Top Travel Days of 2024, A Winter Escape to Troutbeck
After visiting every nook and cranny of New England and New York state over my lifetime, I thought I’ve seen it all. But I was wrong! One day last February, we dropped the kids off to ski at Catamount in the Berkshires while we climbed Monument Mountain, the peak Herman Melville and Nathaniel Hawthorne made famous when they made the same climb in 1850. Then we headed south for an hour into the heart of Hudson Valley’s farmland. I had visited the towns just over the border in Litchfield Hills, Connecticut, like Kent, Sharon, and Salisbury, but had never ventured into the New York state side to see Millbrook, Millerton, and Armenia, home to the 250-acre estate hotel called Troutbeck. We would spend a glorious winter weekend here, dining at their exceptional restaurant, playing games of pool, and reading by the freshly lit fires both inside and outside.
Come summer, this bucolic getaway, which has a rich history as being the site where the NAACP originated, is a serene getaway, replete with tennis courts, outdoor pool, fishing stream on premises, and nearby bike trail to take in the velvety green fields and mountains. Yet, we loved it in winter, especially exploring the nearby towns. We stopped at the well-known teahouse, Harney and Sons, a winter food market, wonderful Oblong Books, and a historic one-room schoolhouse in Millerton. Next stop was Salisbury and the classic White Hart Inn for a lunch of hot soups, salads, and freshly made breads. That night, we visited the village of Millbrook for an intimate dinner at Canoe Hill. Then it was back to Troutbeck for another game of pool and nightcap at the fireplace. We’ve sent a number of clients to Troutbeck over the years, so it was good to finally go in person and happily give it our stamp of approval.
The Trustees
Lisa and I spent two nights in the Berkshires last week checking out 
With mild October temperatures, many of the classes were held outdoors. We pounded those drums on a grassy patch near the large pool. Some fitness classes like spin cycling are still on hold until after the pandemic, but the spa was open for massages and facials. When weather cooperated, dining was outdoors on a large patio. Otherwise, you’ll be having meals indoors in a large restaurant, Harvest Moon, with high ceilings. They do a good job of limiting and separating people in the restaurant, especially during dinner, when you have to reserve a time in advance. The food, like most classes, is included in the price. As you would expect, they try to make it healthy, with numerous vegetarian and fish options. Everything we tried was delicious, from the fresh greens to avocado toast to grilled salmon and tuna ceviche. Unlike Canyon Ranch, they do serve alcohol. There’s also have a café next door, Roost, to grab lattes and yummy cookies and casual fare, all-inclusive. Rooms were spacious with large balconies outdoors for taking in the view.
Every other year, Lisa travels to Las Vegas in the heat of August to meet with hundreds of travel suppliers, hotel GMs, cruise companies, and many other faces in the travel industry for Virtuoso Travel Week. This year, we had those meetings for 4 very full days from the comfort of our office thanks to Google Meet. I have no idea how they can organize hundreds, if not thousands of meetings, at the same time without crashing. But, lo and behold, every 10 minutes we clicked on another link and had our private sessions with the people we most wanted to speak with. This week, I will present the highlights from those meetings: