Portland ghost stories pair surprisingly well with a bar stool. This Boos and Booze crawl ties together Portland’s darker legends and real-world hangouts, with guides like Kris and Victoria bringing the spooky parts into focus. I especially liked the way the tour uses specific stops in the Old Chinatown area, and how the stories feel aimed at keeping you entertained while you walk.

Two things stand out for me: first, the guides. Kris, Victoria Rose, Houston, Jessica, and Lori all sound like they prepared for real questions, not just cookie-cutter scares. Second, the route gives you more than one flavor of Portland spooky, from old theaters to the Shanghai Tunnels theme and an end stop with actual food.

One drawback to keep in mind: alcohol is not included, and not every location is set up for full access. Several spots are often just a curbside story moment, and on some days a planned stop can end early or be less accessible than you hoped.

Key takeaways before you go

• Small group vibe (max 20): easier conversations and less chaotic walking at night
• Real guide energy: names like Kris, Victoria Rose, Houston, Jessica, and Lori come up for a reason
• Old Chinatown focus: the stories are anchored to actual neighborhoods and landmarks, not generic ghosts
• Tunnel-themed stop: the Shanghai Tunnels segment is part of the planned flow
• Food at the end: you finish at Old Town Pizza & Brewing rather than ending with just a final scare
• Plan for extra costs: drinks cost extra, so decide early what you’ll order

A 5:00 pm crawl that turns Portland’s Old Town into a walking story

This tour starts at 5:00 pm and runs about two hours, which is a smart window. You get some daylight fading, then the streets feel moodier without it turning into a late-night slog.

I like that you are not sent out solo to find the spooky parts. You move as a group, and the guide keeps the evening organized, so you’re mostly thinking about the stories and the next stop instead of safety math on your phone.

Also, the timing matters for the “feel.” One reviewer noted that daylight can shrink the ambience, so if you’re hoping for peak creepiness, show up a few minutes early and be ready for twilight energy.

Price and what $36 really buys you

At $36 per person for about two hours, the value is in the structure: guided storytelling plus multiple stops where the guide sets the scene. The tour includes all fees and taxes, and you get a mobile ticket.

What’s not included is the easy part of the budget: alcoholic beverages. That means your final cost depends on what you choose to drink at each stop, but it also means you control the pace and spending. If you’re traveling with a friend who wants cocktails, and you want soda or water, you can still enjoy the tour without feeling locked into a bar tab.

One more “value” point: some stops are quick (around 5–15 minutes), so you’re buying lots of variety rather than lingering at a single location. If you want a slow, long sit-down pub night, this format may feel fast.

How the evening moves: walking, pacing, and staying comfortable

The itinerary is built around short story-and-drink moments, plus a bit of walking between stops. The tour is listed as requiring moderate physical fitness, which to me reads as: expect walking and standing, not a fully seated experience.

Pacing seems to vary by guide and group needs. In one case, a guide was praised for a slow pace that worked well for older folks, with guests feeling like they had some control over how fast things moved.

Bring practical gear. Wear shoes you can stand in for a while, and add a light layer because Portland evenings can cool off quickly. If you’re worried about keeping up, you can still plan to enjoy the stops at your own speed while staying with the group.

Stop 1: The Benson Portland and the first ghost story with a drink

You start at The Benson Portland, Curio Collection by Hilton at 309 SW Broadway. This is a classic way to begin because a hotel landmark immediately sets a “something happened here” tone.

The format at this early stop is simple: grab a drink and let the guide start layering Portland’s haunted history. Drinks are not included, so this is your first budget decision of the evening.

What I like about starting here is the momentum. You’re not walking into the tour already tired or distracted; you’re settling in while the guide builds the theme for the rest of the crawl.

Stop 2: Kelly’s Olympian and the pleasure of switching scenes

Next up is Kelly’s Olympian, another well-known watering hole. Again, the model is the same: short time, ghost story, and the chance to order something if you want.

This stop works as a contrast. The Benson gives you grandeur; Kelly’s gives you neighborhood pub energy. That shift makes the stories feel like they belong to different corners of Portland, not one single setting.

If you don’t drink alcohol, you still get the main event: you hear the story and you keep moving.

Stop 3: Roseland Theater for the quick hit of haunted venue lore

At Roseland Theater, the stop is brief—around 5 minutes. This is where the crawl format shines for people who like variety, because you get a taste of the theater-world vibe without a long wait.

The value here is that the guide can connect a famous location to a specific kind of Portland mystery. Even if you are not spending much time inside, the story gives context to the building and why it fits the theme.

One thing to watch: some venues may not be set up for deep access, so think of this as a story stop where you take in the mood from outside or near the entrance.

Stop 4: Kells Irish Restaurant & Pub and the basement story question

The crawl continues at Kells Irish Restaurant & Pub. This is one of the stops people tend to notice because it mixes pub culture with a darker angle, and it is one of the places where you might expect access deeper than a curbside chat.

That said, access can vary. Some guests reported situations where a basement area connected to the haunted element was closed off. Translation for you: don’t plan your expectations around going into every claimed haunted space.

Your best move is to show up ready for the experience to be story-driven, not always door-by-door exploration.

Stop 5: Shanghai Tunnel Bar & Venue and the vibe shift

Then you hit Shanghai Tunnel Bar & Venue, and the theme tightens. The crawl starts talking more directly about Portland’s tunnel mythology, and the atmosphere of a tunnel-themed bar naturally fits the narrative.

Even if you’ve never heard of the Shanghai Tunnels before, this stop helps you catch up fast. The guide uses it to make the underground concept feel more real and less like a random legend.

Also, this is another drink option stop. You’ll likely be deciding by now whether you want to order one more round or keep it light so you can enjoy the walking comfortably.

