Cumberland Gap National Historic Park The sign reads - The Cumberland Gap, before you lies the first southern route opened for settlement through the barrier of the Appalalians. Following a Indian and Buffalo trail, Danial Boone & 30 axemen blazed a westward route in 1775 for future settlers. Within a generation nearly 200,000 had filed through the gap passing near to where you are standing. Welcome to Kentucky. From the hills and hollows of eastern Kentucky through the rolling bluegrass of our heartland to the massive lakes and flatlands of the west, Kentucky has much to offer.