Heading "north," the route runs northeast, west, southwest, then turns northwest to its northern terminus.

After about 5 miles (8.0 km), the road curves to the west and crosses the Back River at the Cowsegan Narrows, entering the town of Wiscasset.

Route signage begins at this point and SR 144 turns to the southwest heading through a cleared area lined with houses.

From there, it ran northeast to Eustis, then turned southeast, passing through Kingfield and New Portland and into Anson, with its eastern terminus located at New England Route 20 (which became US 201 in 1926 and is now US 201A).

In 1931, the route was truncated back to Eustis, with its segment west to Rangeley becoming part of the newly designated SR 4.