The ultimate spooky weekend in Portland, Oregon

Not everybody knows this, but Portland, Oregon, has a hidden spooky side. The largest city in this Pacific Northwest state is a paradise for horror fans and a top spot for a Halloween weekend getaway. We’re not just talking about ghost tours, although these are definitely on the table. The city's shops, bars and lounges embrace all things eerie and macabre, and these aren’t your typical pop-up haunts. These places have a year-round dedication to the dark and mysterious.

Having visited Portland over a long fall weekend, I can promise that three days will barely scratch the surface of what Portland has to offer – especially if you plan to dive into the city's spookier side. To experience Portland’s haunting charm, here’s how to craft a perfect spine-tingling Halloween weekend.

• When to arrive: Halloween falls on a Thursday in 2024, so check in by the afternoon for your three-day weekend to make the most of the quirky, haunted and delightfully eerie experiences that await in Portland.

• How to get from the airport: From Portland International Airport (PDX), hop on the red line of the MAX Light Rail to Pioneer Square. It’s about a 40-minute train ride, with trains running every 15 minutes, and tickets cost less than $3 (one-way). A rideshare will get you the nine miles into town for around $40.

• Getting around town: Portland is wonderfully walkable and easy to get around. You’ll find most spots easy to reach on foot. But if you need to cross the Willamette River or venture further, rideshares are fairly inexpensive and quick.

• Where to stay: For convenience, staying centrally near Pioneer Square is a smart move. The Hampton Inn & Suites Portland-Pearl District is a great mid-range option, with rates starting from around $150 per night. For something a bit more upscale, the Kimpton RiverPlace Hotel along the Willamette River offers stays for under $300. If you’re on a budget, the Hotel Rose on SW Morrison St is a solid pick, with rooms for less than $80 per night.

• What to pack: Portland’s weather can be unpredictable, so pack layers and be ready for anything. The city gets about 36 inches of rain a year, but showers are usually light. Portlanders don’t even bother with umbrellas; just throw on a jacket, and if the rain does start, pop into a cozy coffee shop. Chances are, the rain will have stopped by the time you’ve finished your latte.

Thursday night: Hang out with the spooks and ghouls

Halloween falls on a Thursday in 2024. If your trip coincides with the Halloween weekend, there are plenty of themed events to check out if you still have energy after the journey. If not, you're sure to find a creepy movie on hotel cable TV.

Friday: Spooky shopping, food cart eats

Morning: Rise and shine; it’s time to explore. But first, breakfast. Head over to The Daily Feast, a hip spot where breakfast and brunch are served until 2pm. Dig into dishes like smoked salmon scramble, fluffy buttermilk pancakes and avocado toast. While it’s not spooky, it’s the perfect fuel for the day ahead.

How to spend the day: After breakfast, it’s time to embrace the odd and unusual. Just two blocks away, you’ll find The Skeleton Key Odditorium, a treasure trove of curiosities. This quirky shop features gothic art, tarot cards, crystals, collectibles and appropriately unsettling taxidermy. Wander through its 2500 sq ft museum, with exhibits that dive into local legends, vampires and circus sideshows.

Next, make your way to Paxton Gate for more peculiar finds. This shop offers hands-on taxidermy workshops where you can learn to prepare, stuff and mount creatures like rats, skunks or even a mythical jackalope.

From here, head to Freakybuttrue Peculiarium – the name alone makes it worth a visit. This anti-museum is filled with wild creations from local artists, all celebrating a passion for urban legends, cryptozoology and weird science. It’s as bizarre as it is fascinating.

Dinner: No trip to Portland would be complete without eating from a food truck, though in Portland, they're known as “food carts.” With more than 500 food carts to choose from, you’ll be spoiled for choice when it comes to dinner on the go. For first-timers, Cartopia on Southeast Hawthorne Boulevard offers a good introduction to the scene. This food cart pod and beer garden features eight food carts, including Pyro Pizza for wood-fired pies and BKK Pad Thai for flavorful Thai street food.

After dark: As night falls, dive into Portland’s creepy bar scene. Naturally, you’ll want to start at Creepy’s where you can sip on cocktails with names such as Ghost Machine and Dark Arts, surrounded by eerie clown paintings, animatronics and dolls that seem to watch your every move. Wrap up your evening at The Coffin Club, a dark and moody nightclub that celebrates all things macabre, as goth, dark wave, post-punk and industrial beats fill the air.

