Portland Ghosts Boos and Booze Haunted Pub Crawl

Portland Ghosts Boos and Booze turns an evening walk through downtown Portland into a string of ghost stories, old crimes, haunted bars, and local oddities. The route starts at The Benson and finishes at Old Town Pizza, passing through the old Chinatown and downtown districts. I like the mix of Portland history and spooky folklore, especially when the guide explains why a plain-looking building has an unsettling past.

I also like the small-group feel. With no more than 20 people, you are not lost in a huge crowd, and a good guide can adjust the pace. Guides including Kris, Victoria Rose, Houston, Jessica, and Lori have received strong praise for their humor, local detail, and ability to make a short walk entertaining.

The main caution is simple: this is not always the full pub crawl suggested by the route. Bars may be closed, areas may be inaccessible, and some stops are viewed from the street. Several outings have included only three or four locations, or just one actual bar, so you should book this for the stories and atmosphere, not for a guaranteed night of drinking.

Key points before you book

• The route covers about two hours: You start at The Benson at 5 p.m. and finish at Old Town Pizza.
• Drinks are not included: The $36 price covers fees and taxes, but you pay separately for every beer, cocktail, or soft drink.
• The route includes Portland’s old downtown: Expect stories around The Benson, Kelly’s Olympian, the Roseland Theater, Kells, the Shanghai Tunnel Bar, and Old Town.
• The Shanghai Tunnels are not guaranteed: They appear in the planned route, but access has been unavailable on some outings.
• The guide makes the difference: Kris, Victoria Rose, Houston, Jessica, and Lori have all been praised for good storytelling and an easygoing manner.
• The experience suits adults only: Nobody under 21 may join, and the group can include up to 20 people.

What the $36 price really buys you

At $36 per person, this tour sits in the reasonable range for a two-hour guided walk, but the value depends on what you want. You are paying for a guide, a planned route, local stories, and the convenience of moving through several downtown locations without doing the research yourself. All fees and taxes are included.

You are not paying for alcohol. That matters because the name suggests a drink-focused evening. Any beer, wine, cocktail, food, or tasting comes from your own wallet. If you stop at several bars, your final cost can rise quickly.

I would see the price as fair if your goal is an entertaining introduction to Portland’s darker stories. It is less convincing if you expect admission to special underground spaces, several included drinks, or a carefully managed crawl from bar to bar. The route has enough places listed to suggest a full evening, but two hours is short for eight stops, walking time, ordering drinks, and storytelling.

The best value comes when you get a guide who brings the material to life. Victoria Rose has been praised for her confidence and Portland character. Houston has been noted for explaining small details about the city, including why Portland’s blocks are unusually short. Kris received especially warm praise for answering questions and making the experience feel lively. Those guide-led details are what you cannot get from a quick internet search.

Starting at The Benson at 5 p.m.

The meeting point is The Benson Portland, Curio Collection by Hilton, at 309 SW Broadway. The tour begins at 5 p.m., which means the first part of the experience may still have daylight, depending on the season. That timing is practical for a two-hour walk, but it can weaken the spooky mood during the brighter months.

The Benson is both a grand downtown hotel and a useful first stop because it gives the guide a setting with a strong sense of age and place. You begin with a haunted story and the option to buy a drink. Drinks are not part of the ticket, so you can order something or simply listen.

This first stop is also where you can judge the evening’s pace. A 15-minute stop does not allow for a long drink service and a lengthy story, especially with a group. If you want a drink here, order promptly and keep your expectations modest.

Kelly’s Olympian and the old downtown mood

Kelly’s Olympian is planned as another drink-and-story stop. It is the kind of location that suits this format: a local watering hole with enough character for a guide to connect a building, its past, and its legends.

The scheduled stop lasts about 15 minutes. That is enough time for a quick drink and a short story, but not enough for a leisurely pub visit. In practice, the group may spend less time inside if the bar is busy or if the route needs to keep moving.

