of Central Oregon, and that means one thing: volcanoes. Well, at least to start. Pack up and stop at Big-O-Bagels for a sack lunch and a great bagel dog. Then point the car south and make your way to Newberry Volcanic Monument, right in the caldera of an active volcano. Visit the spectacular obsidian mountain with trails that wind right through the middle of the glassy black rock pile. Stop at Lava Lands Visitor Center to get your bearings and take an interpretive walk. Check out the geology displays, plus learn the cultural history of Central Oregon. Don't miss Lava Butte, not that you could. Then head for Lava River Cave, where you can explore a mile into this natural tunnel through the ancient lava flow. Bring a sweatshirt, because it's a cool 42 degrees in Mother Nature's basement.

Next, it's on to the High Desert Museum, where you can explore the art, wildlife, natural resources, and culture of the high desert. Plan at least three hours to take it all in. Haven't seen enough? On the way back to town, take a detour to stunning Benham Falls, one of the largest waterfalls on the Deschutes. Back in Bend it's dinner at Zydeco for some of the best service and most flavorful dishes in town. Save room for the Wet Almond Cake and take home free homemade doggie treats to your canine friends. Afterward, drive to the top of Pilot Butte for a Cascade skyline sunset. Tonight, you'll dream of volcanoes, majestic waterfalls, and fire sunsets.


Wheels in Motion

Tumalo Loop Ride

Ride Time: 1.5 hours
Directions: From town, ride west out Newport Avenue through the rolling hills and mountain views around Tumalo, returning on OB Riley Road. Stop by Sunnyside Sports on Newport for loop options.

Grab some coffee and your road bike. Didn't bring yours? Rent one at Sunnyside Sports and don't forget to ask them about the best rides, because if anyone knows, they do. Or just head out toward the town of Tumalo for a nice loop of about 20 miles or so. Wherever you go, we ask that you remember to look at the road once in a while instead of the amazing landscape as you cruise along. Once you've worked up an appetite, head for McKay Cottage on OB Riley Road (you'll ride past it at the end of the Tumalo Loop Ride) for some well-deserved breakfast served in the boyhood home of a former US Senator, no less. Here, the best sports drink is their Mango Mimosas sure to take away all your pain. Now that you've worked your body over, head down the road to Jinsei Spa. Let them work you over, and finish up with a dip in their soaking tub. Still need some relaxation? It's time for sushi and around Bend, that means Kanpai. Try the nigori, or unfiltered sake to really decompress (happy hour is a hit here, too). So you've biked, breakfasted, spa'd and sushied yourself up. Time to head back to your room at the Hilton Garden Inn for the best mountain and sunset views in town. If there's a concert at the Les Schwab Amphitheater, you can listen from your balcony. Other nighttime options include heading over to the Old Mill 16 for a movie, or a nighttime treat of Ben & Jerry's. Feeling like a cocktail? Grab a handcrafted martini at Level 2. The amazing views come free with your drink. Head back home and dream of the perfect day; the one you just had.


Thirty-Six Holes

Aspen Lakes Golf Course

Drive Time: 30 minutes
Directions: From Bend, drive west on Highway 20 toward Sisters, turn east on Highway 126 toward Redmond, turn left on Camp Polk Road, turn right on Aspen Lakes Drive.
Tee Times: 541.549.GOLF

Today is the day we play golf. Head out early and grab your morning meal at CHOW. Fresh coffee, baked goodies, and a burly breakfast burrito are the order of the day. Fully loaded, it's off to Widgi Creek for your first round. Your morning 18 is hosted in the Deschutes National Forest, where giant ​​​Ponderosas frame 6,900 yards of Robert Muir Graves-designed golf. But bring your game -- tight fairways and undulating greens abound, as do the distractingly beautiful views. Sign your scorecards (or pocket them) and head back to town for a little rejuvenation. It's lunchtime. Park your golf bag at High Tides for seafood (choose from the specials sheet, handwritten every day) or settle in at ​La Magie Bakery for salad and sweets. Your afternoon round awaits at Aspen Lakes. Immaculate bent grass fairways and red sand bunkers make this a unique playing experience, even for those of us who live here. Or find your game at Lost Tracks, just southeast of town. Carved from a stand of ​Ponderosa pine and marked with lava rock outcroppings. Brian Whitcomb designed this course to be classic and walkable with 7,000 yards of golf every bit as challenging as the landscape is amazing. With 36 under your belt, head back to town for a well-earned evening of dinner and wine from one of Bend's local dining fave -- the nationally-acclaimed Blacksmith, which features Bend's most extensive wine list. Then tuck in your clubs for the night, and try to figure out how you are going to make tomorrow an even better day.

 

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