Transcendental idealism was an integral part of the American psyche ever since Emerson, Thhoreau and Witman becomes the staunch advocates of it. It holds that human can reach higher level of existence which is more fulfilling and meaningful. Transcendentalism speaks of the invisible in the visible, and the ideal behind the real. Fitzgerald, being a romantic writer belongs to this transcendental tradition of writers. Therefore, he upholds this American cultural tradition of Emerson and Thoreau in his fictional world. This paper try to reveal the deep transcendental longings infused into a few charecters in his writings especially, in his masterpiece ‘The Great Gatsby’ and other mature novels like, ‘This Side of Paradise’, ‘The Beautiful and Damned’, ‘Tender Is the Night’ and in Fitzgerald’s last novel ‘The Last Tycoon’.