Best events in
Ossining

Looking for events or things to do in Ossining, NY? Community life revolves around two key areas: the walkable, historic downtown and the scenic Hudson River waterfront. The village's rhythm shifts from daytime community gatherings to evening concerts and dining with river views.

A typical weekend can begin downtown at the year-round Ossining Farmers Market before an evening of local culture at Sing Sing Kill Brewery or a performance at the historic Olive Opera House.
Bethany Arts Community is a hub for creative workshops, art exhibitions, and a monthly open mic night for poetry, spoken word, and music.
Outdoor events are centered on the waterfront, where Louis Engel Park hosts the RiverJam Summer Concert Series and Henry Gourdine Park features a summer jazz series.

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Popular in Ossining

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Cigar Night on October 5th

Tomorrow • 6:30 PM

The Briarcliff Manor

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Sound Bath at Bella Maiya Day Spa, The Final Harvest

Tomorrow • 7:00 PM

Bella Maiya Day Spa

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FGT H.E.R. Women's Ministry's 5th Annual Women's Empowerment Symposium

Saturday • 9:00 AM

15 Brandreth St

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Ossining Elks - Paint and Sip

Fri, Oct 16 • 7:00 PM

118 Upper Croton Ave

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Pizza Making Class with 2 Hour Beer & Wine Open Bar

Sat, Oct 17 • 11:00 AM

3 Westerly Bar and Grill

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Kiddie Academy Fall Fest 26 [FREE]

Sun, Oct 18 • 10:00 AM

325 S Highland Ave

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Here We Go, Yo! October Halloween Edition!

Fri, Oct 23 • 7:30 PM

Karma Lounge Restaurant

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Terror Tales: A Halloween Ten-Minute Play Festival

Fri, Oct 23 • 7:30 PM + 7 more

Westchester Collaborative Theater (GPS 21 Water St.)

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Cigar Night on October 5th

Tomorrow • 6:30 PM

The Briarcliff Manor

Check ticket price on event

Sound Bath at Bella Maiya Day Spa, The Final Harvest

Tomorrow • 7:00 PM

Bella Maiya Day Spa

Check ticket price on event

FGT H.E.R. Women's Ministry's 5th Annual Women's Empowerment Symposium

Saturday • 9:00 AM

15 Brandreth St

Check ticket price on event

Ossining Elks - Paint and Sip

Fri, Oct 16 • 7:00 PM

118 Upper Croton Ave

Check ticket price on event

Pizza Making Class with 2 Hour Beer & Wine Open Bar

Sat, Oct 17 • 11:00 AM

3 Westerly Bar and Grill

Check ticket price on event

Kiddie Academy Fall Fest 26 [FREE]

Sun, Oct 18 • 10:00 AM

325 S Highland Ave

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Here We Go, Yo! October Halloween Edition!

Fri, Oct 23 • 7:30 PM

Karma Lounge Restaurant

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Terror Tales: A Halloween Ten-Minute Play Festival

Fri, Oct 23 • 7:30 PM + 7 more

Westchester Collaborative Theater (GPS 21 Water St.)

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Online Events

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A Norman stitch-up? The story behind the Bayeux Tapestry

Wednesday • 7:30 PM GMT+1

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AI Kids Music Video Studio: Produce Black Nursery Rhyme for YouTube

Thursday • 6:00 PM EDT

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HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

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HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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A Norman stitch-up? The story behind the Bayeux Tapestry

Wednesday • 7:30 PM GMT+1

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AI Kids Music Video Studio: Produce Black Nursery Rhyme for YouTube

Thursday • 6:00 PM EDT

Check ticket price on event

HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

Check ticket price on event

HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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From nearby cities

Nocturnal Night Walk

Friday • 6:30 PM

Rockefeller State Park Preserve

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An Evening of Spirit Connection with Mediums Daisy & Arlene

Sun, Oct 11 • 5:00 PM

Shames JCC on the Hudson

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Class of 1996 30 Year High School Reunion

Sat, Oct 17 • 7:30 PM

Crowne Plaza Suffern-Mahwah by IHG

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The Duprees in Concert with guests, Classic Sounds. Host Dennis Nardone

