How long does it take to walk through Portland's Old Town?

The walk typically takes between 90 to 120 minutes. The distance is roughly 1.5 miles (2.4 km) on flat terrain, including time to stop and read about the history of the Shanghai Tunnels and historic saloons.

Are the Shanghai Tunnels in Portland real?

Yes, the tunnels are real physical structures beneath the streets of Old Town. While historians debate the extent of the 'shanghaiing' that occurred there, the underground passages were definitely used for transporting goods from the Willamette River to basement storerooms.

Is the Haunted Shadows and Shanghai Tunnels walk family-friendly?

Yes, it is generally family-friendly, though some of the stories involve crime and ghosts which might be spooky for very young children. The route stays on public sidewalks and visits well-known local landmarks.

Can I go inside the Shanghai Tunnels on this walk?

This self-guided audio walk focuses on the street-level history and building exteriors. Access to the actual underground tunnels is restricted and usually requires a separate entry through specific businesses like Old Town Pizza or specialized heritage organizations.

What is the best time of day for a walking tour Portland experience in Old Town?

Late afternoon or early evening is the best time. This allows you to see the historic architecture in the daylight while the shifting shadows of dusk enhance the atmosphere of the ghost stories.

Is the Old Town neighborhood safe to walk at night?

Old Town is a vibrant nightlife district but can have quiet pockets. It is safest and most enjoyable to complete the walk before 9:00 PM, especially if you are exploring solo, to enjoy the pub atmosphere at the final stops.

Where does the Haunted Shadows walk begin?

The walk begins at the Benson Hotel located at 309 SW Broadway. It is easily accessible via the MAX light rail system at the SW 6th & Pine station.

Is this walking route accessible for strollers or wheelchairs?

Yes, the entire route follows the city's sidewalk grid which includes curb ramps. However, be aware that Old Town has some older, uneven paving stones and bricks that can be slightly bumpy.

Haunted Shadows and Shanghai Tunnels | Self-Guided Walking Tour

About This Guided Walking Tour

Portland, Oregon, is known for its quirky spirit and lush greenery, but beneath the modern surface of the Rose City lies a darker, more mysterious past. This neighborhood stroll through Old Town and Chinatown invites you to peel back the layers of history, from the high-society elegance of the early 20th century to the gritty reality of the infamous Shanghai Tunnels. As you follow this walking route, you will discover the legends of 'shanghaiing,' where unsuspecting sailors were said to be kidnapped through trapdoors in saloons and forced into labor on ships heading to the Orient. The journey begins at the majestic Benson Hotel, a beacon of luxury that is rumored to still host its original owner in spirit. From there, the path leads you into the heart of Portland’s oldest district, where cast-iron architecture hides secrets of vice, prohibition, and paranormal activity. You will encounter the Roseland Theater, a venue with a tragic backstory, and visit the site of Erickson’s Saloon, which once boasted the longest bar in the world and served as a central hub for the city’s underground dealings. What makes this self-guided walk truly special is the atmosphere of Old Town. You will see landmarks like Old Town Pizza, where a resident ghost named Nina is said to watch over diners from an old elevator shaft, and the Merchant Hotel Building, a stunning example of Victorian craftsmanship that served as a gateway to the city’s subterranean network. This exploration of Haunted Shadows and Shanghai Tunnels provides a unique perspective on Portland’s development, blending architectural appreciation with the eerie folklore that continues to fascinate locals and visitors alike. Whether you are a fan of true crime, ghost stories, or urban history, this walking tour Portland experience offers a deep dive into the shadows of the Pacific Northwest. Experience the city's transition from a rough-and-tumble port town to a modern metropolis at your own pace.

Tour Highlights & Things to See

The haunted legacy of the historic Benson Hotel
Stories of the infamous Shanghai Tunnels and 'shanghaiing' lore
The site of Erickson’s Saloon, once the world’s longest bar
The ghost of Nina at the historic Old Town Pizza
Stunning 19th-century cast-iron architecture in the Merchant Hotel Building
The dark history of the former Glisan Street morgue at Kell's Irish Pub

Route Map

Numbers indicate the order of stops on the tour.

