Wander Old Port after dark for spooky, walkable stories. This 2-hour guided haunt threads through Portland’s waterfront and historic streets with a mix of ghost lore, true-case legends, and uncanny personal tales.

What I like most is the storytelling pace and the way each stop gives you something specific to look for, from a floating restaurant’s supposed shipboard whispers to hotel-room oddities. Second, you get solid landmark orientation fast, so you’re not just chasing scares—you’re also learning how this part of Portland works.

One possible drawback: this is more haunted history + paranormal storytelling than a pure ghost-hunting experience, so if you want only tightly documented, classic “spirit sightings,” you might want to set your expectations.

Key highlights

• Starts at 8:00 pm and finishes back at the waterfront meeting point, making it an easy evening plan
• Up to 30 people keeps the group small enough for lively guide interaction
• Mobile ticket for a smooth check-in without fuss
• Alex Tanous and a declassified CIA file show up on the route, alongside traditional spooky stops
• “Jukebox from Hell” and phantom-music details make the later stops feel extra specific
• Several stops are linked to Portland’s historic buildings, including the WL Blake Building and Longfellow-associated lore

Walking the Old Port’s haunted loop, starting at DiMillo’s

This is the kind of night tour that fits the way Portland evenings actually play out: you can eat, stroll, and still do something memorable without committing your whole night. The route runs through the Old Port waterfront and down familiar downtown streets, with a roughly 10-minute story window at each location. Total time clocks in around 1 hour 30 minutes to 2 hours, depending on the pace of the group and how much your guide likes to linger on the juicy details.

The tour launches from DiMillo’s Old Port Yacht Sales, at 1 Long Wharf. Ending back at the same place is a big practical win. You don’t have to figure out a second transport plan, and you can fold this into dinner nearby.

And yes, it’s spooky—but it’s also built like a city walk. You’re getting oriented while you’re listening, which makes the “I’m new in town” feeling shrink quickly.

Stop-by-stop: what you’ll see and what the guide will focus on

Below is the heart of the tour: the set pieces. Use this to decide what kind of ghost stories you’ll probably enjoy most.

DiMillo’s On the Water: floating restaurant, old-engine vibes

Your first stop is DiMillo’s On the Water, a floating restaurant tied to maritime history. The story leans into the idea that chatter and sound could linger in a place that once worked like a machine—specifically pointing to the ferry’s former engine area. Even if you’re not fully bought in on ghosts, this is a good opener because it uses the setting itself: water, old wood, and a ship-turned-world that feels naturally haunted.

Why it works: it hooks you immediately with place-based atmosphere, and it sets the tone for the rest of the route.

Custom House Wharf: maritime legends with a “don’t look away” mood

Next comes Custom House Wharf. This is where the stories turn toward maritime tragedy and the darker end of local legend. The tour frames the idea of a famous ghost ship returning for the unfortunate, and it asks the right kind of question for this style of tour: is it possible to be frightened to death, or is that just the legend trying to explain something people couldn’t process?

Practical tip: keep an eye on the group’s spacing here. Waterfront stops can get crowded fast, and you’ll want a clear view when the guide points out the spot they’re talking about.

Andy’s Old Port Pub: a ghost with more attitude than subtlety

At Andy’s Old Port Pub, the legend gets lively. You’ll hear the warning: watch for flying dishes. This isn’t the quiet, “maybe you heard something” style—this one is described as more active than most, with items allegedly tossed off shelves and with the ghost also enjoying a game of pool.

This stop tends to be fun because it gives you something visual (shelves, angles, the feel of the room) while still staying outside the “Hollywood special effects” lane.

US Attorney: Alex Tanous, Patty Hearst, and a declassified CIA file

The route makes a big genre pivot here. The story centers on legendary psychic Alex Tanous, including claims about his assistance with law enforcement and high-profile cases. One highlighted claim ties his help to the Patty Hearst kidnapping, and the segment also references a declassified CIA file.

Why I think this matters: it turns the tour into more than just ghost folklore. It’s closer to the “true crime + paranormal claims” corner of the spooky world, which some people love and others skip past mentally.

Rosie’s Restaurant & Pub: jukebox chaos in the wee hours

At Rosie’s Restaurant & Pub, the spooky angle comes with a sound-based threat: a so-called Jukebox from Hell that unexpectedly blasts rock ’n’ roll during the wee hours. The legend frames this spirit as ornery and impatient with being ignored.

This is one of the stops where the imagination does the work. You’re listening to a story about noise turning into a haunting presence, which is exactly the kind of “could happen, but probably won’t” fear that fits a walking tour.

Henry’s Public House: a 19th-century setting with phantom piano energy

Then you’re at Henry’s Public House, described as a charming 19th-century pub. The story focuses on a ghostly pair spotted on the stairs and the notion of phantom piano music riding the wind.

If you like “place details” in your supernatural stories, this stop has it. Stairs and the way sound carries in older buildings are the kind of cues that make legends feel slightly more plausible.

