Oregon Girlfriends Fall Trip: Reuniting Through Travel

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On an Oregon girlfriends fall trip, Julie Diebolt Price, from JDP Travels, reunited with high school friends through a fun travel experience. Read why this is the ultimate in boomer girlfriend reunions. 

When a visiting high school chum suggested that I host a reunion of our baby boomer girlfriends in my Oregon home, I thought the proposal had some merit.

We discussed the guest list, and I queried her to see if she thought these people would actually come. She assured me that they would. I hadn’t seen some of these gals in more than 40 years, so I had my doubts.

Maintaining friendships is good for your boomer health

It’s a fact that friendships positively impact your health and wellbeing. Nurturing friendships and surrounding yourself with good friends creates a strong bond. So, with this in mind, a plan was hatched, and the game was afoot.

Following the “Planning a Girls Trip” outlined in a previous article here on My Itchy Travel Feet, I counted the number of beds, the guest list was drawn up, the private Facebook page built, and the invitations sent.

Imagine my surprise and delight when ALL of my gal pals accepted my invitation. Not only that, they had their airline reservations within two weeks of receiving the message—almost eight months in advance. That made the advanced planning all the more exciting.

Oregon girlfriends fall trip itinerary

Group of boomer women sitting by a lake in Oregon
All the gal pals at Trillium Lake

With an itinerary that covered Portland to Hood River, Oregon, and many points in between, this multi-day event included sightseeing, outdoor walks, dining out, dining in, shopping, playing cards, reconnecting, and massage.

The weather plays a significant role in an event like this. We chose September because the weather is usually very nice with warm, sunny days, cool nights, and no rain. Unfortunately, this girlfriends reunion encountered a rainy fall forcing us to alter our outings strategically between rain showers.

Coordinating a large rental vehicle became a challenge, so we settled for a minivan rented at the airport that accommodated seven passengers (which became a clown car for a day—see below) and the host’s vehicle.

The getaway starts in Hoodland

Mountain surrounded by green hills
A view of Mt. Hood

In early September, nine baby boomer gal pals descended on the Hoodland. Hoodland is the name of the combined Villages of Mt. Hood in Clackamas County, Oregon, where our house is located at the foot of Mt. Hood.

The Hoodland makes a strategic base camp for day trips to see some of the best of what Oregon has to offer. Rhododendron—an unincorporated community in Clackamas County, was the perfect location to make day trips into Portland, to tour the mountain, shop, eat, hike, and commune with nature.

Arriving late at night from PDX (Portland airport), there was little time to appreciate the chocolates on the pillows. When the guests quickly found their sleeping accommodations, it was lights out until a leisurely breakfast the following morning.

A plastic bag filled with chocolates, tissues and a map for participants of an Oregon girlfriends fall trip.
Goodie bag with map, tissues, chocolates on the pillow labeled with bed assignment

CAPTION: Goodie bag with map, tissues, chocolates on the pillow labeled with bed assignment

As soon as the sleep was wiped from our eyes the following morning, relationships picked up right where they left off all those years ago. We had a lot of catching up to do.

We laughed, we cried, we ate, we consoled, and we hugged. We learned new things about each other, and someone even asked, “Did we really go to the same school?!” and, “You’ve gotta watch the quiet ones!”

This group of baby boomers converging on the Pacific Northwest hailed from Michigan and Utah and had never been to this corner of the world. (The host, that would be me, is from California.) The Pacific Northwest did not disappoint.

We made the best of the rainy weather by rearranging our schedule to do our hike at Trillium Lake on a glorious, sunny day. It was an excellent introduction for our new visitors to the Pacific Northwest.

Reliving high school days crammed into the clown car

boomer women packed into a car
Packed into the clown car, just like back in high school. Photo courtesy Karen Wagner

Our excursion into Portland started with a car dilemma in the host vehicle. A warning light indicated brake trouble. Reluctant to ignore it, the group agreed to drop the car at the dealer on our way to the train station, which was fortunately just a few short miles from the dealer.

sign on a building that says keep portland weird
Keeping it weird in Portalnd

Nine of us piled into the rented van that held seven passengers. With memories of high school and a clown car, we made our way to the train station and into Portland by rail for an exciting day exploring Saturday MarketPowell’s Books, riding the streetcar, and enjoying a fine-dining experience.

No visit to downtown Portland would be complete without a stop at Voodoo Doughnuts and the Keep Portland Weird sign just across the street.

Church and a Massage

Planning a rest day after a full day of touring was welcomed, and that was Sunday during this retreat. For some, Sunday always includes a church service.

During the planning phase, I found a local church for those who wanted to attend. I also arranged for a massage therapist to come to the house after church, as part of the relaxation activities.

Roadtripping around Mount Hood 

Bridge spanning a gorge surrounded by green trees and hills
Historic Bridge of the Gods taken from the Washington side of Columbia Gorge.

Our drive around the mountain started in the rain with a hearty, early morning breakfast at Shirley’s Tippy Canoe in Troutdale. The winding road, Historic Columbia River Highway US 30, rose up to meet us with stops at world-famous Multnomah Falls and Vista Point.

A spur-of-the-moment stop, coordinated by cell phone between vehicles, resulted in an itinerary change. We crossed the Columbia River to Washington and back over the historic Bridge of the Gods.

Next stop was a 90-minute layover in Hood River. The guests scattered to enjoy the town at their own pace, taking in what interested them.

A brief stop for fresh homemade hand pies at an apple orchard on the homeward-bound segment, got us home for one of those pre-planned crockpot meals ready to serve at suppertime.

Design and print a simple guide for all destinations on this tour. There will be many tourist questions and having answers to some basic questions and links for online searching is a handy addition.

What They Said

Boomer women sitting around a table in a restaurant
A fine-dining experience at Enzo’s Caffe Italiano with gal pals

Jeanne said, “My expectations were surpassed. This was a much-needed trip.”

Karen’s favorite excursion was the day exploring with a hike around the lake, the visit to historic Timberline Lodge, and the scenic views across the Cascades. “Trillium Lake was majestic. I enjoyed the picnic at the lake the most.”

Charlotte said, “This has been a trip of a lifetime.”

Ann shared, “It has been so wonderful meeting up with you again after all these years.”

“This trip has been fabulous…”, Michelle wrote.

“I look forward to our Chicks Retreat, the Sequel, next year!”, Maureen exclaimed.

Kristine shared, “What an experience to reconnect with friends…”

Jackie summed it up very eloquently. “Wednesday was the end of our incredible week of reconnecting and reminiscing, sharing memories, secrets, and recapturing a bit of our past, which at times seemed as though it were just yesterday!

Fabulous food prepared by our gracious host, ample beverages, conversation, laughing, crying, silence, walks, and playing cards made our downtime even more memorable and special. Just sitting in the same room and enjoying one another’s company. New memories were made, and friendships rekindled.”

A successful girls trip in Oregon

Picture this: Nine women in one house, everyone completing their assigned tasks, getting out of the house on time for every excursion, starting as friends, and ending closer than ever before.

Proper advanced planning allowed the group to swing with the punches and make the best of the challenges with weather and car trouble. Providing creature comforts, good food, and drinks, relaxation and entertainment, brings out the best in everyone.

This retreat was all that we could ask for and more. The best part was the renewal of friendships created in childhood that will endure for our lifetimes.

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