Summer Traditions in Central Oregon: Making the Most of Our (Limited!) Summers

Do you have a beloved vacation spot that you return to again and again? This week I’m sharing our family’s very favorite and special location for an off-grid vacation everyone will enjoy.

Kids having fun swimming on a summer vacation in Oregon

I read an article long ago that mentioned parents get a total of 18 summers with their children – it sounds like a lot but the time flashes by quicker than you’d expect!

When the kids were younger, securing real vacation time was always tricky, but we made it a point to spend at least one week each summer on a family trip with our kids, Mia and Dylan, and their cousins, Ellie and Cole from Pennsylvania.

Most years, our destination of choice was a rented house at Caldera Springs, a gem of a spot just 3.5 hours from Portland in the heart of Sunriver, Oregon. Both Bret and I grew up in Oregon and were lucky to visit Sunriver when we were younger — despite how much it has grown over the years, it’s still an amazing destination spot for families.

This place isn’t just a getaway; it’s a slice of paradise with family-friendly amenities: swimming pools, biking trails, and a bunch of outdoor activities to keep everyone entertained (and off digital devices) — even for reticent teenagers.

Choose Your Own Adventure

Our summer trips were packed with activities that were great memory makers. Here’s a taste:

  • Whitewater Rafting and Jet Skiing: If laughter were a water sport, we’d have won gold medals. Between the waves and the “I swear I won’t fall in” moments, it was an adrenaline-packed splash fest.
  • Paddleboarding and Horseback Riding: Each year, they would ride horses and tell us stories about their adventures and how silly their horses were on the trail ride.
  • Exploring Nature Trails and Lava Caves: The beauty of this place is the abundance of outdoor activities — some years we would do a guided tour from Wanderlust (to experience the Lava caves) or just set out on our own to explore the vast number of nature trails.
  • Fishing and Ski Lift Rides to Mt. Bachelor: The kids were always open to trying new things so if something didn’t hit the mark, we didn’t do it the next year. Let’s just say fishing was in that camp — despite amazing views on the lake, holding a slimy fish wasn’t a “do again” 🙂  The ski lift ride up Mt. Bachelor in the summer however WAS a highlight — the thrill of being on the chair lift and the views at the top were absolutely stunning.

Evening Routines

As the day wound down, our evenings were filled with simple joys:

  • S’mores and Ice Cream at the Lodge: A sweet reward for surviving the great outdoors—one sticky marshmallow at a time.
  • Star Gazing and Night Swims:  There’s something magical about floating under the stars while swimming at night.
  • And if the weather didn’t cooperate? No problem. It was the perfect excuse for indoor games, hide and seek, and movie marathons, making sure the fun didn’t stop.

Here are a few resources we used to plan our adventures:

Horseback riding: Saddle up | Sunriverstyle

Whitewater rafting: Big Eddy Thriller – Exciting Whitewater Rafting Adventure | Sun Country Tours

Wanderlust tours: Wanderlust Tours

Fishing Guide: The Hook Fly Shop – Home of Cascade Guides (hookfish.com)

Pine Marten Lodge Sunset Dinner: Dining & Shopping | Sunset Dinners | Pine Marten Lodge | Mt. Bachelor (mtbachelor.com)

Family trip with Danielle Cullivan, whitewater rafting

Creating Memorable Moments

The highlight of these trips was undoubtedly the kids’ laughter, creativity and independence. Reuniting after a year apart, they dove back into their close bond without missing a beat, planning pranks and enjoying spirited water balloon fights. Saying goodbye at the end of each trip was bittersweet, marking another precious summer spent together.

We even celebrated significant milestones like my dad’s 80th birthday with all the grandkids which made it all the more special.

Reflecting on Our Adventures

When COVID-19 changed the world, we adapted by exploring the Oregon coast with the six of us packed in an RV called the Bounder, a story for another time. These trips, though a lot of work in planning and managing four kids, were invaluable. The memories we’ve created are cherished not just by us, but by the kids as well. Our very own videographer (Mia Cullivan Film) created a highlight reel each year which acted like a little time capsule and gave us the chance to relive these special memories. Here’s a short video from 2016 so you can see the adventure in action.

Do you have summer vacation traditions? Please share in the comments below so other working parents can benefit!

Thank you for reading and reminiscing with me!

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 and high-school-aged son, and visits her college-age daughter as often as possible! 

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