Things to Do in NYC This Friday on Columbus Day Monday, Oct 12

Hand-picked every week — checked against organizers’ own pages.

Stumblday's hand-checked ranking of the best things to do in NYC This Friday on Columbus Day Monday, Oct 12: 15 picks, refreshed weekly.

15 picks · checked Sep 28

The 10 picks

#4
The Headless Horseman Files at Philipsburg ManorPhilipsburg Manor, Sleepy Hollow, Hudson Valley
Fridays–Sundays, October 2–31, 2026, timed entry 10am–4:15pm (open Fri Oct 9, Sat Oct 10 and Sun Oct 11, 2026; closed Mondays, including Oct 12)Adults $35

The Headless Horseman Files at Philipsburg Manor

Historic Hudson Valley's daytime Sleepy Hollow headliner: a 45-minute guided walk through Philipsburg Manor where costumed characters hand you clues to the disappearance of Ichabod Crane.

HalloweenSleepy HollowDay trip

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