Waldo was born in Vermont in 1832. By 1864 he had settled in Oshkosh, Wisconsin, where as a self-taught artist, he began to earn a living as a sign painter. View of Island Park, one of Waldo's earliest known landscapes, was executed about ten years after the artist moved there.

The view is across Lake Winnebago, one of the largest inland lakes contained in one state. Among the buildings depicted in the distance can be seen the old Oshkosh Court House. (In reality it would not have been possible to see the Oshkosh Court House from Island Park, so Waldo took some creative liberties with this view.) Island Park, also known as "Garlic Island," was used as a summer resort and had cottages and a hotel. The island first came into prominence during the War of 1812, when Captain Dickson of the British Army and his Native American allies spent a starving winter there. In more recent times, the building of dams on the Fox River, which empties Lake Winnebago, has resulted in increased water levels and a reduction of the island's size.

A similar view of Island Park by Waldo is in the collection of the Oshkosh Public Museum. Another painting by the artist is presently in the "ladies warming room" in the Opera House also in Oshkosh.