Hudson Valley & the Catskills in Two Days: Grand Gardens, Mountain Waterfalls & Stories Beyond New York

Just beyond New York City, the scenery opens into river valleys, wooded mountains, and small towns with remarkable stories to tell. This two-day private tour combines the Hudson Valley’s gardens and presidential history with the waterfalls, spiritual retreats, and mountain landscapes of the Catskills and the Shawangunks.

With an overnight stay along the way, we’ll have more time to explore—and discover how much lies within a few hours of the city.

Day 1: Discovering the Hudson Valley

Our journey begins at Untermyer Park and Gardens in Yonkers, where landscaped gardens, striking architectural details, and views of the Hudson River make a beautiful introduction to the region. We’ll explore its inviting paths and discover a place where garden design and architecture work together to frame the surrounding landscape.

Next comes New Croton Dam and Reservoir. Its monumental stonework and dramatic spillway turn an essential part of New York City’s water supply into an extraordinary sightseeing stop.

At Bear Mountain, we’ll enjoy sweeping views of the Hudson River and the surrounding hills, with time to take photographs and appreciate the valley from another perspective.

Then we’ll continue to Hyde Park, where American history becomes personal. At the Franklin D. Roosevelt Presidential Library and Museum, we’ll explore the challenges and decisions that shaped his presidency, from the Great Depression and the New Deal to World War II. A visit to Springwood, the Roosevelt family home, brings a more intimate dimension to the story, connecting the president’s public life with the place he called home.

Our final sightseeing stop is the gardens and grounds of the Vanderbilt Mansion, where a walk offers a glimpse into the world of the Hudson Valley’s grand country estates.

We’ll spend the night at a hotel in Hyde Park or the Catskills region, with the location chosen according to the season and our route.

Day 2: Waterfalls, Woodstock & Mountain Landscapes

Our second day takes us into a different world: wooded slopes, cascading water, and places that invite us to pause and look a little closer.

At Kaaterskill Falls, we’ll discover one of the Catskills’ most memorable natural sights. The waterfall and its forest setting offer a dramatic contrast to the gardens and estates of the previous day, with opportunities to enjoy the scenery and take photographs.

Near Woodstock, we’ll visit a Buddhist monastery and temple, where we’ll explore the setting and learn about the traditions reflected in its architecture and sacred imagery. We’ll also stop at a nearby Orthodox church, adding another perspective on the spiritual life of this mountain community.

Then it’s time for Woodstock itself. We’ll explore the town’s artistic character, browse its shops and galleries, and discover the place behind a name known around the world.

At Ashokan Dam and Reservoir, the landscape opens into broad views of water and mountains. After the intimacy of Woodstock’s streets and the enclosed woodland around the falls, this is a place to appreciate the scale and quiet beauty of the region.

Our final destination is Minnewaska State Park Preserve, where we’ll enjoy its mountain lake, waterfall, and scenic surroundings. It’s a fitting finish to our journey: fresh air, beautiful water, and time outdoors before returning to the city.

We’ll arrive back in New York with photographs of gardens and waterfalls, stories of presidents and artists, and memories of two days spent discovering a quieter, greener side of New York State.