(This is the first installment of PretentiousPDX’s new series of “Get on My Level!” recommendations and reviews.)

Every year in the first part of November, I take my annual trip to Central Oregon for a little late fall R&R. This tradition started rather accidentally when I inherited my grandmother’s WorldMark timeshare membership a few years back. While WorldMark boasts a very respectable selection of resort offerings, my Rock Star Lifestyle (RSL) affords me precious little time to travel around the country and visit timeshares. So, at the end of every year, I find myself scrambling to use up my allotment of timeshare days before they expire – which usually involves making reservations at whatever’s close and still available (another place I’ve frequented several times due to this scenario is the charming hamlet of Long Beach, Washington – and you can just imagine how bumpin’ Long Beach is in the middle of December).

One year, the only option available was a unit at WorldMark’s collection of condos the Eagle Crest Resort in Redmond, Oregon. On my first visit there, I immediately fell in love with Central Oregon. Although Bend and its environs are normally bitterly cold by mid-November, after two months of the Portland rainy season, Central Oregon’s cold, dry climate and reputed 300 days of sunshine a year offer a much-welcome dose of Vitamin D during the fall and winter months. After that first visit in 2009, I’ve gone back every November.

This year, I decided to take things to the next level by inviting three PretentiousPDX’s most notorious co-conspirators to come partake in festivities for our first annual Executive Retreat: PretentiousPDX co-founder and the other half of “Yume and Jenna Are Cooler Than You,” the inimitable Jenna B; up-and-coming downtown socialite and Instagram aficionado Paulette; and wilderness expert and violin virtuoso, Erielle.

Early this last Saturday, the four of us loaded our collection of over-sized suitcases (given our mutual commitment to the Rock Star Lifestyle, neither Jenna, Paulette or myself are capable of packing light) into the trunk of my Toyota Camry, cranked the Mackelmore, and headed out.

GETTING THERE
Unless you’re a fan of small commuter airlines, the best way to reach Bend is by car (covered wagons are also quaint, but they’re not good for a weekend getaway). From Portland, there are two main routes that you can take: East on US-26E around Mount Hood and then South on US-97S, or South on Interstate 5 and then East around Detroit Lake on OR-22E and US-20E.

Which route you take is largely a matter of personal preference (and/or which town you’re trying to visit) – the Mount Hood route takes you through the mountains fairly quickly, followed by a long, fairly straight drive through the high desert.  The Detroit Lake option involves a rather tedious interlude on Interstate 5 (“Oh, Wilsonville! How quaint.”), followed by a long, winding drive through the mountains (although the Alpine vistas are quite picturesque) and then a quick sprint through the desert at the end. If you fancy a drive in the desert, I’d go with the former. If you wish to see the Willamette Valley in all its verdant glory, I’d stick with the latter. Anecdotally, I’ve heard that US-26 is the first to get attention from the snow plows this time of year.

SATURDAY
When we arrived in Bend, our first stop was for lunch at Hola!’s downtown location. Hola! is a small chain of Mexican-Peruvian restaurants in Bend and Sunriver. Bend has a small but competent dining scene, and by these standards, I don’t think Hola! was a disappointment (Yes, I know that’s a back-handed compliment. Deal with it.). They have a fairly imaginative menu, and their entrees are both reasonably portioned and reasonably priced – both characteristics that are refreshing to find in Mexican cuisine. All too often, I find that Mexican/Southwestern eateries either offer paltry portions at unreasonable prices, or – even worse – ridiculous portions and reasonable prices… and often questionable quality.

