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.

Exhausted from far too many 5 am wake-up calls, 90-minute drives in and out of Quito to the airport, and long longboat rides in the Amazon, my family was in poor spirits when we arrived in the Galapagos Islands for the last segment of our summer trip to Ecuador. But it’s amazing how a motorboat cruise on the ocean and all that water can wash away the toxins of travel. Listening to our iPods and watching the dolphins and orcas swim beside us, we were relaxed by the time we reached the sea lions lounging on the docks of Floreana. A driver brought us to our lodging for the next two nights,
The ferry ride from Piraeus to Spetses island is a little under 3 hours or you can take the long drive we did through the Peloponnese peninsula to reach the town of Kosta, then take a 10-minute boat ride over to the island. Either way, it’s worth your effort. On Spetses, time stands still, especially when we ran into a large group of bikers circling the island in Victorian garb for the annual Tweed Day celebration. A 26-kilometer loop circles the island past beaches and the rugged shoreline, ideal for bikers since Spetses is a car-free island. Soon we were back at the main square in town, dominated by the classic façade of the
I often joke with my kids that they grew up in the pages of The Boston Globe (the photos on the left are Melanie from a story on mid-coast Maine and Jake from a story on Costa Rica). Lately, I’ve been writing about our family trips for Virtuoso Traveler, like the 
Last Wednesday in Puerto Vallarta, I took a fast zodiac boat ride with the family across glorious Banderas Bay. Led by the outfitter 
The Trustees purchased the 36-acre