I recently just got back from an INCREDIBLE trip to Bend, Oregon with the Babes that Wander, and I can’t wait to share all the awesome things we got up to! If you’re looking for what to do in Bend, Oregon I have an action packed, EPIC 4-day winter itinerary to fully take advantage of all Bend has to offer.
As a winter sports kinda gal, I had a blast on our winter trip to Bend. Nate and I love to ski, but we never really get to do other wintery activities on our ski trips. He’s more focused on getting in all the runs we can, so it was so fun to get to try things like snowmobiling and snowshoeing. If you DO love to ski or board, Mount Bachelor has some incredible terrain. Its only about a 20 minute drive from downtown. I’m definitely going to come back with Nate and check the mountain out one of these days!
One thing I loved about visiting Bend was how conscious they are of the environment and preserving their wild places and wildlife. From our stay at Element and their sustainable practices to the tours we went on with Wanderlust Tours and their practice of leaving no trace, I really appreciated this city’s commitment to protecting the environment. Bend is a beautiful destination and the locals are incredible custodians of their city’s natural beauty.
Getting to Bend
If driving to Bend is not feasible, you will want to book a flight into the Redmond Municipal Airport. This is a really small airport! When you arrive and depart you’ll be walking right out onto the tarmac. Make sure to bring a coat on the flight with you…the walk from the plane to the gate was pretty chilly!
The flight from Los Angeles was pretty quick, just under 2 hours in duration. I actually flew on Avelo Airlines, which is a newish budget friendly West-coast airline I’ve been wanting to try. They offer direct flights to Bend from the Burbank airport. Stay tuned because I’ll be reviewing my experience flying Avelo very soon if you are interested!
Once you land in Redmond, you’ll definitely want to rent a car. While Bend does have public transportation, you won’t be able to get to some of the more outdoorsy areas without your own wheels. If you’re visiting in the winter I’d also recommend a 4 wheel drive vehicle just in case it snows during your visit. If you aren’t renting a car, there are a couple bus routes that will get you from the airport to downtown Bend.
Where to Stay in Bend
On our stay in Bend, Element Bend hosted the Babes that Wander. This hotel was the perfect home base for exploring all that Bend has to offer. The Element is located a couple minutes drive from Downtown Bend and about 20 minutes from the mountains, so its truly so convenient to so many of the best activities in Bend.
I love how the hotel’s design is inspired by the peacefulness of nature and all the sustainable practices the hotel implements. They have an amazing breakfast in the lobby each morning. You can choose between fruits and cereals, or have a hot breakfast made to order, and it is all included in your stay. Another thing I thought was really cool was their daily complimentary happy hour in the lobby. We took advantage of this a couple times during our stay and the best part: the wine the serve is made by the hotel’s owner.
While all the guest rooms at Element are very spacious, we stayed in the Studio Commons, which is a super cool concept and perfect for a group trip. The studio commons features a large living room and kitchen space that is connected to four guest rooms. Each room has their own room key which gives each person their own private space. We loved being able to hang out in the common room and make food in the huge kitchen. Its basically the perfect combo of the comforts of home in a hotel.
What to do in Bend, Oregon: My Epic 4-Day Winter Itinerary
What do in Bend, Day 1 (The Podski, Ice Skating, Wine Tasting)
Check out the Food Carts at The Podski
On our first day, I flew in early and arrived in Bend around 9:45am. I was ready to hit the ground running! After getting settled at the Element in Bend, we went in search of food. I happened upon this place called The Podski, which is a quirky and cute collection of food trucks and local beer. Anyone can find something to love here as they have cuisines from all over. You can take your pick from fried chicken, Middle Eastern comfort food, awesome Vegan offerings, tacos, sushi, and more.
