
Welcome to the city of weird. Portland is the largest city in Oregon and is known for it’s craft beer and amazing coffee. There are many things to do in this amazing city. The outdoor enthusiast has everything at their disposal the person that wants to be weird, well…I guess they can continue to be weird! If you like like beer, coffee and waterfalls, I suggest that you give Portland a chance.
Top 5 Things To Do
- Breweries – There are too many to mention for this list. Rogue, Deschutes, Ecliptic, and many more are at the heart of this city. There are plenty of amazing breweries to go to in one of the worlds best beer towns!
- McMenamins – Various buildings that this family has redone and you won’t be disappointed. We went to the Kennedy school and it’s so neat to see how they have changed these places. The school is now a hotel and where else can you be sent to detention and find yourself smoking a cigar and having a drink?
- Mt. Hood – A great day trip if you have the option. It can be so different to get to the top of Mt. Hood and visit the famous hotel that Jack Nicholson chose as his playground in “The Shining”.
- Multnomah falls – There are many waterfalls to view in the land of amazing waterfalls, but this one is rated as one of the tops in many lists around the world. It’s a spectacle to see.
- Japanese garden – It’s a great place to relax, enjoy the view and have a traditional Japanese tea ceremony. If you choose, you can stop off at the zoo in very close proximity. Either way, it’s my favorite Japanese Garden that I’ve been to.
Itinerary
Day 1
- Pearl District
- Rogue Distillery and Public House
The first day in the city really depends on how early you get in at the airport. The airport is very conveniently located right outside the city. The train station is right out of the airport and is very easy to locate. Take the system into the city and get your day started off right with a trip through one of their most famous districts of the city.
Pearl District: There is a lot within this district of the city. Powell Book store and plenty of eclectic stores that you can take your time and go through in your first day in the city. There are also plenty of options for you to dine and relax. If you get to the city early, you can take some time and walk through the area and get accustomed to the city.

Rogue Distillery and Public House: We decided to get our two main breweries in Portland out of the way. When we first got into the city, we went to Deschutes, which we were pretty disappointed in. The beer was very average and commercialized. The food was also pretty mediocre. The line getting into the place would have said otherwise. We preferred going down the road to Rogue. Rogue didn’t originate in Portland, but they opened a brew house here later on. Their beer is so much better than Deschutes in my opinion. Try a flight and you will more than likely find a beer that you will enjoy. The service was also very kind here and it felt like a much different crowd than the previous brewery. Try out Rogue and you will experience what craft beer is all about. Their famous Dead Guy ale is one of the top ranked beers that you can find across the US.
Day 2
- Voodoo Doughnut
- Tom McCall Waterfront Park
- Pioneer Courthouse Square
- McMenamins Kennedy School
- Alberta Street
- The Grilled Cheese Grill
- Lan Su Chinese Garden
- Ecliptic Brewing
- Portland City Grill
Stumptown coffee roasters: Portland is known for breweries and coffee right? Stop in to Stumptown as they are probably their most famous coffee roasters. They have some delicious coffee single origins and are located many places in the city. They have gotten quite large to where they distribute many places. This is a great first stop to make if you are a coffee enthusiast.

Voodoo Doughnut: The famous donut shop to go to while in the city. Across from the graffiti that says to keep Portland weird, this place definitely adds to that flavor. They make some of the most unique donuts that you will ever see. There are so many random types of donuts and they continue to make new flavors weekly. Are you big with trix cereal? They probably have a trix donut! Try your favorite types as they have a certain donut for everyone. I’m not a huge donut fan, but you’ve got to stop in at this donut shop while in Portland.
Tom McCall Waterfront Park: We originally wanted to grab some bikes and head down the waterfront as we have had some amazing times just biking cities. As it was pouring out, every day of our trip…it was a little hard to fulfill that situation. Our next best thing was walking down the waterfront. It’s a nice area and it has some great views of Portland that you can stroll down. Enjoy your walk and keep to the trail. You’ll even pass by the famous Portland sign on top of the hotel.

*Pioneer Courthouse Square: This square is a nice area to visit in the middle of the city. They have some great restaurants in the area. They also have a coffee shop in the middle if you’re feeling like a coffee again!

McMenamins Kennedy School: This famous family has many places around Oregon, so when you get the chance, tour as many of them as possible. They purchase buildings and repurpose them. This place was originally a school and they changed it into a hotel and restaurant. They also brew their own beer. It’s probably a pretty cool hotel to stay in if you get the chance. Where else would you get a chance to have a cigar in detention? Yes, they have a cigar lounge with drinks that is open for you to indulge…but only if you have been sent there right? Who wouldn’t have enjoyed this during their school years?!
*Alberta Street: This street has some wonderful shops on both sides to visit and some great eateries as well. Take a walk down the street, which is heavily trafficted by locals in the area. They have farmers markets and everything that you could want with a great local feel.

