Sleepy Hollow & Tarrytown
A driving day from Midtown up the Hudson to the Rivertowns: the Gothic Revival mansion at Lyndhurst, lunch on Tarrytown's Main Street, the working mill and manor house at Philipsburg Manor, Washington Irving's grave and the Old Dutch Church in Sleepy Hollow, and a late-afternoon walk around Swan Lake in the Rockefeller preserve.
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From late September to early November the lower Hudson Valley usually brings cool mornings, mild and often sunny afternoons, and chilly evenings, with occasional rain as fronts pass. Fall color in the lower Hudson Valley usually arrives in the second half of October. Days are short: by mid-October sunset is a little after 6 pm, and earlier after that. Wind off the river can make Lyndhurst's lawns feel colder than Midtown. These are seasonal expectations, not a forecast for your travel date; check the NWS forecast the evening before and the morning of your trip.
Admission and parking are separate. Check current conditions before departure.
A driving day from Manhattan up the Hudson Highlands: the riverside lawn at Boscobel, Main Street and the waterfront in Cold Spring, an easy loop and cliff overlook at Little Stony Point, the big daylit galleries of Dia Beacon, and an early dinner on Beacon's Main Street.
A long day up the Hudson from Midtown: Franklin Roosevelt's Springwood home and presidential library, lunch cooked by students at the Culinary Institute of America, the Gilded Age Vanderbilt Mansion above the river, Eleanor Roosevelt's Val-Kill and a late-afternoon walk across the Walkway Over the Hudson in Poughkeepsie.
A long driving day from Manhattan to the far end of Long Island's North Fork: a quiet bay beach and maritime forest at Orient Beach State Park, lunch and the antique carousel on the harbor in Greenport, one unhurried winery tasting on Route 25, and pies from a Sound Avenue farm stand on the way home.
A fall-color driving day up the Palisades Interstate Parkway from Manhattan: the cliff-top view at State Line Lookout, the summit road and stone tower on Bear Mountain, a walk around Hessian Lake, the Trailside Museums & Zoo beside the Bear Mountain Bridge, the West Point Visitors Center and a quiet lake in Harriman State Park on the way home.