Poughkeepsie in January has options: outdoor, comedy, theatre, food… basically everything except an excuse to stay bored.
1.Walkway Over the Hudson “First Day Hike & Festival” — Thu, Jan 1 @ 11 AM–2 PM
Start the year with a view that makes your phone camera feel inadequate (in the best way).
Cost Box: Free
2.Flag Changing Ceremony (Walkway Over the Hudson) — Fri, Jan 9 @ 12–12:30 PM
Short, meaningful, and easy to pair with lunch nearby.
Cost Box: Free
3.Michael Blaustein (Bardavon) — Sun, Jan 18 @ 7 PM
A comedy night that’s perfect for couples, singles, and anyone trying to laugh their way through winter.
Cost Box: $35.50–$65.50
4.Computing Venus (Vassar College, Martel Theater) — Jan 23–25
A real “date that isn’t dinner” option with multiple showtimes—so you can actually make it work with your schedule.
Cost Box: Free / ticketed depending on performance entry (varies)
5.Hudson Valley Wingfest (MJN Center) — Sat, Jan 31 @ 5–8:30 PM
Bring appetite and strong opinions. (You will absolutely declare a winner. Loudly.)
Cost Box: Ticketed (price varies by ticket type)
My top pick: Wingfest (because January should include at least one event that’s purely joyful).
Team Comedy, Theatre, or Wings? Comment your team name like you mean it.