The Town of New Ashford, with its rough and mountainous terrain, was established in 1781.  The town lies in the northern part of Berkshire County and has always been one of the smallest communities in the Commonwealth.  New Ashford is well supplied with water, since the Green River rises in town before flowing north, but has never had very much arable land.  Despite that, the earliest settlers, Evans Roys and Hezekiah Beach, arrived from Connecticut in 1762 and Peregrine Turner felt optimistic enough to open the first store in town shortly after. 

Several town residents were actively engaged in the battles of the Revolution and were present at the Battle of Bennington in 1777 and the surrender of Burgoyne.  In the 19th century, a census of the town showed that of 44 adults listed in a business directory, 38 reported farming as their primary occupation,  with only a half dozen working as laborers in the saw and grist mills or selling farm equipment.  In 1885, the Berkshire County Gazetteer noted that "no doctor or lawyer has ever been located in town".  

New Ashford is sited in a picturesque gorge, lying between the giant foothills of Saddle Ball and a spur of the Taconics.  The beauty of its natural surroundings very early on dictated a new business for residents, the tourist business, and the first hotel was opened by William Starkweather.  A tourist guide of 1889 describes the views in town as creating the effect of "the Switzerland of Berkshire".  The view from the summit of Saddle Ball, one of the prominent peaks in northern Berkshire County, was generally felt to be one of the grandest in the area. 

In addition to Saddle Ball, a portion of 2700' high Brodie Mountain is in New Ashford, which became the site of a growing winter recreation industry in the 1930's, bringing in skiers and ski racers from around the state.  The town had some valuable beds of marble and an interesting cave over 100' long, with 20' high arches inside and glittering stalactites adding to its enticements for tourists.