4. Sleepy Hollow, Hudson Valley
381 N Broadway, Sleepy Hollow, NY 10591, map
Don’t Miss: 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 Avg: 65° / 46° F
It’s best known as the setting of Irving’s The Legend of Sleepy Hollow, so naturally, October is the best time to visit! Since peak foliage starts earlier in the Hudson Valley than NYC, 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 with over 7,000 hand-carved pumpkins.
We really wanted to go while we lived in NYC, but we planned too late, and tickets sold out before we knew it. In other words, get them ASAP.
October Events in Sleepy Hollow: Sleepy Hollow Cemetery at Night (1-31), Great Jack O’Lantern Blaze (1-31), Sleepy Hollow International Film Festival
See More: 21 Best Places to Visit in Upstate NY
