Michael Rogovin provided the following information on the Berkshires:
The Berkshires offers beautiful country for hiking, walking, biking, fishing, boating, and golf (plus skating and skiing in the winter). It is also one of the most art & culture saturated areas of the country, with numerous theatre, music, dance, opera and museums, along with more ceramic, glass, craft and antique shops in all price categories than one could visit in a lifetime. There are many activities for children, both cultural and recreational. In addition to many specialty shops featuring locally produced items, there are more conventional shopping centers and malls, including several outlet malls with major bargains.
There are many options for the kosher traveler. Accommodations range from motels to resorts, plus many fine inns and B&Bs. However, we chose to stay at the Ponds at Foxhollow. The Ponds offers 1 bedroom condos that sleep up to 4 and 2 bedrooms sleeping up to 8, with deck and fireplace and a full electric kitchen in each unit. It is located right on Route 7 near Lenox. When we arrived, the oven was still warm from the self clean cycle--ready to use as kosher! There is no eruv, but the rooms and clubhouse were spacious and we were able to enjoy a peaceful and active Shabbat. Ponds units rent by the weekend, or week (Fri-Fri) or day during off season.
The nearby Super Stop and Shop on Dan Fox Drive stocks fresh chicken and glatt beef, along with a large selection of cheese, frozen prepared foods and everything you could possibly need to cook or reheat meals--no need to shlep food with you. Price Chopper also has a good selection of foods. The Berkshires do not have an orthodox community, although a Chabad House just opened in Pittsfield.
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