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Greenport (Columbia County)

Why we love it

“I can make more and better landscapes in this way than by tampering with canvas and paint in the studio,” said renowned Hudson River School painter Frederic Church. He was referring to the grounds of Olana, his hilltop home near Hudson. Running the 5 miles of carriage roads he laid out offers a great way to explore the full extent of his designed landscape of flower-filled meadows, woodlands, a lake, and — everywhere — breathtaking vistas of the Hudson River and Catskills. The course can be hilly at times, but you’ll gasp as much in awe as in exhaustion.

More to explore

Take a guided tour of Church’s mansion, one of the Hudson Valley’s most interesting and unusual historic houses. A trail from Olana connects to the Hudson River Skywalk (across the Rip Van Winkle Bridge) and the Thomas Cole National Historic Site, home of Church’s mentor.


  • 5 miles of carriage roads traversing beautiful, varied landscape
  • Spectacular views of Hudson River and Catskill Mountains

Directions, hours, etc.: