Portland Ghosts Boos and Booze Haunted Pub Crawl

Portland’s Boos and Booze crawl ties spooky tales to a walk through the Old Town and Chinatown area, with stops linked to the Benson, Shanghai Tunnels, Kelly’s Olympian, Kells, and Old Town Pizza. The best part is the way a guide can turn ordinary blocks into a string of eerie stories.

I like the small maximum of 20 people, which makes it easier to hear the guide and ask questions. I also like the mix of local history and drinks, especially when guides such as Victoria Rose, Houston, Jessica, and Lori bring their own energy and storytelling style.

The main catch is important: the advertised route does not always match what happens on the night. Bars may be closed, basements may be off-limits, and some groups have visited only three or four stops, or just one bar, during the two-hour tour.

Key points to know before booking

• The route begins at 5 p.m. outside The Benson Portland and ends at Old Town Pizza & Brewing.
• Drinks and food cost extra, so the $36 ticket is not the full evening budget.
• The Shanghai Tunnels are not guaranteed, despite being a major part of the advertised theme.
• Guides make a big difference, with Victoria Rose, Houston, Jessica, and Lori earning especially warm praise for their storytelling and humor.
• The walk covers roughly 20 blocks, according to one detailed account, so comfortable shoes and moderate fitness help.
• This is for adults age 21 and older, and the group can include up to 20 people.

What the two-hour Portland ghost crawl is really like

The experience starts at 5 p.m. at The Benson Portland, a grand downtown hotel and a fitting place to begin a ghost tour. You are meant to hear a haunted story here while having a drink, though the drink is not included and the actual amount of time inside can depend on the evening’s plan.

From there, the group moves through downtown Portland toward the Old Town and Chinatown area. The tour is part walking tour, part pub visit, and part local-history talk. I would approach it as a guided story walk with drinks available along the way, not as a guaranteed bar-hopping night with a new drink at every stop.

The two-hour time limit shapes the whole experience. There are many planned locations, but a quarter of an hour at each stop leaves little room for long meals, relaxed drinks, or extended time inside each bar. If the group stops for service, waits for a venue to open, or takes a longer route, some locations may be shortened or skipped.

The tour is also scheduled at 5 p.m., which means part of the walk may take place in daylight, especially outside the darker months. That can reduce the spooky mood, though it also makes it easier to see the streets and buildings as your guide explains Portland’s past.

The Benson starts the evening with atmosphere

The Benson Portland is the opening stop and one of the more natural places to begin. You get a drink opportunity, a haunted story, and a recognizable downtown meeting point at 309 SW Broadway.

The strength of this stop is atmosphere. A historic-feeling hotel gives a ghost story more room to breathe than a plain street corner. The weakness is time. Fifteen minutes is enough for a quick tale and perhaps a drink order, but not a leisurely start to the evening.

Bring a little patience if you want to buy something here. Alcohol is not included in the ticket, and the tour continues on a schedule. I would not arrive expecting a full cocktail hour before the walk gets moving.

Kelly’s Olympian adds a classic watering-hole stop

Kelly’s Olympian is planned as another place for a drink and ghost story. This is the sort of stop that best fits the tour’s promise: a working bar, a local tale, and a chance to sit down briefly while the guide connects the place to Portland’s darker side.

Still, the stop is not guaranteed in practice. Some bars have been closed or inaccessible when groups arrived, and one evening’s route may not include the places you most want to see. If Kelly’s matters to you, confirm its availability close to the tour date rather than treating the published route as fixed.

The tour can work well for a solo visitor here. You are walking with a group, not trying to find unfamiliar downtown bars alone, and the guide provides structure. That does not remove every concern about the area, but it gives the evening a clear route and a shared purpose.

Roseland Theater brings a quick dose of haunted history

The Roseland Theater is listed as a five-minute stop, so this is more of a storytelling point than a full venue visit. You should expect to hear about its haunted past from outside or nearby, rather than spend time exploring the theater.

That short pause helps the guide cover more ground, but it also shows the limits of the experience. Several locations are story settings, not places where you spend much time inside. If you want a tour with building access, room-by-room exploration, or underground visits, this may feel too brief.

I like this format when the guide is lively and well prepared. A strong storyteller can make five minutes work. A flat delivery can make the same stop feel like a quick address on a street corner.

Kells Irish Restaurant and Pub may be the biggest variable

Kells is planned as a drink-and-story stop, with a haunted angle tied to the building and its basement. In practice, the venue has sometimes been closed, and the basement has not always been open to the group.

That matters because Kells is one of the places most likely to shape your expectations. If the basement is unavailable, you may hear about the haunted side without seeing the part that makes the story feel tangible. Staff service can also affect the mood, and one account described an unpleasant experience at the bar. That is separate from the guide’s work, but it is still part of the evening you are buying.

The best approach is to treat Kells as a possible stop, not a promise. If it is open and accessible, it could be a strong pub moment. If not, the guide may need to tell the story from outside or move on.

Shanghai Tunnel Bar and the tunnel question

The Shanghai Tunnel Bar & Venue is another planned place for a drink and ghost story. It connects naturally with Portland’s famous Shanghai Tunnels, a subject that draws many people to this tour in the first place.

Here is the key practical warning: several groups have not visited the tunnels, and some have not reached the Shanghai Tunnel Bar. The tour includes a short stop described as a Haunted Underground Shanghai Tunnels Tour, but access is not assured. Venue closures, outdated route details, and changing operations have all affected the experience.

