Everything Awesome To Do In Bend During Ski Season | Bend Oregon Travel Guide

We recently visited Bend Oregon to see my brother, his fiancé, and my little niece who moved there several months ago. My future sister-in-law, Annie, used to live there for quite some time so she gave us the best to-do list while we were there. I decided to share her local tips for where to stay, what to do, where to shop, and restaurants to enjoy. Most of these place we tested out ourselves and some others are on our list to come back to next time. 

Several of these photos are actually cell phone snaps. Normally, I only share pro photos on my blog, but there were many places I visited where I did not have my camera or my cell phone was the more polite option. And some places I could not take photos at all. If you’re planning a visit to Bend, especially during the winter season, I have the best recommendations for you. No guide book can compare to the inside scoop from a local who loves the land they live in. 

Places To Stay

• McMenamin’s is the Old St. Francis School, which is now a hotel, pub, and public bath house! (More on the bath house later.) As far as budgets go, it is not over the top and very doable for a short trip. It is right in walking distance of the best shops, boutiques, and restaurants in Bend. 

• Airbnb is the way to go if you’re a budget traveller like myself. Thankfully, we stayed with family for this trip, but if you do not have the luxury of knowing a local, Airbnb can give you a similar experience. 

Places To Play

• Winter Sports: For all your outdoor winter sports you can visit Mt. Bachelor   or Hoodoo. These are the two best places for skiing and snow boarding. 
• Caves: You can see incredible caves and lava tubes in Bend. Lava River Cave has a great website you can check out. 
• Take a drive and explore
• Blockbuster: This is a funny recommendation for a travel guide, but I had to put Blockbuster in here for nostalgia’s sake. This Blockbuster is the last one in the world! If you loved to browse Blockbuster for a movie as a kid, then you’ll want to stop here to pick up a DVD for a movie night. 

• Outdoor ice rink
• Dudley’s Bookstore Cafe  There are a few bookstores in Bend, but Dudleys was my favorite because of the selection, the cafe, and the atmosphere. 

• So many great cafes and tea houses to choose from. 
• The Vector Volcano Classic Arcade with $5 beer on tap. My brother took up to this place and I jammed out to Pac Man, Frogger, and many of my old favorites while the boys spent an hour racing Off Road. 

• If you enjoy breweries, Bend is your place. There are so many to choose from. 
• Hike at Smith Rock

• McMinnemin’s Greek style open-air bath house is a great place to soak after a day on the slopes. It is designed to look like an old fashioned Greek bath. 

Places To Eat: There are so many places to choose from, but these two are my brother’s favorite casual places. 

• Spork
• Kababa’s

Places To Shop

• Bend Outlets: A great place to find winter gear. We loved the discounted prices at Columbia for long underwear and snow pants. 
• Goodwill: The Goodwill in Bend has lots of great finds. 
• Vanilla: My sister-in-law says this is the place where the hip girls go and is popular with the ski crowd.