Portland in October with Kids: A 2-Day Fall Weekend Itinerary
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We drove to Portland, from Seattle, in Mid-October for my oldest’s birthday in a way that best celebrated her - with all things spooky. Whether she loves Halloween because her birthday is right before it or whether it is just a nice coincidence is not known. We came up with this fun fall weekend itinerary together, highlighting some of the best things to do in Portland in October as a visitor. Portland is an amazing place to visit in the fall and its wet and dreary weather only adds to it. This quirky city is a perfect destination for soaking up the spooky season even if you just have 2 days.
Multnomah Falls
Where to Stay
Wildings Forest Farm Stay
Some trips we choose accommodations that are practical - ones that fit within the budget and close to the sights we want to see. Some trips we choose accommodations that are an activity or sight for themselves. This trip we did the later. We did a farm stay just a short distance outside of Portland. We got to tour the farm, feed the animals, hear stories of how the animals were rescued. We got to wave to the llamas before bed at night. I’d recommend a farm stay for almost any trip, but for this one it felt very fitting. We stayed at Wildlings Forest and loved it – it was a good location between St. Helen’s and Portland. There are also many other farm stays including:
Four Wheels Farm in Hillsboro – large nice home with beautiful views and a peacock that often visits the home
Springdale Farm in Troutdale – peaceful farm stay with alpaca and goats with lots of fun nature activities nearby
Stay on a blueberry farm in Battle Ground, WA – private blueberry patch and pickleball court, along with a beautiful farmhouse to stay in
Santos Family Farm Retreat in Yamhill, OR – beautiful farm you can walk through with animals and produce and surrounded by vineyards
If farm stays are not your thing, there is so many more accommodation options in and near Portland. If you want to stay more within the downtown area, I’d recommend the Pearl District area where you can walk to restaurants, Powell’s books, or nice parks like Canopy by Hilton. If you want more of a neighborhood feel, Nob Hill has nice tree-lined streets and is close to the Japanese Garden. Check out hotels like the Inn at Northrup Station or Park Lane Suites and Inn.
Our Itinerary Overview
This is our itinerary for this trip. There are dozens of fall activities to do in Portland this time of year, so your itinerary very likely will look a bit different. Near the end of the article, I list many more places to see during your fall weekend in the Portland area. I’d recommend picking your favorite 1-4 things per day you are here, mapping them out and creating your itinerary by grouping your activities to reduce your driving time. Portland is a medium sized city with beautiful things to do both within the city and surrounding it on all sides. The first part of this article will focus on our trip and what we choose and the later part will focus on additional things to do. The map below includes all of the fall things to do.
Day 1
Drive from Seattle to St. Helen’s, OR (2.5-3 hours depending on traffic)
St. Helen’s Halloweentown
Check into farm stay
Hidden Creek Park West
Day 2
Drive into downtown Portland (30 minutes)
Portland – Powell’s books, etc
West Coast Giant Pumpkin Regatta
Ole Bolle Troll
Multnomah Falls
Drive back to Seattle (3-3.5 hours depending on traffic)
Day 1
We drove down to Oregon from the Seattle area on a saturday. We left at about 8:45am and ended up arriving in St. Helens, OR at 11:20am.
St. helen’s Halloweentown
The Spirit of Halloween town festival takes place in downtown St. Helens along the water of the Columbia River every weekend of the Halloween season. It typically starts the last weekend of September and goes till Halloween weekend on Saturdays and Sundays. Everyday they have stage performances, entertainers and costumed characters walking around the festival grounds, both free and paid attractions, photo-ops, booths with local artists and food vendors and much more. You can walk around a lot of the festival without paying for any admission. However if you want access to some of the photo-ops, the haunted house, games area, train rides and more - you will need to buy an access pass. Adult tickets are $40 a person and a kids (6-12yo) access pass is $20 a person, with some additional service fees. You can also get an haunted house ($15) only pass, which might be worth it for your family if you are not interested in any of the photo-op areas, train ride, or other paid attractions. We decided to get the access pass since our kids were under 6, so we would only have to pay for the adult ones AND because it was a special weekend and we don't live in the area. However, I think it is still worth it to visit the festival and not pay for the pass. We did enjoy the parts we paid for, but it is fairly pricey.
