There's Always Woodstock is a music infused romantic comedy about a frustrated musician, Catherine Brown who finds herself living a life she never imagined. Stuck at a dead end job in New York City at Abundant Records, a mega music record label with no soul. When Catherine is fired from her job and finds her fiancé in the shower with another women she decides she is going to sell her engagement ring and move back into her family home in Woodstock, reinvent herself and get back to what she has always wanted to do, write music and perform.

Returning to Woodstock for Catherine is bitter sweet. She hadn't been back since the death of her parents when she was only 4 years old. Catherine quickly finds herself in a rut and unable to write music. While exploring the town she meets and befriends a bartender and barista, Emily. After a drunken karaoke performance, Catherine stumbles out of the bar only to have a chance encounter with Noah, the resident town Doctor. There is an immediate attraction but Catherine is in no position to start dating. Little by little, Catherine starts to find herself, write music, and fall in love with Noah.

Just as it all seems to be coming together for her, everything begins to unravel once her fiancé comes back into her life and Abundant Records makes an offer to sign her as an artist. As Catherine struggles to reconcile her two vastly different worlds she ends up not only finding herself but also "true love."