It’s no secret that one of my favorite areas in our tri-state area is across the border in the northern part of Dutchess County, New York. I always recommend a day trip to Millerton, New York. The village is located about half an hour south of Great Barrington, about an hour’s drive from Pittsfield and is a jump from the Connecticut border parallel to Lakeville.
When I was working at a radio station in Sharon, Connecticut in the early 1990s I moved to Millerton and within a year headed east 4 miles from Lakeville due to the proximity from my home port in the northwest corner. It is a pedestrian village which includes many local shops, a cinema, excellent restaurants and a historic library that was established in 1867. But there is more to explore as you take in the natural wealth this region has to offer.
To start, you can walk or cycle the historic Harlem Valley River Trail, a perfect place to commune with your thoughts as local residents and visitors alike give this land a four star rating. If you are brave enough, some Hiking options are available at Bash Bish Falls and nearby Alander Mountain. There are plenty of places to practice paragliding and paragliding (I will pass because of my slight fear of heights).
The mountain valley farm is a picturesque setting for horseback riding as you can verify stunning views of New York’s beautiful Berkshires and Catskill Mountains as the guides will take you to scenic spots and it is even possible to book a rustic or corporate public event and a wedding would be ideal with a breathtaking background. Check out their website to make an appointment and see for yourself.
You can learn more about this beautiful hamlet in our Listening Zone by visiting the Millerton Village website by going here. Guaranteed you will agree with yours truly as to why this region truly is one of my best destinations ever. Meet near Highways 44 and 22 in nearby New York City at some point.
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Most of the cities included jump out to casual observers as popular summer rental spots – Branson of the Ozarks, Missouri, or Lake Havasu in Arizona – it might surprise you to dive deeper into some of the quality of life offerings in the area. beyond the beach and vacation homes. You will likely gain knowledge in a wide variety of Americana: one of the last 50s-style drive-ins in the Midwest; a town in Florida that started out as a retreat for Civil War veterans; an island with some of the best public schools in the country and wealthy people in the middle of a lake between Seattle and Bellevue; and even a Californian town containing a lot more than the blues of Johnny Cash’s prison.