Painted Tugboats on Display at Esopus Tugboat Trail; Auctioned Off at Tugfest

The Tugboat Trail celebrates one Ulster County town’s maritime history

If you drive down Route 9W (aka Broadway) in Esopus during the summer months, you’ll no doubt notice the 25 model tugboats that dot the side of the road. Each about four feet long and two feet high, these miniature vessels make up the Tugboat Trail, an initiative that began in 2011 to commemorate the village’s bicentennial and its history as a thriving port.

Each year, local artists, businesses, schools, and families decorate the models (which are provided by the town) according to whatever design strikes their fancy. Lois Dekoskie, one of the masterminds behind the trail and its current coordinator, recalls two memorable designs: a boat painted like the Headless Horseman, and a Chinese-themed tug with noodles hanging from its stern. “They each take on their own character, they really do,” she says.

Download 2014 Esopus Tugboat Trail Map
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2014 tugboat trail map

This season featured Noah’s Ark, Old Glory, and the Hudson Valley itself — all depicted in tugboat form. The sculptures will be auctioned off at Tugfest — bids start at $250, most boats sell for $400, although some go as high as $700. Held on the grounds of Headless Horseman Hayrides and Haunted Houses, this September 14* event includes food and live entertainment, with all proceeds going directly to the town.

And who bids on the little boats, you might ask? “Everybody bids on them,” says Dekoskie. “Afterwards, they’re set up in shops, in front yards, in gardens. We are very proud of them.” 

*Editors’ note: The original version of this article listed the event for September 13. The event was postponed due to inclement weather.

If you go…

What: Tugfest
When: Sunday, September 14
Where: Headless Horseman Hayride and Haunted Houses, 778 Broadway (Rte. 9W), Ulster Park
Details: Visit Tugboat Trail’s Facebook page at

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