Saturday: Donut breakfast, creepy tunnels, haunted pizzas

Morning: Donuts are practically a Portland tradition, so start your day with one of the city’s sweet specialties. A must-visit is Pip’s Original Doughnuts & Chai, where the mini donuts and artisan chai are unforgettable. If you’re in the mood to explore further, Blue Star Donuts, Doe Donuts and Mikiko Mochi Donuts are crowd-pleasers, and of course, there’s the iconic Voodoo Doughnut – a local institution with two Portland shops to choose from.

How to spend the day: A visit to the Shanghai Tunnels – an underground network of passageways with a shadowy past – is an absolute must while in Portland. Used in the early 1900s for smuggling, gambling and “shanghaiing” – kidnapping unsuspecting, intoxicated men and forcing them into labor on ships – these tunnels are steeped in history and spooky lore. Numerous ghost sightings and paranormal reports have made the tunnels a must-see for those intrigued by Portland’s sinister side. On Saturdays, 90-minute guided tours run between noon and 8pm.

Afterward, re-fuel and calm your nerves at Old Town Pizza & Brewing, one of Portland’s most infamous haunted spots. Located in the historic former Merchant Hotel, this pizzeria is said to be home to a ghost named Nina, who’s been spotted wandering the halls (plus, the pizza is delicious).

Make Glowing Greens your next stop of the day. This indoor blacklight miniature golf course boasts a spooky ghost pirate theme (think skeleton buccaneers, shipwrecks and treasure chests). On-site, you’ll also find Wicked Axe Throwing and Mental Trap Escape Room for more Halloween-appropriate entertainment.

Dinner: Portland is packed with incredible spots to dine, so take your pick based on whatever you’re craving. For Southern comfort food with a twist, head to Screen Door Pearl District. In the mood for Thai? Thai Peacock won’t disappoint. If tacos are calling your name, look to Fabos Tacos for delicious tacos, tequilas and tostadas.

After dark: Ready for some chills after sundown? End your day in the company of Portland Ghost Tours. These one-hour walking tours take you through particularly freakish and ghost-infested corners of this town. With tour names like “Portland Ghosts: Poltergeists and Psychopaths” and “Portland Ultimate Dead of Night Tour,” you’re in for a spine-tingling experience.

Sunday: Haunting views, moody mansions, donuts after dusk

Morning: Portland’s coffee scene is legendary, so it’s only right to start your day with a cup of something strong. Coffee aficionados have plenty of stellar options to choose from, like Fuller’s Coffee Shop, Above Grnd Coffee and Caffé Umbria. If you’re up for something out of the ordinary, how about getting your coffee made by a robot? At Artly, located inside the minimalist Japanese clothes and homewares store MUJI on SW 5^th Avenue, a barista bot brews your morning java. In a city known for offbeat vibes, it seems perfectly at home.

How to spend the day: Head to Pittock Mansion for more of Portland’s haunted history. Perched high above the city, this historic home offers sweeping views and eerie overtones. Rumor has it that former owners, Henry and Georgiana Pittock, still roam the halls; visitors have reported all sorts of encounters, from cold spots to unexplained footsteps and moving objects. While the ghost stories give Pittock Mansion an air of mystery, it’s the stunning architecture and panoramic city views that truly make it worth the trip.

Dinner: For dinner, try Nong’s Khao Man Gai, a beloved spot known for the favorite Thai-Chinese dish khao man gai – broth-cooked chicken over rice, drizzled with a tangy chili-and-soybean sauce. Afterward, take a stroll to Powell’s City of Books, the world’s largest independent bookstore, and pick out a sinister page-turner for the journey home.

After dark: If you’re still craving a spooky vibe, make Raven’s Manor your next stop. This haunted mansion-themed bar is decked out with spider webs, candelabras and skeletons. Sign up for a 1.5-hour mixology class called “Dr Raven’s Elixir Experience” to create your own hauntingly delicious cocktails.

Cap off the night, and your weekend, with a final stop at Voodoo Doughnut – their Old Town location is just four blocks from Raven’s Manor and stays open until 3am, perfect for a last indulgence before you bed down. Be sure to try their famous Bacon Maple Bar, a maple frosted bar donut topped with crispy bacon strips.

As your spooky weekend comes to a close, set an alarm to catch your flight out of PDX, or enjoy a leisurely morning before you check out for the drive home. Either way, Portland’s eerie charm will linger long after you’ve said goodbye.