St. Helen’s Oregon neighborhood streets
Spirt of Halloweentown’s Plaza Square
In addition to the access pass, there is a fee for onsite parking at $25-30 per car. We wanted to avoid that charge and found free parking in the neighborhood streets. It took us a bit to find parking but ended up getting a spot in the neighborhood streets north of Columbia Blvd, near Godfrey and 6th Street Park. It was about a 0.5 mile walk and we saw lots of other groups walking with us to the event. It was a nice walk with sidewalks most of the way and we got to see some of the neighborhood halloween decorations. We wanted to get there as close to event opening time as we could to minimize lines, but with finding parking and the walk and getting on our costumes, we arrived at 11:50am and it was quite busy and got more busy the longer w were there. If you want a better chance of finding closer parking, arrive before 11am or pay for the onsite parking.
We walked into the festival at the 1st and St. Helen’s Rd intersection but there are multiple ways to enter into the event area. There are quite a few craft and food vendors on 1st street, all making the most of the theme. There are also several other food trucks and booths throughout the festival. Our first stop was the most iconic - the Plaza Square. Here they had a variety of photo-ops including ones from the Halloweentown movies including the bus ticket stand, iconic characters, and also other general Halloween photo-ops and decorations like tractors and pumpkins. Jack Skeleton dressed as Santa was even available to take photos with. All of these smaller photo ops had a short to no line. The main photo-op of Jack the pumpkin (or the giant pumpkin) had quite a long line. Initially we saw how long the line was and passed on it in favor of other things, but we did end up waiting in it later when it was considerably longer. We likely should have got in that line earlier in the day since it just grew. The line itself stretched outside of the area requiring a pass but you did need the access pass to take a photo with the giant pumpkin. They checked the line several times to make sure only people with valid tickets were in the line and checked it again once we were at the end. Jack the Pumpkin photo-op was a little different, they had a camera there that took your photo and then you were able to scan a QR code or enter your email to get the digital copy of the photo. The digital copy was included with your access pass. They also had an option there to get a physical photo for an extra price. And while we are not massive Halloweentown fans, it was a nice photo. However, we did end up waiting 40 minutes in line for it.
Spirt of Halloweentown’s Plaza Square
Spirt of Halloweentown’s Plaza Square
Spirt of Halloweentown’s Plaza Square
After the plaza square photos, we headed over to the creature encounters and alien experience. I did not know what to expect out of either but they were both interesting and cute. In total those took us about 15 minutes to go through, but you could have spent more time especially with the creatures. They had snakes, spiders, lizards, parrots and other creepy critters. If you came at the right time they also let you touch and interact with some of the animals. That was not something that interested us so we spent just a short amount of time here. In that same building but in the back is the Haunted House. We were all pleasantly surprised by the haunted house. I did as much research as I could about the haunted house beforehand to make sure it was appropriate for younger kids and it seemed to be, but you can never be too sure. It was a fairly calm Haunted house with no jump scares or live actors. It was definitely creepy and eerie without being scream inducing or traumatic for little kids. As an adult it was also enjoyable. A teenager might think it is “lame” due to the lack of jump scares, but it likely appeals to the general public. Now of course, you know your kid best and if you think that a dark space with creepy elements would be too much - skip it. My kids get scared at any movies with suspenseful scenes like finding Nemo or Toy Story, but they are not scared of ghosts, skeletons, etc so I thought they would be okay. We talked to them multiple times before going in that none of it is real and that seemed to help. Our 4 year old wanted a hand to hold and our 5 year old was out walking in front of us.
Spirt of Halloweentown’s Haunted House
Spirt of Halloweentown’s Haunted House
Spirt of Halloweentown’s Haunted House
What can you expect in the haunted house – animatronics, strobe lighting, dark rooms, creepy decorations, spiders, eerie sounds, and skeletons. We felt they did a good job spacing out the guests so we didn’t feel like we were having to rush through it or we were crammed in there with other people. We were just by ourselves in most of the rooms or scenes. The line for the haunted house was not that long for us at 12pm and moved fairly fast. In total, it took about 8 minutes to walk through at a constant pace.
After the haunted house, we got lunch at one of the food vendors on site and explored the rest of the attractions and performances. We watched the St. Helens witches and the magicians. We checked out the pirate encampment down near the waterfront and watched the cannon demonstrations. Played on the playground nearby – which is just always present and part of the park. We also went over to the paid area with games and some activities. They had pumpkin bowling and a maze that was quite fun. There were also face painters who initially we assumed were included as part of our ticket since they were in the paid zone, but it was an additional fee. This area was fun and not crowded but only occupied about 15 minutes of our time. I don’t think it would be worth it for most groups but if you have the pass, check it out. After this we were going to go on the filming location train ride, but the wait for the next train was quite long so we skipped it. It was also about to rain and continue to rain the rest of the afternoon, so we prioritized our final activity. Which just happened to be waiting in the long line for the Jack the skeleton photo op. We were able to interact with all of the wandering performers and listen on the performances on the stage, so despite it being a long wait, it wasn’t without its enjoyment.
