There’s something freeing about tossing the itinerary and just driving. Recently, we did exactly that—no reservations, no strict agenda. Just the open road and a loose plan to start in Greeley, Colorado, where we kicked things off at Greeley Hat Works with custom cowboy hats in hand. From there, we pointed the car north and followed wherever the road took us.

We made our way into South Dakota, winding through the Black Hills—a place known for its summer traffic and tourist-packed streets. But traveling in the off-season was a game-changer. We hit every major spot:

It felt like we had the entire region to ourselves!