Mount Cleveland stands within the watershed of Lake Champlain, which drains into the Richelieu River in Québec, the Saint Lawrence River, and then eventually into the Gulf of Saint Lawrence. The north side of Mount Cleveland drains into Stetson Brook, thence into the Mad River, the Winooski River, and into Lake Champlain. The south and east sides of Mount Cleveland drain into Austin Brook and then into the Mad River. The west side of Mount Cleveland drains into the New Haven River, thence into Otter Creek, and into Lake Champlain.