Accurate heading estimation is crucial for the autonomous navigation of small-to-medium tractors. While dual-antenna GNSS systems offer precision, they face installation and safety challenges. Single-antenna GNSS integrated with a low-cost Strapdown Inertial Navigation System (SINS) presents a more adaptable solution but suffers from slow convergence and low accuracy of heading estimation in low-speed farmland operations. This study proposes an adaptive trajectory-constrained heading estimation method. A sliding-window adaptive extended Kalman filter (SWAEKF) was developed, incorporating a heading constraint model that utilizes the GNSS-derived trajectory angle. An enhanced Sage–Husa algorithm was employed for the adaptive estimation of the trajectory angle measurement variance. Furthermore, a covariance initialization strategy based on the variance of trajectory angle increments was implemented to accelerate convergence. Field tests demonstrated that the proposed method achieved rapid heading convergence (less than 10 s for straight lines and 14 s for curves) and high accuracy (RMS heading error below 0.15° for straight-line tracking and 0.25° for curved paths). Compared to a conventional adaptive EKF, the SWAEKF improved accuracy by 23% and reduced convergence time by 62%. The proposed algorithm effectively enhances the performance of GNSS/SINS integrated navigation for tractors in low-dynamic environments, meeting the requirements for autonomous navigation systems.