Portland is known for its natural beauty, it’s great food, and it’s “weird” aesthetic. There’s something for everyone in this city which makes it a great place to visit any time of the year. Below are some of my favorite things to do in Portland including sights to see, places to eat, some tips on what time of year to go, and even an itinerary for your weekend trip to Portland, Oregon and the Pacific Northwest. 

What to do in Portland in the Spring

Wooden Shoe Tulip Festival

Late March to Early May

If soaring over beautifully blooming tulip fields in a hot air balloon is on your bucket list then the Wooden Shoe Tulip Festival has you covered. If staying on the ground is more your speed, the festival is a family friendly spring event where you can roam through the fields, have a picnic lunch, ride a hay wagon, grab a glass of wine in the tasting room and head home with a a bunch (or two) of fresh cut flowers.

Portland Cherry Blossoms

April to May

Taking a walk along the Tom McCall waterfront is an activity that I would suggest for most seasons. However, spring is when this place really shows off all that it has to offer when the cherry blossom trees come into bloom. Even if you have seen more than your fair share of pictures of cherry blossoms on Instagram, you still can’t quite prepare yourself for the surreal experience of actually immersing yourself in the scene and standing under rows and rows of blooming trees. I recommend waking up early, packing up a thermos of tea or coffee and catching the blossoms at sunrise as this place gets crowded. The most concentrated area of cherry blossoms is around the Japanese American Historical Plaza.

Silver Falls State Park

Late March to Early June

Spring is a great time of year to chase waterfalls in the Pacific Northwest when the weather is a bit more mild and the streams are full. Silver Falls State Park has 10 breathtaking waterfalls all accessible via one long-ish hike. Park in the lot near South Falls and catch you first waterfall not far down the trail. If you don’t want to hike the whole park, you can see South Falls and Lower South Falls fairly easily and on your way back home you can park at the North Falls Parking for a short walk to Upper North Falls.

Smell the Roses at The International Rose TEST Garden

Late May through October

Before I actually went to the Rose Garden myself I was prepared to be underwhelmed. In reality the place is way more expansive then I ever imagined, full of more rose varietals than I even ever knew existed. There is enough space to lose yourself in your thoughts while wandering and pondering which rose is your favorite. There is also an amphitheater where you can both stop and smell the roses and enjoy a picnic lunch in the sunshine. As a bonus there are also public restrooms and a snack stand right near the entrance of the garden if you forgot to pack this theoretical picnic.

Dog Mountain Wildflowers

Late May to Early June

Dog Mountain on the Washington side of the Columbia River is a steep and challenging hike but the payoff is worth it. As you come out of the woods you will be treated to hillsides covered in yellow Balsamroot flowers and incredible views of the Columbia Gorge. This hike does requires a permit on weekends. If you want to see some wildflowers without the long hike, take a look at Crawford Oaks Trailhead in Washington or the Tom McCall Preserve out past Hood River. Pro tip: Check the bloom status by looking at Dog Mountain on Instagram or All Trails. 

Summer time activities in Portland

Berry picking on Sauvie Island

June through August depending on the fruit.

The Pumpkin Patch and Topaz Farms are two great spots for berry picking. Both locations not only have acres of fields to explore and gather fresh berries but also have cute farm stand style stores where you can snag some local syrups, wines, and other artisan goods. If you venture a bit deeper into the island you can also find stairs that lead to the river coast line. You can snack on your freshly picked berry goods while dipping your toes in the water.

Cool off in the Willamette River

July through August

Swim Dock or Sellwood Riverfront. It may be hot but that water is freezing; don’t forget a personal floatation device! This is also a great place to be a dog lover as pretty much everywhere you turn there are dogs and their owners enjoying this patch of sunshine. There also seems to be no shortage of kayakers and paddle board enthusiasts on the river in the summer. You can either become one of them or enjoy watching them exert their energy while enjoying a snack and a refreshing beverage on the warm sand- either is enjoyable in my opinion.

Fields of Lavender

June to July

Mountain views, aromatherapy, and a lot of honeybees? Lavender Valley Farms is a beautiful place to visit in the summer time and take a walk through the beautiful fields. Pick a bundle to take home with you, purchase some lavender honey, and visit nearby Hood River on your way back.

