Arguably the Best PNW Trip without a Lottery
On the flight home from Redmond, it's hard to not think about the blind shots at Tetherow, the barefoot beers at Caldera Links, and the fact that we played 81 holes in three days and never once felt rushed. That last part is the whole case for Bend as a buddy-trip destination. The golf is genuinely excellent (Juniper Preserve, Tetherow, and Crosswater are all fantastic) but the reason Bend works as a trip is the town itself.
Here's exactly how we did it, and what I'd change.
Thursday: land, eat, get your legs under you
Fly into Redmond Municipal Airport (RDM), not Portland. If your group is flying in from more than one city, RDM covers enough of the map that everyone can usually get a direct flight.
We landed early afternoon, which is the move if you can swing it. Grab the rental cars, skip Redmond entirely, and drive straight into Bend before checking in.
First stop was the river. Bend Brewing Company has a patio that sits right on the Deschutes. It's the correct place to have the first beer of a trip: casual, unpretentious, and close enough to downtown that you can walk to dinner after.
For dinner, head to the Old Mill District. There are tons of good options, but we went to Bos Taurus: steaks, a good wine list, great vibe. If your group wants something more casual with the same river setting, Anthony's Home Port does excellent ahi and a patio for sunset.
Then ice cream. Goody's downtown has been doing this since the 1950s: old soda fountain counter, sixteen flavors, milkshakes built for sharing. It's a fifteen-minute stop that does more for group morale than it should.
From there, drive to Juniper Preserve; most people still call it Pronghorn, and honestly so do I half the time, even though the resort rebranded a few years ago. It's about 30 minutes northeast of Bend. Check in, get to bed. You've got 36 holes tomorrow.
Friday: 36 at Juniper Preserve
This is the one day of the trip built entirely around golf, and it should be. Juniper Preserve has two Signature courses on property (the Fazio and the Nicklaus) and playing both back to back makes for a great day if you can swing it. The Fazio plays the way you'd expect from a Fazio design: wide corridors, strategic bunkering, room to miss without being punished for it. The Nicklaus is the tighter test, more demanding off the tee, more consequence for a bad miss. Playing them in the same day gives you a real sense of contrast rather than just two more scorecards.
Two rounds is a long day, even with a cart and no real wait between them. Build in a real lunch break at the turn between rounds rather than grabbing a hot dog on the fly. You'll play better golf in round two if you actually sit down for ten minutes.
Dinner on property that night, then stay a second night at Juniper Preserve. We didn't leave the resort at all on Friday, and that was the right call.
Saturday: the long, good day; Tetherow, then Sunriver
Saturday is the biggest logistics day of the trip, and it's worth doing right. Breakfast at Juniper Preserve, then about 30 minutes to Tetherow on the west side of Bend.
Tetherow is the course people talk about most when they talk about Bend, and it earns it. David McLay Kidd's design plays over high desert terrain with fescue-lined fairways and greens that demand real thought, not just a good ball-striking day. It's the most difficult golf and most architecturally interesting round of the trip, and if your group only gets one photo-worthy tee shot all week, it's probably here. We kept lunch short and late because there was still a lot of driving and one more course ahead of us.
From Tetherow it's about 25 minutes south to Sunriver Resort, home of Crosswater and Caldera Links. We saved Crosswater itself for Sunday morning when we'd actually have the legs for a Top 100 course, and instead played Caldera Links on Saturday afternoon, the 9-hole par-3 course built into the Caldera Springs community. It's links-style, short, full of pot bunkers, and exactly the kind of low-stakes golf you want after two big days: nobody's tracking their score, everybody's got a beer in hand, and the greens are somehow better than a lot of full-length munis.
That evening we found the lazy river at Sunriver then late dinner and live music on property after.
If your group wants an afternoon completely off the course, the no-brainer decision is to grab some drinks and float the river instead. Load a cooler and let the current do the work for an hour or two. It's the right call for a group with mixed golf appetites, and something Bend is famous for.
Sunday: Crosswater, then home
Save Crosswater for the last morning. It's perhaps the best course of the trip on pure architecture, a Robert Trent Jones II design that's wide enough to be enjoyable but strategic enough to reward good decisions, and it deserves to be played fresh rather than tacked onto the end of a long day. It's also the kind of round you want to be the last memory of the trip rather than the first.
Depending on flight times, that leaves the afternoon for a late lunch back in Bend and a straightforward 20-minute drive to RDM for an evening flight.
If you can stay through Monday
We couldn't, but if your group has the extra night, this is where I'd spend it. Widgi Creek is the locals' course: a Robert Muir Graves design tucked along the Deschutes that doesn't get the same attention as the resort courses but is genuinely well-liked by people who live there. Brasada Canyons is the other option: a Peter Jacobsen/Jim Hardy design with Cascades views that stretch the whole round and wide, forgiving fairways that make it a good closer after a week of more demanding golf. Either one extends the trip without repeating anything you've already played.
Four nights, three anchor resorts, five courses if you skip the Monday add-on, six if you don't. The thing that makes this itinerary work isn't any single course, it's that the drive times are short enough that you never lose half a day to logistics, which means the trip stays about golf and dinner and beer on the river, and not about being in a car.