Portland Ghosts Boos and Booze Haunted Pub Crawl

Portland’s ghosts prefer a barstool. This two-hour evening walk mixes local legends, old drinking spots, and Portland’s darker past, beginning at The Benson and ending at Old Town Pizza & Brewing. I like the small-group format, capped at 20 people, and the chance to hear stories from guides such as Victoria, Lori, Houston, Kris, and Jessica. I also like that the route brings you through Old Chinatown and the Shanghai Tunnel area instead of keeping you in one attraction.

The main caution is that the advertised route can be more ambitious than the actual evening. Stops may be closed, boarded up, inaccessible, or changed, and some outings have included only one or three drinking stops rather than a full pub crawl. At $36, it can be good value for a lively history walk, but you should not book it expecting every listed location or a drink at each stop.

Quick take: what matters most

• The stories are the main event: Guides are praised for humor, energy, local history, and spooky storytelling.
• The pub crawl is flexible: Alcohol costs extra, and the number of open venues can vary sharply.
• The Shanghai Tunnels are not guaranteed: The route includes the area, but access to the underground site may not be possible.
• You walk through central Portland: One outing covered roughly 20 blocks, so comfortable shoes matter.
• The 5 p.m. start changes the mood: Depending on the season, part of the tour may take place in daylight.
• It suits adults who enjoy history with a spooky edge: Everyone must be at least 21, and the pace is generally moderate.

What you are really buying for $36

At $36 per person, you are paying for a guide-led walk, stories, and an evening of Portland context. You are not paying for drinks, food, entry to a tunnel attraction, or a packaged tasting. Every beer, cocktail, or snack comes from your own wallet.

That price is fair if you treat the outing as a haunted history tour that uses pubs as story settings. It is less attractive if your main goal is a classic pub crawl with several guaranteed drinks. The experience has received a 4.2 rating from 44 reviews, with especially strong praise for the guides. The weaker scores center on route changes, missed stops, closed bars, and expectations that the full itinerary would be completed.

I would budget more than the $36 base price if you plan to order drinks at several stops. Since alcohol is not included, check the menu and pace yourself. A two-hour walk with multiple drinks can become less enjoyable than a single well-chosen beverage and a snack at the end.

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., with a drink and a haunted story planned for this grand downtown hotel and local watering hole. The drink is optional and not included.

The Benson gives the tour a polished opening. You begin with a well-known Portland address before moving toward older and more rough-edged parts of downtown. If you arrive early, use the time to find the guide and settle in. Confirmation is sent within 48 hours of booking, subject to availability, so do not leave the meeting details to the last minute.

The early start is worth noting. In summer, the first part of the walk may still feel like a normal city stroll rather than a night of fright. In winter, the mood will be darker, but you will want a warm layer and shoes that can handle a longer urban walk.

Kelly’s Olympian and the first real pub stop

Kelly’s Olympian is the next planned stop. Here, the guide shares more ghost stories while you have the chance to buy a drink. The venue adds a proper bar setting after the hotel opening and helps establish the pub side of the experience.

This is also where expectations can begin to differ. Some outings have included two drinking stops, while others have reached only one open bar. Venue schedules, access, and the timing of the group affect the route. I would enjoy Kelly’s if it is open, but I would not count on it as one of several guaranteed rounds.

The strongest part of this section is usually the guide. Victoria has been praised for her confidence and Portland personality, while Kris received warm marks for answering questions and making the group laugh. Houston has also been praised for explaining local details, including why Portland’s blocks are unusually small. Those touches make the walk more than a string of ghost claims.

Roseland Theater and Portland’s public side

The route then passes Roseland Theater for a short stop of about five minutes. The focus here is the building’s haunted past rather than a drink or a long interior visit.

Short exterior stops are part of the tour’s character. You get a quick story, a look at the site, and then keep moving. That works well for a group that wants variety, but it can disappoint if you expect to enter every haunted building. Much of the experience may take place outside, with the guide pointing out locations and explaining their past.

