False. Alaska does not cross the International Date Line (IDL). The IDL runs at ~180° longitude through the mid-Pacific. Alaska's westernmost point (Attu Island) is at 172°E—still 8° west of the IDL.
Because the Aleutian chain crosses the 180th meridian (antimeridian), some claim Alaska is "both easternmost and westernmost." But the IDL deviates eastward to keep all Aleutians in the same day (UTC-10 to UTC-12). Thus, no US territory crosses the IDL.
If using geographic coordinates only (ignoring IDL), Semisopochnoi Island (179°46'E) is technically "east of" West Quoddy Head. But by legal time zones and date, Maine is unequivocally easternmost.