Since the discovery of 15760 Albion in 1992, over 2,000 more transneptunian objects (TNOs) have been discovered by various techniques. In recent years, several surveys have been conducted to detect TNOs through serendipitous occultations when small solar system bodies eclipse distant stars. Through searches for serendipitous occultations, several constraints have been produced for the population of TNOs below 10 km in diameter. The Very Energetic Radiation Imaging Telescope Array System (VERITAS) in southern Arizona uses photo-multiplier tubes (PMTs) to detect the faint blue/UV Cherenkov light produced though interactions the upper atmosphere by gamma rays from astronomical objects. Since 2018, VERITAS has implemented an additional program to detect predicted asteroid occultations. The angular diameters of magnitude 9 to 12 stars are determined by fitting the diffraction pattern observed by the central VERITAS pixel at the start and end of the occultation. Once VERITAS upgrades all 499 pixels on each of its 4 telescopes to kilohertz sampling over the course of 2024–2025, a new program will begin to detect serendipitous occultations across the full 3.5-degree field of view of VERITAS, simultaneous with regular gamma-ray observations. This presentation will detail several occultations observed with VERITAS over the last few seasons and describe future VERITAS capabilities for detecting serendipitous occultations by TNOs.