After lunch, we headed at Jenna’s recommendation to Boneyard Brewing for a little afternoon beer-tasting. Boneyard is a small brewery tucked away in a rather quiet-looking neighborhood just outside of downtown, near Hwy 97. In keeping with their rather bleak name, there’s nothing ostentatious about Boneyard’s digs – they run their shop out of an low-slung warehouse with a tiny tasting room and the sort of decor you’d expect to see a place called “Boneyard.” There’s a bit of a rough-around-the-edges feel to the place. But don’t let the unassuming venue fool you – these dudes make some seriously good beer – at very affordable prices. When we visited (on a day, it’s worth noting, when the rest of downtown Bend seemed almost deserted), their tasting room was packed. Despite running twenty-odd tastings at once, the two guys behind the counter were extremely affable and attentive (the fact that I was rolling with three hot ladies may have helped with that, but who knows). Boneyard is probably best known in the Portland area for their Hop-Venom IPA, but their RPM IPA and their Diablo Rojo Red Ale are both worth trying, as well. A four or five beer tasting will run you 4 “bones” (ahahaha, I crack myself up), and you can get a filled growler for $15. Be aware, though – these guys only take cash or check, so come prepared.

While Deschutes is probably first and only brewery that most Bend tourists visit, here in Portland I can drink a Mirror Pond anytime I want. For my money, if you only have time to visit one brewery while visiting Bend (like we did), you should check these guys out.

Having spent an enjoyable afternoon in Bend, we headed north to check into our High Desert HQ at Eagle Crest Resort, just outside of Redmond. The resort features a loose conglomerate of hotel rooms, timeshares, vacation rentals and condos, golf courses, spa and exercises facilities, as well as a couple of small cafes – pretty much anything you could want while on holiday. (The only thing they don’t have is a good bar.)

While we stayed in my timeshare on this trip, if you don’t have any ailing relatives and you don’t feel like dropping five figures on a timeshare membership, you can stay onsite at the recently renovated The Lodge at Eagle Crest, which is operated as a Holiday Inn Resort. I’ve stayed at The Lodge before, and the rooms are all very nice (assuming you like the standard Holiday Inn amenities) and include access to all the resort facilities, including the hot tub, pool, and sauna.

That evening, after an in-room happy hour and trip to the spa, we headed back into Bend for an evening of shenanigans. For dinner, we headed to Brother Jon’s Alehouse, right across the street from Deschutes Brewery. I’ve been to Brother Jon’s before, and they consistently offer solid entrees and a great selection of beers on tap. Definitely a place worth checking out, if you want a simple meal and a good beer before heading out for a night on the town in downtown Bend.

One interesting thing did happen while we were at Brother J’s, though. Unbeknownst to our server, they had just blown the keg for the beer Paulette ordered, so when she came back, our server offered Paulette a beer from a newly tapped keg (so newly tapped, in fact, that she didn’t know what it was called) – a nice, light ale with a hint of melon. Much to Paulette’s amusement, when the check came, she found out that the beer she’d been drinking was called “Nice Melons” (which I later found out was made by Flat Tail Brewing in Corvallis). In high spirits, she snapped an Instagram of her bill and uploaded it into the interwebs with the hashtag, #NiceMelons. Now, if you are as world-weary as I am, you can only imagine what other sorts of photos get a hashtag like that – and I said as much as we were paying our tabs. However, a quick perusal of Instagram reveals that your average hash-tagger is not as prurient as one might think. What they are is painfully literal. If you ever do a search for that particular hashtag, you will find, almost without exception, dozens and dozens of photos of various types of melons. Honeydew, cantaloupe, personal watermelons. They’re all represented. The people of Instagram love a good pun, it would seem.

Following dinner, we wandered downtown in search of further excitement. Being the last Saturday of Daylight Savings Time, some members of our group wanted see if the bars exercise their OLCC-given right to stay open an hour later when we “fell back.” (Spoiler Alert: None of them did.)

Our next (and as it turned out, last) stop on our micro-pub crawl, was a place called Velvet, a pleasantly intimate little club occupying a long, thin – almost vestibule-like floorplan split over two levels. Velvet’s interior is almost entirely comprised of unfinished wood and a neo-rustic vibe reminiscent of Portland’s Doug Fir Lounge – perfect for a night of cocktail-swilling in the desert. The main reason that we ended up at Velvet, however, is because Jenna and Paulette happened to know that Velvet has their own Eastern Oregon twist on Bottle Service – a $30 barrel full of cocktails, delivered straight to your table. When we were there, our barrel featured some sort of delicious vodka-hibiscus-lemonade concoction that the girls enjoyed immensely. However, do keep in mind that it can take a rather long time to empty a cask full of cocktails, so plan accordingly. 

SUNDAY
The next day, we went to a late brunch at CHOW, a quaint breakfast and lunch joint near downtown Bend. CHOW specializes in locally sourced ingredients, and offers a simple but tasty array of breakfast and lunch options. The food is great, and they make a mean Bloody Mary, but their bar is limited, so don’t order anything too fancy. And definitely stay away from the Mimosas – $10 is far too much to pay for a very weak mimosa. That said, this is definitely a place worth visiting – just be prepared to wait, as CHOW is PACKED on the weekends.

Following brunch, we decided to do a little sightseeing on our way back to Portland. Our first stop was Pilot Butte, a defunct cinder cone in the heart of Bend. The best way to see Pilot Butte is hike up to the top – there are several trails of varying lengths and difficulties. If you’re short on time (as we were), though, you can also drive up straight up to the scenic viewpoint on the top – just be prepared to endure the stares of every hiker you pass them in a cloud of dust, glaring at you as those you were the biggest asshole on earth. No matter how you choose to get there, once you’re at the top of Pilot Butte, you’ll be treated to a scenic, 360-degree view of the entire Bend area and all of the surrounding mountains – on most days, you should be able to see Three Sisters, Mount Jefferson, Black Butte, and Mount Hood.

After visiting Pilot Butte and checking out of our timeshare, we retraced our route from the day before, stopping at Smith Rock State Park for a very brief bit of sightseeing. There are numerous opportunities for climbing and hiking at Smith Rock, but we had to content ourselves with walking around the campgrounds and taking a shitton of photos so that we could Instagram The Shit Out Of™ out of them. Then, with daylight fading, we got back on the road and drove home to Portland.

IF YOU GO
Bend is a great to visit, and I personally think the late fall is the best time to, since it will offer you a brief respite from Portland’s indeterminably long rainy season. If you go, however, a few, final words of advice:

1. Go early. The passes start getting pretty snowy around Thanksgiving, so either go early in the fall, or be prepared for winter driving conditions.
2. Take a Long Weekend. A Saturday/Sunday trip just isn’t enough time, unless you only want to see a handful of things. Take a long weekend, or drive out right after work on Friday – you’ll thank yourself for the extra time.
3. Buy some Vitamin D. After a couple of days in the sunshine, you’ll come back to Portland refreshed… but the rainy will seem that much more dreary.

Stay sharp, Portland.

LODGING
Eagle Crest Resort  (www.eagle-crest.com), Resort and Golf Course.
1522 Cline Falls Road, Redmond, Oregon.

FOOD & DRINK
Hola!  (www.holabend.com), Mexican-Peruvian Restaurant & Cocktails.
Multiple Locations.

Brother Jon’s Alehouse  (www.brotherjonsalehouse.com), Pub.
1051 NW Bond Street, Bend, Oregon.

Velvet  (velvetbend.com; on Facebook as VelvetBend), Cocktail Lounge.
805 NW Wall Street, Bend, Oregon.

CHOW  (www.chowbend.com), Breakfast and Lunch.
1110 Newport Avenue, Bend, Oregon.

ATTRACTIONS
Boneyard Brewing  (www.boneyardbeer.com), Brewery (duh). Cash or Check Only.
37 NW Lake Place, Bend, Oregon.

Pilot Butte State Scenic Viewpoint (www.oregonstateparks.org/park_42.php)
Bend, Oregon

Smith Rock State Park  (www.oregonstateparks.org/park_51.php)
NE Crooked River Drive, Terrebone, Oregon