From Mansions to Prisons: My Winter Road Trip

I was sitting around a few friends just before Christmas break, and could hear the excitement in their voices about how they were flying back home to visit family. My family in Taiwan and Israel are thousands of miles away, so paying over two-thousand dollars for a flight ticket is not a feasible or economic option. What should I do? What’s a relatively cheap way to travel, but yet would still be fun and adventurous? Bing! A road trip.


So now that you have the basic tips on hand, here are some recommended places to go in Portland:

Pittock Mansion

Most people don’t know about this, but this amazing mansion was built in 1914.

Henry Pittock was the owner of The Oregonian newspaper. Most of the items in the mansion are originals, and it is filled with rich history and intriguing stories. They even have an elevator in there that was constructed originally as part of the house, and it still works!

There are also some hiking trails around which is a great activity either before or after the tour of the mansion.

Hollywood Theater

The non-profit Hollywood theater opened in 1926. It has 1,500 seats and continues to be a popular destination both for locals and travellers. The architecture is fascinating, and you can feel the rich history in the walls. It now functions as a modern-history movie house, and the best part is that you can enjoy beer and pizza while being immersed in the art of film.

San Francisco

Next stop on our list was San Francisco. Here are some places I went to:

The Golden Gate bridge

Looking at it up close, I continued to be amazed as the sheer size of the beaming red suspension bridge. You might wonder why a red bridge would be called the ‘Golden Gate’ and the history is that it was a symbol of Bridging the Golden Gate Association of San Francisco County and Marin County. It was also completed ahead of its scheduled projected time, and was built under budget.

It’s mind-blowing to think that in 1937 people were able to build something of such high quality that lasts till today. I wonder if anyone would be willing to take on such a project, and go under budget? Almost unheard of. This is a must-see, and definitely walk and bike on the bridge. It’s fascinating and extremely fun!

Alcatraz Island

From the Golden Gate Bridge and Fisherman’s Wharf in San Francisco, Alcatraz Island is open for tourists now. A prison (no longer operating) sits on the small island. I got the shivers walking through the hallways, as I listened to the audio recordings, explaining the history of the place.

It was quite strategic to build it on the island, because if you escape, it is hard to survive against the cold strong and dangerous currents of the San Francisco Bay. It was mainly used to house civil war prisoners. However, this was a double edged sword, because it ended up costing too much more to operate than other prisons since everything had to be shipped there, and the salt water severely eroded the buildings which resulted in high maintenance costs.

It finally closed on March 21, 1963, but still remains standing today for locals and tourists from around the world to see and experience a piece of history! You do need to pay for a ferry ticket to get across which is pretty pricey depending on which travel package you get, but totally worth every penny!

There is always more to see, and the key to be a curious adventurer, plan ahead, but not necessarily every single step, and stay thrifty!

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