Things to Do in Portland This Fall: Festivals, Family Fun, and Spooky Events

Fall in Portland is packed with traditions, celebrations, and unique community events. The weather cools, the trees turn shades of orange and gold, and the city fills with activity.

For families, creatives, and anyone who enjoys being part of something local, fall is one of the best times of year. Portlanders take this season seriously. There are festivals, ghost tours, book fairs, and even pumpkin races on the water.

Here are some of the best fall events you can look forward to this season.

Portland Oddities and Curiosities Expo

Dates: October 25–26, 2025

Location: Oregon Convention Center, 777 NE Martin Luther King Jr Blvd Portland, OR 97232

This expo celebrates the unusual and bizarre. Vendors and artists from around the country bring their strangest finds to Portland.

Expect to see everything from taxidermy and preserved specimens to odd jewelry, antiques, and funeral collectibles. There is original artwork, clothing inspired by horror, and plenty of one-of-a-kind items. It is not just about shopping. It is about stepping into a world where strange is celebrated.

West Coast Giant Pumpkin Regatta

Date: October 19, 2025

Location: Lake at the Commons, 8325 SW Nyberg St, Tualatin, OR  97062

This annual event is hard to forget and worth the short trip to Tualatin. People climb inside hollowed-out giant pumpkins, dress up in costumes, and paddle across the lake. Since 2004, the regatta has been a favorite fall tradition.

The day before the race, Stickmen Brewing hosts a pumpkin weigh-off and a Pumpkins and Pints celebration. On race day, there are pumpkin-themed games like bowling and golf. It is free, family-friendly, and full of laughter.

The Corn Maize on Sauvie Island

Dates: Until October 31, 2025

Location: The Pumpkin Patch on Sauvie Island, 16511 NW Gillihan Rd, Portland, OR 97231

This corn maze covers eight acres and is a must for fall outings. Every year, the design changes and surprises visitors. Two observation bridges give you a chance to catch your breath and enjoy the views of Sauvie Island and Mount Hood.

Families often spend the day here because the maze is only part of the experience. There are hayrides, a pumpkin patch, farm animals to meet, and a gift shop and café when you are ready for a break. Open daily with extended hours on weekends in October, this is a fall favorite for both locals and visitors.

Spirit of Halloweentown

Dates: Until October 31, 2025

Location: St. Helens, Oregon

Just 45 minutes from Portland, St. Helens transforms into a Halloween town every fall. The city was the filming site for the Disney movie “Halloweentown,” and it honors that history with a full month of events. There are costume contests, trick-or-treating through Old Town, haunted tours, scarecrow displays, and celebrity appearances.

Families can explore decorated streets, see carved pumpkin displays, and even take photos with a replica of the taxi from the movie. Every weekend brings something new, which makes it easy to turn this into more than one fall outing. It is playful, festive, and filled with community pride.

Dia de los Muertos Festival

Dates: October 16–November 9, 2025

Location: Milagro Theatre, 525 SE Stark St, Portland, OR 97214

For 30 years, Milagro Theatre has hosted Portland’s longest-running Day of the Dead festival. This event is rooted in Mexican tradition and includes altar displays, community gatherings, and the premiere of a new stage production each year.

The 2025 festival introduces audiences to the story of Pedro Linares, the creator of alebrijes, in a bilingual play that blends history, culture, and imagination. The performances, combined with the colorful ofrendas and cultural events, create a space for honoring loved ones and connecting with the community.

Portland Book Festival

Date: November 8, 2025

For readers, writers, and anyone who enjoys creative conversation, this is a highlight of the season celebrating Portland’s strong literary scene. Around 100 authors participate each year, offering conversations, readings, panels, and workshops.

The Portland Art Museum and nearby theaters provide a cultural setting, and food trucks keep visitors well-fed between events. The festival has grown into one of the city’s biggest cultural gatherings and attracts both local and national voices.

A Night with Ghosts

Dates: Until October 30, 2025

Portland has a haunted side, and this tour brings it to life. Local guides share historic ghost stories based on newspapers, journals, and spiritual accounts. The tour stops at three locations where paranormal activity has been reported. Stories include the ghost of Agnes Reid’s son, little Ernest Harp’s poltergeist playmate, and the Lady Over the Bar.

These tours are recommended for adults and anyone over 12. For thrill seekers, it is a chance to explore the city through a different lens. The mix of history and mystery makes this one of the most talked-about seasonal tours.

Why These Events Matter

Fall in Portland feels different when you take part in these traditions. Each of these events connects you to the city in its own way. You can laugh at the sight of people paddling giant pumpkins, enjoy a family day in a corn maze, learn about cultural traditions, or feel a chill on a ghost tour.

This is also what makes living in Portland special. The events are not just for visitors. They are community traditions that bring people together. If you are new to the city, they help you feel connected. If you have been here for years, they give you something to look forward to.

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