Home to prestigious Vassar College, one of the few gay bars in the region (Out Bar, at 206 Main St.), and an attractive downtown that's a great base for exploring the area's many attractions, Poughkeepsie is the site of the 5th Annual Big Gay Hudson Valley Gay Pride, which is tentatively expected to take place again over Memorial Day Weekend (May 24 to 27, 2013).
Organizers of this celebratory weekend in scenic and sophisticated Dutchess County bill this as the "kickoff to summer," and indeed, the entire Hudson Valley is a magnet for gay visitors all summer long, and other Gay Pride events take place a bit later, in early June across the river in New Paltz, and farther north in the small, hip Columbia County city of Hudson. In fact, Big Gay Hudson Valley Gay Pride bills itself a Preview Weekend for the Hudson Valley Gay Pride events taking place throughout the following week across the river, in New Paltz and Kingston.
Events that make up Big Gay Hudson Valley Gay Pride include a party Friday at the new and sophisticated (Canvas Bar & Lounge, at 305 Main St., Poughkeepsie, 845-483-WINE), from 9 pm until 1 am - there's a $5 cover charge. Then on Saturday there are two Pride Cruises on the Hudson aboard the [i]Mystere[/i] (operated by Empire Cruise Lines; there are two cruise options, a 5:30 to 7:30 sunset sailing, and a later 8:30 to 10:30 pm sailing that will benefit Hudson Valley Community Services. The cruise departs from Waryas Park, at 29 Front St., in Poughkeepsie.
And then on Sunday there's the grand finale: a BYOB Pride Preview Picnic held on the lovely grounds of Tymor Park (8 Tymor Park Rd., Lagrangeville, 845-724-5691) from 2 pm until 10 pm. The cost is $10 in advance, and $15 at the door, and entertainment includes DJ Ali Gruber, Freddy and Jay Freeman of Bearapalooza, drag bingo with Trixie Starr, and Super Sounds performing.
Additionally, local gay bars as well as gay-friendly restaurants, hotels, and shops will attract plenty of LGBT folks throughout Pride weekend. An outstanding resource for learning more about the gay scene (as well as gay-friendly businesses) in the region is BigGayHudsonValley.com. Also take a look at the visitor site produced by the region's Dutchess Country Tourism office for general travel advice.