What's on in Pawling for free?
9 upcoming events
See it on a mapVenues at a glanceWe've rounded up 9 upcoming events in Pawling for free — concerts, parties, theatre, exhibitions, family outings — updated every day. Pick a theme or just scroll.
Events in Pawling for free
Sat3
Saturday 3 October
Sun4
Sunday 4 October
Later
Sat 10 · 12 PM$0
💿DJ set
Brunch: Ol' Moose Trio
Daryl's House
Sun 11 · 12 PM$0
🪕Folk / Acoustic💿DJ set
Brunch: The Bargain
Daryl's House
Sat 17 · 9:30 AM$25–35
🏃Running🤾Sports & fitness
EDRRC - Ryan's Run Superhero 5K, Villain 10K and Kids Fun Run
2 Lakeside Park
Sat 17 · 12 PM$0
🎫Concert
Brunch: Kristina Koller
Daryl's House
Tue 20 · 6:30 PM$0
🗣️Talk
Sheplie Travel presents ~ Visiting Ireland!
Pawling Free Library - The Annex
Wed 21 · 6 PMFree
🏛️Politics & Economy
Deep Canvassing in Pawling
Sunflour Bakery
Sun 22 Nov · 1 PMFree
🏃Running🤾Sports & fitness
EDRRC - Beer Mile
2 Lakeside Drive
See also in Pawling for free
At 8 PM$22.03–33.84
🎸Rock✨Pop
Live Coverage - Post-Punk and New Wave
Daryl's House, Pawling
Sun 4 · 4 PM$20–25
🎶Singer-songwriter🪕Folk / Acoustic
Jay Mafale and Catherine Miles in Concert
Unitarian Universalist Congregation of Danbury
Sun 18 · 3 PM$12.51
🎷Jazz🎫Concert
WCSU High School Honors Jazz Ensembles
Veronica Hagman Concert Hall, VPAC, Danbury
Tomorrow
☀️Open air🌳Outdoors
CP2 Mini Festival
Falls Theatre, Wappingers Falls
Tomorrow$25–47.505.0(47)
🎻Classical🎶Singer-songwriter
Candlelight: 90s Unplugged
Living Water Church, Poughkeepsie
Tomorrow · 7 PM
❓Quiz🎫Concert
Trivia Night - Every Friday Night!
King's Court Brewing Company, Poughkeepsie
Sun 4 · 2 PM$28.52
🎷Jazz🌳Outdoors
Big Band Swing at Tompkins Corners
Tompkins Corners Cultural Center, Putnam Valley
Wed 7 · 7 PM$23.18–97.88
🎷Jazz🎙️Small gig
Dave Edwards Trio Feat. Keyboardist Rob Aries & David Jimenez On Drums
La Zingara, Bethel
Today$0
🎪Street party🌳Outdoors
Low and Slow Social Club
Twins BBQ Co, Brookfield
Thu 8 · 5 PMFree
🎉Parties
Grand ReOpening!
487 Federal Rd, Brookfield
Sat 3 · 10 AMFree
🎉Parties
Spanish Heritage Celebration
Grinnell Public Library District, Wappingers Falls
Fri 9 · 10 PM$17.39–38.57
💿DJ set🎤Hip-Hop
The Remix Presents: Spooky Szn (Danbury Edition)
Diamond Club, Danbury
Sat 17 · 10:30 AM$5–1,000
🎪Street party🌳Outdoors
Warren OctoberFest 2026 - 3rd Annual
Warren Woods Town Park
Sat 24 · 11 AMFree
🎪Street party🏰Heritage
REV FEST 250
Ward Pound Ridge Reservation
Sat 10$3
🖼️Exhibition🪡Crafts
2026 Gaylordsville Columbus Day Arts and Fine Crafts Show
Merwinsville Hotel, Gaylordsville
At 4:30 PMFree
🗣️Talk🏛️Politics & Economy
Farmland Protection and Agricultural Viability
Dutchess County Farm & Home Center, Millbrook
Tomorrow · 10 AM
🖼️Exhibition📸Photography
October Artist: Christy Bonaiuto
Burnham Library
Sat 3 · 2:30 PM$31.85
📚Literature🗣️Talk
Author Tessa Wegert in conversation w/Author Deborah Levison 10/3 at 2:30PM
The BookSmiths Shoppe, Danbury
Mon 5 · 11 AM
🗣️Talk
Visiting Artist Lecture - Stephanie Pierce, Painter
Visual & Performing Arts Center, Danbury
Fri 16 · 7 PM$0
🗣️Talk🔬Science
When Giants Die: The Ecological Afterlife of Elephants | in-person
Cary Institute of Ecosystem Studies, Millbrook
Sat 24 · 10 AMFree
👗Fashion & Design🗣️Talk
One Room Two Ways: Design Workshop
227 Federal Rd, Brookfield
Sat 24 · 6 PMFree
📚Literature
Horseman Rising: An Evening in the Hollow: A Willow Bookshop Launch
Willow Bookshop & Lounge, Wappingers Falls
Sat 3 · 2 PM$0
🗺️Guided tour🏰Heritage
Stones & Bones Living History Tour at Wappingers Rural Cemetery
Wappingers Falls Rural Cemetery
Sat 3 · 2 PMFree
📚Literature
Horseman Rising Signing with Regina Bergen - Barnes & Noble, Poughkeepsie
Barnes & Noble, Poughkeepsie
Sat 3 · 2 PMFree
🖼️Exhibition🥂Opening
Opening Celebration for Photo-Design with Artist Sarah Elawad
Frances Lehman Loeb Art Center, Poughkeepsie
Fri 16 · 9 AM$0
🗣️Talk
Weekend with the Prophets
Residence Inn by Marriott Fishkill
Wed 21 · 7 PM$0
🗣️Talk🏰Heritage
The Hudson River and the American Revolution - a multimedia presentation
Wappinger Town Hall, Wappingers Falls
Tue 6
🤝Volunteering
Community Stitchers
Alley Room
Wed 7 · 6 PMFree
🕊️Human rights
Deep Canvassing in East Fishkill
Hopewell Recreation Park, Hopewell Junction
Sat 17 · 12 PMFree
🕊️Human rights🏛️Politics & Economy
No Kings: Vote Early New Milford CT
New Milford Town Green
Sat 17 · 11 AMFree
🕊️Human rights🏛️Politics & Economy
No Kings: Vote Early Bethel CT
Clifford J. Hurgin Municipal Center, Bethel
Sat 17 · 1 PMFree
🏛️Politics & Economy
No Kings: Vote Early [Canvass City of Poughkeepsie,NY]
302A Mill st, Poughkeepsie
Mon 19 · 6 PMFree
🕊️Human rights🏛️Politics & Economy
Mike Mondays: Healthcare Is A Human Right!
Mike Lawler's Mahopac Office
Your passions nearby
Tap what you're into — we'll find the outings around you.
