Ideal duration: 1-4 days
Best Time: September to November
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Located in the gorgeous, green Berkshire County, Lenox is a beautiful small town. It is a famous retreat during the summers usually for hiking, orchestra concerts, visiting mansions previously occupied by famous people. It is also known for housing Shakespeare & Company, Tanglewood and others. This makes it a perfect town to enjoy concerts and go hiking during the summer. It is located between the two airports that have national flights, one in New York and one in Connecticut, which make your travel easy.