Spirt of Halloweentown’s Hay maze
Spirt of Halloweentown’s roaming performers
Spirt of Halloweentown’s pumpkin bowling
Hidden Creek Park West
Once the rain started in St. Helens, we headed back to our car and made our way over to our farm stay to check in. We said hi to some of the animals, waited a bit for the rain to stop and then headed to a destination playground. This wasn’t like your normal basic playground you can find in any park, this playground is worth the bit of a drive to get to. Hidden Creek Park West or as we refer to it “the Giant Monkey playground” features the impressive climbing structure called Oro the monkey. Kids can climb on it, in it and all around it. We saw kids playing on it ranging in ages from 1 to 12+. The park was more than just the monkey and included swings, spinners, sand and water play, forested areas and more. The main play area is also completely fenced in to give you peace of mind if you have an eloper or just multiple kids that you are in charge of. The park itself is very pretty in the fall. Beyond the play area they have outdoor games like ping pong and an obstacle course and fitness equipment that is labelled for adults, but kids were on too.
We grabbed take away dinner on our way back from the park and enjoyed our evening back on the farm.
Hidden Creek Park West - Oro the monkey
Wildings Forest Farm Stay
Day 2
Before check-out, our lovely host and owner of the farm sanctuary gave us a tour of her animals while she fed them. We got to hear about the animals incredible stories, help fed some of the animals, and help accept a delivery of donated produce. Such an amazing morning experience that was just included in our stay. We then packed up our stuff, loaded it in the car for our last day exploring the Portland area.
Wildings Forest Farm Stay
Wildings Forest Farm Stay
Powell’s Books
First up was exploring Portland itself. We have been to Portland on prior trips so our goal was just to stop by Powell’s Books. We are a book-loving family and Powell’s books feels like paradise but also risky at the same time because we end up walking out with far more books than we anticipated getting. Powell’s is the largest independent bookstore in the world. The bookstore covers an entire city block and is 4 floors. It includes new, used and some unique rare books across every genre you can think of. Whether you read often or not, this is a fun store to just walk around and explore - especially on a rainy fall morning.
Voodoo Donuts is another quintessential Portland place in downtown Portland that fit the fall vibes.
West Coast Giant Pumpkin Regatta Festival
Portland is known for being a quirky and fun city and this is just one of the many event that showcase it. We happened to be in town for this festival and once we found out it we had to go. In 2026, it is taking place on Sunday, October 18th. Watching the pumpkin races itself is worth visiting but there is so much more fun activities happening around the lake that are worth checking out. This is a completely free event and takes place in the middle of a large shopping district. There are some parking lots nearby that fill up quite quickly and there are other ones a bit farther out that you can walk from or take their free shuttle to the event. This is a very busy event and the pathways and activities can be quite crowded.
West Coast Giant Pumpkin Regatta
West Coast Giant Pumpkin Regatta
The pumpkin races themselves are broken up into 4 heats with two taking place at 12:00pm and the other 2 at 2:00pm. People find a spot to watch these races hours in advance but there might be some okay viewing spots to find 30 minutes beforehand. If you want a good view, be prepared to wait. While the adults found it interested and fun, our younger kids were not interested enough to watch more than 1 heat. We then checked out some of the other activities which included pumpkin decorating and other art projects, pumpkin bowling and pumpkin golf, a giant coloring mural, magician performances, a costume contest, and a lot more. Around the lake there are also several food vendors for lunch. We had more that we wanted to see elsewhere so we just stayed for about an hour but you could easily spend the entire festival time (10-4pm) exploring everything.
Ole Bolle Troll
We love the Dambo Trolls – I even have an entire article written about them. While we visit them all throughout the year, it still feels like more of a fall activity. The Ole Bolle outside of Portland especially lends itself to being viewed in the fall with its forested surroundings and adorable Scandinavian buildings. The troll is completely free to visit and you can park at the lot for Nordia House. You can go inside the little house that Ole Bolle is looking into to get a cool view.
Ole Bolle Troll
Ghost Little Free Library
Ghost Little Free Library
During the month of October, an amazing woman who lives in Southeast Portland has a Little Free library that gets haunted by ghosts. Rather than books, you can find little ghost figurines, ghost stamps, ghost art, halloween-y stickers and so much more. You can drop of your own fun ghosts to spread Halloween spirit or take one. To find the location of this and learn more about it - check out her instagram @littleghostlibrarypdx. If you are looking for more fun neighborhood things like this, there are so many others in Portland (and beyond). This website called worldwide sidewalk job maps out what they are and their location. It started in Portland but has expanded worldwide. There are other trinket exchanges, mini art galleries, puzzle exchanges, mini blockbusters, and of course mini book libraries.
