Pleasant Drive Through Tarrytown and Sleepy Hollow

Two small Hudson River villages connected by a slow, walkable main street — Broadway here is everything Broadway in Manhattan is not.

Westchester County · Drive · about 20 min · 4 miles · Pleasantness: High

Why this route is pleasant

• Slow village speeds, not highway driving
• Independent shops and restored 19th-century storefronts
• Hudson River appears at every cross street
• Rich tree cover through residential blocks

What you'll see

• Tarrytown Music Hall (1885)
• Patriots Park and the Captor's Monument
• The Old Dutch Church and burying ground
• Philipsburg Manor

Best time to go

Weekday afternoon, or weekends in October during Sleepy Hollow's Halloween events.

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