What I Wish I Knew Before Moving to Bend, Oregon

Greg Powell
Jul 29
2 min read

Updated: Jul 30

Thinking of moving to Bend? You’re not alone. With its stunning natural beauty, thriving craft beer scene, and laid-back lifestyle, Bend continues to attract newcomers from all over. But as with any move, there are things that don’t show up on the brochures or Instagram feeds.

Whether you're already packing or still in the dreaming phase, here are some insights locals wish they had known before relocating to Bend:

1. It’s More Expensive Than It Looks

Yes, Bend feels small-town, but the housing prices say otherwise. While it's more affordable than big West Coast cities, home prices and rent have skyrocketed in recent years. Property taxes are moderate, but don’t underestimate everyday costs—especially groceries, gas, and childcare.

Pro Tip: Budget like you're moving to a mini-Portland, not a rural town.

2. Winter Is Real—and So Is Shoulder Season

Bend gets a lot of sunshine—but don’t confuse that with warmth. Winters can be long, with icy roads, snowstorms, and extended "mud seasons" in between. Locals joke that there are five seasons: summer, fall, winter, spring... and shoulder season.

Pro Tip: Invest in all-wheel drive and a solid puffy jacket. And get used to studded tire season noise!

3. Jobs Can Be Harder to Come By

Remote workers thrive here, but if you’re job-hunting locally—especially in hospitality or retail—wages may not match the cost of living. Bend has a strong entrepreneurial spirit, but it's still growing its professional job market.

Pro Tip: If you're not working remotely, line up a job before moving.

4. Tourism is a Double-Edged Sword

We love our visitors—but summer and ski season can make traffic snarl, trailheads crowded, and restaurant wait times... brutal. That said, tourism keeps Bend’s economy vibrant and supports tons of small businesses.

Pro Tip: Do what the locals do—go early, go midweek, or go off the beaten path.

5. You’ll Never Be Bored (Unless You Want to Be)

From river floats and biking to skiing at Mt. Bachelor and hiking Smith Rock, the outdoor options are endless. And if you’re not outdoorsy when you arrive, you might be soon. There’s also a vibrant arts and music scene that’s only growing.

Pro Tip: Buy the annual forest pass, and keep your kayak or skis on standby.

Most people don’t regret the move—but they do wish they’d arrived with clearer expectations. Bend is beautiful, quirky, sometimes crowded, and often challenging. But if you’re ready for a lifestyle driven by nature, community, and creativity, you’ll probably love it here.