We consider the emission within the fireball model framework of very high energy, ∼ 1 GeV to > 1 TeV photons, on a minute time scale, during the onset of fireball deceleration due to interaction with surrounding medium. Our time dependent numerical model includes exact treatment of electron synchrotron emission, inverse-Compton scattering, pair production, and evolution of electromagnetic cascades (initiated by pair production or photo-production of pions). We find that (i) The 1 GeV– 10 GeV flux is not sensitive to model parameters and is ∼ 10 7 ergcm 2 sec 1 for z = 1 bursts, well within the detection capabilities of GLAST; (ii) The sub-TeV flux depends on the surrounding medium density and on the fraction of thermal energy carried by the magnetic field, ǫB: It ranges from ∼ 10 7 ergcm 2 sec 1 in the case of typical ISM density and ǫB . 10 4 to 10 10 ergcm 2 sec 1 in the case of a source surrounded by a wind and ǫB ∼ 10 0.5 ; (iii) The sub-TeV flux is detectable by high energy γ-ray experiments such as HESS, MAGIC, MILAGRO, and VERITAS; (iv) Combined ∼ 1keV, ∼ 1GeV and sub-TeV observations will allow to determine both ǫB and the ambient medium density; (v) The spectra depend only weakly on the spectral index of the energy distribution of the accelerated electrons. Pion production energy loss of high energy protons may contribute significantly in the wind case to the luminosity of high energy photons. However, it is difficult to distinguish in this case between the electron and proton contributions since the spectral shape is determined primarily by the energy dependence of the pair production optical depth. Subject headings: gamma rays: bursts — gamma rays: theory — radiation mechanisms: nonthermal