The Old Annapolis Road was a planned direct route between Halifax and Annapolis Royal, the current and former capitals of Nova Scotia, in Eastern Canada. Work began in 1784 and was resumed in 1816 as a military settlement plan for Napoleonic War veterans. Known various times as the Annapolis Military Road, the Dalhousie Road and the Kempt Road, it led to some successful settlements but was never completed and was abandoned in 1829. Some disconnected sections remain in use today.
Annapolis Royal was the original colonial capital of Nova Scotia, until the founding of Halifax in 1749. Nevertheless, in the late 18th and early 19th century it was a commercial center and an important fortified garrison for Western Nova Scotia. It was also the principal gateway to New Brunswick by sea. Transportation between Halifax and Annapolis Royal was by a lengthy and indirect route known as the "Post Road" or "Great Western Road" which followed ancient trails from Halifax to Windsor, and then West through roads linking the Acadian settlements of the Annapolis Valley, approximately the same route is followed by Nova Scotia Highway No. 1 today. The Old Annapolis Road was an attempt to quickly connect Annapolis Royal with Halifax and open up the interior for settlement. It was the most ambitious of several roads built in the late 18th century to connect coastal settlements to Annapolis Royal. Other examples were the equally unsuccessful and identically named "Old Annapolis Road" from Shelburne to Annapolis Royal, started in 1785 but abandoned by 1814, and the more successful Liverpool to Annapolis Royal Road built in the 1790s which later grew to become Nova Scotia's Highway No. 8.
The interior of Nova Scotia consists of thick forest, extensive swamps and thin soils with only the occasional pocket of marginally fertile soil. In the early 19th century, the interior, while crossed by long-established Mi'kmaw travel routes was an uninhabited by European settlers. The route of the Halifax to Annapolis Royal road was varied to make areas of potentially-better farmland more accessible.