Ghosts and happy hour, in one walk. This Portland crawl works because it threads haunted history through real neighborhoods and real pubs instead of feeling like a lecture.

I especially like the small-group format, capped at 20 people, which keeps the evening social but still controlled. You’ll also get that Old Chinatown-area route with multiple stops, so the walk feels like exploring, not rushing.

One thing to consider: the tour is tight at about 2 hours, and the pub side depends on what’s open and accessible that day. Alcohol is not included, so your final spend can rise if you go full bar crawl.

Key Things to Know Before You Go

• Small group size (20 max): Easier to hear your guide and keep the pace.
• Old Chinatown-area route: Several stops clustered in the downtown core.
• Haunted storytelling, not just sightseeing: You’re there for the dark narratives tied to each location.
• Shanghai Tunnels are a highlight: But access can vary, so keep expectations flexible.
• Multiple stops for drinks (at extra cost): You’ll likely purchase something along the way.

Portland at 5 pm: the vibe of a ghost pub crawl

This starts at 5:00 pm, which means you’re walking through the city as it transitions from day to night. That timing is good for comfort, photos, and checking out storefronts, but it also means the “spookiness” isn’t automatically at full volume like an all-dark, later-night tour would be. If you’re chasing maximum chills, I’d still go. Just don’t expect the lighting to do all the work for you.

The best part is how the tour blends the haunted angle into places you’d actually choose to visit anyway: hotels, theaters, Irish pubs, a tunnel-themed bar, and a final spot where you can eat. It’s not just standing in a park and listening. You’re moving through working Portland venues, and that makes the stories feel more anchored in daily life.

Also, you’re not doing it alone. One of the practical wins here is that a guide keeps the group together and moving safely through downtown. Portland can feel intense around central blocks at evening hours, so having a planned route with a small group is a smart way to enjoy the night without turning it into a solo scavenger hunt.

Price and Logistics: what $36 really buys

The price is $36.00 per person for about 2 hours. What’s included is straightforward: all fees and taxes. What’s not included is equally important: alcoholic beverages.

That means you’re paying mainly for:

• a guide and the route planning,
• time at multiple locations for stories,
• and the structure of a pub crawl format.

But you should treat this as a guided night out, not a free-drink event. If you skip alcohol, you can still enjoy the stories and take in the stops. If you do drink, the cost can climb quickly since you’ll be deciding drink-by-drink at each location.

The tour uses a mobile ticket, and you’ll receive confirmation within 48 hours of booking (subject to availability). It’s offered in English and capped at 20 travelers, so it doesn’t feel like you’re part of a massive crowd.

Finally, it’s not for anyone under 21, and it’s listed as having a moderate physical requirement. Translation: wear comfortable shoes and expect real walking, even though each stop is only about 5–15 minutes.

Stop-by-Stop: from The Benson to Old Town Pizza

This route is designed to feel like a guided tour of haunted Portland landmarks, with time to grab a drink and hear a story at most stops. Here’s how each part plays out, plus what to watch for.

Stop 1: The Benson Portland (Curio Collection by Hilton)

You begin at The Benson Portland with a drink and a haunted story at this well-known hotel setting. The value of starting here is simple: it’s a strong “opening scene.” Hotels also tend to have enough interior space and staffing to absorb a small group before you head out.

The only catch is that the drink is on you. Still, this first stop is a nice way to settle in, get your bearings, and let the guide set the tone.

Stop 2: Kelly’s Olympian

Next is Kelly’s Olympian, another classic Portland watering hole with ghost stories attached to the location. This stop keeps the pub-crawl rhythm going—one part narration, one part atmosphere.

If you’re sensitive to crowds, this is one to pace yourself. It’s a bar stop, so you’ll want to stay aware of personal space and keep moving with the group.

Stop 3: Roseland Theater

Then you shift to Roseland Theater for haunted history, with a shorter visit (about 5 minutes). The benefit here is variety. A theater location gives you a different kind of Portland story than a pub or a tunnel bar.

Because the stop is brief, it’s best if you’re listening instead of multitasking. If you stop for a drink here too long, you may feel like you rushed through the story.

Stop 4: Kells Irish Restaurant & Pub

At Kells Irish Restaurant & Pub, you get another shot at a drink plus a haunted tale. This is often where people start to connect the “stories + Portland pub culture” idea.

One practical consideration: some parts of venues can be closed or inaccessible on certain days. If you expect specific areas to be open as part of the haunted theme, keep it flexible. You may hear the story while standing outside or in a limited area rather than going deeper into the venue.

Stop 5: Shanghai Tunnel Bar & Venue

Now the tour leans into its signature theme. Shanghai Tunnel Bar & Venue is where you’re likely to feel the Portland-meets-legend vibe most strongly. The stop includes time for a haunted story and, again, an opportunity to buy a drink.

If you’re the type who likes photos, this is one of those locations that tends to feel good on camera because of the tunnel/old-city branding. Still, aim to keep your phone put away during the narration so you don’t miss details.

