Prior to European colonization, present-day Westmoreland was inhabited by numerous indigenous tribes.

The upper Connecticut River valley was a popular region for short-term Indigenous villages mostly used for hunting and fishing.

[4] Indigenous peoples did not understand the concept of individual land ownership, which resulted in numerous misunderstandings and conflict between them and English settlers.

[4] The English settlers purchase of land and construction of permanent settlements disrupted the hunting and fishing traditions of the indigenous tribes.

[5] The Pow-wow Rock is a large boulder that was deposited by glaciers and is measured at 12 by 14 by 8 feet (3.7 by 4.3 by 2.4 m) in height.

This part of the river was a favorite Indian campsite, and the settlers who came beginning in 1741 were several times victims of attack.

Hyland Hill, elevation 1,510 feet (460 m) and the highest point in town, is on the eastern border and although it is now private land, it is a local hiking and hunting destination.