Keep Portland Weird , Beer, Mexican Food and A Strip Club

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It’s just an average night in Portland.

Keep Portland Weird. You hear that phrase all the time, in fact it’s even painted on the side of a building like a badge of honour. Whether it is earned or not is for you to decide but I had a few “weird” Portland experiences and one of them happened while my friend John Biehler was still in town visiting me. At the time, we were staying at The Benson, just a short walk from our hotel is Bailey’s Taproom (post to come) and across the street from Bailey’s is Tugboat Brewing and Santeria restaurant. Bailey’s was becoming the place that John and I would pop into for a quick beer to make plans for that nights adventures and also where we would return for a nightcap before heading to sleep. After a few visits to Bailey’s we saw how popular Santeria was and so decided that we would check it out for ourselves. And so begins 30 Days In Portland tale of “Keep Portland Weird”.

Keep Portland Weird

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To start off our evening we went to Tugboat for Happy Hour. It’s a fairly small brew pub that of reminds me of The Storm Crow back in Vancouver. Books and games line the walls behind the bar. It’s an intimate bar and no matter how bright it is outside I get the feeling it’s dark and cozy inside.

Tugboat Brewing Co

Book and games line the walls behind the bar

It’s counter service at Tugboat so John and I saddle up, order a beer, a cheese plate and then find a spot to sit. I said this place was intimate right? From what I can see there are only 3 staff working, 1 behind the bar, 1 doing clean up and 1 person preparing the food. It’s actually a fun little place. I don’t think I could spend an entire evening here but the beer was good, cheap and best of all it’s right next door to Santeria. So far though nothing weird has happened.

Marc at the Tugboat Brewing Bar

Cheers to Beer with John Biehler at Tugboat Brewing

Menu board at Tugboat Brewing

After two pints at Tugboat John and I are getting seriously hungry so we head next door to Santeria. the gods are with us because we scooped the last table for two in the tiny little restaurant. First thing we ordered was a Blackberry Margarita. The lighting inside Santeria is very dark and atmospheric, great to set the mood for a cozy intimate dinner with friends or a date but not good for my pictures Smile

Inside Santeria Restaurant

Blackberry Margarita from Santeria

With the Margarita going down smoothly and after snacking on Chips & Salsa we are ready to order our dinner. John goes for a Quesadilla and I order a Carne Asada Burrito with guacamole & chipotle sour cream. OMG I am so looking forward to this, I love Mexican food and I’m really hoping the line-ups of people I’ve seen the past few nights mean the food is great.

Chips and Salsa from Santeria

While we wait for our dinner to arrive I decide it’s time to visit the washroom and this is where it gets weird. I get up from our table and head back to the door marked restroom. I push it open and enter the dark corridor on the other side. To the left of me is a wall so I look to the right and what do I see? A woman wearing only a g-string swinging around a stripper pole. I’ve walked into a strip club! I have seen a live “that” for over 20 years. To say I’m shocked is an understatement. I find the restroom, do my business and return back to my table as quick as I can. Then I start to laugh. Only in Portland would a restaurant and a Strip Club share restroom facilities. That is definitely a Keep Portland Weird moment.

Dinner arrives shortly after I return and it’s everything I’ve hoped for. Delicious and massive portions for under $10 each. My Burrito was so big I could only eat half of it. I took it back to my hotel and had it for breakfast the next day, yummy!

John's Quesadilla

Carne Asada Burrito with Chipotle Sour Cream

What a night, we got to have dinner and a show. If you are thinking of checking out Santeria for yourself I say do it. The food is worth it and honestly where else can you say you enjoyed Beer, Mexican Food and a Strip show all within 25 feet of your first stop.

Santeria on Urbanspoon

Certainly not what I expected but I guess i shouldn’t be too surprised after all Portland has more strip clubs per capita than any other city in the USA. Coffee, beer, tax free shopping and now strip clubs, what else does Portland have up it’s sleeve? I can’t wait.

I want to thank my sponsors Roam Mobility and GM Canada for helping me make this series possible. Roam of course for their awesome product to help me stay connected at a reasonable price and to GM for providing me with a sweet ride to make the road trip in. I don’t know what I’ll be getting yet but I’m looking forward to exploring and test driving a brand new GM.


Roam Mobility is a Canadian wireless company that eliminates US roaming fees by connecting you directly to its nationwide network in the USA.  To get started with Roam, all you need is one of their USA Travel SIM Cards or devices, then you can enjoy unlimited talk and text, plus data anytime you cross the border. Just pick a plan that fits your needs, schedule when you want it to start and travel free from USA roaming fees with Roam Mobility! To learn more, visit


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About Author

Marc Smith is a former event planner turned vagabond adventurer. He loves strong Americano's, great wine, cold beer and zip lining over tree tops. Formerly of Vancouver, most of Marc's time when not travelling is in Canada's largest city, Toronto. Follow along on his nomad adventures and discover places to stay, things to do and where to eat & drink as he explores the world one city and region at a time.

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