Although efforts to restore floodplain forests are becoming more popular in the northeastern United States, best management practices are not well defined. In this study, we demonstrate the success of a planting effort in western Massachusetts to increase the extent of a floodplain forest along the Housatonic River. Over 1700 floodplain-adapted tree saplings were planted in an old field and in two hayfields at Bartholomew's Cobble, a property located in Sheffield, Massachusetts, and individually tagged to follow their growth and survival. Planted trees had relatively high rates of survival over a 6 y period, especially the two most commonly planted tree species: silver maple (Acer saccharinum, 42.5% survival) and boxelder (Acer negundo, 71.7%), although plantings were more successful in the old field compared to the two hayfields. Tree dbh after 6 y differed across fields for silver maples and boxelders with those planted within the old meadow significantly larger than those planted into hayfields (silver maple dbh 9.8 cm old field vs. 6.5–6.6 cm hayfields; boxelder dbh 10.4 cm old field vs. 4.4–6.6 cm hayfields). By documenting which floodplain-adapted tree species were successful in establishing under which conditions, our observational study provides valuable insights for future restoration efforts.