Complex sentence: While there, he enjoyed frequent trips to his birthplace Staunton where he visited with cousins, and fell in love with one, Hattie Woodrow, though his affections were unrequited.
Split into simpler sentences: While there, he enjoyed frequent trips to his birthplace of Staunton. He visited with cousins, and fell in love with one, Hattie Woodrow, though his affections were unrequited.