A system for a dynamically orienting adjustable shelter is provided. The system generally comprises a base, lever arm, counterweight, boom, canopy, canopy supports, and support cables connected to said canopy supports. The boom and lever arm connect to the base in a way such that the boom may be in an upright position when a counterweight is placed on the lever arm. A canopy assembly may be rotatable attached boom in a way that allows it to rotate about said boom, which allows the canopy assembly to reduce the cross-sectional area of the canopy exposed to the wind. A cable may be attached to the front end of the canopy supports, which may prevent the back end of the canopy from tipping too far down when there is no wind that the system may use to stabilize the canopy by naturally reducing the cross-sectional area exposed thereto.