In 1648 it was recorded in the old record book that a vote was taken to build a bridge over the Ipswich River, four miles from Reddinge. Its accompanying road ran from Nahant Bay in Lynn through Reddinge, now Wakefield, and then northerly to the present Middleton-North Reading line, proceeding through North Reading into Andover.
The old records describe this road as “the first highway formally laid out” and “Captain Richard Walker, Thomas Marshall, and Nicholas Holt, being appointed by the General Court to lay out the County Highway from Andevour to Reddinge, have thus agreed to follow the cart-way from Andevour to Goodman Holt’s farm, leaving his house about a quarter mile on the left hand, and so on in a strate south or nere a south lyne to the Ipswich River according to the marked trees, and so from the river upon a like strate lyne to the head of a meadow, called great meadow to the saw mill in Reddinge thence through common cornfields to the meeting house.”
In 1658 the General Court “Ordered that there be a highway of tenn poles broad left at each end of all those lotts of upland beyond the Ipswich River.” William Cowdrey, John Smith, John Brown and Jonathan Poole, were selected to divide that tract of land recently acquired by Reddinge, located north of the Ipswich River. They surveyed the land into lotts leaving a “tenn pole highway” at either end. This land then became common land for the use of the town as a highway, watering place and other public uses as it became necessary. The land left for the highway ran parallel to the river on the north side, bypassing the marsh and meadow and staying with the lowland, avoiding the fertile high ground.
In 1707, a way was laid out northward from the vicinity of the present common to the Andover line. This was known as “Sixteen Pole Way” and led through Sergeant George Flint and John Eaton’s land. In 1715 Sgt. George Flint complained to authorities that the road ran through his fertile fields and cut his farm in half. He offered to exchange land to the north with the town if they would relocate the highway westerly of the then existing position. The course of the new road was laid out by Timothy Wiley, Joseph Burnap, and John Goodwin. The old record show “At the north meeting house it is goe next to John Eatens land until it comes within twenty poles of sum low land that joynes to Sart. George Flints orchard, and then goes a slant over to Sargent Flints land fourty pole. Then turns a slant by the hill over to said Eatens line at ye end of the hill, then it is to ly by said Eatens line cross three swamps, then turnes a slant to said Flints line at ye middle mark. Then it is to turn a slant over to Eatens line at ye norwest end of Rattle-snake Rock. Soe by Eatens line till it comes to the foot of the hill at this side Jebit Plaine then it is to turn a slant to Flints line at a Valle at the hether end of said Jebit Plaine.