79 Commercial St (WL Blake Building): author Nomar Slevik’s ghost encounter

At 79 Commercial St and the WL Blake Building, the tour leans into a specific paranormal-author experience. The name Nomar Slevik comes up along with the account of his own ghostly encounter at this address.

Why this stop is different: it’s anchored to a named person, not just a spooky vibe. That helps the story feel more like a local “this happened to someone” tale rather than a general campfire loop.

26 Exchange St (Art Alley): cobblestones, Longfellow, and ghost belief

The route heads to 26 Exchange St and the Art Alley area. This is framed as a place where alleys become hidden art spaces and cobblestones add charm. The story also brings in a Portland connection: Henry Wadsworth Longfellow, with the question of whether he believed in ghosts.

This stop works well late in the walk. It’s less about frantic activity and more about the long, old-town feel—the kind of setting where a legend can sit naturally.

Portland Regency Hotel & Spa: moving items and a TV that won’t behave

The final story set is at Portland Regency Hotel & Spa. One guest noticed odd room behavior: items shifting, a closet door rattling, and a TV turning on and off by itself.

This end-stop “creep factor” is a classic walking-tour closer: it’s personal, domestic, and plausibly nightmarish because it’s happening inside a room people actually stay in.

What makes the tour feel worth $29

At $29 per person for about 1.5 to 2 hours, the value depends on what kind of experience you want.

If you want a guided evening that:

• gives you a simple route through the Old Port,
• adds story stops you wouldn’t find on your own,
• and keeps you moving with a clear schedule,

…then $29 can feel like a fair price. It’s also presented as admission-free at the stops (each location is marked as free admission in the route notes), so you’re not paying extra to enter rooms or pay for attractions.

Also, the small max group size (up to 30) is a hidden value lever. Big groups can turn guides into voice actors. Here, the setup is designed to keep the guide present and the audience engaged.

How guides drive the experience (and why it matters)

The tour’s quality shows up in the “human” layer: the guide’s tone and timing.

Multiple guides have appeared for this route, including Jeff, Grace, and Jordan. The strongest praise clusters around:

• serious-but-funny storytelling,
• fast, confident pacing,
• and guides staying aware of the group’s comfort level (including families).

That matters because this tour isn’t just “read a story from a plaque.” The best versions feel like you’re on a guided set walk—your attention gets pulled forward, and the spooky beats land at the right moment.

That said, one thing to plan for: the pace can be fast-moving, and some people want more detailed grounding in Portland’s foundation and early development rather than a straight line of spooky episodes. If that’s your preference, go in knowing the goal is entertainment plus eerie local lore—not a full city-history lecture.

Good fit for you if you want…

This tour is a strong match if you:

• want a fun, themed way to see the Old Port and historic downtown in one evening,
• like specific addresses and landmark-based storytelling,
• enjoy a mix of ghosts, local legends, and paranormal claims rather than only one flavor of spooky.

It’s also a good “first night in Portland” option. In a couple hours you’ll learn the geography of the waterfront spine and the downtown grid around it.

Families can work too, as long as you think of it as spooky-fun rather than horror. Some groups have described it as not too scary and manageable for all age groups.

Considerations before you book

A few things can shape whether you’ll love this or feel only okay:

• This is not purely about visible ghosts. You’re listening to stories, plus haunted history and paranormal legends. If you want a classic ghost-tour feel only—hard origins, very “documented” claims—this may feel looser.
• You may encounter supplemental materials during the walk, including photo-style references. One person disliked the heavy use of binder-style handouts, and another didn’t like AI images. If visual style is a big deal for you, keep that in mind when choosing a night.
• You’ll do a fair amount of walking over the 10-minute stop blocks. Comfortable shoes matter.

Should you book the 2-hour Portland Old Port Ghost Walk?

Yes, book it if you want an easy evening activity that combines Old Port scenery with entertaining, landmark-based haunted stories, and you’re open to a paranormal mix that includes true-case legends (like Alex Tanous and the Patty Hearst connection).

Skip or reconsider if you’re very strict about “only classic ghosts” or you want the tour to focus heavily on Portland’s early founding and civic history rather than eerie episodes. This walk is built for spooky storytelling first, city orientation second.

If you do book, go expecting a smart, fast, story-forward stroll at 8:00 pm—then let the Old Port do the rest.

FAQ

What time does the tour start?

The tour starts at 8:00 pm.

How long is the walking tour?

Plan for about 1 hour 30 minutes to 2 hours.

Where do I meet for the Old Port ghost walk?

Meet at DiMillo’s Old Port Yacht Sales, 1 Long Wharf, Portland, ME 04101.

What does the tour cost?

It costs $29.00 per person.

Is the tour offered in English?

Yes, it is offered in English.

What group size should I expect?

This activity has a maximum of 30 travelers.

Are service animals allowed?

Yes, service animals are allowed.