Questing in New Marlborough. As the town of New Marlborough was being settled in the first part of the eighteenth century, one of the first cluster of homes was built atop Leffingwell Hill. Houses and outbuildings were built atop feld stone foundations while pasturage and roads were bounded with carefully crafted stone walls. Also present was a fortified enclosure built of logs and stone where the earliest settlers took refuge if they felt threatened. In the early 1700s Philip Brookins and his wife were one of the families that lived at Leffingwell. According to tradition it was in the log-and-stone fort that Mrs. Brookins gave birth to twin girls, the first non-Native American babies born in the Berkshires. The location of the fort is not exactly known, but local custom holds that the fort stood at the edge of the field a few yards east of the brook where the path first enters the field. Leffingwell was abandoned during the economic depression of the late 1800s when the remaining families left the hilltop and New England and moved to the Midwest.

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