The small, riverfront city of Hudson (population 7,500) has become one of the most popular locales in New York's Hudson River Valley among gays and lesbians - both weekenders and full-time residents. A workaday city that experienced a sharp decline in the '60s and '70s, Hudson has experienced a renaissance in the past 15 years and is now home to a number of hip eateries, lively bars, noteworthy coffeehouses, and funky shops. Each June, the city hosts a Hudson Gay Pride celebration - the date this year is June 20 and 21, 2014.
Events that make up Hudson, New York Gay Pride include a Sunset and Moonlight Boat Cruises on the evening of Friday, June 20; a Hudson Gay Pride Parade along Warren Street at 2 pm on Saturday, June 21; and a Pride Festival that same afternoon at Waterfront Park (Broad and Ferry Sts.).
Additionally, local gay bars as well as gay-friendly restaurants, hotels, and shops will attract plenty of LGBT folks throughout Pride weekend. Outstanding resources for learning more about the gay scene (as well as gay-friendly businesses) in the region are BigGayHudsonValley.com and GayHudson.com. Also take a look at the visitor site produced by the region's Columbia Country Tourism office for general travel advice.
Note also that Gay Pride events take place father south a bit earlier, including New Paltz/Hudson Valley Gay Pride in early June, and Big Gay Hudson Pride Preview Weekend in Poughkeepsie over Memorial Day Weekend.