Hidden Gem One Hour from Portland: Our First Farm Stay Experience

Who knew the best adventures could be so close to home? To end summer, we swapped city noise for a farm stay and left with memories we’ll be smiling about for a long time. It turns out, it doesn’t take a big trip to make big memories.

Highland Farms

Sometimes the best reset isn’t found in a productivity hack or a new planner. It’s in trading the busy week for wide open skies. That’s exactly what we did to wrap up this summer: a quick adventure that started in Hood River and ended at the sweetest little farm stay called Highland Farms.

Family Traditions, Growing Up (and Busy Times)

When the kids were younger, we made it a tradition to head to Central Oregon every summer for a week with their cousins. Now that they’re older with jobs, schedules, and actual lives of their own, coordinating a family trip feels more like a project plan with too many dependencies. Still, we pulled it off with a mini getaway before summer officially wrapped up.

First Stop: Hood River

We started our adventure with a yummy lunch at Riverside in Hood River. Sitting outside with the Columbia River as our backdrop felt like a two-for-one special…good food AND a postcard view. After a little window shopping in Hood River’s charming old town, we packed up and headed for Brightwood.

Riverside Restaurant View Hood River

The Stay: Highland Farms

Highland Farms sits in a forested valley of Mount Hood, and it’s as charming as it sounds. We stayed in the three-bedroom, one-bath cottage…a bit rustic, very cozy, and made instantly better by Cowboy, the black barn cat who greeted us like we were long-lost family.

The farm offers fresh eggs and other food items you can order from their online store and have delivered to your door. Breakfast in pajamas with farm-to-table eggs? Doesn’t get any better than that!

Highland Farm Images

Day Two: Lakeside Picnic

The next day we grabbed sandwiches from a nearby coffee shop and drove about 30 minutes to Trillium Lake. For a $10 day pass, we scored a picnic table with a front-row view of Mount Hood. If only every picnic came with scenery this good…next time, we would plan to stay longer and get on the water. They have kayaks you can rent right there for as little as $25.

Trillium Lake

Farm Tour + Animal Encounters

Back at the farm, we met up with one of the nice farm hands for a little tour of the five acre property (the tour is a great add on to the experience). We learned about the history of the farm, brushed the sweet highland cows, and fed them beets (a.k.a. “cow lipstick”). The cows were thrilled with the beet treat but it’s a messy job 😉

Of course, the animals (who were literally right next to the cottage) provided endless entertainment:

The peacock who roams free, fell in love with its reflection in our car and wouldn’t stop pecking at it.

The barnyard soundtrack of squawks and barks, which quickly separated the heavy sleepers from the light sleepers (Pro tip: if you’re the latter, be sure to pack earplugs).

When Dylan got out of the warm outdoor soaking tub and told me the trip was a “solid and fun experience,” I knew it was a good choice.

Final Thoughts

If you’re looking for a family getaway that’s a little unique, a little rustic, and highly memorable, Highland Farms is worth checking out. It’s easy to get to — only an hour from Portland and there’s so much to do around the area. You’ll leave with funny stories, fresh eggs, and maybe even a new barn cat best friend.

Thanks for reading & sharing! xx

Danielle Cullivan Signature

Danielle Cullivan

Career Insight Studio

Danielle Cullivan is a seasoned leader in tech with over 20 years of experience in Fortune 500 companies. She is also the creator of Career Insight Studio, a career and lifestyle blog dedicated to providing insights and new perspectives for working women. Danielle lives in the Pacific Northwest with her husband, cheers on her son in college, and supports her daughter as she launches her career.

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2 thoughts on “Hidden Gem One Hour from Portland: Our First Farm Stay Experience

  1. This looks like a really fun trip. And seeing you with those cows made me appreciate what a natural you are in those green acres.😊

doses of inspiration

@CAREERINSIGHTSTUDIO

Happy long holiday weekend! 🇺🇸
We wrapped up our summer by trading city noise for wide open skies…a quick Oregon getaway with Hood River eats, a cozy farm stay, and a picnic by the lake. 
It was simple, close, and such a memorable experience. 
Get all of the details on the blog. Link in bio 👆
#workingmom #travelportland #summervibes☀️ #highlandfarms #farmstays
A little Career Insight Studio inspo to start the week…
Progress over perfection.
It’s the pep talk I give myself every. single. day.
Show up.
Experiment.
Learn.
Grow.
Because the messy first draft is still a step forward. 
And moving forward is the whole point.
So take the step. 
Hit publish. 
Raise your hand. 
Send the email.
Ask for the help you need.
It’s not comfortable but your future self will thank you. 
At least that’s what I say to myself on repeat these days 😉
#workingmom #over50 #progress #progressoverperfection