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What to Do in Bend Oregon: 3-Day Winter Itinerary

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What to do in Bend Oregon, by travel blogger What The Fab

The Babes just got back from such a fun trip to Bend, so today I’m sharing all the deets on what to do in Bend Oregon for a three-day winter trip!

I’m usually more of a warm-weather gal, and I tend to hit up a lot of tropical destinations. Combine that with the fact that I’m a born and raised California girl, and I’m pretty useless when it comes to dealing with the snow.

So Bend was a bit of a different adventure to me, and guess what? I freaking loved it.

There are SO many fun things to do in Bend no matter which season you’re visiting during. But all the winter and snow activities were a total blast.

Plus, I got to put together some new cold-weather outfits. 😉 Check out my post on what to wear in Bend Oregon if you’re in need of some inspo!

I know a lot of people are opting for domestic travel within the United States right now over dealing with ever-changing rules and restrictions around international travel. So Bend is the perfect spot to add to your bucket list!

This mountain town is absolutely beautiful—from Deschutes National Forest to Oregon Badlands Wilderness, to Smith Rock State Park, you’ll be met with scenic views of the Cascade Mountains and endless adventuring options.

Getting to Bend Oregon

If you’re too far to drive to Bend, you’ll want to fly into the closest airport in Redmond (RDM). It’s a very small airport with just a few gates, which means that getting through it is a breeze.

My flight from SFO to RDM was short and sweet (about 1.5 hours), but do note you might be on a very tiny plane. I flew United and both ways the plane was so small that the overhead compartments weren’t big enough to store roller/carry-on suitcases.

They’ll store your carry-on suitcase for free as you board your flight, but just something to be aware of—I had things like my DSLR camera and my drone in my carry-on, and I don’t like letting those out of my sight so I took them out before having my bag stored below.

From RDM, Bend is just a short 20-minute drive. The airport also has super easy access to rental cars—no shuttles needed, you just walk outside and the rentals are right there.

Where to Stay in Bend Oregon

We stayed at the Element Bend and it was the perfect homebase for us. It’s centrally located with plenty of free parking, and the room rates are very reasonable.

The Babes stayed in Element Bend’s new Studio Commons room set up, which is great for a group! There’s a common area with a living room, kitchen, and dining table and four rooms connected to the common area.

They also provide free breakfast (that includes a freshly made hot option that rotates daily—no sad continental breakfast here!), a swimming pool and hot tub, and a gym. We were set!

There is legit something for everyone in Bend. Obviously if you’re into skiing and snowboarding (I am not, lol) that’s an option, but there are a lot of other really unique experiences too, as you’ll see in this itinerary all about what to do in Bend Oregon.

Into cycling? There are tons of mountain biking trails. Just want to relax, eat, and drink? We did plenty of that too and you can easily find a cool distillery or brewery to hit up (Crux Fermentation Project is a fun one!).

Alright, let’s get into all the juicy deets for what to do in Bend Oregon on your next epic snowy adventure trip!

What to Do in Bend Oregon: 3-day Itinerary for a Winter Trip

Day 1: What to Do in Bend Oregon

What to do in Bend Oregon, by travel blogger What The Fab
What to do in Bend Oregon, by travel blogger What The Fab
What to do in Bend Oregon, by travel blogger What The Fab

Go on a Snowmobiling Tour

Our first adventure was heading out on a snowmobiling tour with Central Oregon Adventures! This was my personal favorite activity from our trip.

This was my first time snowmobiling so I was a little nervous at first. I didn’t want to tip over!

But the tour includes a guide who goes over all the safety instructions with you and then takes you to an open area where you can practice and get the feel for your snowmobile.

This was super helpful and after just five minutes I was feeling confident and ready to go!

We rode through some absolutely beautiful trails and made it up to a scenic viewpoint where we stopped and took a bunch of gorgeous photos.

The whole experience was about 2.5 hours and like I said, it was SO much fun!

If you’re worried about getting cold, you’ll be happy to know that there are actually heat warmers on the handlebars and foot rests that you can adjust—these kept me super warm and toasty while cruising around.