Ice Skating at the Pavillion
After some delish eats, I headed to the Pavillion for some ice skating. You might not know this about me, but I was a competitive figure skater for most of my childhood. When I saw photos of this rink online, I knew I had to check it out. The Pavillion is an open air skating rink with a roof and endless windows allowing so much natural light and air to flow in. Because it is open air, the ice is only available from November-April. If you visit in the summer, it transforms into a roller rink! Make sure to check out their schedule for open skate times or their cheap skate sessions which are only $6!
Wine Tasting + Dinner at Domaine Serene
One of my favorite meals (and experiences) on our trip was getting the VIP treatment at Domaine Serene Wine Lounge. If you’re wondering what to do in Bend and you are a wino, this is a must stop! Several locals told me this is their favorite winery in town, and its so easy to see why.
First of all, the space is STUNNING. We got a little tour that included a peek downstairs at their members only area, and learned a bit about the history of the historical Spheir Building. I loved the high ceilings and exposed brick coupled with the dim lighting…truly the perfect setting for sipping on Domaine Serene’s delectable vintages.
Like I said, we got the VIP treatment. One of Domaine Serene’s Sommeliers walked us through our custom wine flight with food pairings and shared their production process in both their local Dayton Ohio winery as well as their Bordeaux estate. They specialize in Chardonnay and Pinot Noir, two of my fav varietals, so of course I was in wine heaven.
Oh, and the food? Absolutely delish! I had a hard time choosing between the Waygu Steak Frites, Oxtail Pappardelle Ragot, and the Hazelnut Crusted Salmon, but in the end, my seafood craving won out!
What to do in Bend, Day 2 (Snowmobiling, Prohibition Cave + Distillery Tour)
Snowmobile Excursion with Central Oregon Adventures
If I had to pick my favorite thing we did in Bend, it has to be the Snowmobiling Excursion with Central Oregon Adventures. I’ve been wanting to try snowmobiling for a long time, but since it never seems to happen on our past ski trips, I was so excited to finally try this high speed snowsport out!
Central Oregon Adventures was about a 25 minute drive from our hotel. Upon arrival, we headed into their yurt to grab helmets and goggles. Next, we were paired up with a snowmobile and received a brief lesson on how to drive them. Nervously, we started our engines and followed our guide to a big open field so we could get the feel of the snowmobiles and practice our turns before heading out on the trail. To my surprise, I got the hang of it quickly! My dad loves to race dirt bikes so I have some experience on a motorcycle which definitely helped I think.
After our warm-up laps, we headed single file onto the trail for our excursion. We rode for about an hour and a half to the top of a mountain with the most incredible views where we stopped to take a break, and of course, take pictures. The ride was exhilarating and I definitely got my dose of adrenaline for the day. The excursion lasted about 2 hours total and by the end, I definitely felt like a pro!
Some things to know before you go on this excursion:
- Dress warmly! I basically wore what I might wear skiing, which is warm socks, a base layer, my snowsuit, a neck gaitor, snow gloves, and snow boots.
- Your hands stay super warm because the handlebars are actually heated!
- Snowmobiling is a workout! You will feel it in your arms and your chest from gripping the hande bars and steering such a heavy piece of machinery
- If you want to bring anything with you, be aware that there is no storage on the snowmobiles. I recommend packing a small backpack…this one is my favorite for skiing and hiking!
Prohibition Cave Tour with Wanderlust Tours
Later that afternoon (after a quick outfit change), we got picked up at our hotel by Wanderlust Tours to embark on their Prohibition Cave Tour. This is a two part excursion, consisting of a tour of Boyd Cave, followed by a tour of Oregon Spirit Distillery with a tasting. For the cave portion of the tour, we were provided with helmets and headlamps before descending into the subterranean caverns of this 1880 foot long lava tube.
Boyd Cave is anywhere from 75,000 and 400,000 years old and was created from volcanic activity from nearby Newberry volcano. During Prohibition, this cave (and the others in the surrounding area) were used to distill and store illegal alcohol. Not a bad idea, since the cave makes for the perfect cellar. The temperature down here is around 45 degrees all year round, so you’ll want a warm coat and possibly some gloves!