Stop 6: The Haunted Underground Shanghai Tunnels Tour

This is the segment that many people come for, and the tour lists it as 10 minutes: the Haunted Underground Shanghai Tunnels Tour.

If you’re into place-based spooky—stories that connect to a real-looking location—this is where your attention should sharpen. The value isn’t just fear; it’s understanding why Portland’s “underground” shows up in the city’s folklore and how people have used tunnels as part of the legend for years.

Do keep expectations grounded. Some guests said they did not get the full tunnel portion during their run, and that can happen if the schedule or access tightens. If the Shanghai Tunnels is your top reason for booking, it’s smart to keep a flexible mindset and be ready for the story to be part explanation even if time is compressed.

Stop 7: 9 NW 2nd Ave and the darker street-corner stories

After the tunnel theme, the tour moves to 9 NW 2nd Ave for another quick ghost-history moment—listed at 15 minutes. This is the kind of stop that makes a crawl feel real: you’re not just in bars. You’re learning how the city’s past leaves marks on ordinary street addresses.

This is also where you start to notice the route as a whole. The guide’s job is to stitch together why Portland blocks and neighborhoods look the way they do, including the idea that street layouts can tie into the city’s growth and survival stories.

If you like learning why a place looks the way it does, this is your payoff stop.

Stop 8: Old Town Pizza & Brewing to end with food and closing stories

The tour finishes at Old Town Pizza & Brewing at 226 NW Davis St. The ending is 15 minutes, and it’s built for a proper wrap-up: a final drink option plus food.

I like this structure because it helps you land after walking. Instead of sprinting to dinner afterward, you have a built-in transition from spooky talk to real-life calories.

This is also a good moment to recap what you remember. If the first half felt heavy on legends, the last stop feels more like Portland in full swing: a normal evening out, just with ghosts layered over it.

The biggest praised ingredients: guides who make the stories stick

The consistent theme in high ratings is the guide. People mention guides being funny, engaging, and prepared to answer questions, and names like Kris, Victoria Rose, Houston, Jessica, and Lori come up repeatedly.

Here’s what that likely means for you, practical and not mystical: you’ll get better pacing, clearer context, and stories that connect rather than just list dates. When a guide knows the route and knows how to read a group, it makes short stops feel worth it.

One guest also liked that the pace felt adjustable. That matters because a pub crawl can go either way: either you move too fast and feel rushed, or the guide keeps it comfortable.

Things that can affect your experience (and how to handle them)

A few realities can shape your night.

First, some stops may be limited to standing outside while the guide tells the story. If you’re imagining full access to every location’s haunted interior, you might feel a little deflated if it’s mostly exterior.

Second, the crawl is short at each location, so you won’t get long, deep dives on-site. You’re getting bite-size storytelling across multiple points, not one long guided deep history session.

Third, downtown ambience can swing with timing and weather. With a 5:00 pm start, you’ll probably catch dusk, but if the light level is still bright, it can soften the spook factor. Bring layers and lean into the experience as an evening walk, not a horror-movie set.

Who this tour is best for

You’ll enjoy this most if you like:

• Portland legends tied to real places, not just generic ghost talk
• a group format where someone else handles the route
• mixing pub culture with short, story-led stops
• a quick stop-and-go pace that fits a couple hours in the city

It might not be your best match if you want:

• a long, sit-down ghost tour with fewer stops
• guaranteed interior access to every location
• a night where drinks and snacks are included in the ticket price

Tips so you get the most spook per minute

A few simple moves can improve the whole evening.

Arrive a bit early and settle in before the first story starts. When you’re not rushing, you’ll actually hear the details when the guide talks.

Since alcohol isn’t included, decide ahead of time if you’re getting one drink, two, or going non-alcoholic. That prevents mid-tour budget stress.

Finally, focus on the guide’s connections. This crawl is strongest when the story ties the neighborhood together—why the theater fits the legend, why the address matters, and how the tunnels concept becomes part of Portland’s myth.

Should you book Portland Ghosts Boos and Booze?

If you want a fun, social way to see Old Town and hear Portland hauntings tied to specific addresses, this is a solid pick. The guide quality is a clear selling point, and the ending at Old Town Pizza & Brewing helps the tour feel like a real evening, not just a haunted sprint.

I’d only hold off or switch to a different format if your top priority is guaranteed access to every haunted interior space or a longer session at fewer stops. For everyone else, $36 for two hours of guided spooky plus multiple landmarks is good value, especially when you treat it as story-first and budget-friendly with your own drink choices.

FAQ

What is the duration of the Portland Ghosts Boos and Booze pub crawl?

It runs for approximately 2 hours.

How much does the tour cost?

The price is $36.00 per person.

Where does the tour start and end?

It starts at The Benson Portland, Curio Collection by Hilton (309 SW Broadway, Portland, OR 97205) and ends at Old Town Pizza & Brewing (226 NW Davis St, Portland, OR 97209).

What time does the tour begin?

The start time listed is 5:00 pm.

Are alcoholic beverages included in the price?

No. Alcoholic beverages are not included.

What places does the tour include?

The tour lists stops including The Benson Portland, Kelly’s Olympian, Roseland Theater, Kells Irish Restaurant & Pub, Shanghai Tunnel Bar & Venue, an Underground Shanghai Tunnels tour segment, 9 NW 2nd Ave, and Old Town Pizza & Brewing.

Do I need to be 21 or older?

Yes. The tour is not for travelers under age 21.

How large is the group?

The tour has a maximum of 20 travelers.

Is confirmation provided after booking?

Confirmation is received within 48 hours of booking, subject to availability.

What about accessibility and getting there?

The tour notes that it is near public transportation, allows service animals, and requires a moderate physical fitness level.