Lunch at Cafe Sintra

After your snowmobiling trip you’ll definitely be hungry, so head to downtown Bend to grab lunch at Cafe Sintra.

They serve delicious Portuguese food for lunch, plus yummy espresso drinks and pastries. Basically everything you could ever want after being out in the snow for a few hours!

What to do in Bend Oregon, by travel blogger What The Fab
What to do in Bend Oregon, by travel blogger What The Fab

Prohibition Cave Tour

Next up, we were picked up by Wanderlust Tours for a Prohibition Cave Tour!

This was another super cool experience, and our guide Katie was amazing! She was so knowledgable about the caves, and just an all around cool chick.

Bend has over 800 caves to explore. This particular cave tour is called the Prohibition tour because these caves were used to distill and store alcohol during prohibition.

We also learned that NASA tests their spacesuits here because the terrain is so similar to the moon!

If you’re not looking to drink afterwards, Wanderlust Tours also has a Lava Tube Cave tour. (This is different than Lava River Cave, part of the Newberry National Volcanic Monument in Deschutes National Forest, where you can go on a self-guided exploration of a mile-long lava tube. Start at the Lava Lands Visitor Center for that one.).

For this tour, I’d recommend wearing hiking boots as the terrain in the caves is rocky, uneven, and sometimes a bit jagged. And I’d wear a small backpack to hold your water bottle/things so you can be hands free, because some parts are a bit of a scramble.

What to do in Bend Oregon, by travel blogger What The Fab

Oregon Spirit Distillers

As part of the Prohibition Tour, you get to stop at Oregon Spirit Distillers and get a tour of their distillery.

We sipped on some of their whiskeys, learned about their distilling process, and a bottle of their bourbon maple syrup definitely made it home in my luggage. SO good!

Dinner at 900 Wall

Wrap up your first day in Bend with dinner at 900 Wall in downtown Bend.

I loved the ambiance and brick walls here, and highly recommend the shrimp risotto.

Day 2: What to Do in Bend Oregon

Brunch at Boxwood Kitchen

Head to the Old Mill District for day two and kick things off with a delicious brunch at Boxwood Kitchen.

They’re known for delicious comfort food and American fare. Don’t miss their brussel sprouts!

What to do in Bend Oregon, by travel blogger What The Fab
What to do in Bend Oregon, by travel blogger What The Fab

Shopping in the Old Mill District

After brunch, stroll through the Old Mill District and do a little shopping. If you’re from out of state, you’re really going to enjoy that tax-free situation! 😉

It’s right by the water, so it’s lovely on a sunny day.

You’ll find a mix of standard stores like Athleta and Banana Republic here, as well as some very cute local boutiques. My favs were Vanilla Urban Threads (where I scored my pink Dolce Vita boots in the above pics) and Hello Sunshine (where I bought way too many cute earrings).

What to do in Bend Oregon, by travel blogger What The Fab
What to do in Bend Oregon, by travel blogger What The Fab

Visit the Last Blockbuster

Yes, you read that right. The LAST Blockbuster.

I had no idea there was still a Blockbuster in existence, but apparently there is, and it’s in Bend.

It happened to be located right around the corner from our hotel and when we passed by, we knew we had to stop in!

Get ready for all of the Friday night circa 2002 nostalgia vibes. I seroiusly felt like I was transported back in time.

It’s definitely worth a visit and popping into.

Be Kind, Rewind. 😉

What to do in Bend Oregon, by travel blogger What The Fab
What to do in Bend Oregon, by travel blogger What The Fab

Early Dinner at Joolz

Next up, you’ll want to have an early-ish dinner (in prep for your next evening activity!), and Joolz is a great spot.

This Middle Eastern restaurant was SO delicious. Share some apps (baba ghanouj, the flash fried cauliflower, and the chicken wings), and then get a beef shawarma plate (it’s big enough to share between two people, especially if you’re doing apps).

