A Family Vacation to Portland, Oregon

I knew I was in Portland when I saw a woman and her boyfriend walk out with a big pink box of Voodoo Doughnut and when approached by a grimy and shirtless homeless man outside the donut store, she promptly and perkily opened the said box and offered him his pick! This could have totally been an episode from Portlandia!

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Portland is definitely one of those cities that has an identity that can’t really be compared to anything else. Add to that, the Pacific ocean, the mountains, the trees (oh the trees), and of course, the fog which appears and disappears so mysteriously; together all of it makes Portland seem so magnificent and magical.

I am all about the downtown in a new city. And while, downtown Portland is charming and has a lot to offer in terms of restaurants and an extensive waterfront, it was the countryside that really won my heart. We drove by so many idyllic farms with gentle rolling fields and the mountains in the background, that at times it felt like I was in a storybook.

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Our travel companions included four cousins and their families – two from Chicago and two from California – making for a total of 9 kids ranging in age from 9-months to 5-years (yay to not letting parenthood stop the travels). In spite of so many little humans I am amazed at how much stuff we did! Thanks mostly to auntie Lisa who prepared a day-to-day itinerary to make sure we didn’t get caught in the daily cycle of snacking and napping at home for the littles.

Usually this is where I would stop typing and just post my gazillion pictures. However, in an effort to be more helpful to anyone who is wondering about Portland, and how we travel as a family of five, I have divided the information into Transportation and Luggage, Stay, Eat, See-Do-Hike, and Tips. Plus the gazillion pictures of course. [I have talked about travel tips with kids before, but an updated is much needed as our family has grown]

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Transportation and Luggage

We traveled with Southwest Airlines from Raleigh to Portland (with a 3-hour layover in Chicago). On the way back home to Raleigh, we opted for Alaska Air which took us through San Francisco (with a 12-hour layover). [We lucked out and got a Virgin America plane which is infinitely more fun for the kids; Alaska Air acquired Virgin not too long ago]. Once in Portland, we rented our car using National’s Emerald Club. We brought two booster seats from home and got an infant carseat from National.

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Our luggage included two duffle bags (I swear by Patagonia’s 60lb blackhole duffle which has amazing capacity, feels really good to carry for my size, can be carried onboard or checked in), one Baby Zephyr pack and play (which is easy, compact, and lighter than the conventional pack and plays; we needed one since this wasn’t a hotel), a Deuter Kid Comfort hiking pack (without which hiking would have been infinitely more stressful knowing Arjun would be on the loose to test out all his daredevil moves), and then an Ikea clear DIMPA storage bag to hold booster seats, slings, extra shoes, and any miscellaneous items we might acquire later (we have traveled with the same DIMPA bag every single time in the last few years and at under $10, the value can’t be beat; it has been abused a lot but still going strong). We also had our double stroller.

I was in charge of carrying my Patagonia duffle, Ajay (in his sling), the two kids in the stroller, and the Deuter’s pack which fit nicely on top of the stroller. Devang carried his small back-pack for the plane, the other duffle, the pack and play, and the DIMPA. It was really very efficient. Especially once we checked in the 5 bags, all we had was the back-pack and the stroller. Southwest didn’t charge us for the checked-in bags because they are awesome that way. By the time we checked in with Alaska Air, we were down to just 4 bags and paid $100 total in fees. Thankfully we have a credit card that reimburses us for these kind of things.

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We booked a house near Sauvie Island using Airbnb because there were a lot of us. Staying in a hotel wouldn’t have been the same since we would have lost out on the kitchen and the common areas for the kids to hang out. This home also came with lots of outdoor space which included blackberry brambles, strawberry vines, wild flowers, roses, herbs, a small pond, and a fountain. Making all of it a lot of fun for the kids, especially the blueberries which we picked each morning for breakfast.

During the day, the house had views of both Mt. St. Helens and Mt. Hood. At night, once the kids were all asleep, the adults hung out on the back patio catching up over some libations and shooting stars. Not bad at all.

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We did a lot of grilling and cooking at home but we also had a night of take-out Thai, Bao from XLB, pFriem (super excellent for food, beer, and location which is right on Hood River Waterfront Park with an awesome playground and a beach for the kids). Alder Street food trucks in downtown Portland, Ruby Jewel Ice Cream, Sizzle Pie pizza, the Tillamook Creamery and Cheese Factory, Pelican Brewery, Voodoo Doughnuts Deschutes Brewery, and a few other places names of which I don’t remember. All in all, there is a lot of variety of foods in downtown Portland, however, the pickins are slim when driving around the state parks.

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Nursing Bebe + Beer


The natural beauty of Portland and the surrounding area makes it ideal for long drives, which is good, because many of the destinations are quite spread apart. Auntie Lisa planned our itinerary based on regions which basically included a day of Mt. Hood, Sauvie Island, downtown Portland, Oregon Coast, and Willamette Valley respectively.

