It's no secret one of my favorite areas in our tri-state region is located across the border in New York's northern portion of Dutchess county. I always recommend a day trip to Millerton, New York. The village is located about a half hour south of Great Barrington, about an hour's drive from Pittsfield and is a hop, skip and jump from the Connecticut border parallel to Lakeville.

When I was working at a radio station in Sharon, Connecticut in the early 1990's, I relocated to Millerton and within a year headed east 4 miles to Lakeville due to the close proximity of my home base in the north west corner. This is a walkable village that features plenty of local shops, a movie theater, great restaurants and a historical library that was established back in 1867. But there's more to explore by enjoying the natural bounty this area has to offer.


For starters, you can walk or bike at The Historic Harlem Valley River Trail, a perfect place to commune with your thoughts as local residents and visitors give this terrain a four star rating. If you're brave enough, some hiking options are available at Bash Bish Falls and neighboring Alander Mountain. There are plenty of places to participate in para sailing and para gliding (I'll pass due to my slight fear of heights).

Cowboys riding a horse over the mountains

The Mountain Valley Farm is a quaint setting for horseback riding as you can check out awesome views of the beautiful Berkshires and New York's Catskill Mountains as guides will take you to scenic locations and there is even an opportunity to book a public rustic or corporate event and a wedding would be ideal with the breath taking background. Check out their web site to make an appointment and see for yourself.

You can learn more about this beautiful hamlet in our listening area by checking out the village of Millerton's web site by going here. Guaranteed, you'll be in agreement with yours truly on why this area is truly one of my all-time top destinations. See you at some point in the vicinity of routes 44 and 22 in neighboring New York.

LOOK: Here are the best lake towns to live in

Many of the included towns jump out at the casual observer as popular summer-rental spots--the Ozarks' Branson, Missouri, or Arizona's Lake Havasu--it might surprise you to dive deeper into some quality-of-life offerings beyond the beach and vacation homes. You'll likely pick up some knowledge from a wide range of Americana: one of the last remaining 1950s-style drive-ins in the Midwest; a Florida town that started as a Civil War veteran retirement area; an island boasting some of the country's top public schools and wealth-earners right in the middle of a lake between Seattle and Bellevue; and even a California town containing much more than Johnny Cash's prison blues.

More From WBEC FM