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Best events in
Chester

Events and things to do in Chester, NY, are centered around its historic villages and community gathering spots. The hamlet of Sugar Loaf is a primary cultural draw, with its walkable streets lined with 18th-century buildings housing artisan studios and galleries. Meanwhile, local breweries provide casual backdrops for live music and social gatherings.

Spend an afternoon exploring the artisan craft village of Sugar Loaf before catching a national touring act or film festival at the Sugar Loaf Performing Arts Center.
Find live music and trivia nights at local craft breweries like Tin Barn Brewing and Rushing Duck Brewing Company.
Catch a stand-up act at Jester's Comedy Club or enjoy year-round activities from roller skating to go-karts at The Castle Fun Center.

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Fall City Escape - Upstate Hike + Farm Visit

Saturday • 7:15 AM

Esty and Hellie Stowell Trailhead

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Class of 1996 30 Year High School Reunion primary image

Class of 1996 30 Year High School Reunion

Saturday • 7:30 PM

Crowne Plaza Suffern-Mahwah by IHG

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Bootcamp For Boobs!

Saturday • 8:00 AM

Apex Performance Gym

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Sizzle & Serve: One-Pan Cooking with Executive Chef Brian Walter primary image

Sizzle & Serve: One-Pan Cooking with Executive Chef Brian Walter

Sunday • 11:00 AM

All One One All Farm

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HALLOWEEN SIP-N-PAINT AT HOUSE OF BIRRIA primary image

HALLOWEEN SIP-N-PAINT AT HOUSE OF BIRRIA

Sat, Oct 24 • 4:00 PM

House of Birria Tacos & Cantina

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Fall Candle-Making Class in Warwick, NY | Scripted Fragrance primary image

Fall Candle-Making Class in Warwick, NY | Scripted Fragrance

Sat, Oct 24 • 3:00 PM

Scripted Fragrance

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SAINT RITA's PRESENTS: Vinny DePonto - Mind Reader primary image

SAINT RITA's PRESENTS: Vinny DePonto - Mind Reader

Fri, Nov 6 • 7:30 PM

Saint Rita's Presents at The Masonic

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Breakfast with Santa primary image

Breakfast with Santa

Sun, Dec 6 • 1:00 PM

Kruckers, Call Hollow Road, Pomona, NY, USA

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Fall City Escape - Upstate Hike + Farm Visit primary image

Fall City Escape - Upstate Hike + Farm Visit

Saturday • 7:15 AM

Esty and Hellie Stowell Trailhead

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Class of 1996 30 Year High School Reunion primary image

Class of 1996 30 Year High School Reunion

Saturday • 7:30 PM

Crowne Plaza Suffern-Mahwah by IHG

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Bootcamp For Boobs! primary image

Bootcamp For Boobs!

Saturday • 8:00 AM

Apex Performance Gym

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Sizzle & Serve: One-Pan Cooking with Executive Chef Brian Walter primary image

Sizzle & Serve: One-Pan Cooking with Executive Chef Brian Walter

Sunday • 11:00 AM

All One One All Farm

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HALLOWEEN SIP-N-PAINT AT HOUSE OF BIRRIA primary image

HALLOWEEN SIP-N-PAINT AT HOUSE OF BIRRIA

Sat, Oct 24 • 4:00 PM

House of Birria Tacos & Cantina

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Fall Candle-Making Class in Warwick, NY | Scripted Fragrance primary image

Fall Candle-Making Class in Warwick, NY | Scripted Fragrance

Sat, Oct 24 • 3:00 PM

Scripted Fragrance

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SAINT RITA's PRESENTS: Vinny DePonto - Mind Reader primary image

SAINT RITA's PRESENTS: Vinny DePonto - Mind Reader

Fri, Nov 6 • 7:30 PM

Saint Rita's Presents at The Masonic

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Breakfast with Santa primary image

Breakfast with Santa

Sun, Dec 6 • 1:00 PM

Kruckers, Call Hollow Road, Pomona, NY, USA

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Nearby cities

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43 miles away

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Perfectionnement en programmation Python [en ligne, PYT102]

Thursday • 9:00 AM EDT

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Thu, Oct 22 • 6:00 PM GMT+2

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Perfectionnement en programmation Python [en ligne, PYT102]

Thursday • 9:00 AM EDT

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HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

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Coming Together for Multilingual Children with DLD

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(ONLINE) Women on the Move with Ann Patchett primary image

(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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Fri, Oct 30 • 2:00 PM GMT

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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 primary image

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Frequently asked questions about Chester

Where can I find comedy shows in Chester, NY?

Jester's Comedy Club is the local spot for stand-up comedy. The club hosts its Saturday Night Comedy showcase weekly, a popular event featuring a rotating lineup of comedians in an intimate setting.

What are some venues for live music events in the Chester area?

The Sugar Loaf Performing Arts Center hosts major national and international tours. For a more casual scene, local spots like Tin Barn Brewing and Pennings Farm feature regular live music events in their taprooms and beer gardens.

Are there family-friendly things to do in Chester?

The Castle Fun Center provides year-round entertainment for all ages. It offers a wide range of activities including go-karts, laser tag, and roller skating, making it a reliable destination for family outings.

What kind of art events happen in Sugar Loaf?

Sugar Loaf is a historic artisan village known for its creative community. The area hosts events like the annual Sugar Loaf Fall Festival, and visitors can explore independent studios and galleries year-round to see local craftsmanship.

What is the nightlife like in Chester, NY?

Chester's nightlife is relaxed and centered around local pubs and breweries. Places like Rushing Duck Brewing Company host trivia nights and music, while Jester's Comedy Club offers weekend shows for evening entertainment.

Do you have any date night ideas in the Chester area?

A great date night could involve seeing a show at the Sugar Loaf Performing Arts Center. Alternatively, enjoy a more casual evening with craft beverages and live music at Pennings Farm or catch a comedy act at Jester's.

Are there any annual festivals or major events in Sugar Loaf?

Sugar Loaf hosts several notable annual events at its performing arts center. These include the Sugar Loaf Film Festival in the fall and the Dead Ahead Festival, a full-day outdoor music event celebrating the Grateful Dead.

How can I experience the local community vibe in Chester?

The seasonal Chester Farmer's Market is a great place to connect with the community. Held on weekends, the market features local vendors selling fresh produce and goods, reflecting the town's small-town, community-focused atmosphere.