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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Nearby cities

New York

45 miles away

Jersey City

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Newark

43 miles away

Stamford

43 miles away

Upper Montclair

37 miles away

Norwalk

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Danbury

41 miles away

Hoboken

44 miles away

Harrison

43 miles away

Englewood

36 miles away

Kingston

42 miles away

Pompton Lakes

25 miles away

Yonkers

35 miles away

Woodstock

48 miles away

Beacon

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White Plains

34 miles away

Elizabeth

48 miles away

New Rochelle

40 miles away

Morristown

40 miles away

Garwood

49 miles away

Poughkeepsie

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Hackensack

35 miles away

River Edge

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Mount Vernon

38 miles away

Mount Arlington

37 miles away

Madison

42 miles away

Rutherford

38 miles away

Dover

35 miles away

Westport

50 miles away

Tuckahoe

36 miles away

New York

45 miles away

Jersey City

45 miles away

Newark

43 miles away

Stamford

43 miles away

Upper Montclair

37 miles away

Norwalk

47 miles away

Danbury

41 miles away

Hoboken

44 miles away

Harrison

43 miles away

Englewood

36 miles away

Kingston

42 miles away

Pompton Lakes

25 miles away

Yonkers

35 miles away

Woodstock

48 miles away

Beacon

19 miles away

White Plains

34 miles away

Elizabeth

48 miles away

New Rochelle

40 miles away

Morristown

40 miles away

Garwood

49 miles away

Poughkeepsie

30 miles away

Hackensack

35 miles away

River Edge

32 miles away

Mount Vernon

38 miles away

Mount Arlington

37 miles away

Madison

42 miles away

Rutherford

38 miles away

Dover

35 miles away

Westport

50 miles away

Tuckahoe

36 miles away

Online Events

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Lean Global Connection 2026

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Sat, Nov 14 • 1:00 PM EST

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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The World of Bunny vs Monkey Workshop with Jamie Smart

Saturday • 10:00 AM GMT

Check ticket price on event

Managing Your Emotions - Prof Ethan Kross

Tuesday • 7:00 PM GMT

Check ticket price on event

This Little World: a New History of Tudor and Stuart England

Wednesday • 7:30 PM GMT

Check ticket price on event

Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

Check ticket price on event

Gestion de l’anxiété dans le traitement des troubles alimentaires

Fri, Nov 13 • 1:00 PM EST

Check ticket price on event

Physicians Financial Wellness Conference 2026

Sat, Nov 14 • 1:00 PM EST

Check ticket price on event

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Thu, Dec 3 • 1:00 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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Events near Chester

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Sip & Decorate with Marie Béatrice Interiors: Workshop #1, The Blueprint

Saturday • 2:00 PM

Westtown

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Vinny DePonto - Mind Reader

Saturday • 7:30 PM

Saint Rita's Presents at The Masonic

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

Sat, Nov 14 • 2:00 PM

Scripted Fragrance

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November 2026 Grade A Compliant Lab Course. STOP!-See below before paying

Tue, Nov 17 • 8:30 AM

Wallkill Town Hall

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Unforgettable Fire - The U2 Experience at Silk Factory

Fri, Nov 20 • 8:00 PM

Silk Factory

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Heart Mending: Hawthorn Medicine, Magic and Lore, $55

Sat, Nov 21 • 10:00 AM

Vulgaris Herbs

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Breakfast with Santa

Sun, Dec 6 • 1:00 PM

Kruckers, Call Hollow Road, Pomona, NY, USA

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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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Sip & Decorate with Marie Béatrice Interiors: Workshop #1, The Blueprint

Saturday • 2:00 PM

Westtown

Check ticket price on event

Vinny DePonto - Mind Reader

Saturday • 7:30 PM

Saint Rita's Presents at The Masonic

Check ticket price on event

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

Sat, Nov 14 • 2:00 PM

Scripted Fragrance

Check ticket price on event

November 2026 Grade A Compliant Lab Course. STOP!-See below before paying

Tue, Nov 17 • 8:30 AM

Wallkill Town Hall

Check ticket price on event

Unforgettable Fire - The U2 Experience at Silk Factory

Fri, Nov 20 • 8:00 PM

Silk Factory

Check ticket price on event

Heart Mending: Hawthorn Medicine, Magic and Lore, $55

Sat, Nov 21 • 10:00 AM

Vulgaris Herbs

Check ticket price on event

Breakfast with Santa

Sun, Dec 6 • 1:00 PM

Kruckers, Call Hollow Road, Pomona, NY, USA

Check ticket price on event

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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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.

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Nearby cities

New York

Jersey City

Newark

Stamford

Upper Montclair

Norwalk

Danbury

Hoboken

Harrison

Englewood

Kingston

Pompton Lakes

Yonkers

Woodstock

Beacon

White Plains

Elizabeth

New Rochelle

Morristown

Garwood

Poughkeepsie

Hackensack

River Edge

Mount Vernon

Mount Arlington

Madison

Rutherford

Dover

Westport

Tuckahoe

New York

Jersey City

Newark

Stamford

Upper Montclair

Norwalk

Danbury

Hoboken

Harrison

Englewood

Kingston

Pompton Lakes

Yonkers

Woodstock

Beacon

White Plains

Elizabeth

New Rochelle

Morristown

Garwood

Poughkeepsie

Hackensack

River Edge

Mount Vernon

Mount Arlington

Madison

Rutherford

Dover

Westport

Tuckahoe

Online Events

The World of Bunny vs Monkey Workshop with Jamie Smart

Managing Your Emotions - Prof Ethan Kross

This Little World: a New History of Tudor and Stuart England

Lean Global Connection 2026

Gestion de l’anxiété dans le traitement des troubles alimentaires