Thinking about retiring in Bend, Oregon, or relocating here from the East Coast? Nicole and I just did it. We’re a couple in our 50s, empty nesters, and semi-retired, and we traded Frederick, Maryland, for the high desert of Central Oregon.
This isn’t a generic relocation guide. It’s our story: why we chose Bend after years of visiting, how we picked a neighborhood and a house from 2,500 miles away, and what has been scary and exciting along the way.
The short version: Bend gives us mountains, trails, golf, breweries, and four real seasons in a town small enough to feel like home.
For an active couple heading into semi-retirement, nowhere else we’ve been has checked as many boxes. (Glenn has been to all 50 states, so that’s not a casual claim.)
Why We Moved to Bend: Our Story
Who We Are: Glenn and Nicole
We both had full lives before we met in Frederick, MD, in 2020. Glenn was a technology executive based in the Washington, D.C. area. Nicole, originally from Edmonton, Alberta, had recently relocated to Maryland for her work in HR.
Since then, we’ve built a life around what we share: travel, the outdoors, and good food and wine. We try new restaurants, wineries, and breweries constantly, and we travel often, both close to home and internationally.
Nicole is a certified fitness instructor who loves mountain sports. She grew up near the Canadian Rockies, after all. Glenn is a sports buff and golfer who does his best to keep up with Nicole hiking, biking, skiing and paddling.
We started EpicBend and EpicFrederick to share our secrets for living the best life possible in both places. More than anything, we’re adventure seekers.
Our Move at a Glance
| Who we are | A couple in our 50s, empty nesters, semi-retired, plus three cats |
|---|---|
| Moving from | Frederick, Maryland |
| Moving to | Bend, Oregon (west side) |
| Bend history | Glenn: nearly 20 years of visits. Nicole: a few trips, then fully on board |
| Home search | Months of online research, then one long weekend touring 15+ homes |
| What we bought | A new build on a rim-facing lot near Phil’s Trails and Shevlin Park |
| Our must-haves | A nature-facing backyard (Nicole) and golf nearby (Glenn) |
| Not on our list | School districts and work commutes |
A Lifelong Pull Toward Western Mountain Towns
I grew up on the East Coast: a kid in Maryland, college in Virginia, then a career in Atlanta and Washington, D.C. But 30+ years of work travel took me across the country. I’m a million-mile traveler on two airlines, and I’ve been to all 50 states.
That gave me years to think about where I’d ultimately want to live once life’s constraints loosened. A long time ago, I decided it would be Bend, Oregon.
While living in Frederick, Nicole and I kept up a kind of parallel life in western mountain towns.
She showed me Canmore, Banff, and Jasper in Alberta. Together we skied Steamboat, tasted wine in Paso Robles, and explored the desert around Sedona. And we kept coming back to Central Oregon.
We love Frederick. But places like these call to both of us. Nicole will always be a mountain girl, and I’ve dreamt of living in a West Coast mountain town my whole life.
How Bend Won Me Over, One Trip at a Time
Falling for Bend was gradual. My parents moved to Southern California when I went to college. (“Boy, the weather here sure is nice.”) Ski trips to Colorado and Utah and summers in Idaho followed. I knew I’d leave the East Coast eventually.
Then work took me to Seattle and Portland for extended stretches, and I discovered the Pacific Northwest. The green, the variety of landscapes and the volcanic peaks mesmerized me.
One family road trip from Portland to Sun Valley, Idaho, took my kids and me through Sisters, Redmond, Bend and the heart of Oregon. (“I think I love this state more than all the others.”)
When my kids were old enough to mountain bike, we started taking summer vacations in Bend, and I brought their grandad along. (“Hey Dad, this town has everything we like to do.”)
As the kids grew up, I came on my own for weeks at a time each summer. Working remotely made it easy. (“Bend also has breweries!”)
When COVID hit in 2020, I got in my car and drove straight to Bend for a month. I did a lot of fly fishing. That’s when I officially fell in love with the place.
Convincing Nicole (It Wasn't Hard)
Not long after COVID, Nicole became the center of my world, and a new question took over: how could I convince her to move to Bend with me?
It wasn’t hard. For an outdoor-loving mountain girl, Bend sells itself. A few trips together and she was fully on board.
Figuring Out What Life in Bend Would Look Like
Moving across the country is hard, even to a place you know well. It’s a long chain of steps, decisions, and details, and it can easily be overwhelming.
We started by researching neighborhoods, partly by driving around on visits but mostly online. Zillow, Redfin, and the many YouTube channels run by local real estate agents were incredible resources. (We’ll share our favorites in an upcoming article.)
