Mountains along the northwestern coast of Ellesmere Island, Canada, possess the highest peaks nearest the Pole. This geography, combined with an atmospheric thermal inversion restricted to below similar to 1000 m during much of the long arctic night, provides excellent opportunities for uninterrupted cloud-free astronomy - provided the challenges of these incredibly remote locations can be overcome. We present a miniaturized robotic observatory for deployment on a High Arctic mountaintop. This system tested the operability of precise optical instruments during winter, and the logistics of installation and maintenance during summer. It is called Ukpik after the Inuktitut name for the snowy owl, and was deployed at two sites accessible only by helicopter, each north of 82 degrees latitude; one on rock at 1100 m elevation and another on a glacier at 1600 m. The instrument suite included at first an all-sky-viewing camera, with the later addition of a small telescope to monitor Polaris, both protected by a retractable weather-proof enclosure. Expanding this to include a narrow-field drift-scanning camera for studying extra-solar planet transits was also investigated, but not implemented. An unique restriction was that all had to be run on batteries recharged primarily by a wind turbine. Supplementary power came from a methanol fuel-cell electrical generator. Communications were via the Iridium satellite network. The system design, and lessons learned from three years of operation are discussed, along with prospects for time-domain astronomy from isolated, high-elevation polar mountaintops.