Multnomah Falls
For our final Portland area activity, we debated between a pumpkin patch or a hike. We ended up with visiting the iconic Multnomah Falls. The most iconic waterfall in Oregon is just a 35 minute drive from downtown Portland. This is a gorgeous waterfall but can be a bit tricky to visit with how popular it is. There are two main parking areas. The main lot is off the highway I-84 on exit 31 that is run by recreation.gov, during the more popular months you need a permit to access this parking lot. Unfortunately though, the permit does not guarantee you a spot as the limit the permits per day but now how long people can stay at the falls. The other option is park along the historic Columbia river highway (U.S. 30) and either park for free near Wahkeena Falls and hike a bit to Multnomah Falls or park in the private Multnomah Falls parking lot along this road. The private lot can be quite pricey at $20+. There are also shuttles that will take you to falls including the $5 shuttle from the Multnomah Falls Park and Ride from Sasquatch Shuttle or a longer shuttle tour that will take you multiple other attractions in this area.
Multnomah Falls
Multnomah Falls
Once you get out of your vehicle and have arrived at the falls, you can walk the short distance to the main viewing platform to get a beautiful view of the falls. You can also take a 0.2 mile uphill switchback walk to the bridge between the falls. If you are ready for a longer hike, there is a 2.4 mile hike up to the top of the upper falls. The waterfall itself is the tallest in Oregon, with a total of 620 feet, the upper falls is a 542 feet drop and the lower falls is 69 feet and some 9 feet between the two falls. There are lots of other hikes in this area that take you past many other falls. You could spend a whole day or more exploring the Columbia River Gorge sights.
Multnomah Falls and this whole area is absolutely gorgeous in the fall time, despite or perhaps enhanced by the misty or rainy weather.
More things to do
Places to enjoy the colorful Fall Foilage
Multnomah Falls
Peak fall color in the Portland area is often best from late October to early November. Leaves start changing earlier in the higher elevations and if you are heading around Mount Hood or similar high elevation trails, your best bet is to visit early to mid-October if you want to see the spectacular color. Here are some of the best places to immerse yourself in scenic fall near Portland:
The Portland Japanese Garden – one of the most authentic Japanese Gardens outside of Japan and one of the most popular spots in Portland. This garden really shines in the fall time with the stunning Japanese Maples changing colors. Along with the colorful trees, there are koi ponds, waterfalls and serene paths. Admission is currently $22.50 for adults and $16.50 for kids between 6-17 years old and is well worth it if you are into gardens.
Pittock Mansion – a historic 1914 Mansion which you can visit through a self-guided tour along with walking around the beautiful grounds that includes a viewpoint of Portland and Mt. Hood. The view showcases Portland with fall colors scattered all around it.
Silver Falls State Park – A hike that is at the top of my bucket list is the Trail of Ten Falls, which features 10 beautiful waterfalls that you can either go behind or get an up-close view of and beautiful fall colors from the golden maples on the trail. This 7.7 mile trail is best done though without kids or with older kids who are capable of hiking that long.
Latourell Falls – in the Columbia River Gorge like Multnomah Falls, this waterfall is another jaw-dropping waterfall in the forest that will be in the process of changing colors when you visit. The trail is popular and can get crowded.
Washington Park – the large urban park is home to the Portland Japanese garden but also the Zoo, Hoyt Arboretum and lot more. Everywhere in this park is worth visiting during this time of year but if you are specifically looking for fall colors head to the Hoyt Arboretum or the Secret Garden.
Powell Butte Nature Park – beautiful park with trails through meadows and forests. You get views of mountains and the stunning fall colors.
Overlook Park – a neighborhood park in North Portland with mature trees that turn orange and yellow in the fall. As the name suggests, the park also features views of downtown Portland.
Forest Park – this massive park is urban wilderness at its best. There are 80 miles worth of trails that take you through this beautiful forest. One of the more popular hikes takes you to what is referred to as the Witch’s Castle. You can get there by taking the Wildwood trail in the Macleay Park section of Forest Park. The witch’s castle along with the mossy on the trees and the fall leaves is the perfect vibe for October.
Hike to Multnomah Falls
Pumpkin Patches and farm outings
Here are some of the many great farms in the Portland area that offer either pumpkin patches, you-pick-experiences or other fall festivities.
The Pumpkin Patch – A lot of Portland area families head to Suavie Island north of Portland to go to one of the many farms located there. This spot claims to be the original pumpkin patch and has hayrides, cow train, a petting zoo, a large corn maze and yummy food options. It is free to visit the farm but some of the activities cost extra.