Bring realistic expectations about access. A haunted walking tour often depends on businesses being open and willing to receive a group. The route is not a museum visit with doors guaranteed at every stop. If a particular building matters most to you, ask before booking if it is currently included.

Kells Irish Restaurant and Pub

Kells Irish Restaurant & Pub is planned as another stop for a story and a drink. The venue is meant to add the familiar pub atmosphere that gives the tour its name. You can order your own drink, but it is not part of the tour price.

Kells is also a clear example of why you should treat the route as changeable. The pub has been closed during some outings, and the basement area tied to its haunted appeal has not always been available. Staff service can also affect the evening, even though that is outside the guide’s control.

If Kells is open, this can be one of the more satisfying pauses because the story and setting match. If it is closed, the tour may move on or replace it with an outdoor explanation. That is not necessarily a bad tour, but it changes the value of a booking sold as a pub crawl.

The Shanghai Tunnel area and the biggest question mark

The Shanghai Tunnel Bar & Venue is listed as another story and drink stop, followed by a short visit to the famous Shanghai Tunnels area. This is likely the most anticipated section for many people. Portland’s underground tunnel stories are central to the city’s darker folklore, and the idea of hearing them near the actual site gives the walk its strongest sense of place.

Here is the practical warning: seeing the Shanghai Tunnel area is not the same as taking a full underground tour. Access has not been guaranteed, and some outings have not entered the tunnels at all. In other cases, the guide has discussed the haunted secrets of the tunnels from above ground.

I would book this experience for the stories around the Shanghai Tunnels, not for guaranteed underground access. If going below street level is your top priority, confirm the current arrangement before paying. Otherwise, you may feel shortchanged, especially because the tunnel stop is one of the main reasons many people choose this tour.

9 NW 2nd Avenue and the darker side of Old Chinatown

The planned route continues to 9 NW 2nd Ave for a drink and the location’s darker, more sordid history. This part of the walk places the ghost stories within the old Chinatown district, where the guide can connect individual buildings with broader Portland stories.

The value here is context. You are not only hearing about spirits. You are also getting a quick look at how old downtown spaces changed, how nightlife shaped the area, and why certain addresses became part of Portland’s folklore. The guide’s ability matters a great deal. A confident storyteller can make a short sidewalk stop memorable, while a less engaging presentation can leave the same building feeling ordinary.

The group format helps in this area. You are not wandering alone while trying to locate dark historical sites. The tour keeps you with a guide and other adults, although you should still use normal city awareness and stay with the group.

Finishing at Old Town Pizza & Brewing

The final stop is Old Town Pizza & Brewing at 226 NW Davis St. The tour ends with the option to buy food and drinks while hearing odd and haunted stories connected with Portland and Old Town Pizza.

This is a sensible finish. After roughly two hours on foot, you may want a table, food, and a chance to discuss the stories. It also gives the evening a more relaxed ending than simply stopping on a sidewalk. Food is not included, so plan to pay separately.

The ending point is different from the start. That makes it easy to continue your night in Old Town, but it also means you should know where you are going afterward. If you are staying elsewhere, use the nearby public transportation options or arrange your next ride before the final story.

The guides make or break the evening

The most praised part of this experience is the guide. Several guides have received strong personal praise, including Victoria, Victoria Rose, Lori, Houston, Kris, and Jessica. Their strengths vary, but the pattern is clear: the best outings depend on a guide who can tell a story, answer questions, manage the pace, and keep the group interested while walking between stops.

Victoria Rose has been praised for leading confidently through the city and for making the history engaging. Lori has been described as energetic, creative, and detailed in her storytelling. Houston has been credited with explaining small but memorable Portland facts, including the city’s compact blocks. Kris has been praised for being welcoming, funny, and willing to answer questions.

The guide also controls the rhythm. One family group appreciated a slower pace that worked well for older members. That is useful to know if you do not want a rushed march between bars. At the same time, a two-hour tour cannot give every location much time. You may hear a short story, walk several blocks, and then move on before the mood has fully settled.

Walking, safety, and group size

The tour lasts about two hours and requires moderate physical fitness. One outing covered around 20 blocks, so comfortable walking shoes are more important than a costume or special equipment. You may be standing outside at several stops, so dress for Portland weather.

