Portland Ghosts Boos and Booze Haunted Pub Crawl

Portland’s haunted pub crawl links old hotels, bars, theaters, and the city’s notorious Shanghai Tunnels area in one short evening walk. You begin at The Benson Portland and finish at Old Town Pizza & Brewing, hearing spooky stories along the way while buying your own drinks.

I like the mix of local history and ghost lore, especially when guides such as Victoria Rose, Houston, Lori, Jessica, and Kris add personal energy to the stories. I also like the small group limit of 20, which makes it easier to hear the guide and less awkward to move through downtown together.

The main catch is important: the advertised route includes several stops, but the actual experience can change sharply when bars are closed, basements are inaccessible, or the guide has another group to lead. Some outings have reached only one bar or three to four stops, so confirm the current route before paying if the Shanghai Tunnels or a true pub crawl is your main reason for booking.

Key points to know before you book

• Start at 5 p.m. at The Benson: The tour begins inside Portland’s downtown core and ends in Old Town.
• Drinks are not included: The $36 price covers the tour and fees, but you pay separately for every beer, cocktail, or food order.
• The route covers about 20 blocks: Expect a walking tour with several outdoor storytelling stops, not a night spent sitting in bars.
• The Shanghai Tunnels are not guaranteed: The area is part of the planned story line, but access and actual visits have not been consistent.
• Guide quality matters: Kris, Victoria Rose, Houston, Lori, and Jessica have all received warm praise for humor, energy, and storytelling.
• You must be 21 or older: The group can include up to 20 people, and a moderate level of fitness is expected.

What this Portland ghost walk is really like

This is best understood as a walking history tour with pub stops, not a traditional bar-to-bar crawl. The two-hour format packs a lot into a short window, moving through downtown, Old Chinatown, and Old Town while the guide connects buildings and streets to Portland’s darker tales.

The stories cover haunted hotels, old drinking spots, the city’s sordid past, and the legends surrounding the Shanghai Tunnels. Some stops take place outside, where you hear the story and look at the building rather than entering it. That matters if you are picturing a candlelit tour through several interiors.

The experience starts at 5 p.m., which can mean at least part of the walk takes place in daylight, depending on the season. That is useful for finding your way and seeing the buildings clearly, but it can soften the spooky mood. If you want maximum darkness, late autumn and winter offer a better setting, though the tour still begins at the same stated time.

Your guide can make or break the evening. Kris has been praised for answering questions and making the history fun. Victoria Rose has a confident Portland manner and has led groups through the downtown area after dark. Houston has been singled out for explaining local details, including why Portland’s blocks are so small. Lori is described as energetic and imaginative, while Jessica has been praised for making the ghost stories accessible and entertaining.

That range tells you something useful. The basic route may be fixed, but the tone depends heavily on the person holding the flashlight, figuratively speaking. A strong guide can turn a closed bar or outdoor stop into a good story. A weak storyteller leaves you with a walk past locked doors.

The Benson sets the tone at 5 p.m.

The Benson Portland, Curio Collection by Hilton is the meeting point at 309 SW Broadway. The first stop allows about 15 minutes for a drink and a haunted story, though your drink is not included.

A grand hotel is a fitting place to begin. It gives the evening a clear starting point, and you can get settled before the group heads into the streets. Since the tour is mobile-ticketed and offered in English, you should have your ticket ready on your phone and arrive early enough to locate the group without a last-minute rush.

The Benson stop also shows how the tour handles alcohol. You are encouraged to order a drink, but the $36 fee does not cover it. The same rule applies at later bars. If you want to visit every drinking stop, budget beyond the advertised price.

Kelly’s Olympian brings the first real pub stop

Kelly’s Olympian is planned as another 15-minute stop for a drink and ghost story. It is one of the places where the pub part of the evening should feel most direct: you enter, order something, and listen while the guide ties the location to Portland’s past.

The short timing keeps the tour moving, but it also limits what you can do. You are not getting a relaxed meal or a long conversation over a pint. Think of each bar as a brief pause in a walking route.

