Little is known of the Downeast coast prior to the mid 1700's. While exploration of Maine had begun in 1524 when Giovanni da Verrazzano, an Italian explorer made land fall in what is believed to have been the Casco Bay. What he found in Maine was vastly different than the welcome that he received in Rhode Island, New York and the Carolina's. Here he found the Natives to be hostile. He labeled the natives of this area "Terra Onde di Mala Gente" which means "Land of the Bad People". Thankfully this title did not stick.

There was little recorded contact with Native American's in 1524. There is discrepancy regarding the names of Native American groups. At this time, Samual de Champlain described them in four large groups. The Souriquois thought to be the present day Micmac tribe were located mainly in New Brunswick, Nova Scotia and along the coast of Maine. The Etchemin were located between the Kennebec and St John river. Bothe the Souriquois and the Etchemin relied solely on hunting, gathering and fishing. A third group the Almouchiquois, located west of the Kennebec were able to farm as well as hunt for survival. Because of the milder climate they were able to grow corn, beans and squash. The fourth group were the Abenaki located between the Chaudiere river and Kennebec River.

At this time what we know as Pembroke was undiscovered. The earliest permanent settler of what is now Pembroke was Hatevil Leighton. Along with several other early settlers he envisioned great potential in this area. William Clark cleared land for a farm on the eastern shore now known as Clark Side. Captain Robert Wilson, formerly of the English Army settled on Campobello Island but remained an active participant in the lumbering operation that he established with Hatevil Leighton and William Clark. William Wilson, a relative of Captain Wilson also settled nearby. Also a great contributor at the time was Edmund Mahar (Meagher). He built a tidal falls that was later named for him. He was known to be a skilled pilot of boats and mastered the treacherous waters of the falls. Now known as Reversing Falls. Later assisting many explorers as they journeyed through the falls. John Denbow, Hatevil’s father in law came from Narraguagus to be closer to his daughter. He built his home at a point east of Hatevil’s cabin. James Blackwood, a former English Soldier from Burgoyne’s defeated army, settled at Young's Cove and Ox Cove. He raised a large family and perpetuated his name in the area. Joseph Dudley a former English Soldier from Burgoyne’s defeated army, settled at Young's Cove and Ox Cove. He raised large families and perpetuated his name in the area. Richard Smith, little is known of him other than he had a son named John. John had numerous descendants, many who were sea captains. Daniel Gardner was a wounded veteran of the Revolutionary War. He settled at the lower end of Young's Cove. Captain Richard Harper moved to the Leighton's Point from Township 10 (now Edmunds) about 1780 and built a house on a small cove a little south of Young's Cove. David Reynolds a Revolutionary War Veteran only lived on Leighton Neck for a short time before he moved to Township 10 in 1792. Joseph Bridges settled in 1780 at Birch Point in Township No 1, now Perry. After being annoyed by the dogs of a nearby Native American Village he moved to Ox Cove in Pembroke. Scipio Dalton (Dutton) was an African American man who was once a slave of the Bowdoin family of Boston. He and his family lived on the eastern peninsula near the Narrows. Both Sipp’s Narrows and Sipp’s Bay is named for him. James Wood took over an abandoned clearing on the eastern shore less than a mile north of Scipio’s cabin.

In 1786 General Benjamin Lincoln of Hingham, Massachusetts lead the first organized effort to colonize what is now known as Downeast Maine. He led the Hingham Colony in what is known to be the first planned colonization of Township No. 2