Boyd Cave is also home to bats! During the winter they are in hibernation mode, so you may not see many, but we saw two! During our tour, our awesome guide Katie gave us some really interesting info and facts about the bats as well as the cave and its various properties. She was super fun and very knowledgeable…we definitely consider her an honorary babe!
Before embarking on this tour, make sure to dress warmly, even if you visit in summer. My vegan down puffer from Noize kept me super warm, and chic if I do say so myself! Snag yourself one here, they come in tons of colors and are pretty flattering as far as puffer coats go!
Be prepared for a bit of climbing and scrambling over rocks…you may even crawl at some point! Definitely wear something you are fine with getting a little dusty, as well as comfortable shoes.
After we made it out of the cave, we hopped back into the van for a short drive over to Oregon Spirit Distillery. One of their staff took us on a tour of their distillery and explained in great detail how the distillation process works from start to finish. Their distillery is known for their award-winning whiskeys, but they also make vodka, gin, brandy, and absinthe. Its always fascinating to learn where your booze comes from!
After the tour, we each got a flight of their whiskeys to taste and a cocktail of our choosing from their cocktail menu. Our tour guide Katie supplied a big plate of assorted cheese and crackers to snack on during our tasting. I have to say, their whiskey is SO GOOD. They source their ingredients from local farms and of course their oh so fresh and delicious Oregon water. The result is so yummy!
Dinner at 900 Wall
When discussing what to do in Bend, Oregon, of course, great food comes into play! Bend has some incredible restaurants, so there is no shortage of great places to get a bite to eat. 900 Wall is a local favorite and it is located in downtown Bend. The space is very sleek and they have a great menu and cocktail list. Their menu can be described as modern American with Italian and French influences, and their dishes are seasonally inspired and responsibly sourced.
Of course, I got the Seared yellowfin tuna (newsflash, it was amazing), but we also shared some of their pizzas and those were definitely a crowd pleaser with all the girls.
What to do in Bend, Day 3 (Shopping, Wine Tasting, Snowshoeing)
Shopping at the Old Mill District
Of course, you can’t go on a girls trip and not do some shopping, am I right?! The historic Old Mill District sits on the Deschutes River. It used to be a mill, and is now an outdoor shopping area. You’ll find something for everyone here. They have lots of great dining options, a movie theater, art galleries, and some great local boutiques as well as mainstream stores everyone knows and loves, like Sephora, American Eagle, Athleta, and more.
Everyone knows you shouldn’t shop hangry, so we started the day with lunch at Gregg’s Grill. Gregg’s serves up American food in a comfortable space with high ceilings and huge windows that look out onto the river and the mountains. If you love a good lunch with a side of views for days, this is a great spot!
The Old Mill district also has some really fun art installations and murals scattered throughout. If you are always on the hunt for a cute mural for the ‘gram, here are my three favorites:
I love to shop local when I travel, and you can find several great local boutiques at the OMD. My favorites were Vanilla Urban Threads for great fashion, Hello Sunshine for fun accessories, and Ticket Mill for great souvenirs and gifts.
After a successful afternoon of shopping, you deserve some wine. Make sure before you leave the Old Mill District that you pop into Va Piano for a wine tasting and charcuterie board. This local Oregon winery specializes in big, bold reds, so their selections were definitely speaking my language. We definitely took a couple bottles back to our hotel to enjoy later.
Private Chef Dinner + Snowshoeing to a Bonfire!
My second favorite thing we did while in Bend was our second tour with Wanderlust Tours. Katie picked us up again and brought us to what really seemed like the middle of nowhere for a private chef dinner in a warming hut. Our meal was delicious and consisted of butternut squash soup and fresh bread to start, followed by short ribs and roasted root vegetables with mashed potatoes. Our host served up red wine from another local Oregon winery.