Tour Stops & Points of Interest (6)

1

Benson Hotel

Welcome to the Benson Hotel, a masterpiece of French Second Empire style built in 1913. This hotel was the dream of Simon Benson, a logging tycoon and philanthropist. As you admire the Circassian walnut and Italian marble in the lobby, keep an eye out for Simon himself. Guests and staff have reported seeing a man in a dark suit and hat—believed to be Benson—walking the halls to ensure his hotel is still being run to his high standards. Benson was also the man behind the 'Benson Bubblers,' the bronze drinking fountains you see on the street corners outside. He installed them to discourage his workers from drinking beer during the day. This stop sets the stage for a walk that balances Portland's high-class ambitions with its darker, more spirited history.

2

Roseland Theater

Now standing before the Roseland Theater, you are at a site with a heavy history. Long before it was a premier music venue, it was the Star Theater. In the mid-20th century, it became the scene of a notorious crime involving the theater's owner and a publicity agent. This dark event cemented the building's reputation for being haunted. Today, performers and stagehands often report unexplained cold spots and the feeling of being watched from the shadows of the wings. The Roseland serves as a reminder that Portland’s entertainment history isn't just about the music; it's about the dramatic and sometimes tragic lives of those who worked behind the velvet curtains. The energy here is palpable, especially as the sun begins to set.

3

Erickson's Saloon

You are standing at the site of the legendary Erickson’s Saloon. In the late 1800s, this was the epicenter of Portland's vice district. It famously featured a 684-foot-long bar that supposedly required 50 bartenders to staff. But the real stories happened beneath your feet. Erickson’s was a primary access point for the Shanghai Tunnels. It is said that trapdoors behind the bar or in the floors allowed 'crimps' to drop drugged or drunken patrons into the tunnels below. From there, they were ferried to the waterfront and sold to ship captains in need of a crew. While much of the 'shanghaiing' history is debated by historians, the physical tunnels and the grim reputation of this saloon remain a core part of Portland’s waterfront identity.

4

Old Town Pizza

Old Town Pizza is located in the historic Merchant Hotel building, but it is perhaps most famous for its resident ghost, Nina. Legend has it that Nina was a woman of the evening in the late 19th century who was pressured into acting as an informant for the police. She was allegedly found dead at the bottom of the building's elevator shaft, which still exists today inside the restaurant. If you look closely at the brickwork near the elevator, you might see her name carved into the wall. Visitors often report the smell of perfume or the sight of a woman in a black dress watching them from the upper balcony. This stop perfectly encapsulates the intersection of Portland's architectural heritage and its enduring ghost stories.

5

Merchant Hotel Building

The Merchant Hotel Building is one of the finest examples of cast-iron architecture in the Pacific Northwest. Completed in 1880, it represented the height of Portland’s Victorian-era prosperity. However, its basement tells a different story. Like many buildings in this district, it was connected to the network of tunnels used for moving goods—and allegedly people—away from the prying eyes of the public. The cast-iron fronts were not just decorative; they were a sign of fire resistance and modern engineering. As you look up at the intricate details, imagine the contrast between the elegant guests staying in the rooms above and the rough sailors and laborers navigating the dark passages just a few feet below the pavement.

6

Kell's Irish Pub

Our walk concludes at Kell's Irish Pub, housed in the historic Glisan Building. While today it is a place of celebration and Irish cheer, its past is much grimmer. During the 1918 flu pandemic, the basement of this building served as a makeshift morgue because the city's facilities were overwhelmed. This history has led to numerous reports of paranormal activity, from mirrors shattering without cause to the sound of footsteps in empty rooms. Look up at the ceiling and you’ll see thousands of pennies stuck there—a local tradition, but some say it’s also a way to appease the spirits of the past. It’s the perfect place to grab a drink and reflect on the layered, often shadowed history of Portland’s Old Town.

Start Free on iPhone

Start your private guided tour now

Explore “Haunted Shadows and Shanghai Tunnels” with your very own Private Tour Guide with Zigway. Start free on iPhone, skip the large group and the fixed routes, and hear the city come alive as you go.

Start free on iPhone

Your Private Tour Guide

Frequently Asked Questions

This self-guided route through Old Town is widely considered the best for ghost stories and legends. It covers iconic 'haunted' locations like the Benson Hotel and Old Town Pizza, allowing you to explore at your own pace without a group.