PORTLAND, Maine — It might be Portland’s best kept secret.

Every Valentine’s Day for 41 years, Portlanders wake up to a blizzard of red hearts across the city. On storefronts from Peaks Island to North Deering, from the West End to Munjoy Hill, the valentines help lift spirits and loosen the grip of winter.

On Monday night, as temperatures plunged into the teens and sky-high snowbanks turned streets into luge runs, the Valentine Phantom struck again.

BDN Portland followed along for the evening to see how the phantom works. In return, the bandit insisted on anonymity.

A wily force — more like a secret society — the bandit and crew have managed to shun all media.

“Most people are dying to be in the paper. This is the opposite. This is not ego-driven,” the bandit told us. “It’s not about how we do it; it’s why we do it.”

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The bandit has completed feats that might give other daredevils pause.

From tying giant heart banners onto lighthouses and bridges to clambering up civic landmarks, the playful phantom has done it all. Hoisting sail-like Valentines atop abandoned buildings as winds howl, the phantom, like the postman, delivers in rain, sleet or snow. Since 1976, plans have been modified but never outright dashed.

But there is always room for another caper. This year, the prize was Fort Gorges, reached somehow in the dead of night. In a major coup, the bandit affixed a giant heart banner on the wind-swept fortress in Casco Bay, a feat last completed in 1986.

It’s part of the phantom’s tradition of reaching for new heights each year.

On Monday night, the bandit started early.

The first stop was Rufus Deering Lumber. As the sun set over Portland Harbor and snowplows were the only activity in the Old Port, a banner was hoisted onto the 162-year-old Commercial Street building. Soon to be torn down to make way for new development, the legacy building was festooned with love.

It wasn’t a perfect execution — the banner was lopsided — but time was of the essence. The bandit had miles to go before sleep.

The phantom worked in shifts, even breaking for food and a beer, and had volunteers who appeared spontaneously to keep the phenomenon alive.

The phantom powered mysteriously through the city. Access was granted. Doors opened as if by magic. Seeming to pass unobstructed, locked gates and doors unlatched.

If a plan was foiled on the fly, the phantom nixed it fast. On Monday night a target at Baxter Academy went awry and ended before it began. No matter. Onto the next.

Soon after, the apostle of love was let into Planned Parenthood on Congress Street.

Though the office was closed because of Monday’s storm, an employee ushered the bandit in. “What floor?” she asked as the elevator whisked the Valentine bandit inside. The bandit is usually apolitical. But this year, “we feel we can be a little progressive.”

Walking through the deserted health center at night, the phantom identifies the right windows, cuts rope, unfurls a giant sail-like banner — a relic of Valentine’s Days past — and goes straight to work. It’s not easy.

On the street the flag flaps in the wind, like a billowing sail. An SUV drives by and the driver beeps in approval. Moments later Portland police cruise by too without slowing down. They know not to give the phantom any guff.

At times, it feels the whole city colludes in this affectionate display of humor and love.

And humor is necessary when each location poses challenges requiring ad hoc adjustments.

“It’s a new set of problems every year,” the bandit said, inside Planned Parenthood’s historic Monument Square building, fidgeting with a window.

But problems vanish come Valentine’s Day morning.

“It’s a fun tradition. We are thrilled to be part of it,” Nicole Clegg, Planned Parenthood’s vice president of public policy, said. “It makes people smile.”

As a former city of Portland employee, Clegg didn’t hesitate to give access when she was contacted by a phantom liasion a few weeks back.

The anonymous midwinter performance started long before Portland had cachet.

In 1976 the city’s working waterfront needed a spark. The national mood was grim. Nixon had been driven out of office. The Vietnam War was still raw. That’s when the bandit first festooned the city with paper hearts. A legacy was launched.

The echo of that time lingers today with the nation’s political turmoil.

Last night, as banners anchored against the buffeting wind, the bandit was busy affixing paper hearts to storefronts and windows everywhere. The masking tape froze in the cold, but Congress Street shops, banks and institutions soon bloomed in red and pink.

As the few bars that were open let out, a second phantom wave fanned out across the city, spreading love into the wee small hours with a sea of hearts.

Out in Casco Bay early morning ferry commuters posted on Instagram, delighted photos as the rugged military fort showed a new look: a large banner blazing with a heart.

Somewhere in Greater Portland, the phantom slumbers until next year.

Kathleen Pierce

A lifelong journalist with a deep curiosity for what's next. Interested in food, culture, trends and the thrill of a good scoop. BDN features reporter based in Portland since 2013.