This part of the walk is one reason the tour can work well for a solo visitor. You have a group around you, a guide leading the way, and a clear route through central Portland. That does not remove the need for normal city awareness, especially since one account described downtown as feeling unsafe. Still, walking with a group is generally more comfortable than trying to find unfamiliar bars alone.

Roseland Theater and stories from the street

The Roseland Theater receives only about five minutes on the planned route. It is not a drinking stop. Instead, you pause to hear about the building’s haunted past and move on.

That short stop tells you something about the tour. This is not a sequence of long bar visits. Several locations function as story points, with the guide speaking outside or near the building rather than taking the group inside. If you enjoy architecture, local scandals, and quick pieces of urban history, that can be fun. If you need to enter every haunted site, it may feel thin.

A good guide can make a brief stop worthwhile. Jessica has been praised for combining general Portland history with the city’s scarier stories, while Lori has received strong praise for energetic, detailed storytelling. The guide’s presentation matters more here than the building access.

Kells Irish Restaurant and Pub

Kells Irish Restaurant & Pub is planned as another short stop for a drink and a haunted story. The route gives it about 15 minutes, and the haunted material is linked with the location’s darker past, including its basement.

This is one of the stops you should treat as conditional. Kells has been closed on at least one outing, and the basement has not always been accessible. Staff service has also not been consistent for every group. That is not necessarily the guide’s fault, but it affects the evening because the pub is part of what you are paying to experience.

If Kells is open and the relevant areas are available, it can be a memorable part of the crawl. If not, you may hear the story from outside or skip the stop entirely. I would not book this tour solely because you want to visit Kells.

Shanghai Tunnel Bar and the famous underground stories

The Shanghai Tunnel Bar & Venue is one of the most appealing names on the route. Portland’s Shanghai Tunnel stories have long been tied to tales of underground passages, coercion, crime, and hidden movement beneath the city. The bar gives those stories a natural setting.

The planned visit includes a drink and a short talk, again with drinks sold separately. The next stop is a brief look at the haunted secrets associated with the Shanghai Tunnels. On paper, this is the part most likely to attract people who want something distinctively Portland.

In practice, access has been a major uncertainty. Some outings have not visited the Shanghai Tunnels at all. Others have encountered closed or inaccessible locations. You should see this material as a possible subject of the tour, not a guaranteed underground visit.

That distinction is important. If your main reason for booking is to physically enter the tunnels, this may disappoint you. If you are happy to hear the stories and see the area from above ground, the stop can still add a strong sense of place.

9 NW 2nd Avenue and the city’s darker side

The stop at 9 NW 2nd Avenue is designed around the sordid history of the location. It includes another chance to buy a drink and hear a story, with about 15 minutes set aside.

This part of the route helps explain why the experience is more than a standard ghost walk. The guide connects haunted tales with the less polished side of Portland’s past. Expect stories about questionable characters and grim episodes rather than only friendly spirits and theatrical scares.

The stop may also be another example of the tour’s limits. A short talk outside a building can be interesting, but it is not the same as exploring an interior. You should be comfortable with a walking lecture format, with occasional pub visits, rather than expecting private access to every address.

Finishing at Old Town Pizza and Brewing

Old Town Pizza & Brewing at 226 NW Davis Street is the endpoint. The planned finish includes food, drinks, and more strange Portland history. Since you pay for food and drinks yourself, this is a good place to budget for an optional meal rather than treating it as part of the ticket.

Ending at a pizza restaurant is practical. You can sit down, order something substantial, and continue the evening without having to search for dinner. The stop is listed at about 15 minutes, but you may want to stay longer after the official tour ends.

Old Town also gives the tour a fitting final setting. The area connects to Portland’s older downtown stories and to the city’s reputation for unusual, sometimes grim local lore. Just keep in mind that the formal experience lasts about two hours. A longer meal is your own add-on.

The guide matters more than the ghost claims

I would not choose this tour based only on its list of buildings. The biggest variable is the person holding the lantern, figuratively speaking. A strong guide can turn a closed bar or a brief street stop into an amusing lesson. A weak storyteller can make even the Shanghai Tunnel subject feel flat.

