This is a brief story of a quick extended weekend trip that occured close to my home town in Vancouver, Canada. I ended up planning a last minute weekend getaway to Mount Hood, Oregon, United States of America to get in a little summer skiing. This was quite an impromptu trip where I decided to head off just two days prior to the trip itself. This trip would allow me to re-experience a trip that I took when I was in my twenties approximately thirty years later. It’s always a great opportunity to travel down memory lane at a different part of life. Hopefully you’ll join me on this adventure.

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This post is one chapter on a weekend trip from Canada to Portland, Oregon, United States of America. This trip was enhanced through Marriott Bonvoy Elite Status, and Hertz Gold Plus Rewards. For parts of the trip, please see this index.

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Trip Introduction: Returning to Timberline Resort – Mount Hood, Oregon, USA for Summer Skiing.

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In the summer months of 2024, MrsWT73 had started a contract job which took her overseas to Europe for several weeks at a time. I ended up staying behind during her travels.

Due to this arrangement, I ended up having a lot of spare time on the weekends. Before boredom set in, I came up with some ideas on how to fill the longer weekends. As a result, I struck up an idea of revisiting summer skiing at Mount Hood in Oregon.

I had previously visited Timberline Resort on Mount Hood for summer skiing in the summer of 1991. This would mark my first trip back in 31 years. It is always unusual returning to a travel destination when you’re in a completely different life, experience, and financial bracket as you get to see things differently while comparing the journey to the times before.

The Travel Objective:

Vancouver, Canada to Portland, USA – solo travel.

When I was initially putting this trip together in my mind, my first thought turned to flying down to Portland. It was about a five hour drive by car from Vancouver Canada to Portland, Oregon, which I wasn’t so keen on given summer weekend traffic.

Using Aeroplan points, I located the Air Canada Express flight from Vancouver to Portland on their Dash 8 aircraft. Since Air Canada Aeroplan offers a distance based award chart, and with Air Canada Elite Status lead status offering Priority Award vouchers with a 50% mileage reduction, I was locating flights as low as 5000 miles each way. I debated renting a car for the weekend at the Portland International Airport, in order to get around for this adventure.

While I was debating my options on whether to pull the trigger on this adventure, the cost of the air ticket portion rose quite substantially to over 28,000 Aeroplan points. As a result, the value proposition when it came to flying changed quite substantially.

Instead, I went with the secondary option: renting a car from the local edition Hertz Rental Car. With an intermediate booked, I ended up with a 2023 Chevrolet Malibu LT. While not the most exciting ride, it was a better option than throwing a thousand kilometres on my Audi for a weekend journey.

In the end, it took about eight hours to drive down as a result of some weekend traffic. The Chevfoelt ended up being quite fuel efficient with heated and cooled seats and a generous dose of air conditioning for the summer weekend.

Planning Hotels:

Being fans of the Marriott Bonvoy program I ended up researching the Portland options. The weekend rates were much softer than the weekday rates and, even in the middle of summer, there was quite a bit of availability for all properties.

I ended up booking into The Nines – A Luxury Collection Property Portland. Ever since the Starwood Preferred Guest days, I had been curious about trying this particular property. Aside from some minor service mishaps, it ended up being a relatively good stay.

While I also considered the Portland Marriott Downtown Waterfront, and the Hi Lo Autograph Collection, The Nines – A Luxury Collection Property seemed to be the most appealing of the group. While, the Ritz Carlton Portland looked to be appealing, given that I wasn’t likely to be on the hotel property for much time, I decided I would pass on this new property for this particular visit.

Planning Activities:

This trip was all about leisure activities. During the trip, I was able to reexplore some summer skiing at Mount Hood.

I was also able to get two visits into Résonance Winery and Argyle Winery, offering a small taste of wine making in the Oregon Willamette Valley and surrounding regions.

Ultimately, it would end up being an enjoyable trip, despite the last minute nature of organizing it.

My Thoughts on Planning Mount Hood:

This was a fairly simple trip to put together, given that I was returning to an area that I had some familiarity. My biggest decision was with the hotel selection, along with activities to complete during my down time. There were also a few activities I was able to organize as well.

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Have you explored the Portland, Oregon area for a leisure holiday ?

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