Some of our favorite places included: Bridal Veil State Park Trail and Falls which is an easy half mile hike that leads to a magnificent waterfall. Above mentioned Hood River Waterfront Train & Park Hood River Lavender Farms, the breathtaking Timberline Lodge on Mt. Hood (don’t miss this!), Beaches at Sauvie Island (beware of the nude beaches), the huge Rose Garden in Washington Park (which is HUGE and also includes a zoo, Japonese Garden, a children’s museum, and many other natural attractions). My absolute favorite thing we did while on our trip was drive to the Oregon Coast and hike the Ecola State Park to go to Cresent Beach. That hike, up and down the mountain, amongst those huge green trees, landed us to a quiet beach that was perhaps the best beach I have ever seen in my life. The water was ice cold, but we still had a ton of fun splashing around! Cape Meares Lighthouse (very small but beautiful area and drive) Brooks and Stoller Family Estate wineries in the Willamette Valley rounded out the last day very very nicely! It you want more outdoor ideas, Best Oregon Hikes covers even more hikes around Oregon for all family sizes and levels!

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Bridal Veil Falls
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Bridal Veil Falls
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Bridal Veil Falls
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Bridal Veil Falls
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Bridal Veil Falls
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Hood River Lavender Farms
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Hood River Lavender Farms
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Hood River Lavender Farms
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View of Mt. Hood from Timberline Lodge

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Summit of Mt. Hood
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Escola State Park Hike To Crescent Beach
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Escola State Park Hike To Crescent Beach
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Escola State Park Hike To Crescent Beach
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Escola State Park Hike To Crescent Beach
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Crescent Beach
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Crescent Beach
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Crescent Beach
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Crescent Beach
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Crescent Beach
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Crescent Beach
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Crescent Beach
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Crescent Beach
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Escola State Park Hike To Crescent Beach
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Escola State Park Hike To Crescent Beach
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Escola State Park Hike To Crescent Beach
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Rose Gardens At Washington Park
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Rose Gardens At Washington Park
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Rose Gardens At Washington Park
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Rose Gardens At Washington Park
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Cape Meares Light House
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Cape Meares Light House
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Deer sighting at Cape Meares Light House
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sea views from Cape Meares Light House
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Brooks Winery
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Chicken coop at Brooks Winery
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Brooks Winery
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Brooks Winery

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Wine Tasting at Stoller Family Estate Winery
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Stoller Family Estate Winery
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Stoller Family Estate Winery
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Cheese Plate at Stoller Family Estate Winery
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Stoller Family Estate Winery

Tips for traveling with kids in Portland and the surround area

  • Definitely rent a car since there is a lot to see and all of it is spread out.
  • Plan activities ahead of time based on regions. Try to tackle one region per day to get the most bang for your travel buck.
  • Internet and phone signals are pretty good but they do disappear when driving at higher elevations. Make sure you know roughly how to get somewhere. Carry a paper map if you are not good at remembering directions.
  • Long distances between sights make it ideal for kids to nap and rest.
  • Pack layers when it comes to clothing. It was a 100 degree scorcher on the day we started our drive towards the Oregon coast where we needed jackets before starting the hike.
  • There is so much to see and do in and around Portland. Try to pick sights that you don’t have at home (ex: we skipped the zoo and children’s museum at Washington Park even though they came highly recommended and I know all 9 kids would have loved it).
  • Downtown Portland has a lot of homeless people. If you have kids, they will notice, and they will ask questions about it. Be prepared to explain to them what is going on.
  • Walking around downtown Portland is not as scenic as one would hope. The waterfront area is nice but not very clean, the splash pads have a lot of homeless people around, and crossing the bridges can get very hot in the summer time.
  • Powell’s Books, the worlds largest independent book store is in downtown Portland. You can plan a visit based on their calendar of events.
  • The Alder Street food trucks in downtown Portland is GREAT! However, there are no good places to eat that food. If you have a big group, you might have to just scatter and each on the sidewalk. Watch the little kids who can easily just run on to traffic.
  • There were a lot of pick-your-own farms everywhere we drove. While we didn’t stop at any of them, I imagine they would make for an excellent stop if one has the time.
  • If your kids are little, definitely consider bringing a hiking pack. Asha at 5-years-old did just fine on all the hikes with help, but 3-year-old Arjun would have either hurt himself or gotten tired because he isn’t as careful.
  • Don’t miss Stoller Family Estate winery if you can help it! There is plenty of space for the kids to run around while the parents leisurely sip their amazing wine.
  • The time difference can be hard if, like us, you are coming from the East Coast. However, it only took a day for our kids to adjust to the local time given the amount of activities we had planned which kept them busy and awake. However, the struggle is real once home when it took us 2-3 days before being completely back to our normal schedule. Consider yourself warned.
  • Regarding booster seats and car seats for rental cars, I have noticed that our company, National, didn’t charge us for the one car seat that we needed to “rent”. Each time, they sent me to a room full of car seats and just asked me to pick what I wanted. I can’t speak for all car rentals, but I have a feeling that at least National is trying to get away from charging parents for car seats since they are required by law. I would love to hear your experiences with this, with National and other car rentals.

If there is only one thing I remember from this year, it is that turning 40 is the perfect excuse to plan a trip with the people you love. Our Portland trip was second such trip this year where we got to take a fabulous trip and be part of a milestone birthday! This one was for our cousin Mukund who is easily one of my favorite people in the world! Happy birthday Mukund. Here is to 40 more! I might only be 36, but my wheels are already churning for what destination I might pick! = )

Thank you for reading this tremendously long post. The only thing I love more than travel is to talk about it, so thank you for being my muse. Please share your comments and let me know how I can make content on this website even more useful and fun for you! xoxo

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