Charles Swift was a 19th Century newspaper editor and historian. His 1884 history of Yarmouth, available on Google Books, has a map of Old Yarmouth in 1644 (Old Yarmouth including the current towns of Dennis and Yarmouth).
The Pilgrims reached Plymouth in 1620. Written records place English settlers in Old Yarmouth along Cape Cod Bay by 1638-39.
Early on, some began to settle along the upper ponds of Bass River. Samuel Rider was evidently there about 1639 and Francis Baker on the east side of Follins Pond about 1641. One person lived close to Nantucket Sound by 1644, and Swift's map shows a road running from north to south on the western side of his map. Swift doesn't mention other settlers between Follins Pond and the mouth of Bass River, except for Richard Berry who lived near the mouth of the river by about 1649.
Map of Yarmouth (which included what is now Dennis) in 1644 (From Swift via Google Books)
The Google edition is dated 1884, so this is Swift's conjectural map of the area 240 years earlier. He doesn't describe his sources, but I don't think he had sketch maps circa 1644. I assume the map is an amalgam of information about the places where early settlers made their homes, a knowledge of the 19th century road system, local tradition, and common sense. These roads must have been more like primitive trails at this early date. The map doesn't show any Indian trails.
The main road ran from east to west, a mile or so south of the Bay. The map shows another road branching south from this, running around the southern side of Mill Pond, and then north and around the northern and eastern sides of Follins Pond.
Compare this to the road net in 1832: The Bass River Road Net - Late 1832.