Forewarning: this is an unsolicited blog written from a genuine place of love by a Bend native. The following builds a solid itinerary for those who like to wake up with the sun and be tucked in around 9 pm.
We are so fortunate to live, work, and play in Bend, Oregon especially amongst such synergy and creativity. We wanted to take a moment to boast a few local must-sees, -dos, -tastes, and -experiences around Central Oregon as “day plans” during the Winter season.
We hope this list gets you excited to make the most of Bend during the winter season and packs up your time while here with our best of the best—getting you off your phones googling and researching in-the-moment needs, with more time to look around and soak it all up! For those that just want a bulleted list and none of our romantic narrative; skip to the bottom two, darlings:
Jacq XC skiing downtown to open the shop after a big night of snowfall in late February 2019.
Indulgent Downtown Bend Day
Begin with an anything but light brunch at The Lemon Tree (shakshuka and crab cake benedict to name two menu winners), walk it off around the iconic Drake Park to circle back around and find FOUND Natural Goods and other like-minded downtown boutiques and shops (Cowgirl Cash & Arrange and Feathers Edge Finery are two must-shop shops). Take a warm coffee break at Lone Pine’s new location and wander around a bit more until happy hour to find yourself sampling from over 300 tequilas y mezcals at M&J Tavern (order the jojos if you want the full experience). After you’ve built up your liquid confidence, get some of the best PNW Lebanese food at Joolz with a warm and gooey date cake, and a shot of arak to end your day of indulgence.
Pro-tip: go for a long run in the morning or XC ski into town to make room for a day of indulging, bring your own shopping bags, take home some coffee beans for the morning, and detour to The Lot if you’re not into shopping.
Cabin Four at Loloma in the winter.
R&R at Loloma Lodge
If you’re craving some nature time surrounded by a rushing river, fragrant green scenery, and moody cloud systems—all via a radiant floor heated MCM cabin—then we know to send your lucky self to Loloma Lodge. Bring a notebook, comfies, some reading you’ve been meaning to catch up on, even a movie or two and some light paperwork with a facemask and you’re in business. The McKenzie General Store has all the fixings you’ll need and Takodas will leave you ear-to-ear if you want to see other humans.
Pro-tip: book in the off/winter season for a 1-night stay! Also, you can easily ski HooDoo from Loloma or go into Eugene for the day but we recommend staying local to get the true essence of this magic McKenzie River-front property.
Stella and Jacq at Suttle Lake in January 2019 enjoying a moment after running around the lake for the daily cardio.
Sisters Afternoon by Foot
If you have the whole day, you should begin with a BC tour into the Three Sisters Wilderness to earn what’s ahead of you. Or, resort ski at HooDoo! But if you have to work in the AM, kick things off in the afternoon with a coffee break from Fika Coffee where you can have a sweet and adore the Scandinavian environment before your treatment inside Shibui Spa. Steam before and soak after in their killer amenities and remember to leave an offering with Buddha. Three Creeks Brewing and a quaint movie theater are all within walking distance of the spa and the brewery offers a delicious juniper berry crusted wild salmon dinner with micro-brew flights to accompany. If you’re a treasure hunter, the Habitat for Humanity Re-Store is downtown Sisters and is a great detour to hunt and gather. Next door to the Re-Store is Oliver Lemons for a snack para llevar.
Pro-tip: stay the night at Five Pines, or the weekend if you’re game. Another rad option in this neck of the woods is Suttle Lake as pictured for delicious food and lodging that’s close to HooDoo too.
Pro-tip No. 2: Extend your weekend and stay at The Suttle Lodge (now owned by Ace Hotel people and recently renovated) on your way back via Portland.
Jacq & Jacob at Mount Bachelor on a bluebird day, 2019.
Ski Then Soak
Get yourself to Mount Bachelor and slide down the fluffy white hill (with a break at our absolute favourite, Sun Bar). After you’ve felt the burn de groomers, soak in salty waters at McMenamins Turkish Pools, and continue to warm up from spice level three while dining on Khao Soi Curry at Wild Rose Thai. Bonta is next for a local, fresh gelato dessert with a nightcap at San Simón for the big kids will leave you toasty, stoked on Bend and ready for the hay. Oh! Simón is interactive—he’ll take an offering too.
Pro-Tip: order the chili and hot toddies from Sun Bar, and if you have a friend who doesn’t ski we highly recommend you delegate the task of getting your names on the Turkish Bath list asap!
