How to Have a Spooktacular October in Portland

October in Portland is a bewitching time of year — one when the city transforms into a whimsical wonderland of fall foliage, autumnal activities, and Halloween celebrations that are certain to send shivers down your spine. Planning a visit to Rose City this fall? Here are some events calendar entries certain to help you get the most out of your autumn adventures.

The Spirit of Halloweentown

Located just a short trek from Portland in St. Helens, “The Spirit of Halloweentown” is an enchanting attraction that brings the spirit of the season to life. Inspired by the cult classic Disney movie, “Halloweentown,” this event is a must-visit for fans of all ages. As you step into St. Helens, you’ll be transported to a world of witches, ghosts, and spooky goings-on. The entire town embraces the spirit, with storefronts decorated in eerie themes and characters from the film. Visitors can pose for photos with giant pumpkins, explore a creepy carnival, and shop for unique, Halloween-themed keepsakes. The highlight of “The Spirit of Halloweentown” is undoubtedly the grand lighting of the Great Pumpkin, an event that draws visitors from every corner of the state. Join the festivities as the pumpkin is lit with a theatrical ceremony, marking the official start of “spooky season.” It’s a magical experience that captures the essence of Halloween and fills the air with a sense of wonder and nostalgia.

Crawl With Us Halloween Bar Crawl

For those seeking a more grown-up Halloween experience, the Crawl With Us Halloween Bar Crawl is the perfect opportunity to celebrate the season with friends while enjoying spooky sips and chilling thrills. Don your most creative costume and join fellow Halloween enthusiasts as you embark on a pub crawl adventure through some of Portland’s most vibrant neighborhoods. This annual event promises a night of devilish drinks, bewitching brews, and lively entertainment. As you traipse from one tavern to another, you’ll encounter themed drink specials, costume contests, and a chance to revel in the Halloween spirit with fellow revelers. It promises to be an unforgettable event filled with laughter, fun, and the thrill of exploring Portland’s nightlife in your spookiest attire.

West Coast Giant Pumpkin Regatta 

This whimsical event is held annually in Tualatin (just south of Portland), and epitomizes the spirit of fall in the Pacific Northwest. The Regatta is a unique festival that features an inventive aquatic race — one held among costumed captains navigating makeshift watercraft carved from massive pumpkins that can weigh hundreds of pounds! Participants paddle their pumpkin vessels, vying for victory in their grandest gourds as spectators line the shores, creating a carnival-like atmosphere filled with laughter and excitement. It all adds up to a great way to combine the essence of autumn and the quirky community spirit of the region, making it a cherished and lighthearted tradition that delights both locals and visitors alike.

Hood River Hops Fest

This renowned event (the largest beer fest in Oregon) celebrates the region’s vibrant craft brewing culture with infectious enthusiasm. Beer enthusiasts from all over the area convene to sample an extensive selection of fresh, locally brewed craft concoctions, particularly highlighting the unique flavors and aromas of the botanical element that gives many craft beers their special floral character: the humble hop. Live music, food vendors, and picturesque views of the Columbia River Gorge enhance the festival experience, making it an unforgettable celebration.

Portland Retro Gaming Expo

The Portland Retro Gaming Expo is a beloved annual event in Oregon that transports attendees back in time to the golden era of video gaming. Gamers, collectors, and enthusiasts all come together to celebrate the nostalgia of classic digital entertainment, including both consoles, and vintage arcade machines. The expo features a vast collection of retro games for sale, as well as tournaments, panel discussions, and guest speakers from the gaming industry. Cosplay contests, free-play areas, and a vibrant, inclusive community atmosphere make this event a must-visit for anyone passionate about vintage video games and the timeless joy they’ve brought to generations of players.

The Corn Maize at the Sauvie Island Pumpkin Patch 

Don’t miss this beloved autumn tradition, a must-visit for families and thrill-seekers alike. Spanning several acres, this intricate corn “maize” offers visitors an engaging and challenging adventure amidst a vast field of sky-high stalks. The maze’s design changes annually, featuring intricate patterns and themes, ensuring a fresh and exciting experience each season. Guests of all ages can test their navigation skills as they wind their way through the towering twists and turns, making it a perfect fall outing for groups and families. Alongside the corn maze, the Sauvie Island Pumpkin Patch also offers pumpkin picking, hayrides, and a delightful assortment of seasonal activities to complete the autumn experience.

Fear PDX Haunted House

Ready for your blood to run cold? This premier haunted attraction promises a spine-tingling Halloween experience for those brave enough to venture within. Every autumn, this immersive haunt delivers heart-pounding scares and thrilling moments, making it a popular destination for spooky season enthusiasts of all stripes. Get ready for a dizzying selection of elaborately designed haunted houses (such as “Don’t Split Up”, “Smiley’s Fun House” and “Radioactive Rampage”), each with its own terrifying theme and a cast of skilled “scare-acters” who bring the nightmares to life. With pulse-pounding attention to detail and a commitment to top-flight frights, this attraction offers visitors a night of intense and chilling entertainment — ensuring that the Halloween season in Oregon is unforgettable for those seeking an adrenaline rush. 

The Portland Film Festival 

Cinema enthusiasts won’t want to miss this annual showcase of artistry and storytelling celebrating the best of the silver screen. Attendees can look forward to a diverse range of independent films, documentaries, and shorts from both local and international filmmakers. With a commitment to fostering creative expression, the festival offers a platform for emerging talents to connect with industry professionals, as well as engage with enthusiastic audiences. Beyond taking in screenings, attendees can also participate in workshops, panel discussions, and networking events — making the festival a hub for film enthusiasts, creators, and industry insiders to come together and celebrate the magic of the movies.

Your Autumnal Adventures Begin at The Hotel Zags

No matter your areas of interest, one thing’s for sure: Portland is the place to be this fall. And there’s no better place to call home during your seasonal escapades than The Hotel Zags! Not only are we centrally located, but our stellar service, excellent accommodations, competitive rates and unexpected amenities (including our famous Gear Shed) all add up to an unforgettable stay. Take a look at our Special Offers page for all the best Portland travel deals, and we’ll see you soon!