This essay explores the political significance of John Thelwall’s engagement with the discourse of the picturesque in his travel writing of the 1790s. E. P. Thompson asserted that Thelwall’s turn to travel writing in the immediate aftermath of his metropolitan radical career demonstrated the success of the authorities in driving him out of politics. For Thompson, Thelwall’s essays “A Pedestrian Excursion” and “The Phenomena of the Wye” (1798-1801) were “conventional” and “unremarkable” examples of the picturesque tour, in which Thelwall reneged on his reformist principles by failing to engage with the working people he encountered. Recent critical accounts have defended Thelwall against Thompson’s charge by accentuating the sociological emphasis of the pedestrian tours and playing down Thelwall’s engagement with the picturesque. This essay argues that it is precisely through an exploration of the picturesque that Thelwall finds a new medium for the articulation of his political ideals. Thelwall’s turn to the picturesque is not just a response to political harassment. The Peripatetic (1793) demonstrates Thelwall’s long-held fascination with visual forms, though it expresses distrust at the abstracting effects of spectatorship. In The Peripatetic, Thelwall begins an exploration of alternative means of “seeing,” namely the material exploration of both the landscape and social configurations. This exploration is continued and refined in the “Pedestrian Excursion” and “Phenomena of the Wye,” where the language of Thelwall’s descriptions of landscape anticipate his engagement with the politics of free speech in his elocutionary writings of the next decade.