This is one of the oldest maps I’ve been able to find, showing the core of Portland in the early years. The large parcels on the right are owned by Francis Pettygrove and Benjamin Stark, both prominent place-names of early history.
This map dates to the inital history of Portland – with the initial land claim by William Overton and Asa Lovejoy, and the subsequent ‘coin-toss’ by Lovejoy and Pettygrove, giving the City is current name. From City of Portland’s Historic Portland Timelines, 1843-1901:
“1945: Overton sells his share of the claim to Francis Pettygrove. Pettygrove and Lovejoy survey the land, deciding to build a city. Previously called The Clearing, Portland gets its name with the toss of a coin with Pettygrove’s home town in Maine winning over Lovejoy’s birthplace in Boston.”