Summer Night Fun

Open-Air Cinema

NW Film Center regularly hosts a series of open air movie screenings through the months of July, August, and September. Check our their website for locations, movie selections, and screening times. Make sure to purchase your $20 tickets ($30 for VIP seating) in advance as these events tend to sell out. You can pack your own treats or purchase selections of drinks (both alcoholic and non alcoholic) from on site vendors and food trucks,

Roller Skating at Oaks Bottom Park

Whether you are an expert roller skater or someone who needs to hold onto the wall for a few rounds before getting your bearings, roller skating at Oaks Bottom Park is a perfect way to spend a summer evening. A $10 admission covers the cost of a skate rental. There are always new specials and events at the rink including Gay Skate and glow in the dark skate night.

Fall in Portland

See the Fall Color

Locations around Portland

Peak fall color is usually mid to late October

Unlike some areas of the country, Portland actually has seasons and fall in Portland can be full of color. You can see some color at the Japanese Garden, Hoyt Arboretum, or Silver Falls State Park, or even just taking a walk around most Portland neighborhoods. We are a city of trees and it is hard to avoid seeing patches of beautiful color this time of the year.

Halloween Fun

Sauvie Island Corn Maze

Mid September through Late October

Sauvie island isn’t only a summer destination. Both Topaz Farm and The Pumpkin Patch transition from berry picking destinations into a pumpkin lovers paradise. Caramel corn, elephant ears, hay stacks and intricate corn mazes complete this fall dreamscape.

Halloween Town

Mid September through Late October

Halloween Town is not just a “classic” Disney movie, but a real celebration in the town of St. Helens that usually ranges from Mid September through Halloween. This celebration includes costume contests, tarot readings, themed shopping areas and even a haunted hotel. While there is not parking available on the city streets during this time you can get free parking in the paid lot with validation from a vendor that you spend at least $15 with.

Swift Migration

Chapman Elementary

September

Every September the largest roost of migrating Vaux Swifts puts on an evening show at Chapman Elementary in Northwest Portland. Just before sunset, thousands of swifts dance throughout the sky before going to bed in the school’s large chimney. It’s a really cool and mesmerizing display of nature. For more information follow the Swift Watch on the Portland Audubon website.

apple picking

Assorted locations throughout Hillsboro or Hood River

September - October

Apple picking no longer means just filling a bucket of apples and taking them home with the intentions of making elaborate pies and treats. With apple picking at Oregon Heritage Farms you can reward yourself for all your harvesting work by enjoying an apple cider slushie or eating a few (dozen) very Instagram worthy tiny apple cider donuts.

Winter Activities in Portland

Snowshoe Trillium Lake

December to Early March

Trudging through snow in regular shoes is not a fun experience. Moving through the crisp landscape on snowshoes is a refreshing, exhilarating (and tiring) activity. A scenic place to test out your snowshoeing skills is Trillium Lake. While this is a beautiful location in the summer, the blanket of snow surrounding it during the winter months make it just that much more dazzling.

Timberline Lodge

Timberline is open year round but for a snowy, cozy scene try November to March

After your trek around Trillium, make your way up the mountain to Timberline Lodge and enjoy a hot chocolate by the fire.  The classic and cozy lodge will warm you up while you gaze through the large windows at the beautiful natural scenery that surrounds it. You can also order a full meal to go along with your whipped cream topped hot chocolate to really satisfy the appetite that you worked up with all that snowshoeing.

Deck the Halls at Peacock Lane

December

The houses on Peacock Lane are adorable to look at any time of the year. Their classic architecture and sloping roofs make this street a fun detour on a walk year round. However, this street transforms into a winter wonderland with each house decked out with lights and whimsical decorations. You can enjoy the sights while sipping on apple cider and generally soaking up all the holiday cheer.

something warm to drink

There is no shortage of alcoholic and non alcoholic drinks to try out in Portland. Some of my favorite winter drink experiences have been at Smith Teamaker. They have a well rounded menu of hot teas and tea lattes. For those new to tea (or just those with an adventurous spirit) you can choose a tea flight, which includes a selection of flavors that are consistently rotated and updated. If alcoholic spirits are your thing you can check out a few (or all) of the locations listed on the Distillery Row map. You can grab a distillery row passport and embark on a self guided tour where you can check out Wild Roots, Freeland Spirits, and Straightaway Cocktails (and many others).

Bonus Portland Places to Visit Year Round

Below are some bonus locations that are wonderful all year round.

