Facing yet another failed relationship and a full-blown identity crisis after losing her job in a corporate merger, unemployed executive Amber Shaw realizes she hasn't been happy in a long time. Who is she if not a CEO, and if everything she's worked for hasn't made her happy, what will? Inspired after learning about the Appalachian Trail, Amber sets off in hopes of figuring it all out.

Leslie Brown lives life on her own terms with nothing to tie her down. She's an experienced hiker and has one final trail left on her bucket list, the Appalachian Trail. Only problem, all her friends have settled down and started lives that don't allow for seven months away from responsibilities. She's out there alone.

Amber and Leslie assume they are polar opposites based on their first impressions of each other, but the more their paths cross, the more this hike of a lifetime begins to look like a love of a lifetime.