First Round at the Benson, Then Drinks at Old Town Pizza
Two hours of Portland ghost stories that start at The Benson's bar and finish in Old Town.
This is a walking ghost tour with bar stops, and it starts inside a hotel. The guide meets the group at The Benson on SW Broadway, the hotel lumber baron Simon Benson built downtown, and the listing puts the first drink and the first story there. Everyone on it has to be 21 or older.
Two departures run each evening, at 5:00 PM and 7:00 PM. The listing sells the night as two hours, and the operator's own booking record says it runs an hour and a half to two.
Booking here locks in a 5:00 PM or 7:00 PM start on the date you choose, at a per-person price that changes with the day of the week and the season. Tips for the guide are not in the ticket, and the operator says they are greatly appreciated.
Portland Ghosts Boos and Booze Haunted Pub CrawlA two-hour evening ghost walk with bar stops, leaving at 5:00 PM or 7:00 PM from The Benson on SW Broadway. Guests have to be 21 or older.www.viator.comThe Bar Lineup Shifts With the Night
The operator's booking record names four bars: The Benson's own bar, Kelly's Olympian on SW Washington Street, Kells Irish Pub on SW 2nd Avenue and the Shanghai Tunnel Bar on SW Ankeny Street. The same record says the lineup depends on the day of the week and the season, that bar hours vary, and that it will do its best to find an alternate when a stop is unavailable. The listing ends the night at Old Town Pizza on NW Davis Street.
The venues' own websites show where the gaps fall. Kells posts hours for Wednesday through Saturday only. Old Town Pizza's downtown taproom lists hours from Wednesday to Sunday, so it shows none for the Monday and Tuesday nights the listing also sells. The Benson's Palm Court lists dinner from 4:30 PM daily, and the Shanghai Tunnel Bar opens at 5:00 PM every day. By those posted hours, Wednesday through Saturday are the nights when every stop named here is open during the walk.
Travelers who wrote about the crawl between 2023 and 2026 describe the same flexibility. Several counted only one or two bars, with the others closed that night or pointed out from the sidewalk. One traveler in September 2026 named four: the hotel, an Irish bar, a speakeasy and the tunnel bar. Treat it as a ghost walk with drinks along the way, and a full crawl on the nights the doors line up.
The Shanghai Tunnels Stay Underfoot
The listing sets aside ten minutes for the secrets of Portland's Shanghai Tunnels, the underground passages the operator links to the shanghaiing of sailors. Travelers who mention the tunnels say the group did not go down into them. The Shanghai Tunnel Bar on SW Ankeny Street is one of the four listed bars, a drink stop that shares the name.
Between bars the walk moves through the Old Chinatown district the listing names as its setting. The operator's Portland pages lean on Old Town landmarks such as Erickson's Saloon, which it describes as a saloon that once spanned a full city block, and on The Benson itself, where it says the founder's spirit still scowls at anyone drinking in his hotel.
Paying as You Go, Bar by Bar
The ticket includes all fees and taxes, and the listing excludes alcoholic drinks. Each round is bought at the bar. The listing ends at Old Town Pizza with drinks and food, and that food is ordered and paid for there as well. The operator suggests bringing a water bottle and a snack.
House rules come from the operator's booking record. Open drinks cannot be carried out of the bar where they were bought, and smoking is not allowed on the tour. Guests who arrive intoxicated can be refused service, and severely intoxicated or disruptive guests can be removed. Pets are not permitted on the crawl, though the listing accepts service animals.
Who Walks With You, and How Far
One booking holds up to twenty people, and the listing sells up to twenty places on a shared departure. The operator's own booking system caps its departures at fifteen. Some nights run small: a traveler in 2024 described a Monday walk that turned into a one-on-one, and another in 2026 said nobody else had booked.
The listing asks for a moderate level of fitness, and the operator's Portland page puts the route at about a mile. The listing also ticks wheelchair and stroller boxes on a tour that admits no one under 21. The operator's FAQ says not all of its tours are wheelchair accessible and asks guests to contact it to confirm a specific one.
📍 Meet at The Benson, 309 SW Broadway. The guide wears a black US Ghost Adventures T-shirt and carries a lantern. Arrive 15 minutes before your 5:00 PM or 7:00 PM start.
The walk runs rain or shine, and the operator says it will contact you if it has to cancel. Cancel at least 24 hours before departure for a full refund; inside 24 hours there is none. The operator's own site sells this crawl under stricter terms, and those apply only to bookings made there. Bring a photo ID for the bars and a way to pay at each one.
Early arrivals can look around the hotel first: The Benson invites visitors to its Historic Stairwell, a twelve-story marble stairwell lined with more than 160 photos and stories of Portland. On the nights Old Town Pizza is open, the listing's route ends there on NW Davis Street, with one more helping of haunted history alongside the food.