Bella Organic Pumpkin Patch and Winery – A Suavie Island farm with lots of activities including a corn maze, train, pumpkin picking, and a great halloween atmosphere.
Topaz Farm – Another Suavie Island farm with a sunflower field, pumpkin patch, yard games, hayrides, animals and more.
Packer Orchards – On the Hood River Fruit loop and includes a pumpkin patch and apple picking, a bakery, along with other fun fall activities.
Plumper Pumpkin Patch – This farm hosts a fall festival through the beginning of November and has so many fun kid activities from pumpkin cannons to slides and fall treats to taste.
Sherwood Orchards – If you don’t want all of the fall festival frills and just want a nice U-pick orchard to get apples - visit this orchard for a more relaxed and less crowded atmosphere.
West Coast Giant Pumpkin Regatta
Spirit of Halloweentown Plaza Square
Wildings Forest Farm Stay
Tips for visiting Portland in the fall
The Pacific Northwest really goes all out creating the cozy and spooky vibe for fall. This means fog, misty rain, cold mornings, and also changing leaves and fun cafe specials and fall events. If you version of the perfect fall outing includes farms, a short hike or two, bookstores, deliciously comforting food, cozy neighborhoods maybe with some cool Halloween decorations and unique activities – then Portland is your place. Some preparation is required. October is a transition month between the beautiful sunshine and the more frequent rain showers. Your weekend may not have a drop of rain or it may be raining the entire time. Temperatures are also likely to be comfortable with highs in the 60s but you might also have an odd 75+ degree day or a chilly one in the low 50s. Here are some things I’d recommend packing:
Rain Jackets – starting with the most obvious.
Fleece jacket or a warm layer – for the chilly but not rainy mornings and evenings.
Rain boots or Waterproof hiking shoes – for the muddy farms or hikes after rain
Extra socks
Clothes that can get muddy or rainy
Travel Umbrella – like Seattle many Portlanders skip umbrellas in favor of just wearing waterproof jackets, however that doesn’t need to stop you from bringing one.
Daypack for hikes
Don’t let rain in the forecast or the idea of rain prevent you from taking this trip. Portland rain is often misty and intermittent. It won’t be an all-day downpour. After a while, with a good rain coat, you won’t even notice it. As they say, there is no such thing as bad weather, just bad clothing. If you make sure you aren’t walking around in wet shoes and socks (the worst) and are warm and comfortable – you will have an amazing time. I will also note that for farms and hikes, be sure to also check what the weather was the day or two before. Even if it is a sunny warm day the day you go, if it rained the day before, you will likely encounter mud.
Pacific Northwest Recommendations from Powell’s Books in Portland, Oregon
However, if rain does affect your desire to go outside – then keep your itinerary flexible and plan out your days based on the forecast. If it is dry and nice – head out to a park to see the fall colors, go to a farm or Halloweentown. If it is raining, maybe focus on visiting Powell’s and other bookstores, doing a long food tour of different Portland restaurants and their fall offerings, go to the zoo which has lots of indoor areas or a museum. Or do some fall or early Christmas shopping, note that Oregon has no sales tax.
Books to read
One of my favorite ways to immerse myself more in a place that I am visiting is by reading a book that is either set in my destination or at least has a similar vibe. Here are some books that would be perfect for reading during, before or after an amazing fall weekend in Oregon. This list includes books across multiple genres and for various ages. Feel free to wait to buy your pick once you go to Powell’s books!
The Book Witch by Meg Shaffer – a fun book set in a fictional Oregon town called Fort Meriwether, in which a third-generation book witch is able to go into novels to fix any issues. This is a captivating magical realism romance books.
Chaos at the Lazy Bones Bookshop by Emmeline Duncan – inspired by St. Helens, OR, this book takes place in a Halloween-themed town and follows a bookshop owner discovering her town’s dark side
Ferris by Kate Dicamillo – A great middle grade novel for kids 8+, about ghosts and found family
The Caretaker by Marcus Kliewer – A horror that follows a woman who is taking care of a strangers home in the Oregon Coast wilderness.
Spooky Oregon: Tales of Hauntings, Strange Happenings, and Other Local Lore by S.E. Schlosser – Non-fiction book about spooky happenings all around Oregon.
The Orchardist by Amanda Coplin – A historical fiction novel that places in rural Oregon on a Orchard detailing a moving story about a non-traditional family.
Kitty series by Paula Harrison and Jenny Lovlie – book series for kids aged 5-10 about a girl with catlike superpowers who helps solve problems around her cozy fall town
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