I highly recommend all of the properties run in the Berkshires (and the Hudson Valley) by Posto Property Management because the management team did a great job of communicating with us and stocking the home with everything we needed. It was a great option for us because we were a larger group and needed 4 bedrooms and Monterey is a quick, 10-minute drive to Great Barrington. When we visited Great Barrington, we rented an Airbnb property in nearby Monterey through Posto Property Management. The dining room at our Posto Property Airbnb Where to Stay: And lastly, in the fall, visit during peak foliage to take in the magical colors of the leaves. Plus, the region really comes alive with a variety of cultural events and festivals. Summertime means you can enjoy all of the typical outdoor activities. There are also many great museums in the area where you can take in some culture. In the spring, you can enjoy hiking or a stroll through town. If you visit in the winter, you can go skiing and enjoy a variety of winter sports. One of the things I love about Great Barrington and the Berkshires, in general, is that it’s an area worth exploring year-round. The Best Time of Year to Visit Great Barrington From there, it’s a 45-minute drive to Great Barrington. An alternative is to take an Amtrak train to Hudson, NY. Pittsfield is about a 30-minute drive to Great Barrington and car share services are readily available in the area. This option is only available during the summer but it’s a great alternative if you don’t have access to a car. Amtrak has just introduced its Berkshire Flyer direct service between Manhattan and Pittsfield, Massachusetts. The con is that this bus service is currently only offered 3 times a week, Fridays through Sundays, at 9:30 am. The pros of taking the bus are that it’s only a 3-hour ride and the bus drops you directly in Great Barrington. You can also take a Peter Pan bus from the Port Authority bus station. There are three ways to get from New York City to Great Barrington, by bus, train, or car. Great Barrington was also officially named an Appalachian Trail community in 2009, which makes it a popular stop for hikers and the perfect weekend getaway in the Berkshires for city dwellers alike. Its main thoroughfares are lined with well-curated shops and popular restaurants. Great Barrington is also the largest town in the Southern Berkshires and offers a very pedestrian-friendly town. According to Airbnb, it’s the most popular town to visit in the Berkshires. And I’m not the only one who feels this way. While the Berkshires is full of small, charming towns like Lenox, Stockbridge, and North Adams, Great Barrington is the perfect town to base yourself for exploring the entire region. Great Barrington is located in the Berkshires, a rural region in the mountains in Western Massachusetts. So keep reading for all of my travel tips and recommendations! Now I want to share everything we did so you can plan the perfect weekend in Great Barrington as well. I recently spent a weekend getaway in Great Barrington in the Berkshires with my husband’s family and we had such a great time hiking, eating, shopping, and exploring. And that’s exactly how I feel about Great Barrington, in the Berkshires in Massachusetts. One of the things I love about travel is revisiting a place I’ve been to years ago and rediscovering everything I loved about the destination in the first place.
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