Overview:
The Berkshires are not an exact location that you can simply enter into your GPS. They encompass the totality of rural western Massachusetts as New England mingles with the Hudson Valley of New York. They also represent a feeling of escape. A century ago, they were a popular spot for the gilded urbanites of Boston and New York to decamp; a pastoral Newport if you will. Nowadays, the Berkshires offer a different freedom. A chance for those same urban denizens of the northeast corridor to temporarily give up their ersatz connections to constant connectivity and hyperproductivity and seek out a bucolic and verdant holiday to recharge with friends and family and let the mind meander. A fuel for introspection and creativity, the area has been a residence to famed authors Herman Melville and Elizabeth Kolbert, artists such as Norman Rockwell, and even tempting Hollywood glitterati such as composer John Williams and Meryl Streep to buying vacation homes. While peak season in the Berkshires is the summer, we went with some friends in late March as a spring getaway from New York post-vaccination. Read below for our recommendations.
WHERE TO STAY:
There are multiple towns that dot the North-South axis of western Massachusetts, all of which could serve as a potential place of stay. To minimize driving time, it is best to pick a location based on the activities/interests you are likely to pursue. Along the southern edge is Great Barrington. Along the middle are Stockbridge, Lee, Lenox, and Pittsfield. And along the northern edge is Adams. We picked an AirBnB in Lee which offered easy access to multiple points of interest.
WHEN TO GO:
As one could imagine, Summer is the peak season here. Tanglewood music venue (the summer home of the Boston Symphony Orchestra since the 1930s) serves as a magnet to many tourists. Of course, that would result in a commensurate increase in prices for lodging, etc. If you are looking for some value, the shoulder seasons of Spring and Fall have a significant decrease in costs. However, please note, that some restaurants are often closed for parts of Spring/Fall.
WHAT TO DO:
This was a pretty leisurely trip for us. We went with 2 other couples (all of whom had left our respective kids at home) for a trip seeking rest, relaxation, and mirth among the company of friends. So we balanced our time between catching up at the AirBnB and exploring the confines of the Berkshires. Instead of a robust itinerary, our recommendations will be more of what can be paired together geographically.
MONUMENT MOUNTAIN (Great Barrington)
-A great hike that affords some tranquil views of Housatonic River Valley.
https://www.tripadvisor.com/Attraction_Review-g41586-d2008981-Reviews-Monument_Mountain-Great_Barrington_Massachusetts.html
https://thetrustees.org/place/monument-mountain/
NAJI’S (Great Barrington)
-If you did the above hike, you definitely deserve this hearty meal. Understated (or as the kids would say “low-key”) flavorful Lebanese eatery
https://www.yelp.com/biz/najis-lebanese-restaurant-great-barrington
NORMAN ROCKWELL MUSEUM (Stockbridge)
-Honoring one of the many creatives that made the Berkshires home, the Normal Rockwell Museum has the largest collection of Rockwell art anywhere. This museum really captures his evolution as an artist and we strongly recommend it.
https://www.nrm.org/
https://www.tripadvisor.com/Attraction_Review-g41850-d108873-Reviews-Norman_Rockwell_Museum-Stockbridge_Massachusetts.html
HILLTOP ORCHARDS (Richmond)
-Apple orchard with Artisanal Craft Ciders, Cider Donuts, and Wine/Cider Tastings. A fun stop as you explore the Berkshires
https://www.yelp.com/biz/hilltop-orchards-richmond
https://www.hilltoporchards.com/
LENOX, MA
-walking, browsing, and eating in the different boutiques and restaurants in this well-maintained town that feels like Pleasantville
BERKSHIRE MOUNTAIN BAKERY (Pittsfield)
-We were skeptical. After all, we live in NYC. And this was a pizza spot in the Berkshires in a strip mall. But if you love sourdough bread, this was some phenomenal pizza. There was a reason it was featured in a Netflix documentary: “Cooked”. We strongly recommend it.
https://berkshiremountainbakery.com/
https://www.yelp.com/biz/berkshire-mountain-bakery-pittsfield-4
DISTRICT KITCHEN & BAR (Pittsfield)
-A fun well-done gastropub.
https://www.yelp.com/biz/district-kitchen-and-bar-pittsfield
https://district.kitchen/
