Throughout much of history the low lying valley of the upper River Forth was an impassable marsh. Even today, when much of it has been drained for agriculture, a good number of squares on the 1:50,000 Ordnance Survey map are largely featureless save for the words "Flanders Moss".
Settlement in the area, and roads through it, were largely confined to the higher ground on either side of the valley. Kippen lies in a commanding position on the slopes of the Gargunnock Hills with extensive views to the north to the mountains beyond Callander.
The growth of the village owes much to the building in the 1700s of the military road from Stirling to Dumbarton. Kippen lay at the junction between this and a traditional drove route south over the hills to Fintry.
Kippen's church was first mentioned in public records in the 1300s, though by this time it had been used as the burial place for the Earls of Menteith for many generations.
The earliest buildings in Kippen today date back to the late 1600s and early 1700s and are gathered around the mercat cross and war memorial to the north of the main junction in the village. The remains of the nearby Old Kirk of Kippen date back to 1691, while the Black Bull Inn (now a private house) was built as a coaching inn in 1729. Also close by is the Smiddy, now in the care of the National Trust for Scotland.
Cattle droving was not an easy job. Local folklore relates an incident in 1691 when local men failed to prevent Rob Roy and his band of MacGregors from stealing a herd of cattle passing through en route to Stirling. To discourage other villages from interfering in their banditry the MacGregors returned and stole all the village cattle as well. In 1750 Rob Roy's son, Robin Oig abducted or eloped with a local heiress, Jean Keag, and married her. This led to his later execution.
Uphill from the older part of the village the pleasantly wide main street passes the Cross Keys Hotel and, next door to it, the old Free Church, now converted into a car showroom. Opposite are the Kippen Reading and Recreation Rooms, built in 1906.
Kippen was served by a railway that ran along the lower ground north of the village from 1856 to 1934. In 1971 part of the line of the old railway was reused for a new road, the A811, which now bypasses Kippen.