Over time, a vision took shape: the kind of house we wanted and the neighborhoods we liked. This part is very personal. As empty nesters heading into semi-retirement, our priorities were:
- A nature-facing backyard with no house behind us, like our home in Maryland. This was Nicole’s non-negotiable.
- Golf nearby. We toured golf clubs before we toured houses. That one was mine.
- Everyday access to trails, parks, coffee shops, restaurants and groceries.
We didn’t have to weigh school districts or work commutes, which matter a lot to many families. Everyone’s budget, priorities and situation are different.
Choosing a Real Estate Agent and Researching on the Ground
Know this going in: those online tools and YouTube channels are lead generation for real estate agents. You will get contacted, like we did. That’s not necessarily bad. A good agent is critical when you’re relocating to Bend, especially from far away.
Ours guided us from start to finish and became a friend and an essential partner in making the move happen.
After many months of research, we scheduled a long weekend in Bend for on-the-ground neighborhood research and house hunting. Our agent arranged most of it. We toured 15+ homes we had pre-selected and explored neighborhoods extensively.
We visited new home communities being built by builders, mostly on the west side of Bend.
We also checked out golf courses, coffee shops, parks, bike trails, restaurants, and grocery stores: all the places that would become part of our daily life.
Choosing Our Neighborhood and House
Despite all the long-distance research, nothing beats being there. It’s amazing how quickly our opinions solidified.
A home usually speaks to you within two minutes of walking in. Bend has lots of great neighborhoods, but after two or three days of touring, we’d narrowed it to the few we liked best.
Was It FOMO?
Things happen fast. Toward the end of our tour, we found a new home in one of our top neighborhoods that checked most of our boxes.
It was one of the few left on a desirable street with a rim-facing backyard, and the builder had priced it aggressively to sell. It was close to Phil’s Trails, Shevlin Park, the golf courses I like and much more.
“This house feels too good to pass up.”
Within weeks, our agent was helping us with an offer, then a negotiation, then a closing. After several eventful and sometimes stressful weeks, the house was ours.
What's Been Scary, and What's Exciting
Buying a home in Bend set off a long series of follow-up decisions. We had to sell our house in Maryland. Our jobs are disrupted. We had to find movers and figure out how to get three cats across the country.
I’ll share more about each of those decisions in upcoming posts.
Now that the initial move is done, we’re thrilled. For me, it’s the culmination of a 20-year dream. We’re finally living in the town we love, with no flight back East to plan.
Follow Our Move to Bend
This is the first post in our Moving to Bend series. Coming next: the neighborhoods we toured, the house we chose, finding the right real estate agent, selling our Maryland home, and moving three cats cross-country.
Subscribe to the EpicBend newsletter to get each one as it’s published, and join our Living in Bend group to ask locals your own questions.
FAQs About Retiring in Bend, Oregon
Is Bend, Oregon a good place to retire?
For active retirees, we think so. Bend puts trails, golf, skiing, rivers and a strong food and brewery scene minutes from home, in a town that still feels small. The trade-offs are home prices well above the national median, snowy winters, and long flights back to family on the East Coast.
Why are so many people moving to Bend, Oregon?
Mostly for the lifestyle: year-round outdoor recreation, a lively downtown and the Cascade Mountains on the horizon. Remote work made it possible for many people, including us, to spend long stretches here before committing to a move.
How long did it take you to find a house in Bend?
We researched online for many months, then spent one long weekend in Bend touring 15+ pre-selected homes. We found our house at the end of that weekend and closed within a few weeks.
Do you need a local real estate agent when relocating to Bend from out of state?
We’d strongly recommend one. Our agent set up our tours, guided our offer and negotiation, and handled countless details we couldn’t manage from 2,500 miles away.
What should retirees look for in a Bend neighborhood?
Start with how you’ll spend your days. For us, that meant a nature-facing backyard, golf nearby, and easy access to trails, parks, coffee shops, restaurants and groceries. School districts and commutes didn’t factor in.
What's the hardest part of moving to Bend from the East Coast?
For us, it was everything that followed the purchase: selling our Maryland home, adjusting our jobs, finding cross-country movers, and getting three cats to Oregon.
Are you fully retired in Bend?
Not quite. We’re semi-retired, which gives us the freedom to enjoy Bend on weekdays while still working part of the time.
About Nicole and Glenn
We’re Nicole and Glenn, the couple behind EpicBend and EpicFrederick. After years of visits to Central Oregon, we moved from Frederick, MD, to Bend’s west side.
Everything on this site comes from our own experience: the trails we hike, the courses we play, the restaurants we love, and the questions friends ask us about moving here. More about us.
