[3] The name[4] Ashtabula derives from the Lenape language phrase ashte-pihële, which translates to 'always enough (fish) to go around, to be given away'[5] and is a contraction of apchi ('always')[6] + tepi ('enough') + hële (verb of motion).

Grapes are a popular crop and there are several award-winning wineries in the region due to the favorable microclimate from the nearby lake.

At the time of contact, Ashtabula County appears to have been divided between the Erie people in the east and the Whittlesey culture in the west.

[9] The Erie were an Iroquoian people, who were organized like the Iroquois, believed in a similar religion and lived in longhouses in palisaded villages and may have had a burial ground at what is now Erie, PA, whereas the uncontacted Whittlesey are mostly believed to have been Algonquians, who also lived in longhouses at the time of contact (after having gone through prior periods of living in wigwams and Fort Ancient style houses) in villages surrounded by earthen berm walls and had smaller, local burial grounds near each settlement.

The French were the first to explore the Great Lakes by ship and, having never met the inhabitants, saw the continuation of longhouses and mistakenly assumed the entire region had belonged to the Erie.

The Jesuit Relations claim rumors of infighting between the Erie and an unknown nation to the west of them who were similar to other Algonquian peoples the French had already encountered in the years prior to both tribes' eradication.

Three known village sites have been documented by archaeologists from this period in Windsor [11] (located inside what is now a private children's Summer Camp) and two at Conneaut.

After Europeans arrived in the Americas, the land that became Ashtabula County was originally part of the French colony of Illinois Country, which was ceded in 1764 to Great Britain, along with the rest of Canada (New France) and incorporated into the Province of Quebec, though generally came to be referred to as Ohio Country.

This group, known as the Wyandot,[13] later ceded settlement of most of the territory roughly between what is now Cleveland, Akron, the Mahoning River and the Ohio-PA border to be a common hunting ground, shared by themselves, the Seneca, Shawnee, Lenape and even the Ottawa, or Mississauga, who lived at the western end of Lake Erie, at the time.

The Ottawa were the only residents, who maintained two known hunting camps in Ashtabula County- one at Conneaut, and the other at Andover.

After the end of the Northwest Indian War, (a conflict which erupted shortly after the American Revolution between the fledgling United States and all the remaining tribes of the Great Lakes region in territory the US claimed) in the 1790s, the Natives were made to turn over ownership of the area to the US via the Treaty of Greenville, and the remaining Ottawa residents were evicted.

[15][16] That being said, early settlers recalled that some of the Ottawa remained in the region for an additional thirty years, having been sighted all over Trumbull, Geauga and Portage Counties until sometime around the War of 1812, along with Senecas who lived around Streetsboro.

During the pre-Civil War period, the entire Western Reserve area of Ohio was anti-slavery, but Ashtabula County was at the center of the resistance.

[34] According to the accompanying table, Ashtabula County voted for the Democratic candidate for president in every election between 1988 and 2012.