These 22 activities are worth leaving the house for.
Ask me what you're after.
October 25 at 11am (This weekend) +1
Locust Grove Historic Site · Poughkeepsie • $10-$15
Grovetober brings seasonal festivities to the grounds of the Locust Grove Historic Site. The day features live music, pumpkin displays, and hands-on workshops ranging from ornament making to Morse code jewelry.
November 7 at 5pm +1
Cunneen-Hackett Arts Theater · Poughkeepsie • $60-$65
Vegas glitz lands in Poughkeepsie: sequins, casino tables, and vintage cigarette girls kick off this adults-only dance spectacle. The cocktail hour alone is worth dressing up for.
November 15 at 2pm
Millbrook Vineyards & Winery · Millbrook • $50
Watch the 2026 Wine Label Competition winner emerge while sipping Millbrook wines in a loft overlooking the Hudson Valley.
October 23 at 7pm
Womenswork.Art · Poughkeepsie
A Halloween figure-drawing party where the costumes are as much the show as the art. Sketch a burlesque muse, show off your own look, and you might end up drawn by the emcee.
Beacon
This airy industrial brewery sits just outside Beacon's main drag with panoramic views of Mount Beacon from its sprawling deck. Their Wrench pilsner is the main attraction: crisp, hoppy, and dangerously drinkable.
Bannerman Castle · Beacon
Cruise to Bannerman Castle for an annual fundraising dinner featuring a boat tour, live guitar, and a five-course locally sourced meal with sweeping Hudson Highlands views.
Browse Dutchess County neighborhood by neighborhood, get ideas just for you, or ask me anything.
22 activities · Page 1 / 1
Sat, Oct 24 · 10:00 PM
The Academy · Poughkeepsie
$10
Tue, Oct 27 · 8:00 PM
Hudson Valley Food Hall · Beacon
$$
Tue, Oct 27 · 7:00 PM
Hudson Valley Food Hall · Beacon
$$
Tue, Oct 27 · 4:00 PM
Pershing Avenue Park · Poughkeepsie
Free
Thu, Oct 29 · 12:30 PM
East Fishkill Community Library · Hopewell Junction
Sat, Nov 14 · 7:30 PM
Locust Grove Historic Site · Poughkeepsie
$0-$35
Kindred Creeks Farm · Poughquag
Poughkeepsie Public Library District - Adriance Memorial Library · Poughkeepsie
Veterans of Foreign Wars · Beacon
Tymor Park · Lagrangeville
The Derby Poughkeepsie · Union Street Historic District
$$
The Academy · Poughkeepsie
Majed J. Nesheiwat Convention Center · Poughkeepsie
Lathrop Center at Lakeside Park · Pawling
Poughkeepsie Public Library District - Adriance Memorial Library · Poughkeepsie
Wassaic Project · Wassaic
I go through what's actually on nearby and keep only the ones worth the trip. Nobody pays to be on this list.
Finished events drop off the list. Check the listing for times and booking details before heading out.
Tell me when you’re free, where you’ll be, and what sounds appealing. “Live music near me, somewhere I can sit, under $30” gives me more to work with than “something fun.” You can keep narrowing it down with me.
You can browse these pages without an account. Sign in to save activities and help me learn your taste, so future suggestions have a better starting point.
Outgoing is free to use. Events have their own admission prices, including some that are free. Check the listing for prices and booking details before making plans.