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Eastanollee's land was inhabited long before European settlement by Indigenous cultures, including the Mississippian period people who established villages along rivers and creeks. Later, the Cherokee and Creek talents shaped the region, with trails and waterways guiding movement and sustenance. Through the 18th and early 19th centuries, the lands around what is now Eastanollee remained largely wilderness, interspersed with homesteads as the frontier pushed northward.

In the early settlement period, agriculture, small mills, and timber comprised much of the local economy. Families who arrived cleared land along the creeks, farmed subsistence crops, raised livestock, and harvested timber. Water power from streams enabled sawmills and small grist mills to operate, serving both local needs and trade with neighboring communities.

As time progressed, roads were laid down to connect Eastanollee with larger hubs. A post office was established in the latter half of the 19th century, anchoring the community. Bridges were built over streams, and paths were improved into roads, often following earlier Native and settler trails. Though Eastanollee never became a large city, its proximity to the county seat and to Toccoa brought increasing access to services, markets, and transport.

Community character has always leaned rural, with a strong sense of local identity. Churches, such as early Baptist congregations, played central roles in shaping community gatherings, education, and social life. Families, many with deep roots in the area, held together networks of kinship and neighborliness. Through the 20th century, Eastanollee retained its quiet pace, valuing natural surroundings, the creeklands, forested hills, and views that draw those seeking calm outside densely populated areas.

Today Eastanollee is appreciated by homeowners who want to balance natural beauty and rural tranquility with access to amenities in Stephens County. The area offers modest commercial options, community institutions, and is not far from larger shopping, schools, and medical services. Outdoor recreation, low traffic, and scenic landscapes contribute to its appeal.