Nantucket bustles in the summer, when water temperatures hit highs and festival crowds enliven the streets. High season runs from the end of May to the beginning of September, but early June can bring unexpected values (room rates don’t hit their peak until after children get out of school).
Nantucket’s Indian summers mean that the weather stays warm through early fall. By mid-October, the air turns crisp, sea breezes chill the shores, and autumnal colors settle into the moors. By then, the vacation crowds have thinned and ferry schedules slow for the off-season.
The town dresses up for Christmas Stroll, the first week of December. Fireplaces glow through decorated windows, and carolers make their rounds on lit-up Main Street. After the Stroll, the shops hold sales before halting business for the rest of the year.
Activity picks up again in early spring. The Daffodil Festival (late April/early May) greets spring with three million cheery blooms, while the Nantucket Wine Festival (end of May)—celebrated with sips from 165 wineries—marks the start of another busy season.