After dinner, we headed outside and grabbed a pair of snowshoes and a headlamp. Katie instructed us in how to put them on, and I do have to say, I struggled a bit with it…I’m blaming the wine! The great news is between my babes and our awesome guide, I did end up getting those snowshoes strapped on so we could trek out to a bonfire in the snow!
We hiked a little over a mile in the dark to find a roaring bonfire in the snow, complete with hot cocoa, hazelnut vodka, and desert. It was magical to be in the middle of the Oregon wilderness cozied up to the fire and looking up at the stars…not a sight this city girl gets to see very often! If you’re in Bend in the winter I can’t recommend this tour enough. It was truly something so unique and unlike anything I’ve ever done on any of my travels before.
What to do in Bend, Day 4 (Brunch, The Last Blockbuster, Spa)
Brunch at Lemon Tree
One of the spots in Bend that came highly recommended by our hosts was The Lemon Tree, which is a cute little cafe in Downtown Bend. Their menu features dishes inspired by international cuisine and they have a great list of cocktails. I loved the decor too. It definitely felt very Amalfi Coast inspired.
The LAST Blockbuster
I was shocked to find out that there is in fact one Blockbuster left in the world and it was located right around the corner from our hotel in Bend. If you’re in Bend, this is definitely a spot you gotta stop and check out just for the nostalgia. It felt like I had stepped back in time to a Friday night in the 90’s getting to pick out the movie for the weekend.
Yes, it is a functioning Blockbuster, so you can rent a movie! They also have a lot of great merch to take home as souvenirs.
Spa Day at Anjou Spa
What to do in Bend, Oregon if you aren’t super outdoorsy? Get a massage! After all the very adventurous activities of this trip, we were all ready for some relaxation and pampering. Anjou Spa was just what we needed to cap off our trip. At Anjou, they strive to help you look and feel your best, inside and out! I booked the Anjou Custom Body 90 minute massage which includes a foot scrub…I’m fairly certain I fell asleep at one point I was so relaxed!
I also tried out their facials and believe me when I tell you, I was glowing after that treatment! I mean, look at us, we all were!
Dinner at Joolz
For our last dinner, we made a reservation at Joolz. This restaurant is a blend of Middle Eastern and South Western cuisine. That unique combination is perfectly exemplified in their decor.
Their menu was incredible and its a perfect spot if your crew is a mix of vegetarians and meat lovers because Mediterranean food always has tons of veggie options. We loved the hummus, baba ghanouj, halloumi, and the beef shawarma. Make sure you save room for their desert! They are known for their date cake and it definitely lived up to the hype!!!
Do you prefer travel vlogs? Check out my Bend Travel vlog here!
Bend, Oregon FAQ’s
Is Bend, Oregon worth visiting?
Absolutely, and especially if you love being outdoors! Bend offers something for everyone, from hiking, mountain biking, snow sports, and more. I can’t wait to visit in the summer because I just know it will be a totally different experience.
What is the best month to visit Bend?
This depends on what you want to get out of your trip! I don’t think there is a bad time to visit Bend, as there is always something great to experience year round.
What is Bend, Oregon known for?
Bend is known for its pristine beauty as well as all the fun outdoors activities you can do there. They are also the beer capital of Oregon with over 22 breweries. Bend is also known as the Palm Springs of the north because they have 10 golf courses.
How many days do you need in Bend?
I would suggest at least three to have time to get out and take advantage of all the adventures Bend has to offer.
What to do in Bend, Oregon for free?
- Go the Heritage Walk
- Take a tour of the award winning Deschutes Brewery
- Go look at the stars at Pine Mountain Observatory
- Float/go kayaking on the Deschutes River
- Go Caving (see above!)
Thanks for checking out this what to do in Bend, Oregon travel guide + itinerary! Stay tuned as I’ll have more Bend, Oregon posts coming soon!
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