The song "Highway Song" by James Taylor tells a story of a man who is always on the move, constantly traveling and unable to settle down. The lyrics start with the protagonist addressing his father and brother, expressing his desire to escape from his current situation and embark on a new adventure by building a boat and sailing away. The song highlights the protagonist's restless nature and his longing for freedom and exploration. He mentions a broken heart and a sweet misunderstanding, hinting at the difficulties he has faced in relationships. Despite the challenges, he finds solace in the open road and the unpredictability of his journey. The lyrics also mention a past relationship with a woman in Memphis who wanted him to stay with her, but his wanderlust proved stronger. He recalls hearing a "highway song" on a Saturday night, which seemed to call him back to the road. This suggests that he is drawn to the excitement and freedom that traveling provides, unable to resist its allure. The song acknowledges that one day, the protagonist may tire of the highway life and desire to settle down. However, until that moment arrives, he embraces the adventures and challenges that come with his nomadic lifestyle. The repetition of the line "Back on the highway, yeah, yeah, yeah, back on the road again" emphasizes his perpetual movement and constant return to the road. Towards the end of the song, the protagonist acknowledges that despite the hardships and uncertainties of his journey, there is a certain joy and exhilaration in being on the road. The lyrics mention the Holiday Inn, symbolizing the familiarity of being on the go and staying in hotel rooms. He expresses a sense of contentment in being back on the road, even though it means leaving behind the comfort of being home. Overall, "Highway Song" explores themes of wanderlust, freedom, and the search for meaning and fulfillment through an adventurous and nomadic lifestyle. It reflects James Taylor's own experiences as a traveling musician, as well as the universal desire for exploration and the longing for something beyond the ordinary.