If seeing the tunnels is your main reason for booking, I would not rely on this two-hour crawl alone. Ask the operator before paying whether tunnel access is scheduled for your date. If the answer is unclear, book this for the ghost stories and neighborhood walk, not for a guaranteed underground visit.

9 NW 2nd Avenue brings the darker local stories

The stop at 9 NW 2nd Avenue is presented as a place for a drink and the area’s sordid past. It appears to be another story-focused pause, with the guide using the address and surrounding streets as the setting.

This kind of stop can be one of the most interesting parts of the tour because it links Portland’s modern streets to difficult chapters in the city’s past. It also carries the same limitation as several other stops: you may hear the story from outside rather than enter a haunted room.

The guide’s skill matters more here than the building itself. Houston was praised for explaining local details and for covering around 20 blocks while explaining why Portland’s blocks are unusually small. That sort of context gives the walk more value than a string of disconnected ghost claims.

Old Town Pizza closes the night with food and a drink

The final stop is Old Town Pizza & Brewing at 226 NW Davis Street. This is where the tour is meant to finish with food, drinks, and strange stories about Portland and Old Town.

I like the practical ending. A pizza restaurant gives you an easy place to sit, eat, and keep talking after the walk. Food is not included, so plan to pay separately, but ending at a casual restaurant is more useful than finishing on a random sidewalk.

The stop is also a good reason to keep the rest of your evening flexible. You may want to order food here, but the exact timing can vary if earlier stops change. The stated stop length is about 15 minutes, which is enough to get oriented but may not be enough for a full meal during the official tour.

The guides are the heart of the experience

The strongest praise goes to the guides. Victoria Rose is repeatedly described as engaging, confident, and well suited to leading a group through Portland. Her personality and holiday-themed costume added character for one autumn group, while another group appreciated her answers and unusual local facts.

Houston was praised for clear research and for connecting ghost stories with Portland’s street layout and history. Jessica was described as both fun and informed, with a talent for keeping the mood light while discussing the city’s unsettling past. Lori received especially warm praise for her energy, detail, and ability to make the stories feel personal.

That range tells you something useful: the quality can vary by guide, but a good guide can rescue a route with fewer stops. I would pay attention to the guide’s storytelling more than the number of bars. The best version of this experience is a social walking tour led by someone who knows how to hold a group’s attention.

Is $36 a fair price?

At $36 per person, the price is reasonable if you receive a well-led two-hour walking tour with several active stops and a few drinks along the way. The guide, organization, local stories, and group setting provide the main value.

The calculation changes if you are expecting a true pub crawl. Since alcohol is extra, two or three drinks can push the evening cost well above the ticket price. Some groups have stopped at only one bar, while others have had two drink opportunities. You are paying for the guided experience, not a package of beverages.

For me, the price works best when you want an introduction to Old Town’s darker stories and prefer company while walking downtown. It is weaker value if your priorities are tunnel access, a full drink at every listed location, or a long evening with time to settle into each pub.

Who will enjoy this Portland experience?

This tour suits adults who like ghost stories, local history, casual drinks, and a little theatrical suspense. It can be a good fit for couples, solo visitors, and small groups who want a planned evening rather than a self-guided search for Portland’s haunted places.

You should have moderate physical fitness, since the route is on foot and may cover about 20 blocks. Wear comfortable shoes, and keep your schedule open enough to handle route changes. Service animals are allowed, and the tour is near public transportation.

I would be cautious about booking it for children or anyone under 21, since the experience is restricted to adults. I would also think twice if you dislike uncertainty. Bars may close, access may change, and the advertised number of locations may not be the number you reach.

My call: book it for stories, not guarantees

I would book Portland Ghosts Boos and Booze if I wanted a social evening of Portland ghost tales, a walk through Old Town, and the chance to buy a drink or meal along the way. A strong guide such as Victoria Rose, Houston, Jessica, or Lori can make the night memorable even when the route changes.

I would not book it solely to see the Shanghai Tunnels or to visit every named pub. Those parts have not been dependable, and the two-hour format leaves little margin when venues are closed.

The ticket includes fees and taxes, and you can cancel for a full refund up to 24 hours before the 5 p.m. start. That gives you some flexibility, but I would still check the current route before booking. Go in expecting a guided ghost walk with pub stops, and you have a fair shot at a fun Portland evening. Expect a guaranteed bar crawl and underground tour, and you may be disappointed.

FAQ

Where does the Portland Boos and Booze tour begin?

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

What time does the tour start?

The tour starts at 5 p.m.

Where does the tour end?

It ends at Old Town Pizza & Brewing at 226 NW Davis Street.

How long does the experience last?

The tour lasts approximately two hours.

Are drinks included in the $36 ticket?

No. Alcoholic beverages are not included. The ticket includes all fees and taxes, but you pay separately for drinks and food.

Is the tour suitable for anyone under 21?

No. The experience is not for anyone under 21.

Are the Shanghai Tunnels guaranteed?

No. The advertised route includes the Shanghai Tunnel area, but access and the exact stops can change. Several scheduled groups have not reached the tunnels.

How many people can join the tour?

The maximum group size is 20 people.

Can I cancel for a full refund?

Yes. You can cancel at least 24 hours before the local start time for a full refund. Cancellations or changes made within 24 hours are not refunded.