Portland Ghosts Boos and Booze Haunted Pub Crawl

Ghosts and happy hour share the same route. This Portland walking tour pairs Old Chinatown stops with spooky storytelling, plus a final food-and-drink finish near Old Town. It is timed as a 2 hour evening activity, so the city feels like it belongs to the legends.

What I like most is the structure, short story stops tied to real places, so you do not lose the thread. You also move with a small group, up to 20 people, which helps when you are out after dark and not trying to navigate solo.

One thing to consider: alcohol is extra, and several stops are more about hearing the story while you are outside than full indoor access. Drinks not included means your final cost depends on what you order.

Key highlights to know before you go

• Old Chinatown focus with multiple stops clustered around a famously storied area
• A big emphasis on the Shanghai story, including the Shanghai Tunnel Bar and the Shanghai Tunnels segment
• Short, punchy stops that keep the pace friendly for an evening walk
• The Benson start and Old Town Pizza finish, so you get an easy start and a solid end
• Small group size that makes the experience feel less chaotic and more watchable

Why Portland’s Old Chinatown is the right setting for this crawl

Portland has a habit of making history feel close up, especially downtown where the blocks and buildings sit close together. This tour leans into that. You spend your evening in the Old Chinatown orbit, which makes the stories feel less like generic campfire talk and more like a guided walk through places with shadows attached.

The tour also helps you see the city differently. Instead of treating landmarks like photo spots, you treat them like evidence, what happened there, who might have used the walls and basements, and why the streets around it became part of local lore.

The best part is you get variety in the pacing. You do not just hit one bar and stay there. You get several quick stops, then a final longer food moment at the end. That matters if you have a time window, like an early evening in Portland, or if you want something fun without committing to a full night.

Price and logistics: is $36 a good value?

At $36 per person for about 2 hours, this is priced like an evening activity you can do without going too heavy on spending. The value is in the guided route and the number of story moments you get during your walk.

Here is the practical tradeoff. Alcohol is not included, and the tour is built around having a drink available at certain stops. That means your base ticket price is just the story and the group experience. If you order nothing but water, you will still get the ghost narrative. If you plan on buying cocktails or beer at multiple stops, your total cost can rise fast.

Also, some places may not be fully accessible on a given day. That does not kill the tour, but it can change how immersive it feels. The tour works best when you treat each location as a prompt for a story, even if you are mostly standing out front.

Timing is another big piece of value. The start is set for 5:00 pm, which is nice because you are already in the evening groove before the city turns fully dark. It also means you might still be walking in partial daylight depending on the season, and that can soften the ambience for anyone hoping for full night creepiness.

Your 5:00 pm start: The Benson and the tone of the tour

You begin at The Benson Portland, Curio Collection by Hilton, located at 309 SW Broadway. The start matters because it sets expectations: you are not just doing a history walk, you are doing a ghost walk with a drink option from the first stop.

At the start, you get a drink and a haunted story at a local watering hole feeling like a natural kickoff point. This is also a low stakes way to settle in. You can hear the guide, meet the group, and get oriented before you start moving through the Old Chinatown area.

A practical tip from how these tours tend to work: if you want to minimize the cost creep, decide early whether you will buy one drink for the first stop and then switch to something non alcoholic. The tour gives you multiple opportunities to buy, so early planning helps.

Stop-by-stop: what each location adds to the spooky story

The tour is built like a chain of scenes. Each stop gives you a different slice of Portland’s darker folklore, then you walk to the next layer.

The Benson Portland (Curio Collection by Hilton)

This first stop is short, about 15 minutes, and it is meant to get you into the mood fast. You start with both the vibe of a classic hotel neighborhood and the feel of a local pub setting.

What you should expect here:

• A haunted story paired with the idea of a first drink
• A quick introduction to the tour’s main themes

The drawback is simple: since it is a drink guided opening, your experience depends on whether you are ready to spend on alcohol right away. If you are not, just treat it like a narrative kickoff and go for water or something light.

Kelly’s Olympian

Another quick, about 15 minutes, with a similar formula: drink option plus ghost stories. Kelly’s has that classic bar atmosphere that makes the supernatural feel more grounded.

Why it works:

• The guide can build continuity from the first stop
• The shorter time blocks keep energy up so you do not feel stuck waiting

If you are sensitive to crowded bar noise, grab a spot where you can still hear. The value here is story clarity, not the volume of the music.

Roseland Theater

This one is brief, about 5 minutes. It is less of a drink stop and more of a landmark stop where the guide turns the theater’s presence into a story anchor.

Consider it a palate cleanser. After two pub style stops, you get a different kind of atmosphere, more focused on history and place.

Kells Irish Restaurant & Pub

This stop runs about 15 minutes and is again story plus a drink option. The tour leans into the idea that Kells holds creepy details, including basement lore.

What can be tricky here: access can vary. On some days, you might hear the story but not get the full basement look. On other days, the venue may be closed or not operating as expected. When that happens, the ghost part can still continue, but the setting might not feel as immersive as the pitch.

My advice: do not assume you will go deep into any basement area. If you want to experience the space itself, arrive with flexible expectations.

Shanghai Tunnel Bar & Venue

This is one of the more on theme stops, about 15 minutes, with a haunted story tied to the Shanghai angle. You get a bar atmosphere that directly connects to Portland’s famed tunnels narrative.

