Fall Destination Inspiration: Portland, Oregon

If you are looking for some destination inspiration for your fall travels, look no further than Portland, Oregon.  This beautiful city is not only full of color, but it is extremely eco-friendly and conscious about the environment.  Portland has endless opportunities to explore the outdoors with rose gardens, witches castles, and plenty of waterfalls to visit right outside the city.  Here’s my guide to making the best out of your time in Portland:

Things to Do:

Mill Ends Park (World’s Smallest Park)

In 1971, Guinness Book of Records declared this 2 square feet park the smallest park in the world.  Not only has the park become a must-see for tourists, many residents have contributed to its growth in popularity.  Some of the new amenities include a tiny swimming pool and a small Ferris wheel.  Read the interesting story behind the park here(strangely enough it involves a leprechaun).

Portland Farmer’s Market

If you are looking for some fresh and local grown produce to start your weekend, browse one of the two main markets in Portland.  The farmers markets is a regular weekend occurrence and includes tons of local vendors!

The Grotto

The Grotto is a Catholic shrine that spans 62-acres of fir trees, colorful rhododendrons and other native plants.  The heart of the shrine is Our Lady’s Grotto, which is a rock cave carved into the base of a 110-foot cliff.  The center of the shrine features a large marble replica of Michelangelo’s Pietà. The best part? The lower garden, grotto, chapel, visitor center, and gift shop can all be visited for free.  However, the upper-level garden does require an admission fee.

The Witches Castle

The short half mile hike to the “Witches Castle” will provide you with an intriguing history lesson.  In addition, these ruins are rumored to be haunted.   Even if you don’t believe in ghosts, the ruins make for great photos.  It was mostly abandoned until around the 1980’s, when high schoolers began to use it for their Friday night parties.

International Rose Test Garden

This 4.5 acre rose garden in Washington Park contains over 7,000 rose plants of approximately 550 varieties. The best time to visit is when the roses bloom from April through October with the peak usually in June.   Roses are sent here from all of the world to be tested for color, fragrance, and other attributes.

Catch the Sunset at St. John’s Bridge

Portland really is a city of bridges (12 in total), but the best bridge to visit is always under constant dispute. However, for the neighborhood of St. John, there is a clear winner.  Towering over 400 feet (the tallest bridge in the city), the St. John’s Bridge Gothic structure is perfect for snapping pictures during golden hour.  The thick and elegant arches suspend beautifully over the Willamette River and Cathedral Park.

Go on a Brewery Tour

Portland has incredible beer, why not get it straight from the source? There are even some free brewery tours (yes, FREE): Ecliptic BreweryGround Breaker BrewingHopworks Urban Brewery.

Powell’s City of Books

Located in downtown Portland, Powell’s City of Books currently holds the title for the largest used and new bookstore in the world.  The store occupies an entire city block and is home to approximately one million books. To make things even cooler, this book store has nine color-coded rooms and over 3,500 different sections of material. If you are lucky, you can catch one of the dozens of writers and artists that visit each month to read.  Powell’s also has a one-of-a-kind Rare Book Room that houses an impressive collection of autographed first edition books and other interesting collectables.

Visit the Simpsons Streets

Are you a big Simpson fan?  Well, Matt Groening, the creator of The Simpsons, is from Portland and named a number of characters after streets in his hometown.  Many of these streets are located in the Alphabet District such as Flanders and Kearney.

Portland Art Museum

This museum was founded in 1892, making it one of the oldest art museums in the U.S.  The Portland Art Museum has a collection of over 42,000 pieces that ranges from ancient times to today.  In addition, it’s collection is very diverse as it includes art from native people in North America, contemporary art, photographs, and even drawings.   If you happen to be in Portland on the first Thursday of the month, you can see it all for free!

Portland also has a large amount of murals and street art.  Here are my two favorites:

Everything is Everything by Zach Yarrington

508 SE Grand Ave Portland, OR 97214

Forest For the Trees 2014 Mural by Rather Severe

3602 NE Sandy Blvd, Portland, OR 97232

Check out my Portland clothing essentials:

Chase a Waterfall

Oregon is home to many incredible waterfalls and places of pure green beauty.  A short drive outside the city can take you to a ton of waterfall hikes.  The most popular waterfall to visit is Multnomah Falls, which is only a short visit from the parking lot.  If you want a bit more adventure, try hiking through the huge log jam and a creek to find Lower Oneonta Falls.

Keep Portland Weird Sign & Historic Portland White Stag Sign

What to Eat:

Breakfast: Blue Star Donuts

1237 SW Washington St.

If you are in Portland, you are likely to hear about the ongoing debate of Voodoo vs. Blue Star Donuts. The locals we asked all supported the Blue Star side and that sealed the deal. Blue Star was amazing with incredible flavors like Lemon Poppyseed, Key Lime, and Passionfruit!

Lunch: Pizza Jerk
5028 NE 42nd Ave
Dinner: Mi Mero Mole
32 NW 5th Ave


I had a blast exploring Portland with Andrew and his local friends.  This city has so much to offer that it’s hard to get bored…go outside and explore!  I hope these tips help you in planning your way around Portland.

Want to see more of my road trip? Here the part one video of my U.S and Canada road trip:

Happy travels,

L x


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4 thoughts on “Fall Destination Inspiration: Portland, Oregon

  1. I love farmers markets! Definitely making a note that I should stop by this one in Portland. Oregon is one of the states I haven’t yet visited but I’m dying to go so this is a super helpful guide!

  2. This looks awesome! Portland has been on my radar since I saw that show Portlandia in college, but I’ve still not made it out there. That massive bookstore sounds like heaven.

  3. I’ve always wanted to visit Portland – my dad used to work there many many years ago 🙂 I love craft beer too so those breweries look perfect for me 🙂

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