Route 144 was commissioned in 1932, and took this route from west to east:
- Bushy Hill Road, from Route 145 in Deep River to Main Street in Essex
- Main Street (overlapping the old Route 9) and West Avenue into downtown Essex
- North Main Street and River Road toward the Deep River town line.
In 1934, Route 144 was cut back to end at today's Route 154 in Centerbrook. In 1941, Route 80 was relocated south along Main St. through Ivoryton, and Route 144's east end was truncated to that point. On June 21, 1962, Route 144 was decommissioned altogether.