The group can include up to 20 people. That is small enough to feel more personal than a huge sightseeing group, but large enough that the guide must keep everyone together. Stay near the front if you want to hear every detail.

The group setting also offers a practical benefit for an evening walk. You are moving with other people rather than visiting unfamiliar downtown locations alone. Still, some people have felt uneasy about parts of central Portland, and the city atmosphere may not match everyone’s comfort level. Keep your phone and belongings secure, follow the guide, and make your own judgment about the setting.

Service animals are allowed, and the tour operates near public transportation. The experience is restricted to people aged 21 and older.

What can go wrong, and how to plan around it

The biggest problem is the gap between a planned route and a live city evening. Bars close. Basements become unavailable. Buildings are boarded up. A guide may need to shorten the walk or replace a stop. That is normal for a route built around active businesses, but the changes can feel serious when the advertised stops are the reason you booked.

You can reduce the risk of disappointment by treating the exact route as flexible. Think of the tour as a guided haunted walk through central Portland with possible pub stops, not as a guaranteed eight-venue crawl. If Kells or the Shanghai Tunnels are essential, contact the operator before the tour and ask what is currently open.

The daylight issue is another planning point. The start time is fixed at 5 p.m., and depending on the season, some or much of the walk may happen before full darkness. That may reduce the spooky atmosphere, though it helps you see the streets and buildings more clearly.

Finally, do not assume every listed stop means entry. Several locations may be viewed from outside while the guide tells the story. That is fine for people who enjoy urban history, but less satisfying if you want interior access.

Who should book this haunted pub crawl?

I would recommend it to you if you enjoy local stories, walking tours, and a little theatrical fright without needing a full paranormal production. It works especially well for adults visiting Portland for a short stay, solo visitors who prefer a group, and couples who want an unusual evening before dinner.

It is also a good choice if you care more about the guide’s storytelling than the number of drinks. The strongest outings seem to come from guides who add local facts, answer questions, and adjust to the group. You may learn as much about Portland’s streets and past as you do about ghosts.

I would hesitate if you want a strict pub crawl, guaranteed tunnel access, or a tour that visits every advertised stop. For that kind of certainty, ask detailed questions before booking or choose a separate bar tour and a dedicated tunnel experience.

Free cancellation is available if you cancel at least 24 hours before the 5 p.m. start. Cancellations within 24 hours are not refundable, and late changes are not accepted.

FAQ

How much does the Portland Ghosts Boos and Booze tour cost?

The tour costs $36 per person. All fees and taxes are included, but alcoholic drinks and food are not.

How long does the tour last?

The tour lasts approximately two hours.

Where does the tour begin?

It begins at The Benson Portland, Curio Collection by Hilton, at 309 SW Broadway, Portland, Oregon 97205.

Where does the tour end?

It ends at Old Town Pizza & Brewing, 226 NW Davis St, Portland, Oregon 97209.

What time does the tour start?

The scheduled start time is 5 p.m.

Are drinks included?

No. Alcoholic beverages are not included, so you pay for drinks separately at the pubs.

Can people under 21 join?

No. The tour is not available to anyone under 21.

Is the Shanghai Tunnel visit guaranteed?

The route includes the Shanghai Tunnel area and a planned haunted tunnel stop, but underground access may not be available. The exact route can change if locations are closed or inaccessible.

What is the cancellation policy?

You can receive a full refund by canceling at least 24 hours before the start time. Cancellations or changes made within 24 hours are not accepted for a refund.

Should you book it?

Book this tour if you want Portland history with ghost stories, a social walk, and the chance to stop for a drink along the way. The guide is the key attraction, and a strong one can turn a closed bar or shortened route into a worthwhile evening.

Skip it if the words pub crawl mean several guaranteed bars or if you are booking mainly for the Shanghai Tunnels. At $36, the experience is reasonably priced as a haunted history walk, but the value drops when too many venues are closed or the route ends after only a few stops. Go in for the stories, stay flexible about the bars, and confirm the current route if a specific location matters to you.