When surveying the area now known as Maplewood, Robert Treat found several trails used by the Lenape tribes of Algonquin Native Americans, though there was only sparse settlement. Many of these paths form the basis for the town's main thoroughfares today.
The first European settlers arrived in 1675 via Newark and Elizabeth, previously they had lived in Hempstead, Long Island, and Stamford, Connecticut. The settlers had acquired most of today’s Essex County from the Native Americans and followed three trails that roughly correspond to South Orange Avenue, Springfield Avenue, and Ridgewood Road. These three routes resulted in three separate communities that merged into Maplewood and South Orange.
Six families came up today’s Ridgewood Road and established scattered farms around a center that became Jefferson Village, named after Thomas Jefferson. This village, which roughly corresponds to downtown Maplewood today, developed several mills and orchards. John Durand, the son of Hudson River school painter Asher Brown Durand, describes the place as a picturesque but slightly backwards community. The apple harvest was apparently quite impressive and included “Harrison” and “Canfield” varieties. By 1815, there were approximately 30 families in the village.
Those who traveled up today’s Springfield Avenue settled on a hill crest near today’s intersection between Tuscan and Springfield Avenue and established a hamlet known as North Farms. Over time, this community became known as the Hilton section. It became a stagecoach stop between Newark, Jersey City (then Paulus Hook), and Morristown and thereby a center for trade and light manufacturing. The village changed its name from North Farms to Middleville in 1830, and then to Hilton in 1880 when it was granted a post office. In 1855, Seth Boyden settled in what was then Middleville to retire but innovated a number of agricultural products, especially berries. Boyden also built and put into operation the first steam engines to service the railroad through Maplewood. The area became known for its orchards and related industries, including cider mills and distilleries of rum, but also honey and some livestock.
Maplewood was originally formed as South Orange Township, which was created on April 1, 1861, from portions of Clinton Township and what was then the Town of Orange. The name of the township was changed to Maplewood on November 7, 1922.