Help a Reader Travel: Portland, Oregon

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Welcome to another post of helping a reader travel! As I’ve mentioned before, I have not been to every destination (unfortunately), but do get questions from friends and other blog readers on all sort of travel destination questions. Thus far, we’ve been able to help other readers travel to MauiThe Greek IslandsPacific Coast HighwayArgentina /Buenos AiresCosta RicaCape Cod & The IslandsIcelandGenevaCanadian RockiesRomeIsraelPeru / Inca Trail, StockholmChicagoParisHanoiAustinPuerto RicoBrugesSalzburgIstanbulLas Vegas, Jamaica, India/Golden Triangle, Auckland, Singapore, Moscow, The Oregon Coast, and Seattle.

Since we just hit on Seattle and the Oregon Coast, many readers asked about suggestions in Portland, Oregon. For some Portland is their point of travel, while others will be passing through Portland during a West Coast trip to various cities and sites. This particular question here comes from reader Joe:

“I saw that you’ve hit on the west coast a bunch in the past few weeks and I am actually heading to Portland this summer. Can you see if you can gather some readers suggestions on things to do in Portland. Also, how many days would you suggest? Many people have posted about things to do for day trips right outside of Portland during the Oregon Coast post, but what about wineries right outside? I’ve heard they have some great vineyards. Any overall help would be great! Suggestions on where to stay, length needed in the city, and some things to do/wineries outside of the city. Thank you.”

If you’ve ever been to Portland, Oregon, please help out reader Joe (along with many others who emailed me as well) by commenting below.

Also, if you have any upcoming travel where you need some help, feel free to email me at to be a featured “Help a Reader Travel” Monday special. Thanks!

The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. Portland boring! Not in my experience! Downtown has great food, music, and shopping. You get free light rail transit in the city center. Try the Vinopolis wine shop on SW Washington for a bottle or two of some great wines. Hit the food trucks for an afternoon lunch. Explore, eat, drink, and enjoy. Too much to describe here. Boring? Not!

  2. I am considering a trip up there in August/Sept. Would like to see some recommendations as well. I hear there are lots of good craft beer places to hit up. 3-4 day long weekend sounds like a good plan.

  3. Great foodie town – you can follow food trucks for days and still not touch the vast number of great restaurants in town.

    While in town, you should visit the Rose Garden Park. I would also drive around the city. There are lots of parks and other public places around not screaming touristy and therefore not well documented – but nice nonetheless.

    Right outside of the city is Multnomah Falls (as I stated in the post about the Oregon Coast) where you can hike and participate in a myriad of water sports, and you can find many nice vineyards just a few hours from the city. Nice day trips!

    Personally, I found the people in Portland to be very friendly. I would describe the city as a mix between Seattle and Austin.

  4. As a lifelong Oregonian, there are plenty of great places to explore in this state. Portland, is the largest city and offers the most to do. The downtown area is neat and eclectic. Make sure to visit food carts and breweries. If you’re interested in spending additional time in Oregon, I would suggest visiting Bend. If you like beer, plan your trip around the Oregon Brewer’s Festival!

    Bend has multiple award winning breweries, the river and numerous outdoor activities. Plan a hike, go kayaking, stand up paddle boarding or whatever. There are numerous events in the summer that offer awesome things to do (Bend Brew Fest, Summerfest, Cascade Cycling Classic, etc).

  5. No offense, but your reader who poses this question (and questions like it) seems lazy. Can’t they hit up tripadvisor and figure out for themselves what to do? They have forums there where people can weed out the dubious things-to-do.

    If there is something special about THIS particular readership, it is probably the “deal angle”. IOW, your readers may, instead, consider asking if there are any good *deals* in the Portland area.

    • @bluecat – there are many forums and this is one of many. My assumption is that the readers who are requesting this information love the guidance/recommendations they receive in this forum but also utilize many others (i.e., Tripadvisor). You can never have too many recommendations!

  6. Any city is boring, if you dont know where to go! For the best experience, stay at different locations around town. For a HIlton property, SPG, or Marriott, you can stay at the Marriott downtown, or the Nines Hotel, or the Portland Hilton, and you will have access to MAX (Metropolitan Area Xpress) trains, which will take you up and down for almost nothing. Do visit the Cooper Mountain Vineyards, which is 20 min away from downtown Portland, and drive down Scholls Ferry Rd to Newberg passing through the wine country…where you can tour/taste wineries of your choice. All less than an hours drive from the city!! I recommend The Chart House restaurant (see Yelp for reviews) for an amazing city skyline view while dining on delicious Salmon or steak. Stroll along Waterfront Park, and rent bicycles to ride along the riverside on both sides! Enjoy a cappuccino and pastry near OMSI (Oregon Museum of Science & Industry)sitting riverside, and tour the submarine that was on The Hunt for Red October! I have lived in Portland all my life and would be glad to give you more recommendations! Please contact me if you would like!

  7. The Nines is an awesome Starwood hotel right in the center of anything. Their light rail from the airport was the easiest airport transportation i’d ever taken in any city i’d ever been to. My jaw dropped when the train literally stopped on the Nines Hotel doorstop.

