For the first time in Greenport’s decade-long dog dock-diving tradition, this spring will feature two full weekends of dogs sprinting down a dock and launching into the air — one at Greenport Harbor Brewing Co. in May and the other at the Polo Grounds in June.

The dueling events come after last year’s public split between Harbor Pet owner Kim Loper and brewery owner Richard Vandenburgh. Loper moved the 2025 North Fork Dog Dock Dive event from the brewery to the Polo Grounds after a falling out with Vandenburgh.

The wounds from that split haven’t fully healed yet, based on separate interviews this week, but Loper and Vandenburgh each said their focus is on the same thing: bringing crowds, excitement and charitable support to the community.

Vandenburgh’s event is set for May 16 and 17 at the brewery’s Peconic location. Loper’s North Fork Dog Dock Diving Weekend, being produced in coordination with Rena Wilhelm and Sarah Phillips — the team overseeing this fall’s Maritime Festival — returns June 6 and 7 at the Polo Grounds on Moores Lane.

‘Great jumpers’

Both organizers expect a similar mix of serious competition and comic unpredictability.

Vandenburgh said the brewery’s past events have drawn close to 200 dogs over a weekend. Of those, he estimated about 25% are true competitive jumpers, with handlers who travel with dogs from event to event around the region.

“The other 75% are … really skilled and they’re great jumpers, but they do it as a once a year kind of thing,” he said.

Beginners are welcome. Loper said dogs can be registered ahead of time or the day of the event, and that just about any dog can play ball.

“You could register a Chihuahua if you wanted to,” she said with a laugh.

Some dogs “come screaming down the dock” and launch without hesitation, Vandenburgh said. Others get to the edge, freeze, and need coaxing. Some screech to a halt, too late, and tumble into the water.

“It kind of hooks you in,” he said. “When you see a dog who really is good at it, it’s amazing, really impressive.’”

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Leap frogs

The competitions include the distance jump, in which dogs compete to leap the farthest from the dock into the pool. There is also a speed retrieve event, where the dog races into the water, grabs a toy and returns as quickly as possible, and an extreme vertical contest, where dogs spring into the air to try and snag a bumper suspended above the water.

At one previous brewery event, Vandenburgh recalled, a golden retriever cleared 21 feet.

Loper pointed to dogs that have built real reputations in the sport. For years, she said, a rescue pit bull named Tango competed at past Greenport events and eventually made it to the world championships. Last year, a dog named Piper went on from Greenport to the national championships and placed 25th out of 110 dogs, she said.

Wilhelm said another crowd favorite from last year was a large white dog named Boo the Sammy. The mix of serious players and local dogs willing to just give it a shot is part of the appeal.

Loper said her June event at the Polo Grounds will be more ambitious than last year, but that plans are still in development. Wilhelm said organizers want a “bigger, better, more fun, more family oriented” weekend this year. She said a large inflatable obstacle course that was a hit with kids last year will be back.

Wild cards

The June event has been designated a Wild Card by DockDogs, the national company that runs most of the competitions, giving participating dogs a chance to earn double points. Wilhelm and Loper hope that status attracts more serious competitors from the regional dock-diving world.

Loper said last year’s Polo Grounds weekend brought 21 businesses on board and returned $14,000 to the community — $4,000 to the Greenport Fire Department and $10,000 to Greenport Skate Park Inc. She said the fire department will be a beneficiary “for as long as we do this,” but that they’re still working out where the rest of the proceeds will g0. One idea, Loper said, is to invest proceeds into a new initiative to build a dog park in Greenport.

She said that last year’s dock dive visitors moved easily between the event and the village, going for lunch or shopping before heading back to the dock.

“It was just so nice and relaxed and easy for people to transition from the event into the village.”

Vandenburgh said the brewery’s May event will support the North Fork Animal Welfare League, with all net ticket proceeds earmarked for the shelter.

He said the brewery knows how to handle the event logistics after years of hosting it, including the pool setup, off-site parking and shuttle arrangements.

Loper said that her event will continue to host East End animal shelters offering pet adoptions.

Despite their differences, all three organizers acknowledged in interviews that there’s room in Greenport for a lot of flying dogs.

“There’s nothing wrong with having the two,” Wilhelm said.

“The more the merrier,” Loper said.

Vandenburgh was upbeat too, saying he “hopes their [event] is successful too.”