These 22 activities are worth leaving the house for.
Ask me what you're after.
October 17 at 7:30pm (This weekend)
Stissing Center for Arts and Culture · Pine Plains
Let the triangle and accordion pull you onto the dance floor. Massaranduba brings authentic Forró from Brazil's sertão to the Hudson Valley, with rhythms that demand movement.
October 18 at 12pm (This weekend)
Pete and Toshi Seeger Riverfront Park · Beacon
Celebrate the season at this annual Beacon Sloop Club fundraiser along the Hudson River. Expect a day of pumpkin sales, freshly baked pie, and live music across two solar-powered stages.
October 22 at 6pm
Hudson Valley Brewery · Beacon
Crisp pours and crackling flames: Lager Night rounds up a year's worth of collaboration lagers plus beloved standbys, all anchored by a bonfire. Come for lunch, stay past dark.
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.
October 24 (Next weekend) +1
Wassaic Project · Wassaic
The Wassaic Project transforms the Luther Barn into a spooky, immersive labyrinth of art installations. After the scares, the night shifts to a costume-mandatory dance party featuring live music.
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.
Browse Dutchess County neighborhood by neighborhood, get ideas just for you, or ask me anything.
22 activities · Page 1 / 1
Sat, Oct 17 · 10:00 PM
The Academy · Poughkeepsie
$10
Tue, Oct 20 · 8:00 PM
Hudson Valley Food Hall · Beacon
$$
Tue, Oct 20 · 7:00 PM
Hudson Valley Food Hall · Beacon
$$
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
Beacon
The Derby Poughkeepsie · Union Street Historic District
$$
The Academy · Poughkeepsie
Lathrop Center at Lakeside Park · Pawling
Poughkeepsie Public Library District - Adriance Memorial Library · Poughkeepsie
Bannerman Castle · Beacon
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.