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Writer's pictureCatherine Murton

4-day itinerary for Oregon Trip with Kids

Updated: Nov 29

Oregon has so much to offer - family fun, seafood, quirky towns, coastal gems, and so much more! It makes a great trip in the Fall. We are sharing our 4 full days in Oregon (plus travel days) including a day trip to the Oregon coast, as well an evening in St. Helens where you can celebrate the movie Halloweentown by taking pictures by the giant pumpkin and take part in the events.


Here's how we planned our Oregon Trip with kids during Fall!



Oregon Trip with Kids Highlights:





Day 0 - Travel day, Portland


Fly into Portland. Once you check into your hotel, head to Old Chinatown for dinner and then as the sun goes down you can take pictures with the white stag sign.


Day 1 - Portland


Head out early and drive to Oregon City to visit the End of the Oregon Trail Interpretive Center. This is an interactive museum; kids can even make old-fashioned dolls and candles while they learn about life on the Oregon Trail.


After a bit, head back into Portland and take a ride up the Aerial Tram. You get cool views of the city as well as Mt Hood and Mt St Helen. The fares at the time of this post are $8.50 for a round-trip ticket.


Stop for lunch at Growler Guys if you want some local beer and good burgers. Grab some Voodoo Donuts and take a selfie by the "Keep Portland Weird" sign which is literally right across the street.




Head over to Powell's Books for the afternoon. Powell's Books is a bookstore is a whole city block and several stories high, so you could honestly spend days browsing. They even have a rare book room where you can get special passes and go check out their oldest and most coveted books for sale.


Once you've stocked up your TBR pile, head over to Old Town Pizza and Brewing. This is a haunted pizzeria with spooky vibes. Maybe you'll see Nina, the resident ghost. Adults can tour the old tunnels underneath the restaurant (21+).



Day 2 - Drive to Oregon Coast


Drive out for a day at the Oregon Coast. We drove straight to Cannon Beach and enjoyed tidepooling around Haystack Rock looking for hermit crabs, sea stars, and anemones. When we were there it was so foggy and different than any beach I had ever been to. It was so ethereal! There is public parking at 163 Grower St.



Head to Wayfarer for lunch for a selection that includes fried razor clams, oyster sandwiches, Dungeness crab sandwiches, and clam chowder.


After lunch, go up the coast a little further and stop at Seaside. You can check out the Lewis and Clark Salt Cairn for some history and learning. The Seaside Aquarium is a small but fun stop for kids and you can even feed seals and stick your hands in touch pools! We stopped at Seaside Candyman for saltwater taffy. They have over 170 different flavors of saltwater taffy and some silly mirrors to get the kids giggling. We took our blanket down to the beach and walked in the edge of the water, read some books, and ate some salt water taffy. We marveled at the wide beach with low clouds. Be sure to take a picture by the statue of Lewis and Clark at the End of the Trail monument.



Find a spot for dinner on Broadway Street and end the night with some games at Funland Arcade before you drive back to Portland.




Day 3 - Portland Nature - Multnomah Falls, Japanese Gardens, Cathedral Park, and International Rose Garden.


Start the day off by driving to Multnomah Falls. It's just outside Portland and not a very long drive but the view is amazing. You can do the short hike up to the bridge. There is no permit to visit the falls in the Fall. There is also a restaurant and shop there.


If you didn't get food at the Falls, head back to Portland for a light bite to eat at Elephant Delicatessen at 115 NW 22nd Avenue, Portland, OR. They have a varity of salads, sandwhiches, soups, and deli side dishes. They also have fun gifts to browse.


Head to the Japanese Gardens for some zen. The Koi fish pond was a favorite with our group and the volunteers are very knowledgeable. There are so many pretty spots to stop and admire. They also have Umami Cafe where you can get Japanese tea but you need to make reservations ahead of time as they fill up fast. Please note, the Gardens are closed on Tuesdays.




Stop by Cathedral Park to take a stroll and admire St. John's Bridge. In my Opinion this is the prettiest bridge in Portland and this park is believed to be one of the landing spots of Lewis and Clark.


Lastly, head to the International Rose Test Garden. It's free to visit and there are over 10,000 rose bushes planted there. It was created in the early 1900's as a safe haven for European roses during WWI to protect them from bombings.


Portland has a lot of delicious choices for food. We went to Backwoods Brewing for dinner.


Day 4 - Donuts, Museums, St. Helens and Halloweentown


As soon as you wake up, head to Blue Star Donuts before they sell out! You can preorder for pickup. Once you're fueled for the day, head to the Oregon Museum of Science and Industry and explore and play for the morning. We grabbed a yummy lunch at Shalom Y'all which is a Meditterian spot with bright and fresh flavors. We had a quick stop at Freakybuttrue Pecularium (maybe 45 mins) where we posed with Krampus and Big Foot.

For the evening, we drove to the quaint riverside town of St. Helen's where we saw the Twilight Swan House (this is an AirB&B but we did not stay here) and where some of Halloweentown is filmed. We got to pose by the courthouse and big pumpkin. Because Halloweentown was filmed here the town goes all out with The Spirit of Halloweentown activities and events. We only got a small taste of it because we were there on a weeknight. It's free to walk around the event and take pictures by the signs or pumpkin but if you want to meet/greet celebrities or do something like the haunted house, you need tickets. You can read more about our visit to Halloweentown here.





We drove back to Portland that night and headed back home the next morning. What would you be most excited to check out in Oregon.


For more Fall fun check out:



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