The Dryftwell Guide to



Coffee shops galore in Portland, Oregon. It’s a charming and cozy city only located 70 miles away from the Pacific Ocean and nestled up in the mountains. In the past few years, Portland has seen rapid population growth from more tech offices opening up and West coasters escaping the higher prices in Seattle, SF and LA. It’s growing in popularity because of the smaller scale of the city yet still there are so many world-class restaurants, outdoor activities and open greenspace all within walking distance around Portland. The city walking trail Forest Park and the Portland Zoo are all great family activities within the city limits. The city has been designed to make most of its famous architectural and cultural areas have a lot of other tourist attractions nearby.

In this guide to Portland, we'll tell you about the neighborhoods, cuisines, and local recommendations so you can get the actual environmental and vibrant vibe that this city offers.

When to go


The temperature in Portland in the winter hovers around freezing with lots of rain but surprisingly very little to no snow. Few tourists visit during this winter season from November to March. The city does have a special magic to it during this season with the sparkling Christmas decorations in many parks and public places. Lace up your skates and enjoy one of the ice rinks set up at the Sherwood Ice Area, Hillsboro Winter Village and the Christmas Garden. Or if you’re not a fan of ice skating, still get into the holiday spirit at the Portland Winter Festival and see beautiful flowing light sculptures while keeping warm with hot chocolate. If you’re feeling more adventurous and looking to get a bit outside the city, take a drive to Mount Hood for snowboarding and skiing. Mount Hood also hosts popular music festivals like Snowvana, which feature a range of genres from acoustic to soul to blue grass.


Flowers are in full bloom during the Spring season in Portland from April to May. The fresh fragrance of the flowers wafts through the air. Most days have a slight cloud cover but rain is less common. Due to the cold winters, the spring days are the most awaited days of the year. People rush out of their homes to enjoy the sunshine and all the outdoor activities Portland has to offer. It’s common for folks to hang out in the outdoor spaces at restaurants or bars to enjoy the warmer weather. Pull up a chair at Backyard Social and relax with a nice cold beverage while enjoying the sunshine. Hike to Wahkeena Falls along the historical Columbia River banks and enjoy the views of the lush green forest along the way. There will be some crowds in the city, but it is worth experiencing Portland at a lovely time of year.


Portland is warm and sunny during the summer making it the best time to visit the city if you are looking for clearer skies. Wear your favorite summer outfit and visit the International Rose Test Garden for some gorgeous photo opportunities. The city is alive with many outdoor activities like concerts, festivals and small public events. Flicks on the Bricks is a free outdoor concert series beginning in July. Another popular music festival is The Waterfront Blues Festival. If you prefer a more active experience in June, check out the Pedalpalooze, a full month biking festival. Due to the abundance of activities occurring over the summer, be prepared for higher prices for accommodations during the sunny Portland months.


The days begin to cool and rain showers become more common as Portland moves into the fall months in September and October. If you plan to visit in the fall, make sure to rock your fall coat as there will be a cooler breeze most days. One really fun part about this season in Portland is the city really loves to celebrate Halloween. With haunted houses, corn mazes, pumpkin patches and costume parties galore, Portland is a fun city to celebrate the spookiest night of the year in. Another reason to visit in the fall is the colorful changing of the leaves. Check out the Hoyt Arboretum to witness the leaves erupt into vibrant colors as they transform Portland into an enchanted forest. Don’t forget your camera to capture the beauty yourself.



Downtown Portland is nestled between multiple lush green parks and the Willamette River. On Saturdays you can go to Tom Mccall Waterfront Park and enjoy the Portland Farmers Market and experience the unique art of the local artists as well as enjoy live music. Another great place to stop downtown is the one of a kind Voodoo Donuts that captures the “Keep Portland Weird” slogan so perfectly as well as providing you with delicious treats. Take a street art walking tour of the city and if you still have not had your fill of art you can stop by the Portland Art Museum and experience art from other cultures. A great way to spend an evening after a long day of exploring could be a nice dinner at Portland City Grill with a stunning view of the city and end the evening with a concert or ballet at the Keller Auditorium.

Nob Hill

Nob Hill and Northwest Portland combine both natural and urban style. Walk through the streets and admire the stunningly crafted houses some of which have been converted into a quaint boutique or your local coffee house.  As you leave this area and head toward Northwest Portland the nature will grow around you as you emerge into Forest Park, a nature walkers haven. For a different type of nature you can head southwest from Nob Hill and experience the Rose and Japanese gardens as well as visit the Pittock Mansion.

Pearl District

The Pearl District offers a very different atmosphere than the other neighborhoods in Portland. It has cobblestone roads and riverside docks previously used as warehouses. Now it’s a hip area of Portland. The Pearl district is the most walkable area of the city with many old historic brick buildings converted into coffee shops, stylish boutiques and breweries. Bridgeport Brewing, the oldest craft brewery in Oregon, is found in the Pearl District and is a must stop for beer enthusiasts. Another great stop is the famous Powell’s City Books for a quiet tour of one of the best libraries in the United States.

North Portland

North Portland (NoPo) is home to The University of Portland, the largest university in the city. The area is home to many of the large cargo ports since it is right on the water. The Portland International Raceway is also in this neighborhood with races all year around. One of our favorite eating spots in this neighborhood is the St. John's Food Cart Pod, an outdoor food truck area with many options including burgers, Mexican and Thai food. With ample seating inside and outside with a firepit and beer served in Mason jars, it’s the perfect place for a meal outside with your family.

Powellhurst Gilbert

Powellhurst Gilbert is located in the Southeast area of Portland. This neighborhood is all residential so you’ll really feel immersed in the local lifestyle if you stay in this area. Checkout the Leach Botanical Garden with luscious plants and flowers. Eat at Yuan Su Vegetarian for an unsuspectingly delicious Chinese meal. Make sure you rent a car if you decide to stay in this neighborhood because it is more off the beaten path.



Even though Portland’s public transportation is pretty good relative to other US cities, you’ll probably want a car if you plan on staying longer than a few days or exploring more remote places outside the city. The traffic can be a huge headache with the highways getting congested during rush hour. In Downtown, it can sometimes be hard to find parking. Most street parking charges $4 per hour.

Public Transit
TriMet provides bus, light rail and commuter rail transit services in Portland. Get a Hopcard to load up for your trip at Safeway or our office in Pioneer Courthouse Square. Navigating around Portland on public transportation is very convenient and user-friendly. The Portland Streetcar is a fun alternative if you want to cover short distances. It runs closer to tourist spots and more central neighborhoods. It’s very affordable too at $2.50 per ride. If you want to use it for the full day, you can get a $5 all-day travel pass.

Portland is a bike-friendly city with many designated bike routes. Residents love to get around town on a bicycle. Many locals get to work and other places by just walking and biking. A fun way to explore the city is through a bike tour. Similarly, you can walk around the neighborhoods with a guide to Portland to discover the city like the locals. Just make sure you’re prepared for rain or colder weather if you visit in the dreary months.