Engine failure derails Greenport miniature railroad just before Halloween

A mechanical issue with the engine of Greenport’s popular miniature railroad has forced the village to cut short the train’s 2025 run — derailing this year’s Halloween festivities.

The Greenport Rotary Club will pay for rebuilding the failed engine, though officials have not disclosed the cost.

“The Rotary Club has stepped forward and we’ve said to the village, ‘We will gladly pay for the rebuilding of the engine,’” said Richard Israel, a Greenport Rotarian who has championed the miniature railroad since its inception.

The mini-railroad runs on a Wisconsin motor that has been out of production since the 1970s, making both parts and expertise difficult to find. Two local shops will remove the engine, prepare it for transport, and reinstall after it is fixed.

“It’s going to be sent off to Pennsylvania to be rebuilt, and as soon as it comes back, it will be put back into the locomotive,” Mr. Israel said. “Hopefully that will make the train a lot more reliable, and it can run for more days than it has been.”

The miniature train first began running four decades ago. Frank Field, a Long Island Railroad engineer who moved to Greenport in the 1970s, built the first mini-railroad behind his Webb Street home and offered free rides to local kids on Sundays from 1985 to 2012.

When Mr. Field retired, he approached the Greenport Rotary in hopes of keeping the tradition alive. The revived train, dubbed the “Joe Cherry Choo Choo” in honor of late Rotarian Joe Cherepowich who led the initial campaign, took more than eight years to relocate to its current spot on Moores Lane next to the skate park.

Mr. Cherepowich died in 2019.

Working with village officials, including former mayor George Hubbard Jr., the Rotary explored multiple locations including Mitchell Park and the area near the North Ferry terminal before settling on the village-owned property.

“We want to get through this adventure so that we can make it reliable, so tourists can come and utilize it, just like the carousel,” Mr. Israel said. “It has become a great attraction, and that’s what we had hoped for Greenport, because it helps our local economy.”

The Rotary hopes to have the train back running again by Memorial Day 2026.