The Maine Seafood Shack Locals Say Comes Alive Every Halloween

Floating on Portland’s waterfront, DiMillo’s On the Water serves up fresh lobster, ocean views, and a side of chilling tales that keep guests on edge.

Locals whisper about flickering lights, mysterious footsteps, and the ghostly figure said to roam the old ferry-turned-restaurant.

Yet no one can resist its charm. Between the haunting legends and mouthwatering seafood, this Maine spot proves that a little scare can make dinner even more unforgettable.

Built on a 206-Foot Ferry

Picture a massive car ferry that once shuttled vehicles across Chesapeake Bay, now permanently anchored in Portland’s Old Port. That’s DiMillo’s for you.

The New York ferry stretches 206 feet long and 65 feet wide, weighing around 700 tons. Before its restaurant days, it ran routes between Norfolk and Hampton, Virginia, then Newport and Jamestown, Rhode Island.

Now it serves clam chowder instead of commuters, and some say its maritime past left behind more than rust and memories.

Opening Day: December 6, 1982

Tony DiMillo threw open the doors on a chilly December day in 1982, turning heads all along the waterfront. His vision? Transform a retired ferry into New England’s coolest dining experience.

But Tony wasn’t new to Portland seafood. His first spot opened way back in 1954 with the cheeky slogan, “The clams you eat here today slept last night in Casco Bay.”

That commitment to fresh catch stuck around. Forty years later, DiMillo’s floating restaurant remains a local legend, though some guests swear the original crew never really left.

Family-Owned Marina Empire

Generations of DiMillos have kept this operation running smooth as butter. The family doesn’t just manage the restaurant; they own and operate the entire marina surrounding it.

Walk the docks and you’ll see their handiwork everywhere: gleaming yachts, working fishing boats, and tourists snapping photos. It’s a true family affair, passed down through decades.

Yet employees joke that there might be one extra “crew member” nobody talks about during staff meetings, lingering somewhere below deck where the old engine room hums with more than just machinery.

550 Seats of Floating Luxury

With seating for roughly 550 guests, DiMillo’s ranks as one of New England’s largest floating dining rooms. That’s a lot of lobster bibs in one place.

The sheer size means you can host weddings, reunions, or just a Tuesday night dinner without feeling cramped.

Multiple dining areas spread across different decks, each offering waterfront views and that gentle rocking sensation.

But size also means more shadowy corners, more creaky hallways, and more places for unexplained footsteps to echo when the kitchen crew swears nobody’s down there.

Ghost Tour Favorite Stop

Portland ghost tours regularly anchor at DiMillo’s, and guides love sharing tales of spectral chatter echoing from the old engine room. Visitors report hearing muffled voices and metallic clangs when no one’s working below.

One popular story involves a shadowy figure spotted on the lower deck, vanishing before anyone can get a closer look.

Staff members have their own collection of weird moments: lights flickering, doors slamming shut, cold spots on warm summer nights.

Whether you believe in ghosts or not, the lore adds an extra layer of intrigue to your seafood dinner.

East Coast’s Only Floating Restaurant

When DiMillo’s debuted in 1982, it proudly claimed the title of the East Coast’s only floating restaurant. No other place on this side of the country offered dinner literally on the waves.

That novelty drew crowds from all over New England and beyond. Sure, California had floating spots, but Maine? This was groundbreaking.

Decades later, the bragging rights remain, even if a few competitors have tried to copy the concept. And let’s be honest: none of them come with a resident ghost story quite this good.

Below-Deck Apparition Sightings

Venture below deck and you might encounter more than old pipes and machinery. Multiple witnesses describe a shadowy apparition that drifts through the engine room, never quite solid enough to identify.

Some say it’s a former ferry worker, forever tied to the vessel he once maintained. Others think it’s just tricks of light bouncing off metal surfaces. Either way, late-night staff prefer working upstairs.

The below-deck chill, the strange creaks, and that unsettling feeling of being watched? Yeah, they’ll pass on that assignment, thanks very much.