Sun, Oct 18 • 3:00 PM

Port Chester High School

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Zoo Boo TRAIN Ride only Sunday Day 10-5pm

Sun, Oct 18 • 10:00 AM

Bergen County Zoo

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Receiving and Celebrating the New Liturgy of the Hours

Sat, Oct 24 • 10:00 AM

St. Joseph's Seminary

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12/2 Zoo Kids: Carnivores

Wed, Dec 2 • 3:15 PM

Bergen County Zoo

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Breakfast with Santa

Thu, Dec 24 • 9:00 AM

Kruckers, Call Hollow Road, Pomona, NY, USA

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Nocturnal Night Walk

Friday • 6:30 PM

Rockefeller State Park Preserve

Check ticket price on event

An Evening of Spirit Connection with Mediums Daisy & Arlene

Sun, Oct 11 • 5:00 PM

Shames JCC on the Hudson

Check ticket price on event

Class of 1996 30 Year High School Reunion

Sat, Oct 17 • 7:30 PM

Crowne Plaza Suffern-Mahwah by IHG

Check ticket price on event

The Duprees in Concert with guests, Classic Sounds. Host Dennis Nardone

Sun, Oct 18 • 3:00 PM

Port Chester High School

Check ticket price on event

Zoo Boo TRAIN Ride only Sunday Day 10-5pm

Sun, Oct 18 • 10:00 AM

Bergen County Zoo

Check ticket price on event

Receiving and Celebrating the New Liturgy of the Hours

Sat, Oct 24 • 10:00 AM

St. Joseph's Seminary

Check ticket price on event

12/2 Zoo Kids: Carnivores

Wed, Dec 2 • 3:15 PM

Bergen County Zoo

Check ticket price on event

Breakfast with Santa

Thu, Dec 24 • 9:00 AM

Kruckers, Call Hollow Road, Pomona, NY, USA

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Frequently asked questions about Ossining

Where are the best spots for live music events in Ossining?

The Boathouse and Louis Engel Waterfront Park are top choices for live music. During summer, the park hosts the free RiverJam Summer Concert Series, while The Boathouse offers a more intimate setting with river views. The weekly Ossining Farmers Market also frequently features local musicians.

Are there free events to attend in Ossining?

Yes, Ossining offers many free community events, especially in the summer. The RiverJam concert series at Louis Engel Waterfront Park and the jazz concerts at Henry Gourdine Park are popular annual traditions. The Green Ossining Earth Day Festival is another major free event.

What are some family-friendly events in Ossining, NY?

Bethany Arts Community hosts recurring family-friendly workshops called "CREATE Saturdays". The Ossining Public Library also offers various programs, and the annual Green Ossining Earth Day Festival at the waterfront is a large event with activities suitable for all ages.

What's the nightlife scene like in Ossining?

Ossining's nightlife is relaxed and centered on local gathering spots. Sing Sing Kill Brewery hosts events like trivia, salsa nights, and a monthly open mic, while some waterfront restaurants like The Boathouse feature evening live music. It's a low-key alternative to a bustling club scene.

Where can I find art and culture events in Ossining?

Bethany Arts Community is a central hub for the arts, presenting exhibitions, workshops, and performances. The Ossining Public Library's Budarz Theater hosts film screenings and author talks, and the historic Olive Opera House is being revitalized as a downtown performance venue.

What's the difference between downtown and waterfront events?

Downtown Ossining is the year-round hub for community life, with the weekly farmers market and brewery events. The waterfront is more seasonal, coming alive with outdoor concerts like RiverJam and large festivals during warmer months, drawing crowds for the scenic Hudson River backdrop.

Any good date night ideas in Ossining?

A classic Ossining date involves dinner at a waterfront restaurant followed by a free outdoor concert. For something different, consider a history talk or salsa night at Sing Sing Kill Brewery, or check the schedule for a film or performance at the Ossining Public Library.

Can I find comedy shows or open mic events in Ossining?

Yes, you can find open mic nights that feature comedy and music. Sing Sing Kill Brewery hosts a monthly open mic for music and comedy. For a different vibe, Bethany Arts Community has a monthly open mic night focused on poetry, spoken word, and music.