This is also a place where your guide’s storytelling choices matter. If your guide explains the connections clearly, it clicks. If not, you may feel like you are just standing in a bar while names and facts fly by.

Haunted Underground Shanghai Tunnels Tour

This segment is about 10 minutes and is the core “tunnels” focus. Even though the time is short, the tour is clearly trying to give you a sense of the underground story.

Important expectation to set: the Shanghai Tunnels segment is not the same as a long, full scale tour. It is a short haunted underground add on within the crawl format. In some cases, it may be impacted by access conditions, timing, or what the guide can complete that evening.

If tunnels are the main reason you booked, it is worth asking early in the tour whether this portion will be fully available during your group’s walk. That one question can save you disappointment later.

9 NW 2nd Ave

Another about 15 minutes, and the stop is about dark, sordid local history tied to a specific address. This type of stop is where the tour becomes more than pub trivia. You learn how the street and its surrounding blocks fit into the bigger narrative.

This part can also feel extra unsettling if the guide links it to specific people or routes. The best guides turn a simple address into a story you can picture.

Old Town Pizza & Brewing (the finale)

The last stop is about 15 minutes and it is your food and drink end point at 226 NW Davis St. The tour wraps with more weird haunted talk connected to Portland and Old Town, and this is the moment where the evening transitions from spooky stories to a real meal.

Why this ending is useful:

• You get a chance to sit and recover a bit
• You are more likely to leave with a full stomach instead of just a couple sips

This is also where you can ask last minute questions without feeling like you are holding up the group. It is a good time to connect the dots and figure out what you want to explore on your own afterward.

The storytelling style: what guides do right

The tour is run by Portland Ghosts by US Ghost Adventures, and the guide quality shows up in the details. Several guides named in past experiences stand out for a few common strengths.

Kris, for example, is praised for blending humor with knowledge and for answering questions well. That matters because ghost tours often throw out weird names and dates, and having a guide who can explain and respond keeps it from feeling like a script.

Victoria Rose is frequently mentioned for doing a great job leading the group, with stories that feel genuinely Portland. If you want the personality of the city to come through, guides with that Portland confidence help.

Houston is noted for research and for explaining things you might not think to ask about, like why Portland blocks are so small. That kind of detail does not sound spooky at first, but it makes the whole underground narrative make more sense because it changes how you picture movement, trade, and hidden routes.

Jessica and Lori are also praised for creative, detailed story telling that makes the group feel pulled into the mood. Lori’s style is described as energetic and specific, and one person even connected odd phone photo effects to the tour night. You should not plan your evening around that, but it is a fun reminder that part of the joy is the unexpected.

Common snags and how to keep your evening smooth

No tour like this is perfect every single night. The goal is to know what could happen and respond like a prepared adult.

Some stops may be outside only

Even when a location has a dramatic story, you might not go inside. Some venues can be boarded up, closed, or simply not accessible. Your best move is to lean into the story anyway and treat outside viewing as part of the format.

The crawl can feel shorter than you expect

This tour is built with a tight schedule and short time blocks. On some evenings, circumstances can reduce the number of stops you reach, meaning you might not see every listed location or every planned element.

To protect yourself, anchor your expectations to the tour theme rather than exact completion. If your priority is the tunnels specifically, arrive early, listen closely during the early stops, and ask when the Shanghai segment is planned.

Daylight can soften the spooky factor

At 5:00 pm start time, you might walk in fading light rather than full dark in some seasons. If you are the kind of person who wants maximum creepiness, dress for night anyway. Darker clothes, a light jacket, and good shoes do more than you think.

Kells access can vary

Some accounts mention closed basements or even a closed venue on certain days. That does not mean the guide is to blame, but it does mean you should not count on seeing every room.

Who this tour suits best

This crawl is a smart fit if you want a guided walk, you like local legends, and you are okay buying drinks along the way. It also works well if you prefer moving with a group rather than wandering solo in downtown Portland at night.

It is also a good choice if you want a time efficient evening. About 2 hours means it fits well between dinner plans and late night exploring.

It is not for anyone under 21, and it calls for moderate physical fitness. You will be walking and standing through multiple short stops, so plan comfortable shoes and a pacing mindset.

If you are traveling alone, you may find the group setup reassuring. If you are traveling as a couple or with friends, the story beats can spark good conversation, especially around the Shanghai angle and Portland’s small block layout and movement history.

Should you book Portland Ghosts Boos and Booze?

I think it is worth booking if you want a fun Portland night with a guided spooky storyline and a built in finish for food. The $36 price makes sense for the format, especially because you end at Old Town Pizza where you can refuel.

Book it with a clear expectation, though. This is not a private haunted mansion walkthrough. It is a street level crawl with multiple brief stops where some locations may not be fully accessible. If you go in expecting a guaranteed, long tunnel exploration inside underground areas, you could feel disappointed.

For the best experience, I would do three things:

• Check in mentally that drinks are extra, so decide your budget before you start
• Prioritize listening, not only where you get to enter buildings
• If the Shanghai Tunnels portion is your top priority, ask early that evening if it is on schedule for your group

If you want a Portland haunted evening that mixes atmosphere, short stories, and a practical ending, this tour fits the bill.