This is also one of the stops affected by real-world conditions. Bars may be closed, access may change, or the guide may need to shorten the route. If Kelly’s Olympian is open, it can add atmosphere. If not, the value shifts back toward the guide’s storytelling rather than the drink itself.

Roseland Theater adds a quick haunted-history pause

The Roseland Theater receives only about five minutes in the planned route. That makes it less of a full stop and more of a brief look at a location with a haunted past.

Five minutes is enough for a compact story and a quick exterior view. It is not enough for an extended visit, tour of the building, or time to absorb many details. This is a useful example of the experience’s rhythm: several named places, but only short windows at each one.

If you prefer tours with fewer locations and longer explanations, this pace may feel hurried. If you like covering ground and hearing a new story every few blocks, it keeps the evening lively.

Kells Irish Restaurant & Pub is a key question mark

Kells Irish Restaurant & Pub is planned as a 15-minute drink and story stop. The haunted angle centers on the building’s darker associations, with the basement often treated as the important part of the story.

Do not assume you will enter every part of Kells. The basement has been closed at times, and the pub itself has also been closed during some outings. That can turn an anticipated indoor stop into an exterior explanation, or remove it from the route altogether.

I would treat Kells as a possible bonus, not a guarantee. If you are especially interested in the pub, check its current status with the operator before booking. You should also be prepared for regular bar service rather than a private tasting or arranged drink sample.

The Shanghai Tunnels stories carry the most weight

The Shanghai Tunnel Bar & Venue is scheduled for about 15 minutes, followed by a short stop connected with the Haunted Underground Shanghai Tunnels Tour. This is the part most likely to attract people who want Portland’s darker urban history rather than general ghost stories.

The Shanghai Tunnels have a strong reputation in Portland folklore, and the tour uses them as a major theme. The planned experience includes a story and a drink at the bar, then a look at the underground tunnel history.

Here is the practical warning: the actual tunnel visit has not been reliable. Some groups have not reached the Shanghai Tunnels at all, while others have found that the relevant area was closed or inaccessible. You may hear the stories without going underground.

That distinction is central to the value of the tour. If you simply want to learn about the tunnels, the stop can still work. If you are buying this specifically to enter the tunnels, the risk of disappointment is high. Ask exactly what is operating on your date and what the group will enter, if anything.

9 NW 2nd Avenue shifts from ghosts to grim history

The stop at 9 NW 2nd Avenue is planned for roughly 15 minutes. Here the focus turns toward the location’s dark and sordid past, with time for a drink if the stop is open and functioning as planned.

This part of the walk shows that the tour is not only about spirits. Portland’s rougher history, old nightlife, and unsettling human stories are part of the package. For me, that broader approach is more interesting than a string of generic haunted-house tales.

Again, the drink is on you. The guide may tell the story outside or in a nearby venue, depending on access. The quality of this stop will depend on how well the guide explains the setting and gives the story a clear link to the street around you.

Old Town Pizza & Brewing is the practical finish

The tour ends at Old Town Pizza & Brewing, at 226 NW Davis Street. The final stop is planned for about 15 minutes and is meant to combine food, drinks, and strange Portland history.

Ending at a restaurant is useful. You can stay for a meal instead of hunting for dinner after the walk, and the group has a clear finish point in Old Town. Food is not included in the $36 price, so think of this as a convenient option rather than part of the ticket.

The final stop also gives you a chance to continue the evening on your own. If the route has been shortened, this may be where you get the most value from staying longer, ordering food, and talking about the stories. If you are catching another booking or transit connection, allow extra time because the published duration is approximate.

Is $36 a fair price?

At $36 per person, the tour is reasonably priced if you receive a full two-hour guided walk with several active stops and a strong storyteller. It is less attractive if you reach only one bar and spend most of the time outside without the locations promised by the route.

The price includes all fees and taxes, which keeps the basic cost clear. It does not include alcohol, food, or any special drink tasting. A couple who each order two or three drinks can quickly spend much more than the admission price.

I would compare the tour with what you want from the evening. For a guided introduction to Portland’s haunted history, $36 can be fair. For a dedicated pub crawl, the value depends on the number of open venues and how long you actually spend inside them.

