Hudson is a year-round town, but it peaks in summer and fall. The Hudson Valley's foliage season — roughly mid-October to early November — draws large crowds, and Warren Street is at its liveliest then. Summer weekends fill up fast with New York City visitors; if you want a quieter experience, come on a weekday or in late spring, when the weather is good but the crowds have not yet arrived.
Winter is genuine upstate New York cold, but the antiques shops and restaurants stay open, and the city takes on a more local character. Some smaller galleries and boutiques reduce their hours outside peak season.
The Basilica Hudson arts venue runs its biggest events in summer, including the Basilica Farm & Flea Market. Hudson's Pride weekend, typically in June, draws a visible celebration given the city's large LGBTQ+ community.