Jacq trail running with Stella at Smith Rocks in December 2019 on a mild and beautiful blue day. Photo by Geoff Ragatz.
It’s Warmer on The Rocks
Hike, run, or climb Smith for hours and hours then dine at The Depot after for dinner or happy hour. Need we say more? #willnotdissappoint
Pro-knowledge: Smith tends to be about 10 degrees warmer than Bend; plan accordingly.
Jacq halfway up Tumalo Mountain, 2019. Photo by @trubakerism
Head South for Sunriver
Begin at The High Desert Museum to learn about the history of the area and get in touch with the local animal kingdom. Head further South into Sunriver for a Sintra brunch then have an ice skating adventure. Follow with more coffee or hot chocolate breaks (common you’re ice-skating), and some shopping to stimulate the local economy. Or, if you prefer less consumption, a peaceful walk along the Deschutes River with a hot tea is a great option. And for dinner, there’s of course, Sunriver Brewing for the grand meal to end the evening. Their tacos are so good!
Pro-tip: This is an easy kid design kind of day. There’s also a Sunriver Brewing on Bend’s Westside so you can safely bounce around after dinner rather than winter commute it back. And, if you’re lucky and the weather isn’t too gnarly, you can always take the dirt road home! Conversely, stay out at Sunriver and skin-up Tumalo or ski Bachelor in the morning!
Photo by Adam McKibben/Visit Bend
Best Local Experiences
Explore the downtown shops including FOUND Natural Goods, Cowgirl Cash, and Feathers Edge Finery
Smith Rocks
Stay out at Suttle Lake Lodge and eat the best fish dip, and fish sandwich you couldn’t even dream to be better than it is
Skin up Tumalo Mountain! Ski Mt. Bachelor! Or, HooDoo if you’re on a budget and entertained by Oregonians skiing in blue jeans!
Walk/hike Pilot Butte for sunrise or sunset— do it twice to be a true Bendite
Walk/run The Deschutes River trail south from the Old Mill District
XC ski to Tumalo Falls
Shop at The Iron Horse for a throwback to Old Bend
XC ski or skin around Crater Lake and snow camp if you’re game!
Pine Tavern has a great happy hour in the tavern, but the hot soups and grilled chicken caesar salad will not disappoint
Rent a riverfront cabin at Loloma Lodge
Hang out at the McMenamins fire pits by their cigar bar called O’Kanes
Chill, eat, and drink at The Lot Food Truck Court at Bend’s classic westside neighborhood — they have heated benches! The East Side now has On Tap with a similar charm except much more western feeling
Shop local art at The Workhouse then have a satisfying lunch or baked goods at Sparrow Bakery on 2nd Street
Lava Lands has a stunning aspect of the Cascade Range—hike out on a clear day and bundle up
Grab a hot tea and find a cozy nook at Big Story Bookstore—get inspired by their book installations
The High Desert Museum / Sunriver Day
Have a spa day at any one of our awesome spas; a Sisters Day opens up some time at Shibui Spa
El Sancho tacos by Natalie Puls
Must-Taste Restaurants
Wild Rose Thai Khao Soi Curry
Jacksons Corner
Forbidden Rice Chicken Bowl from Joolz
Beetnik at Dogwood Cocktail Cabin
Stumptown Coffee at The Commons
M&J Tavern - 300+ Tequilas y Mezcals
Lone Pine Coffee
Ramen bowls & sushi at Kanpai
A slice, salad, brownie, and glass of wine at Pizza Mondo
Lettuce wraps at Immersion Brewing
Chicharones and the Salmon Wrap from Parrilla
Everything at Spork
Paella from Barrio is so perfect in the winter
Anything from Village Baker, especially their tomato bisque and rolls
Cocktails, steaks, and fresh crab legs from Bos Taurus
The tasting menu from the bar at Ariana
Charcuterie board at Crux Fermentation Brewery is divine - there’s even honeycomb!
Anything at El Sancho especially the strong and short El Caminos and fried plantains
Fish and chips, the Black Bean Burger, and the naked wings with a side salad from Bend Brewing Company with a Tropic Pines IPA
San Simón for the atmosphere, soundtrack, and stiff drinks
The Lemon Tree shakshuka and crab cake benedict to name two menu winners
MOST IMPORTANTLY:
PLEASE LEAVE BEND AS YOU FOUND IT!