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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Events near Ossining

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Connect NY Cup Nov 14th, 2026

Today • 11:00 AM

New York State

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Westchester Speed Dating for Singles Age 20s/30s ♥ Dobbs Ferry NY

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Bellacosa Wine & Tapas Bar

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Tree Identification Walk

Thursday • 10:00 AM

Rockefeller State Park Preserve

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WCSPP Annual Conference (IN-PERSON)

Sat, Nov 21 • 9:00 AM

Manhattanville University, Reid Castle

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Mini Arrangement Workshop for Families - December 5 , 11am-12pm

Sat, Dec 5 • 11:00 AM

Untermyer Gardens

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Breakfast with Santa

Sun, Dec 6 • 1:00 PM

Kruckers, Call Hollow Road, Pomona, NY, USA

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Neil Berg's New Year's Eve Broadway Celebration 2026!

Thu, Dec 31 • 7:30 PM

Saint Joseph Regional High School

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A Taste of Ireland - The Irish Music & Dance Sensation

Thu, Mar 18 • 7:30 PM

Rockland Community College Cultural Arts Center Theatre

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Connect NY Cup Nov 14th, 2026

Today • 11:00 AM

New York State

Check ticket price on event

Westchester Speed Dating for Singles Age 20s/30s ♥ Dobbs Ferry NY

Wednesday • 6:30 PM

Bellacosa Wine & Tapas Bar

Check ticket price on event

Tree Identification Walk

Thursday • 10:00 AM

Rockefeller State Park Preserve

Check ticket price on event

WCSPP Annual Conference (IN-PERSON)

Sat, Nov 21 • 9:00 AM

Manhattanville University, Reid Castle

Check ticket price on event

Mini Arrangement Workshop for Families - December 5 , 11am-12pm

Sat, Dec 5 • 11:00 AM

Untermyer Gardens

Check ticket price on event

Breakfast with Santa

Sun, Dec 6 • 1:00 PM

Kruckers, Call Hollow Road, Pomona, NY, USA

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Neil Berg's New Year's Eve Broadway Celebration 2026!

Thu, Dec 31 • 7:30 PM

Saint Joseph Regional High School

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A Taste of Ireland - The Irish Music & Dance Sensation

Thu, Mar 18 • 7:30 PM

Rockland Community College Cultural Arts Center Theatre

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Physicians Financial Wellness Conference 2026

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HBR Book Webinar: Unspeakable

Mon, Nov 23 • 1:00 PM GMT

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HBR Press Webinar: Unspeakable

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How to Choose a (New) Career Fast

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Sorted Live: A Food Nightmare Before Christmas

Sat, Dec 5 • 12:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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PLAYFUL ARCHITECTURE: Drawing in Colour and Monochrome

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Physicians Financial Wellness Conference 2026

Today • 1:00 PM EST

Check ticket price on event

Singing & Emotional Regulation

Wednesday • 6:00 PM GMT

Check ticket price on event

HBR Book Webinar: Unspeakable

Mon, Nov 23 • 1:00 PM GMT

Check ticket price on event

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Mon, Nov 23 • 8:00 AM EST

Check ticket price on event

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Thu, Dec 3 • 1:00 PM GMT

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Sat, Dec 5 • 12:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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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.

Events near Ossining

Connect NY Cup Nov 14th, 2026

Westchester Speed Dating for Singles Age 20s/30s ♥ Dobbs Ferry NY

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WCSPP Annual Conference (IN-PERSON)

Mini Arrangement Workshop for Families - December 5 , 11am-12pm

Breakfast with Santa

Neil Berg's New Year's Eve Broadway Celebration 2026!

A Taste of Ireland - The Irish Music & Dance Sensation

Connect NY Cup Nov 14th, 2026

Westchester Speed Dating for Singles Age 20s/30s ♥ Dobbs Ferry NY

Tree Identification Walk

WCSPP Annual Conference (IN-PERSON)

Mini Arrangement Workshop for Families - December 5 , 11am-12pm

Breakfast with Santa

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A Taste of Ireland - The Irish Music & Dance Sensation

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Nearby cities

New York

Jersey City

Newark

Stamford

Bridgeport

Upper Montclair

Norwalk

Danbury

Hoboken

Harrison

Englewood

Northport

Elizabeth

White Plains

New Rochelle

Yonkers

Mount Vernon

Morristown

Pompton Lakes

Poughkeepsie

Beacon

Rockville Centre

Hackensack

Westbury

Garwood

Westport

New Haven

Madison

River Edge

Huntington

New York

Jersey City

Newark

Stamford

Bridgeport

Upper Montclair

Norwalk

Danbury

Hoboken

Harrison

Englewood

Northport

Elizabeth

White Plains

New Rochelle

Yonkers

Mount Vernon

Morristown

Pompton Lakes