Why Last-Minute Road Trips Are the Best Way to Travel (Especially in the Off-Season)

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.

Discovering the Black Hills—Without the Crowds Iconic Destinations With Room to Breathe

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:

• Mount Rushmore: Walked right up, no waiting, no crowds. This monument is FREE to the public however there is a $10 parking fee that is then good for the year purchased.
• Keystone: Quiet shops and easy parking.
• Hill City: Peaceful galleries and friendly locals.
• Custer: Bison and wide-open roads.
• Deadwood: Historic charm without the usual foot traffic.

It felt like we had the entire region to ourselves!