The first-ever dual-frequency multi-constellation Global Navigation Satellite Systems Reflectometry (GNSS-R) polarimetric measurements over boreal forests and lakes from the stratosphere are presented. Data were collected during the European Space Agency (ESA) sponsored Balloon Experiments for University Students (BEXUS) 19 stratospheric balloon experiment using the P(Y) and C/A Reflect Ometer (PYCARO) instrument operated in closed-loop mode. Maps of the polarimetric ratio for L1 and L2 Global Positioning System (GPS) and GLObal Navigation Satellite System (GLONASS), and for E1 Galileo signals are derived from the float phase at 27,000 m height, and the specular points are geolocalized on the Earth’s surface. Polarimetric ratio ( ) maps over boreal forests are shown to be in the range 2–16 dB for the different GNSS codes. This result suggests that the scattering is taking place not only over the soil, but over the different forests elements as well. Additionally to the interpretation of the experimental results a theoretical investigation of the different contributions to the total reflectivity over boreal forests is performed using a bistatic scattering model. The simulated cross- (reflected Left Hand Circular Polarization LHCP) and co-polar (reflected Right Hand Circular Polarization RHCP) reflectivities are evaluated for the soil, the canopy, and the canopy–soil interactions for three different biomass densities: 725 trees/ha, 150 trees/ha and 72 trees/ha. For elevation angles larger than the Brewster angle, it is found that the cross-polar signal is dominant when just single reflections over the forests are evaluated, while in the case of multiple reflections the co-polar signal becomes the largest one. The first-ever dual-frequency multi-constellation Global Navigation Satellite Systems Reflectometry (GNSS-R) polarimetric measurements over boreal forests and lakes from the stratosphere are presented. Data were collected during the European Space Agency (ESA) sponsored Balloon Experiments for University Students (BEXUS) 19 stratospheric balloon experiment using the P(Y) and C/A Reflect Ometer (PYCARO) instrument operated in closed-loop mode. Maps of the polarimetric ratio for L1 and L2 Global Positioning System (GPS) and GLObal Navigation Satellite System (GLONASS), and for E1 Galileo signals are derived from the float phase at 27,000 m height, and the specular points are geolocalized on the Earth’s surface. Polarimetric ratio ( ) maps over boreal forests are shown to be in the range 2–16 dB for the different GNSS codes. This result suggests that the scattering is taking place not only over the soil, but over the different forests elements as well. Additionally to the interpretation of the experimental results a theoretical investigation of the different contributions to the total reflectivity over boreal forests is performed using a bistatic scattering model. The simulated cross- (reflected Left Hand Circular Polarization LHCP) and co-polar (reflected Right Hand Circular Polarization RHCP) reflectivities are evaluated for the soil, the canopy, and the canopy–soil interactions for three different biomass densities: 725 trees/ha, 150 trees/ha and 72 trees/ha. For elevation angles larger than the Brewster angle, it is found that the cross-polar signal is dominant when just single reflections over the forests are evaluated, while in the case of multiple reflections the co-polar signal becomes the largest one.