The Grand River originates as a humble stream in a farmer's field near Dundalk, gradually evolving into a modest river as it meanders through the countryside. The Headwaters section of the Grand Trail encompasses quiet rural roads and a portion of the Upper Grand Trailway, offering scenic views as it intersects the river multiple times. The route passes through two main communities, Dundalk in Grey County and Grand Valley in Dufferin County, providing opportunities for dining and supplies.

Dundalk serves as a hub for the surrounding agricultural areas, with amenities like the CP Rail Trail passing through town, catering to outdoor enthusiasts. Meanwhile, Grand Valley offers a taste of local cuisine, inviting travelers to experience the area's culinary delights. Nearby Luther Marsh, managed by the Grand River Conservation Authority, provides opportunities for canoeing, birdwatching, and hunting, with seasonal restrictions in place to protect wildlife and ensure a safe environment for visitors.