Inn-Hopping in New York’s Hudson Valley and the Bucolic Berkshires

July 9 – 16, 2020

West Point  |  Poughkeepsie  |  Hudson  |  Stockbridge, MA  |  Bennington, VT

Exploring the Culture-Rich Outback of the Northeast

Let’s explore the majestic Hudson River Valley and adjacent Berkshire Mountains – a summertime treat for the senses and soul. We’ll enjoy the charms of three distinctive inns, each serving as our base to explore different regions of the Hudson and adjacent mountain areas. The Buttermilk Falls Inn, just downstream from Poughkeepsie will be our window on West Point, Hyde Park, and the Middle Hudson Valley. The Green River Inn, snuggling into the Berkshire Mountains, will offer beautiful backroads leading to sites around Hudson, NY, and Stockbridge, MA, including the Norman Rockwell Museum. The drive to our last inn, the West Mountain Inn, in rural southwestern Vermont, will take us past Berkshire treats, like Shaker villages, and Herman Melville’s Arrowhead Farm. From the West Mountain, we’ll explore Batten Kill River valley treasures, including Hildene—the Green Mountain estate of Abraham Lincoln’s son, Robert.

Photo credit: Jumping Rocks


• Historic inns: comfortable, inspired accommodations; homemade breakfasts; warm, hospitable personalities

• One-of-a-kind Hudson Valley sites: West Point, the FDR Library, the Culinary Institute of America, the Saugerties Lighthouse

• Hudson Valley and Berkshire estate homes, including Olana, Chesterwood, and Hildene

• Americana in its purest forms: Hudson Valley and New England villages; the Norman Rockwell Museum; Herman Melville’s Arrowhead Farm; the Hancock Shaker village


$4,300 / person (double occupancy; single supplement, $1,075)

Price includes comfortable transportation, accommodation with breakfast for seven (7) nights, 7 dinners, all activities / admissions per the itinerary, guide and concierge service throughout the trip. Price does not include airfare, alcohol, other meals, personal expenditures, or optional trip insurance.

Click the button below to register online, or click here for a printable trip registration form.

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(864) 384 - 6947

Mailing Address

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PO Box 9537
Greenville, SC 29604