Stop 6: Haunted Underground Shanghai Tunnels Tour

This is the scheduled tunnel segment—haunted secrets of the famous Shanghai Tunnels—for about 10 minutes. In an ideal run, this is the spine of the experience.

But here’s the reality check: some people report not getting the full tunnel portion during their tour. That doesn’t mean the tour is “broken,” but it does mean the tunnel piece can depend on access and what’s workable that evening. If Shanghai Tunnels are your main reason for booking, treat this as the stop to prioritize mentally.

Stop 7: 9 NW 2nd Ave

Next is 9 NW 2nd Ave, with time for a drink and dark local history (no alcohol included). This stop can feel like a breather between the big-theme moment of the tunnels and the final meal stop.

Also, downtown Portland details can get surprisingly interesting. One guide’s route explanation highlighted why Portland blocks are so small—so you may leave with more than ghost lore. You might also understand how the city’s layout shaped how people moved through it.

Stop 8: Old Town Pizza & Brewing (finish with food and stories)

Finally, you end at Old Town Pizza & Brewing, where you can grab food and a drink and hear more weird Portland history tied to the area. The end stop works well because it gives you something to do right away: eat, decompress, and let the stories settle in while you’re still in the same night-time mood.

Just remember: food isn’t listed as included. You’re finishing with options, not a prepaid meal. The plus is choice—if you want something filling after a couple hours of walking, this is a convenient place to do it.

The Shanghai Tunnels stop: the one to plan around

The Shanghai Tunnels segment is the headline. People go for the Portland legend tied to underground passages, and it’s easy to see why. It’s a specific story anchor in a tour made of city locations.

But I’d plan for two outcomes:

1. You get the tunnel-themed portion as promised, and it feels like the peak moment.
2. Access is limited, and the tunnel experience becomes more of a storytelling stop than an actual underground moment.

Either way, the guide can still shape the experience with the surrounding context. Still, if you’re booking mainly for the tunnel visit itself, don’t treat it like an automatic guarantee. Ask yourself what you’ll do if that part is shortened: will you still enjoy the rest of the route? For most people who like ghost tours tied to real places, the answer is yes.

Guides and storytelling style: why certain names keep coming up

What makes this tour work isn’t just the itinerary. It’s the person holding it together.

The guide talent seems to run the whole range from playful and theatrical to structured and detail-forward. Names that show up with strong praise include Kris, Victoria (including Victoria Rose), Houston, Jessica, and Lori. People highlight humor, strong storytelling, and the ability to answer questions without making the tour feel like a rigid script.

One detail I like to look for in any ghost tour is pacing. This one is designed as a 2-hour experience, and some guides keep it slow enough that you don’t feel yanked along. That matters if you want to actually absorb the stories while still having time to stop at pubs and take in the locations.

If you’re the type who enjoys history served with a chill, the guide’s style is the difference between fun spooky and forgettable spooky.

Practical tips: how to get the full experience

A few small choices can make a big difference on this kind of walking-and-talking tour.

• Wear shoes you can stand in. You’ll be stopping often, but you’re still walking through downtown blocks.
• Bring your ID. It’s not for travelers under 21, so you’ll want to be ready if asked.
• Budget for optional drinks. Alcohol is not included, and drinks at multiple stops can add up fast.
• Listen during the story moments. Each stop is short—especially the theater and tunnel-adjacent segments—so try not to multitask.
• Expect some places may be limited. Some stops can be hard to access depending on the day, and you may end up hearing from outside rather than inside.
• Take common-sense safety seriously. This is downtown at evening hours. Stay with the group, keep your phone controlled, and watch personal belongings as you move between venues.

If you want the best chance of getting the tunnel highlight, go in with flexibility. You’ll still have a full route of haunted spots even if one portion doesn’t run exactly like you pictured.

Should you book Portland Ghosts Boos and Booze?

If you want a 2-hour guided ghost walk that also functions like a social Portland night out, this is a good match. The small group size, the Old Chinatown-area pacing, and the chance to hear haunted Portland stories tied to real venues make it feel more alive than a standard history walk.

I’d think twice if you’re specifically chasing one guaranteed highlight, like a full underground tunnel moment. Access can vary, and the pub-crawl side is optional since drinks aren’t included. Also, because it’s daylight-leaning (starting at 5 pm), you might want to mentally dial your expectations toward “fun spooky” rather than full horror-movie darkness.

For the right mood—Portland + stories + a drink or two—this is a fun way to spend a few hours.

FAQ

How long is the Portland Ghosts Boos and Booze Haunted Pub Crawl?

It runs for about 2 hours (approx.).

How much does the tour cost?

The price is $36.00 per person.

What’s included in the $36 price?

The tour includes all fees and taxes.

Are alcoholic beverages included?

No. Alcoholic beverages are not included.

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 start?

The start time is 5:00 pm.

Is there an age requirement?

Yes. It’s not for travelers under the age of 21.

What’s the maximum group size?

The tour has a maximum of 20 travelers.

What’s the cancellation/refund policy?

You can cancel for a full refund if you cancel up to 24 hours in advance. If you cancel less than 24 hours before the start, the amount paid is not refunded.

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