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The founding of Guilford is the story of three Roberts: Robert Low, Robert Herring Sr., and Robert Herring Jr. Of course, others helped also. There were the Bennetts, and Evertons, but it is the three Roberts that we have the most details about. Other settlers lived in the area earlier, not to mention the Penobscot Tribe, but they did not go about development in as systematic a manner.
In 1803, Robert Low and Robert Herring Sr., who both became deacons in the Baptist Church, bought a large tract of land from Bowdoin College. They cleared the land, where Guilford now stands, to make homes and farms, and brought their families to the area in 1806. In a historical sketch written by Robert Low, he said they were determined "to admit on their part no person as a settler who was not industrious, orderly, moral and well disposed." In this, they apparently succeeded because "for many years thereafter lawsuits and broils among neighbors were known only in name."
Before coming to Guilford, Robert Herring Sr. was a sailor until he was "struck down with the force of Divine truth" and fell unconscious on his ship. He revived, full of religious fervor and left the sea. He founded the first church in Guilford in 1813. Later when boards were scarce, he started a brick-making operation to help the town grow.
Robert Herring Senior's son, Robert Lowe Herring Jr., was among the first settlers. He brought his family from New Gloucester, ME, during mid-winter with a yoke of oxen and a sled. The trip with his wife (Mary Wagg) and two-year-old daughter Charlotte took a week. They brought a few "absolutely indispensable household articles" with them, including a kitchen chair that Mary used, which was known as "mother's chair" as long as she lived. This chair survived at least until 1907-the posts worn nearly to the lower rungs from constant use.
Robert Herring Jr. and one of the Bennett brothers built the first sawmill in Guilford on Salmon Stream, setting the stage for the town's reputation as an industrial center. After ten years, they abandoned it due to insufficient waterpower. In 1824, Robert Jr. bought the rights to build a mill where Guilford now stands for the cost of a cow. Soon a dam was built across the Piscataquis River and the sawmill was running. Eventually Robert Jr. sold the farm he owned near Low's Bridge and bought a large tract of land in North Guilford and moved his family there. He built a sawmill, which was known as Herring's Mill.
Both Robert Jr. and his father had 11 children each. Robert Jr. died in 1847, about a year after the heartbreak of seeing his youngest son, Alvin, die in a tree-felling accident.
Historical accounts say that Robert Jr. was "well-fitted for pioneer work. Robust in mind and body, no combination of obstacles and hard labor changed his course once he determined upon the accomplishment of a certain purpose. He enjoyed overcoming difficulties-the greater they were, the greater his satisfaction when they were surmounted. The sight of suffering, in man or beast, moved him to tears. No one was ever turned from his door unwarmed or unfed. No neighbor in difficulty or distress ever appealed to him in vain for aid."