9 Must-Do’s While Staying in Downtown Portland, Oregon

I have always wanted to visit Portland as I love both nature and supporting local businesses and this city offers a great mix of both. Mike and I like visiting any cities which still have something unique going for them as every city today seems to resemble a big suburb more and more each year. We took a flight from Tucson for the weekend and booked a hotel right downtown so we could easily walk to most attractions and save money on a car rental.

The city is most famous for being one of America’s quirkiest cities and keeps true to its’ famous “Keep Portland Weird” motto. It’s long been known as one of the country’s most offbeat destinations. From the highly touted foodie scene, to eclectic art and funky shops, oddball attractions & interesting museums, a never ending supply of local coffee shops, and a lineup of strange events throughout the year (did you know that there is an annual Naked Bike run?!), there is something unique to do no matter when you visit.

In addition to all the unique attractions found within the city limits, there are endless natural wonders to explore, many of which are within an hour drive from downtown. Four of the best waterfalls in the gorgeous Columbia River Gorge (the most concentrated waterfall region in the country) are all located within a half hour-45 minute drive of downtown.

Gorgeous hiking trails, parks, waterfalls, scenic drives, and more can all be enjoyed via a short drive (or convenient tour). Here’s my guide to some fun attractions we explored, with a focus on both cultural and natural attractions.

1. Spend the day exploring Washington Park

Washington Park is hands down my favorite attraction in the city. Conveniently, this natural oasis is located just a 10 minute drive (or Lyft/Uber ride) from downtown. This massive park is home to the Oregon Zoo, the Portland Japanese Garden, the Hoyt Arboretum, the Portland Children’s Museum, as well as hundreds of miles of beautiful woodsy trails.

The Japanese Garden is super impressive. I loved the koi ponds, waterfalls, and especially the Sand and Stone Garden which resembles a big zen garden.

The zoo, while small at just 60 acres, is pretty impressive, being that it is home to a diverse mix of animals including many endangered species. Unique features include an underwater seal exhibit, a fantastic elephant exhibit, an impressive polar passage exhibit, and a beautiful Pacific Northwest section featuring native plants and animals. I loved the woodsy setting; I felt like I was on a nature trail. Lots of trees give this zoo a really natural feel as opposed to most others.

The mix of indoor and outdoor exhibits comes in handy weather-wise, as there are plenty of places to escape the inevitable rain. Strangely, we visited on a rare super sunny weekend. I actually love overcast weather so this was a bit of a dissapointment. It seems the locals were enjoying it though as evident by the crowds!

The really unique aspect of Washington Park, which really sets it apart from many other urban parks, is the wonderful trail system. I love how you can choose to hike as a means to get to and from various attractions. This is a great way to get in a nice workout while also enjoying the beautiful natural scenery of the area. Anyone looking to relax can opt to take the free (seasonal) shuttle.

2. Check out the local coffee scene

I love visiting independent coffeeshops and I’ve always seen this city ranked up pretty high on “best coffee cities” lists. With so many local shops lining every street, you never have to resort to a common Starbucks here. Most of the shops feature big open windows so you can people watch while enjoying a great cup of locally roasted coffee. Case Study, Cafe Ponte, Stumptown, and Spella are a few excellent cafes we visited during our trip. St. Honore Bakery is the place to go for amazing pastries. I also love the big open windows here.

In my experience, local coffeehouses focus on high quality single origin beans and roast in small batches to produce a flavorful brew as opposed to the burnt and bitter undertones which are all too commonly present in the mass produced coffee at big chains. My favorite was probably Case Study which offers a really cozy setting with dark wood floors. True coffee connoisseurs should be impressed with the scene here.

3. Take your pic by the famous Keep Portland Weird sign

Most of us are well aware of the city’s status of being the king of weird. In fact, it’s a prime reason the city sees so much tourism each year. While cities like Austin have been losing their weird status in recent years, I definitely felt the strange and creative energy still present here. It’s hard to explain, but the city’s got a weird presence – you just know when you are here. You really cannot leave without getting your picture next to the famous “Keep Portland Weird” sign.

If you have the extra time, you may want to check out the free Secrets of Portlandia tour which will take you past the famous sign, as well as many other interesting sites. Meet up by the Pioneer Courthouse at 11am to partake in this fun and free tour.

A few oddball sights to check out

This city is known for all sorts of eccentric attractions. A few of the weirdest:

• Peculiarium – An odd artifacts museum.
• The Witch’s House – Haunted stone ruins in a creepy forest which were once the site of many murders – old remains can be viewed via a 1/2 mile hike.
• The Vacuum Cleaner Museum – Spotlights more than 100 vacuums from the late 1800’s to 1960.
• Rimsky-Korsakoffee -The oldest coffeeshop and also one of the most haunted places in town (plan for a dessert & drink in this most unusual setting).

Simpsons tour – Fans of The Simpsons will also want to check out this Self Guided Simpsons tour (Creator Matt Groening is from here and many of the characters and places in the show were inspired by actual places in the city).

If you are a sweets lover, you will want to check out the massively popular Voodoo Donuts located right next door to the Keep Portland Weird sign. This chain has expanded throughout the US with locations today in Austin and Universal CityWalk Orlando.

Over 2 dozen specialty donut flavors, with everything from Churro Cheesecake, to a vegan Banana Cream Pie on the lineup. I am not a fan of sweets, but Mike enjoyed a rare sugar loaded treat.

4. Indulge in a scoop of “safe to eat” cookie dough

We’ve all been told never to eat raw cookie dough due to salmonella concerns, however, sometimes it’s just too tempting to resist. I’ve never made a batch of chocolate chip cookies without indulging in a spoon (or 2). Lucky for us, some clever entrepreneurs decided to take advantage of everyone’s love of cookie dough by creating safe to eat cookie dough. This tasty treat manages to skip the raw eggs while still maintaining the same delicious raw cookie dough flavor and consistency that we all love.

I found about this Cookie Dough cafe from the reality show Shark Tank (it was featured on Season 5). Today, it is common to find edible cookie dough in any store, however, I thought it would be more fun to try it out for the first time at the place that started the trend.

You can test out about a dozen flavors of safe-to-eat cookie dough flavors. Everything from Oreo, to gluten-free Oatmeal, to a Naked cookie dough (for those who prefer to skip the chocolate chips) is available. In my opinion, you really cannot go wrong with good old classic chocolate chip cookie dough.

Update: This business reportedly closed in 2024. however, you can still buy a container at various grocery stores.

5. Take a stroll along the waterfront

The lively waterfront district is the perfect place to take a jog or walk on a nice day. This is also the location of the popular Portland Saturday Market, the largest continuously operated outdoor market in the country. Every Saturday & Sunday, all sorts of vendors are out and about showcasing exotic foods, fresh produce, arts and crafts, clothing, jewelry, and much more. We had a fun time just strolling around and enjoying the views and ambiance.

The market is located within walking distance of the thriving Old Town neighborhood. Thus, you can easily stroll over to many fantastic coffee shops and restaurants from here. This is also the locale where you will have the best view of the iconic white stag sign.

I recommend lunch/dinner at Kell’s Irish Pub. This is one of my favorite Irish pubs anywhere. They serve delicious fish and chips and the tastiest appetizers anywhere. Bonus points for all the vegetarian options. More on this in a bit.

Along the waterfront, you will find a nice little paved path where you can jog, walk, ride a bike, or rent a classic 4 person surrey bike, while enjoying the quaint river scenery. It’s a nice little area for tourists, particularly during the summer months when the weather is a bit warmer and sunnier. Portland Spirit Cruises offers a number of themed cruises, including brunch, dinner, and sightseeing cruises.