The Grilled Cheese Grill: I know everyone had grilled cheese and tomato soup as a staple when they were children. This place makes gourmet grilled cheese for you and they are delicious! If you are eating there, eat in their old repurposed school bus. They completely removed seats in the bus to make tables for their restaurant. A very cool destination and some great food that made us feel like children…just more as adults!
Lan Su Chinese Garden: The Chinese garden is in the middle of the city and is a very peaceful area to walk through and relax. You can have a tea half way through the garden, or you can just enjoy the walk. The tickets are very affordable and can be a nice break for the day!
Ecliptic Brewing: Across the bridge is Ecliptic brewing. Their brewery is out of this world! Most of their beers have a cosmic theme. Very good beer and Ecliptic is one of the best breweries to visit when you come to the city. It’s a little off the beaten path, but worth checking out to get a couple of beers in the craft beer capital of the US!
Portland City Grill: To end the night, get a perfect view of the city while you dine. We had some wonderful food and the elevation fo the restaurant also makes for some of the best views of this wonderful city. A perfect ending to a long day of touring the city on your second day.
Day 3
- Heart Coffee
- Mt Hood Day Trip
- Dan and Louis Oyster Bar
- Al’s Den
Heart Coffee: With three locations around the city, I’m sure you can find at least one of their coffee shops. Another gem to visit while you are in the coffee capital of the US. They work with local farmers in some of the best coffee growing regions of the world. Kenya, Ethiopia, Columbia and several others all give a great selection of beautifully roasted coffee.
Mt Hood Day Trip:
Today you will go on a half day trip through the area up north of Portland. There are many amazing places you will see including one of the top waterfalls in the US. There are several tour companies that will take you around the area, but we really enjoyed America’s hub world tours.
After being picked up at the Portland hotel, you will make your drive out towards Multnomah falls. You first stop at several waterfalls along the way and get some beautiful views as you take some quick trails around the area. It was pretty rainy out on the day that we went, but waterfalls are always flowing when it rains! It just made for some pretty wet photos. After stopping by several of the smaller waterfalls in the area, you make your way over to Multnomah.
Multnomah falls is one of the tallest waterfalls in the United States. It’s also an extremely popular waterfall to be photographed. The bridge in front of the double waterfall is gorgeous. This is one of the most visited sites on the west coast so you will more than likely be there with many people. The tour won’t give you time to take the hiking trail to the top, but you can still head up to the bridge for a better view. There is also a gift shop close that has plenty of options for memorabilia.
Heading next to Hood river, you get a change to explore the small city that is actually known for having the most breweries in the US per square mile. There are several great breweries to head to, but we ended up trying Double Mountain brewery. They had some delicious beers and the pizza was also really good here. You get a bit of time to walk through the town before heading back to the tour bus.
Making your way up to Mt. Hood next can be a little bit. There is a bathroom stop if needed at a couple of local places. We stopped at a farm that had several fresh fruits and veggies that you could purchase. They had some delicious treats that we ate while we made our way up the mountain. As you continue up to the top of Mt. Hood, we started to really get hit with snow. What we loved about the snow was that it made for a perfect setting as we made our way up to the top and the Timberland lodge. You might know this famous hotel if you ever watched The Shining. It’s a famous ski resort in the area. We walked through the hotel and had a great meal at their local restaurant. My favorite part was taking an iconic picture with the famous axe that was used in the movie! Here’s Johnny!
Dan and Louis Oyster Bar: As our driver dropped us back off at the Portland hotel, we were getting pretty hungry. A short walk towards this Oyster bar, had us feeling pretty good! Several options for Oysters on their menu. It’s also the oldest family owned restaurant in Portland (opened in 1907). They have many options for local Oysters. The presentation wasn’t overly special, but with delicious food and some great speciality drinks, it really didn’t matter to us!
Al’s Den: The final night cap for the evening has us going to another McMenamin’s property in the city. Al’s den is actually hidden at the bottom of this restaurant on the corner. It has that speak easy feel to it and was pretty busy when we went. It’s very low lit and makes you feel like you are doing something wrong by being there! There was live music and they made a delicious Manhattan, while my partner had a lemon drop. A perfect way to end the night with something different than the previous night.
Day 4
- Coava Coffee
- Oregon Zoo
- Portland Japanese Garden
- Salt & Straw
- Ground Kontrol Classic Arcade
Coava Coffee: Your final day of wonderful single origin coffee in Portland takes you to Coava. The service here is extremely friendly and they love to teach the coffee culture to anyone that wants to talk it! Sit down and have a cup and chat over the notes in your coffee.
Oregon Zoo: The zoo is the oldest zoo west of the Mississippi river, being that it was founded in 1888. It’s located along with several attractions in Washington Park. The zoo is set up based on where you would find the animals in the world and there is a large amount of them at that. Travel from the African Savanah to the Amazon rainforest and be entertained by these amazing animals. They do a great job at the zoo and also talk about the importance of conservation. This can be a 2-3 hour trip as you take a stroll through and enjoy the flora and fauna.
Portland Japanese Garden: Shortly down the path from the Oregon zoo, you will come across this amazing garden. This is my favorite Japanese garden that I have been to. They do a fantastic job of spreading out the gardens enough to where you have a zen like feel when you walk through it. The waterfalls are a beautiful view and make for an iconic picture. The rock and sand garden can leave you contemplating life and the tea garden is wonderful. This is probably the best tea garden I have also sat down at. Spend another half of your day here and grab a bite to eat in the tea garden. You’ll feel just a bit more at peace after leaving.
Salt & Straw: Oprah recommended, this ice cream place has some great combinations that you wouldn’t find at any old ice cream parlor. Their unique ice cream fits into the weird Portland setting perfectly. If you can’t make a decision, decide on a flight of ice cream to taste multiple flavors! It’s a nice treat coming out of a relaxing day.
Ground Kontrol Classic Arcade: Find a place to eat around the area and then head over to your last spot for the evening. This will bring you back to your younger days. This arcade is so fun to go to and just play the classic arcade games that too many people just don’t play anymore. The best part as you get older, they start adding bars into these places! Grab a cocktail and play anything from Mortal Kombat to Donkey Kong or classic Ms. Packman. You’ll be sure to have a wonderful night and you won’t have to worry about your mom yelling at you to go to bed!
*People watching experience