Pips Original Doughnuts

Mini donuts and fresh chai. This combination is made even better by the fact that these delicious treats are made to order. The menu staples (including cinnamon and maple candied bacon) are tasty on their own but they also add in seasonal selections which provides an excuse to visit this place more than once. Pips Mobile also caters weddings and events, which makes for a perfect evening, later night, morning or afternoon treat.

Powell’s City of Books

Get lost in a book, or actually lost, in Powell’s City of Books. A trip to Portland, probably isn’t complete without a visit to one of the largest bookstores around.

Kennedy School

Sometimes when I think of returning to the classroom I need a drink. Good thing that is a reality at the Kennedy School. This creative bar makes the best use of an old elementary school by dividing it up into different lounge areas where you can grab a drink or a bite to eat. An extra bonus is the soaking pool, where you can relax and enjoy the experience of actually feeling relaxed in a school setting. They also have you covered if you get one too many drinks to safely drive home as they have an on site hotel.

Plant Shops and Flower Shops

Portland has no shortage of cool plant shops and flower spots. Some of my favorites to visit are Pistils Nursery , Arium Botanicals, Artemisia Collage with Nature, Solabee, Starflower and Colibri. This is just the tip of the iceberg as this is a town packed with great shops.

Tilamook Creamery

If you find yourself headed out to the Oregon Coast you can stop in to the Tillamook Creamery for all your dairy cravings. The visitors center is open seven days per week from 10:00am-6:00pm. You can take a self guided tour of the factory and finish your day with a taste of Tillamook dairy products in burgers, cheese curds, ice cream and more in the Dining Hall.

CORE PDX

CORE PDX is a food destination filled with Food Trucks and a gorgeous new food hall. This is a great option for big groups where it can be a challenge to get a consensus on one place to have a meal. Some great options at CORE include BKK Thai, Jas Kitchen, Sharks’ Cove and Breakside Brewery.

Portland Night Market

Portland is a city of makers. One of the best ways to seek out the goods that the creative entrpenuers of Portland have to offer is by visiting a Portland Night Market event. There is always good food, good music and good people surrounding the cool products that you can find at the market. Make sure to take a peek at their FAQ page to plan your night out as the event is held on rotating dates throughout the year.

My Perfect Weekend in Portland Itinerary 

Friday Evening

Welcome to Portland! Get settled in at your hotel.

I recommend Woodlark Hotel, Hotel Grand Stark, or The Hoxton. Each of these spots have great places where you can get an after flight/long drive cocktail. 

Woodlark has Abigail Hall

Hotel Grand Stark has Bar Chamberlain

The Hoxton has Tope or 2NW5. 

If you aren’t ready to call it a night, you can visit the rooftop bar at Departure. 

Saturday Morning

Wake up early and grab a bite and some coffee downstairs. 

You’ll want to be quick though! If you’re going to the Columbia River Gorge you’ll want to beat the crowd and arrive at the trailhead before 8:00am. 

I recommend the Eagle Creek Trail. This place gets busy, especially in the summer, so again get there early. 

You could substitute Eagle Creek for a visit to Multnomah Falls. If you planned ahead you can snag a reservation online. See Oregon’s tallest waterfall from the bottom and hike your way all the way to the top! 

Saturday Afternoon

Following your hike you could grab a sandwich for lunch at Baker’s Mark (make sure you get there before they close at 3pm.)

After lunch, there’s more to see! Head to Washington Park to check out the Rose Garden, Hoyt Arboretum, or Japanese Garden. If you want to save the stress of finding parking (it’s hard sometimes!) there is a free shuttle that takes you around the whole park and stops at all the destinations. You can take the Blue or Red Max line and get off at Washington Park. Check station info and routes on the Trimet Website. 

Saturday Evening

Grab dinner at one of Portland’s newer restaurants, Takibi. If you opted for the Max, you can get off at the Providence Park stop and walk 14 minutes to the Northwest 23rd neighborhood.

Walk two blocks up to NW 23rd Ave and window shop your way to ice cream from Salt & Straw.

Sunday Morning

Wake up and grab breakfast. You can pick up a delicious breakfast burrito at Fried Egg I’m In Love. If you want something a little more slow, try the Hazel Room on Hawthorne Blvd.

Walk the waterfront or if you’ve got another hike in you, Mt. Tabor is a lovely park to visit.

It’s probably time for your flight. Have a good trip home!

About Chris Brodell

I’m a wedding and portrait photographer based in Portland. My work takes me all over Portland to different parks, hiking trails, and great places to eat.