Save room for dessert because their date cake is to die for. We were pretty full but after hearing about how it made a grown man cry because it reminded him of home, we had to try it.

What to do in Bend Oregon, by travel blogger What The Fab
What to do in Bend Oregon, by travel blogger What The Fab
What to do in Bend Oregon, by travel blogger What The Fab

Snowshoe Tour

Wanderlust Tours offers day time snowshoeing adventures, but I highly recommend doing a nighttime one!

The stars are incredible, and at the end of your snowshoeing you get to sit around a bonfire and drink hot chocolate spiked with hazelnut espresso vodka (from Crater Lake Spirits—it’s a must-try while in Bend!).

Oh and by the way, the team at Wanderlust Tours hand shovels/carves a little ampitheatre for you to sit around the bonfire. Uhh how cool is that?

Katie was our guide for this tour again and we just loved her! She helped us newbs with our snowshoes and she knows the forest like the back of her hand.

Day 3: What to Do in Bend Oregon

What to do in Bend Oregon, by travel blogger What The Fab

Brunch at Lemon Tree

Don’t miss brunch at Lemon Tree! It’s a super popular spot and so yummy.

I did the Avo Hash Smash with bacon and it was delish.

Drive up to a Scenic Viewpoint

You’ve got several to choose from, but Cascade Lakes Scenic Viewpoint (or continuing on the Cascade Lakes Scenic Byway) and Pilot Butte State Scenic Viewpoint are two very popular ones.

Whether you want to hike around or you’re more of a pull over and take pics kinda gal, you’ve got options!

What to do in Bend Oregon, by travel blogger What The Fab

Spa Day at Anjou

On our last day in Bend, we spent the afternoon having a spa day at Anjou.

This was actual freaking heaven on earth. Especially since our forearms were so sore from snowmobiling (you don’t realize it beforehand but gripping those handlebars and hanging on for 2.5 hours will really work your arm muscles!) and then snowshoeing the night before.

Anjou Spa is beautiful and they have lovely ammenities like a hot sand room and a steam room.

The massages were absolutely amazing and I felt like a new woman afterwards.

Anjou also offers facials and brow streatments, as well as dermaplaning and cupping. The works!

What to do in Bend Oregon, by travel blogger What The Fab

Wine Tasting and Dinner at Domaine Serene

If I had to choose, dinner at Domaine Serene was probably my favorite.

Their wine lounge and restaurant is absolutely stunning (they’re actually situated in the oldest building in downtown Bend!), and my god were their wines good.

Their somm walked us through an amazing wine tasting experience where we got to try wines from their local vineyards as well as from their French estate.

We really enjoyed our dinner here too. With options like wagyu steak frites and oxtail pappardelle ragout, you really can’t go wrong.

Drinks at Dogwood Cocktail Cabin

Wrap up your trip to bend with drinks at Dogwood Cocktail Cabin. It’s super cute and eclectic, with a fun cocktail menu.


That’s our itinerary for what to do in Bend Oregon on a three day winter trip! We had such a blast and can’t wait to visit again soon.

Summertime would obviously involve some different activities, like kayaking (or floating) down the Deschutes river.

We also didn’t even scratch the surface when it comes to hikes. Tumalo Falls, Drake Park, Newbery National Monument, and Misery Ridge Trail (lol, that name) at Smith Rock are just a few on my list that I’m eyeing for next time.

If you head to Bend tag me @wtfab in your Stories, I’d love to see what you get up to! And if you’ve been to Bend before, let me know what I should add to my itinerary for next time.

Planning a trip to Bend? I’ll be adding more Bend recs here!

What to Wear in Bend Oregon

FAQs

What are some kid-friendly things to do in Bend, OR?

Catch an Animal Show at the High Desert Museum, visit the last Blockbuster in existence and explain what VHS is, or visit Smith Rock Ranch.

Is Bend Oregon worth visiting?

Bend is absolutely worth visiting, and at least twice so you can experience all the fun winter and summer activities.

How many days should I spend in Bend, Oregon?

Spend at least three full days in Bend so you can really explore and get some fun activities in.

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