  8. @dealswelike, “You can never have too many recommendations!” ….it sounds good, but I think it’s wrong. If you have TOO many recommendations, you will have a hard time making a decision.

    Look, I know you believe this is a worthy topic and, anyway, it’s your blog and you do what you want. I’m just saying that we know nothing about the people that are asking for advice, and they know nothing about us. One piece of advice I once got from a former boss is to never ask for restaurant recommendations from someone you don’t know—your concepts of what is good can really vary a lot.

    The ONE thing we know about each other is that we are attracted to a blog that discusses DEALS. So if there was one aspect of travel that could differentiate your article from the countless other travel guides, it would be something that concentrates on GOOD VALUE.

    That said, for Portland, this might include the many microbrewery pubs that have great happy hours, the cheap tram ride up to OHSU, the free hikes in Washington Park, etc. Just my 2 cents.

    Anywho, Enjoy Portland!

  9. Portland is friendly w/good MAX rail. And for hotels I have used & get free parking w/excellent rates.
    As to wine country, I have visited 12X over 25 years: my favs include R.Stuart, Willakenzie, Le Cadeaux (by appt only), Amity,& Winderlea or Elk Cove. There are hundreds;get “Oregon Uncorked”. Will need a car-about 1 hr away. Allow 2 days! Tasting rooms in town are good too.
    The food scene is awesome:Wildwood, Higgins, Tora Bravo.Many recommend food trucks-not my thing.

  10. Some unusual things about Portland that you might want to check out:

    We do memorials well:
    >Memorial to the Japanese internment during WW2
    >Vietnam Memorial that is quite moving and striking in Washington Park
    >Holocaust Memorial in another part of Washington Park

    We do parks/gardens in cities well:
    Forest Park
    Washington Park
    Tryon Creek Park
    Rhododendron Gardens if you are here in May
    Japanese Gardens
    and perhaps 100 more!

    Voodoo Donuts!!

    You can take a tour based on the TV shows Portlandia and Grimm which are filmed here. A few others are too.

    More typical tourist stuff, Portland style:
    Nike Town is fun.
    People-watch on Pioneer Courthouse Square.
    Waterfront festivals just about every weekend all summer.
    OMSI (great science museum esp. if you come with kids)

    Explore neighborhoods like The Pearl, Hawthorne Street around 33rd, NW 23rd, downtown, Ladd’s Addition, Multnomah Village, others too.

    Best weather is usually July, August, September. Best month to come in my opinion is Sept.

    Nearby excursions:
    >wine country (rent a car or take a tour if you prefer not to drive)
    >Multnomah Falls
    >Mt Hood (there’s a scenic loop that takes you through the falls, the mountain and the gorge)

    Mentioned in the Oregon Coast info but worth repeating here – get on the Groupon, LivingSocial, Amazon Local, PDXDeals, etc. lists. There are many offers to take advantage of there that range from restaurant deals to a limo to the wine country to hotels to food carts to fishing trips.

    Great biking city.

    Have fun!

  11. I enjoyed my stay in Kennedy School, an old traditional school building converted into a hotel. Plenty of parking, friendly staff, humorous reminders of its original usage (including chalk boards in the rooms).

  12. Take a bike ride around the city! Did it last year and its a LOT of fun!!! If you like to read, definitely check out Powell’s! I’m going back this summer.

  13. Tasty n sons is AWAZING for brunch. There is a French pastry shop just a block or two away that is simply amazing too. The Kenedy school is very cold inside. They give you little space heaters for your room and they do not work very well, but the in-house theater is a neat feature. I would stay again.

  14. BEER FESTIVAL. Oregon makes more than 45% of the of the beer consumed in O. The food at beer festivals almost every summer week end Powells for sure. The food trucks plan ahead as often loooong lines. 7 days no prob no car needed first 3 4 days. Lots of interesting architecture. People very friendly

  15. I volunteer at the visitor’s center-that’s how much I love recommending Portland. So many of the great things about PDX have been mentioned above, but here are a few things I recommend:
    1) Powells Books – best books store in the country – used and new books mixed together
    2) Columbia River Gorge – magnificent sight with lots of terrific hiking and waterfalls (45 min drive)
    3) Oregon Coast – 80 miles away. Gorgeous coast- check out Cannon Beach for Haystack Rock, great food and shopping
    4) Washington Park/Hoyt Arboretum – one of the largest in city parks in the country with over 40 miles of hiking trails, the Japanese Gardens and the Rose Test Gardens – hundreds of different roses
    5) More microbreweries than any other city
    6) Hundreds of wineries close by
    7) River rafting close by
    8) Oregon Museum of Science and Industry, Portland Art Museum, Oregon History Museum
    9) Fantastic public transportation with multiple trains running all over including the furthest suburbs – all for $2.50!
    Check out our website at
    or call to chat: 1-87-portland

  16. Ooh – forgot all our festivals on the waterfront during the spring summer months: Cinca de Mayo, Rose Festival, Blues Festival, Brewers Festival
    Pioneer Square: Italian Festival, Christmas Tree Lighting, music all summer, flowers festival
    Oregon Zoo: summer concerts (also at all the other parks)
    We have a wonderful symphony, ballet, opera and many professional theaters.
    and a soccer team – the Timbers and a basketball team – the Trailblazers.

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