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Sleepy Hollow 150th Anniversary Car Show

May 18 @ 1:00 pm - 5:00 pm


This event offers a delightful blend of nostalgia and respect for Sleepy Hollow’s automotive heritage, featuring an impressive array of classic vehicles that have left an indelible mark on the village’s identity. Alongside classic, antique, and muscle cars, families can enjoy food trucks, music, and a bouncy castle. Rain date: May 19th.

Automobile manufacturing was a staple of the local economy for nearly a century, ending its run in 1996. The Stanley Motor Carriage Company opened a plant on Kingsland Point in the 1890s to produce its steam powered “Stanley Steamer” automobiles. On the other side of the mouth of the Pocantico River was a factory of Ingersoll-Rand Drill Company (see postcard above, Rand is on the bottom half with the red water tower). Sometime in the early 20th century the properties came under control of the Maxwell-Briscoe Company, which manufactured the Maxwell line of automobiles.

After a 1907 fire at the North Tarrytown plant, Maxwell-Briscoe moved the bulk of its operations to Indiana. Financially stretched to the breaking point in a recession following World War I, Maxwell-Briscoe was taken over by Walter Chrysler in 1921. With the formation of the Chrysler Corporation in 1925, the Maxwell line was phased out. Walter Chrysler, however, remains a fixture in Sleepy Hollow to this day—his permanent residence is a large mausoleum in Sleepy Hollow Cemetery.

Chevrolet, not yet a part of General Motors, took over part of the facility alongside Maxwell in 1914. Chevy was integrated into GM in 1918 which operated the plant until June 1996. Over the decades the plant expanded by filling in the bay where the Pocantico River emptied into the Hudson and by acquiring part of the adjoining county park.


May 18
1:00 pm - 5:00 pm
Event Categories:
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Village of Sleepy Hollow
View Organizer Website


Sleepy Hollow River Walk Park
Westward Drive
Sleepy Hollow, NY 10591 United States
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There’s something for everyone in Sleepy Hollow Country—farmers markets, live music, street fairs, historic homes, hiking trails, kayaking and boating on the Hudson River. Halloween season brings even more for the whole family—haunted hayrides, blazing pumpkins, costumed 10K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow.