4. Sleepy Hollow, Hudson Valley
381 N Broadway, Sleepy Hollow, NY 10591, card
Do not miss it: Great Jack O’Lantern Blaze, Headless Horseman Bridge, Sleepy Hollow Cemetery
What to eat: Lefteris Gyro, Bridge View Tavern & Beer Garden, Sweet grass grill
Where to stay: Search for hotels in the area
Weather average: 65° / 46° F
It is best known as the setting of Irving’s The Legend of Sleepy Hollow, so of course October is the best time to visit! Because peak foliage starts earlier in the Hudson Valley than in New York, you’ll get a chance to appreciate all the colors.
They also have festivals and events that celebrate Halloween and the fall season. Don’t miss the Great Jack O’Lantern Blaze, featuring more than 7,000 hand-carved pumpkins.
We really wanted to go while living in New York, but we planned too late and the tickets sold out before we knew it. In other words: get them as quickly as possible.
October events in Sleepy Hollow: Sleepy Hollow cemetery at night (1-31), Awesome Jack O’Lantern Blaze (1-31), Sleepy Hollow International Film Festival
See more: 21 Best Places to Visit in Upstate NY