Kris has been praised for humor, answering questions, and making the evening feel like a shared adventure. Victoria Rose has been singled out for her confidence, personality, and ability to lead a group through downtown. Houston has been praised for doing careful research and explaining small pieces of Portland’s past.

Jessica has received praise for being both entertaining and informed, while Lori has been described as energetic, creative, and detailed. You cannot request a particular guide, so the experience may vary. That is worth remembering when you compare this tour with a fixed museum visit or a scripted attraction.

The tour is not presented as a serious paranormal investigation. It is a social history walk with ghost stories, local legends, and pub stops. Bring a sense of humor. The goal is to be entertained and learn something, not to receive proof of the supernatural.

Timing, walking, and group size

The tour lasts about two hours and begins at 5 p.m. A maximum of 20 people keeps the group manageable, though 20 is still large enough to slow down ordering drinks or hearing a guide near a busy street.

You should have moderate physical fitness. The route covers multiple downtown blocks, and one outing covered roughly 20 blocks. Wear shoes that can handle steady city walking and expect to spend much of the evening standing.

Public transportation is nearby at both the general downtown area and the Old Town endpoint. The activity finishes at Old Town Pizza rather than returning to The Benson, so plan your route home before you start.

The pace can be gentle. One group found the slower rhythm helpful for older members, and the guide was able to adjust the pace. Still, do not confuse slow walking with a relaxed pub evening. The schedule has several planned stops, and delays can force the guide to shorten or skip parts of the route.

Who should book this Portland ghost walk?

I would recommend it to an adult who wants a light, social introduction to Portland’s unsettling stories. It works especially well for a first evening in town, a couple looking for something different, or a solo visitor who prefers exploring downtown with a group.

It can also suit people who enjoy local history but do not want a formal museum tour. The route gives you several city landmarks, short stories, and the chance to stop for a drink. Families with adults over 21 may enjoy the relaxed pace and humor.

I would hesitate if you want guaranteed access to the Shanghai Tunnels, a long pub crawl, included drinks, or a fully nocturnal atmosphere. The early 5 p.m. start may mean daylight for much of the route, and several locations can be closed or inaccessible.

The free-cancellation rule is useful: cancel at least 24 hours before the start for a full refund. Changes or cancellations inside that window are not refunded. Confirmation is sent within 48 hours of booking, subject to availability. Service animals are allowed.

Should you book Portland Ghosts Boos and Booze?

Book it if you value a personable guide, odd Portland history, and a casual walk with possible bar stops. At $36, it is a reasonable introduction when the guide is strong and the route runs close to plan.

Do not book it expecting a guaranteed eight-stop pub crawl or a tour beneath the city. The safest way to judge the experience is to treat the bars and Shanghai Tunnel material as bonuses, while the main product is a two-hour guided walk through old downtown.

If that sounds good, you will likely enjoy the evening. If you need a fixed route and reliable access to every location, choose a tour with fewer promises and more controlled entry.

FAQ

How much does Portland Ghosts Boos and Booze cost?

The listed price is $36 per person. All fees and taxes are included, but alcoholic beverages and food are not.

How long does the tour last?

The experience lasts approximately two hours.

What time does the tour begin?

The tour starts at 5 p.m.

Where does the tour start?

The meeting point is The Benson Portland, Curio Collection by Hilton, at 309 SW Broadway, Portland, Oregon 97205.

Where does the tour finish?

The tour ends at Old Town Pizza & Brewing, 226 NW Davis Street, Portland, Oregon 97209.

Are drinks included in the ticket?

No. You pay separately for alcoholic beverages and any food you order.

Can anyone under 21 join?

No. The activity is not for anyone under 21.

Is the Shanghai Tunnel visit guaranteed?

No. The route includes Shanghai Tunnel stories and a planned stop, but access and the actual stop can change.

How many people can join the group?

The maximum group size is 20 people.

Can I cancel for a full refund?

Yes, if you cancel at least 24 hours before the experience start time. Cancellations within 24 hours are not refunded.