Each spring when the cherry blossoms bloom in Greenport, the village is bathed for moment in a dreamy, soft pink glow.

This year, the cherry blossom season has a new name and a broader ambition.

“Greenport in Bloom,” a month-long celebration organized by AgroCouncil founder Deborah Rivera Pittorino and friends, will stretch across five weekends in May, blending the village’s more than 300 cherry trees with a slate of events, retail promotions and cultural programming designed to animate the transitional season between the icy depths of winter and the crazy busy summer season.

The flower power spring campaign grew out of something far more modest.

“It started back in 2017 when I still owned the Greenporter Hotel,” Rivera Pittorino said. “I used to have customers coming into town because the tree committee used to publish a map with cherry blossom trees. But there weren’t any events associated with that.”

Visitors arrived looking for blossoms, plus something to do, she said.

“So I wanted to integrate the blooming of the trees with kind of the blooming of local businesses after a long winter.”

Greenport Cherry Blossom Fest (Courtesy photos)

‘A very hard time’

That mix of economic development and community celebration is the heart of the campaign. Spring, Rivera Pittorino said, is one of the most difficult times of year for small businesses in Greenport.

“You’ve had to carry your staff and all your costs through the winter, and it’s a very hard time,” she said. “I think that people don’t understand how hard it is for the small businesses downtown.”

Deborah Rivera Pittorino and friends at a special tea and salon stop on the tour (Courtesy photos)

‘Greenport in Bloom’ May schedule

The celebration opens Saturday, May 2, with the “Run for the Petals” 5K, organized by Nicki Gohorel (below), followed by an opening-day rollout across the village. Participating businesses will offer cherry blossom-themed foods, cocktails and retail items, tying the seasonal bloom directly to the local economy.

Organizer Nicki Gohorel (left) with Southold’s Finest at a previous event (Courtesy photos)

The second weekend, centered on Mother’s Day, introduces a new feature: a guided Petal Tour led by Greenport Village Tree Committee member John Quinlan, complementing the long-running self-guided version.

The third weekend shifts toward education and culture, with a children’s program at Floyd Memorial Library inspired by the Japanese tradition of hanami, the appreciation of cherry blossoms. Students will decorate and fly kites bearing written messages, connecting the local celebration to its cultural roots.

By Memorial Day weekend, the focus turns squarely to merchants, with a full slate of vendor offerings and promotions spread throughout the village.

The month concludes with a final weekend performance featuring Japanese Taiko drummers at Holy Trinity Episcopal Church, continuing a growing tradition of international and cultural programming tied to the event.

New guided ‘Petal Tour’

Running through it all is the Petal Tour map, which serves as a floral guide and an economic kickstarter. The map highlights dozens of participating businesses, restaurants and lodging partners, encouraging visitors to move throughout the village.

“It’s not just about the trees,” Rivera Pittorino said. “It’s about getting people into the village, to walk around, look at all the nature … and walk into our businesses and support our businesses, because it’s really important that we support them.”

The expanded format also reflects the practical reality that the blossoms don’t adhere to a fixed schedule.

“With more than 300 cherry blossom trees representing seven distinct varieties, Greenport’s blooms unfold in stages,” Rivera Pittorino said, allowing visitors to encounter peak color at different points throughout May.

“It’s Mother Nature,” Rivera Pittorino said with a laugh. “Even Washington, D.C. can’t get their cherry blossom trees to bloom exactly when they want them to.”

#GreenportInBloom

The unpredictability helped inspire a broader reimagining of the monthlong event, including a rebranding led by Weathered Barn co-owner Rena Casey-Wilhelm.

“The event was always called a festival, and one of the things that I had wanted to do was reposition it as more of a seasonal celebration, not a festival.” said Rena-Casey Wilhelm, who devised the initiative’s new name, “Greenport in Bloom,” and is helping promote the social media hashtag #GreenportInBloom this spring.

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Rena Casey-Wilhelm’s favorite cherry blossom stroll is Fifth St. (Courtesy photos)

“When you use that word, “festival,” people are like, ‘Well, where is it, when is it?’” she added. “It takes away the mystery.”

The new name, and the new hashtag, reflects that shift.

“It’s really that the event is the bloom,” Rivera Pittorino said.

An ‘umbrella of pink’

For Wilhelm, the appeal is deeply visual and rooted in Greenport’s landscape, where at peak bloom entire streets are transformed.

“It’s April and May, so typically what happens almost every year is that as soon as they’re all in bloom, the rain hits, and then it washes all the petals into the streets, which I also think is just as beautiful, because the streets are completely covered in pink … It’s just another thing that makes Greenport kind of special.”

Casey-Wilhelm said her favorite pink block each spring is Fifth St.

“It’s like a canopy, because the trees on both sides are large cherry blossoms. So as they bloom, they’re practically touching each other from the left side of the street to the right … and it almost creates this beautiful umbrella of pink.”

cherry blossom petals
‘Greenport in Bloom’ is headed to a village cherry tree near you! (Courtesy photo)

Rivera Pittorino said the goal is to ensure more people not only see the bloom, but experience the village that surrounds it.

“Really it’s the businesses that provide the vibrancy for the village that we just wouldn’t have without them … There seems to be maybe some sentiment that the businesses are for the tourists, but the businesses are for everybody, and they make our lives there interesting and rich and vibrant And, you know, we need the businesses. I think it’s really important to really drive the message that we need to support the business, the local businesses.”

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