This charming town marks either the start or the finish of the Cowboy Trail. Known as the gateway to the Niobrara River, it’s a great base for kayaking, hiking, or simply soaking up views from the old railroad bridges. Stroll through the laid-back downtown, visit local shops, and grab a bite at a classic diner. With the river just nearby, Valentine offers a perfect blend of small-town charm and natural beauty before or after your ride.