The strongest value comes from the guide. When Kris, Victoria Rose, Houston, Lori, or Jessica is leading with humor and detail, you are paying for interpretation, not just a route between bars. The weakest value appears when the route is cut short and the advertising still suggests a longer experience.

Walking, safety, and group size

The walk covers roughly 20 blocks and calls for moderate physical fitness. You should be comfortable standing, walking on city streets, and keeping up with a group for about two hours. Wear shoes that can handle a full urban walk rather than dressing only for the pub stops.

The maximum group size is 20. That is small enough for a guide to answer questions, though a full group can still feel crowded at a bar or on a sidewalk. A group setting also means you are not navigating the evening alone, which may feel more comfortable for someone unfamiliar with downtown.

The tour is near public transportation, and the start and end points are different. Plan your return trip from Old Town, not from The Benson. Service animals are allowed, and the activity is restricted to people 21 and older.

Downtown Portland’s condition and atmosphere can vary by block and time of day. Some outings have felt less comfortable because of the setting, especially when the walk continues after dark. Stay aware of your surroundings, remain with the group, and do not count on the tour as a substitute for ordinary city awareness.

Who will enjoy this tour most?

I would choose this for someone who likes local legends, short walks, bars with a backstory, and a guide who can make history entertaining. It also suits a couple or small group wanting a structured evening without paying for a long formal dinner tour.

It is a good match if you are visiting Portland briefly. In two hours, you can see part of downtown and Old Town, hear several stories, and finish near a place where you can eat. The tour can also work for a family group of adults, especially if you want a slower pace and the guide is willing to adjust for older members.

I would be cautious if your priorities are a guaranteed underground visit, a late-night ghost atmosphere, or a classic crawl with a drink at every bar. The start time may leave part of the tour in daylight, and the number of active pub stops can be much lower than expected.

The experience is also not ideal for anyone under 21, anyone who dislikes walking, or anyone who wants every stop to be indoors. Several locations may be viewed from outside, and closures can change the shape of the night.

How to make the most of your booking

Book with the route uncertainty in mind. Before you commit, ask whether the Shanghai Tunnels are open, whether Kells is operating, and how many pub stops are expected on your date. This is especially important because the route has not always matched the planned sequence.

Arrive at The Benson a little early. Have your mobile ticket ready, use the restroom, and decide how much you want to spend on drinks. If you want dinner at Old Town Pizza & Brewing, leave room in your budget and schedule for food after the formal tour ends.

I would also keep expectations focused on stories, not paranormal proof. The fun comes from Portland’s odd corners, old buildings, unpleasant tales, and the guide’s delivery. Strange photos and eerie feelings may happen, but they are not a promised part of the activity.

Free cancellation is available if you cancel at least 24 hours before the start time. Inside that window, the amount paid is not refunded and changes are not accepted.

Should you book Portland Ghosts Boos and Booze?

Book it if you want a short, social introduction to Portland’s haunted and disreputable past, and you are happy to buy your own drinks while walking between locations. The best guides bring warmth, humor, and useful local detail, and the Old Town finish makes the evening easy to extend with dinner.

Do not book it solely for a guaranteed Shanghai Tunnels visit or a full bar crawl. The route can be shortened, venues can be closed, and some stops may happen outside. For the best chance of satisfaction, confirm the current plan first and treat the tour as a ghost-story walk with possible pub stops. At $36, that is a fair deal when the guide and route are working well, but a poor one if your must-see locations are unavailable.

FAQ

How much does the Portland Ghosts Boos and Booze Haunted Pub Crawl cost?

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

How long does the haunted pub crawl last?

The experience lasts approximately two hours. The planned stops are short, generally between five and 15 minutes each.

Where does the tour begin and end?

The tour starts at The Benson Portland, Curio Collection by Hilton, at 309 SW Broadway. It ends at Old Town Pizza & Brewing, at 226 NW Davis Street.

What time does the tour start?

The stated start time is 5 p.m.

Can anyone under 21 join the tour?

No. This activity is restricted to people aged 21 and older.

Are the Shanghai Tunnels included?

The planned route includes Shanghai Tunnels stories and a stop connected with the underground tunnels. Actual access is not guaranteed and can change because of closures or other local conditions.