Bend Oregon 2 Day Winter Itinerary

Bend, Oregon is one of the most underrated destinations to visit in the US during Winter. This beautiful small city, located along the Deschutes River has tons of things to do in all seasons making it an amazing year-round destination. Winter is really special because of the convenient proximity to Mount Bachelor which is one of the largest ski resorts in the US. Bend is also a more affordable winter destination to visit compared to other places like Lake Tahoe or the mountain towns of Colorado like Aspen and Vail.

Bend used to be the tribal homeland of the Confederated Tribes of Warm Springs, Wascoes and Paiutes before the arrival of white settlers in the 1850s. If you are wondering why this city is named Bend, it comes from the phrase “Farewell Bend” coined by the early pioneers at the time of planning the town. While the town is vastly different from those times, Bend makes a conscious effort towards Sustainability and Conservation which forms the backbone of life and tourism in Bend.

Have I convinced you to travel to Bend now? In this article, I want to share a perfect adventurous and outdoorsy weekend itinerary for your next Winter Trip to Bend, Oregon.

Best time to visit Bend, Oregon

• Winter – Dec to Mar are perfect for skiing and winter sports in Bend.
• Summer – The weather is hot and summer is a super popular time to visit. So you will see crowds everywhere.
• Fall and Spring – Calmer shoulder seasons to visit. Some trails still have snow in late Spring that is melting away. Fall is also great for leaf peeping!

Our trip to Bend, Oregon was in early December. We landed right after the first night of snowfall so it was an absolutely magical time to visit! The whole city of Bend had transformed into a winter wonderland.

How to get to Bend, Oregon?

The most convenient way to get to Bend if you are located outside of Oregon is to fly into one of the nearby airports.

• Redmond Municipal Airport (RDM) – This is a small and convenient airport only 20 mins from Bend.
• Portland International Airport (PDX) – This is the more popular airport with a lot of different flight and airline options but it is a 3.5 hour drive to Bend.

There are also several routes to Bend by road if you prefer to drive. While the roads are open year round, be prepared for winter conditions and unpredictable weather. For other transportation options, check out this page from Visit Bend.

Where to stay in Bend?

There are four different neighborhoods that you can stay at when visiting Bend.

1. Downtown Bend aka “Old Bend” – the heart of Bend with several cafes, restaurants and local businesses. Proximity to Deschutes River and Drake Park.
2. Old Mill District – Historic Mill Buildings turned into outdoor retail area with shops, restaurants and other stores.
3. River West – Sprawling district with speciality pubs, coffee houses and nice vacation rentals. There aren’t many hotels in this area.
4. Northwest Crossing – a popular residential neighborhood in Bend embodying the “Bend Lifestyle”.

If you are visiting for the first time, Downtown Bend is the most convenient location where everything is just a short walk away. Here are some nice accommodation options in Downtown Bend.

• Oxford Hotel
• Campfire Hotel
• Bunk & Brew
• McMenamin’s Old St. Francis School
• The Newberry Hotel
• SpringHill Suites by Marriott

Winter Packing List for Bend – Snow Essentials

• Merino Wool base layers
• Fleece mid layers/ Sweaters
• Winter Jacket
• Gloves
• Wool Socks
• Winter waterproof boots
• Beanie and scarf
• Rain jacket
• Sunscreen
• Lip Balm with UPF 25+
• A small first aid kit
• A compact umbrella
• Moisturizer
• Sunglasses
• Snow pants and jacket (optional)
• Ski glasses (optional)
• Winter sport specific gear

Two-day itinerary for Bend in the Winter

Day 1 – Mt Bachelor, Hiking and Dinner in Downtown

Start your day by heading out to Mt Bachelor which is only a 30 min drive from Downtown Bend. The Mt Bachelor Ski Resort opens around Thanksgiving. You can check the dates here. Start early to avoid traffic. You can go skiing, snowboarding or take lessons with one of the amazing instructors there. Mt Bachelor also has childcare facilities so your little ones are well taken care of when you are out on the mountain. Call ahead to book childcare services. There are many restaurants and cafes at the West Village Lodge to grab some lunch during your visit.

Get some rest in the afternoon and then head to Smith Rock State Park which is a 35 min drive from Downtown Bend. Enjoy a short hike at this park while admiring its towering rock spires and scenic views. The sunset is beautiful at the park. Smith Rock State Park is popular among climbers but it is also a great spot for hiking or biking. Hike one of their many trails. Here are a couple of easy trails that take you right through the most beautiful parts of the park.

1. Canyon Trail and Homestead Trail, 1.5 mi, 206 ft elevation gain
2. Crooked River Trail, 4.3 mi, 324 ft elevation gain

Head back to Downtown Bend to enjoy dinner at one of the restaurants in the area. Salud, Wildrose Northern Thai Eats and Noi Thai Cuisine are some Vegan/ Vegetarian friendly places in Downtown.

Day 2- Snowshoeing, High Desert Museum and Old Mill District

Bend on average receives 3 feet of snow annually and Mt Bachelor gets an average of 33 feet of snow! This makes snowshoeing one of the most fun things to do during the Winter. There are several Sno Parks in Bend that you can go to with an Oregon Sno-Park Permit. The permit is required for entry between November and April.

We did a Snowshoeing tour with Wanderlust Tours which took us deep into the Deschutes Forest with our 6 month baby in a baby carrier and it was absolutely stunning. Our guide Dylan was so knowledgeable about the local Geology and we had so much to learn from it. This experience is a core family memory that I will forever cherish. You can find a list of all the places you can go Snowshoeing here.

After that, head to Old Mill District to grab lunch. Old Mill District is a happening area in Bend with lots of restaurants, shopping, trails and spaces to hang out. There are many events happening throughout the year so plan your visit accordingly if you want to check out any of them.

The last stop for the day is the High Desert Museum which is only a short 8 min drive from the Old Mill District. The High Desert Museum is often missed by visitors but it is one of the most awe-inspiring places in Bend. This 135 acre sprawling Museum that does a lot of conservation efforts, provides many opportunities to see wildlife up close and includes a ranch and even a sawmill. My favorite exhibit here is the Birds of Prey Center where most animals were rescued or cannot be released into the wild for their survival.

You can end the evening with a late evening stroll in Downtown and grab dinner before you head out. We really en joyed the holiday cheer at night at Dudley’s Bookshop Cafe.

Bend is a stunning small town in Oregon that is totally worth the visit in the Winter. We cannot wait to come back already!

I hope you enjoyed this 2-day itinerary for Bend, Oregon. If you liked reading this, leave a comment and subscribe to my newsletter below to get the latest travel news from my blog!