Best events in
Chesterton

For events and things to do in Chesterton, IN, the local scene is defined by its community spirit and strong connection to the arts. Most activity centers on the walkable downtown area, where historic storefronts house galleries, theaters, and cozy pubs. The town's proximity to the Indiana Dunes also shapes its culture, blending outdoor recreation with local arts and community gatherings.

Stroll through historic downtown Chesterton, where Third Fridays bring the area to life with open galleries at the Chesterton Art Center and extended hours at local shops.
Catch a local production at the 4th Street Theater or enjoy a casual, family-friendly open mic night at Cheers.
Experience large-scale community events at local parks, from the weekly European Market in Thomas Centennial Park to the annual Chesterton Art Fair in Dogwood Park.

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Popular in Chesterton

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Coffee Creek Center Trunk or Treat

Today • 5:00 PM

Allen Law Group / Coffee Creek Professional Center

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Halloween Bash '26 NWI | Open Bar Costume Party + $1,000 Contest

Saturday • 8:00 PM

Duneland Falls All-Inclusive Event Venue

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RISE Around the Region

Thu, Nov 5 • 5:30 PM

Just Breathe

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Paint & Drink at Running Vines Winery: Gingerbread House

Wed, Nov 11 • 6:00 PM

Running Vines Winery, Broadway Avenue, Chesterton, IN, USA

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National Philanthropy Day

Thu, Nov 12 • 8:30 AM

Sand Creek Country Club

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Interwoven Expressions 2026

Sat, Nov 14 • 9:00 AM

Sand Creek Country Club

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C12 Executive Luncheon with Patrick Lencioni Webinar

Wed, Nov 18 • 11:00 AM

Sand Creek Country Club

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The Cigar Maker Experience

Sat, Jan 9 • 12:00 PM + 24 more

3093 Village Point

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Coffee Creek Center Trunk or Treat

Today • 5:00 PM

Allen Law Group / Coffee Creek Professional Center

Check ticket price on event

Halloween Bash '26 NWI | Open Bar Costume Party + $1,000 Contest

Saturday • 8:00 PM

Duneland Falls All-Inclusive Event Venue

Check ticket price on event

RISE Around the Region

Thu, Nov 5 • 5:30 PM

Just Breathe

Check ticket price on event

Paint & Drink at Running Vines Winery: Gingerbread House

Wed, Nov 11 • 6:00 PM

Running Vines Winery, Broadway Avenue, Chesterton, IN, USA

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National Philanthropy Day

Thu, Nov 12 • 8:30 AM

Sand Creek Country Club

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Interwoven Expressions 2026

Sat, Nov 14 • 9:00 AM

Sand Creek Country Club

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C12 Executive Luncheon with Patrick Lencioni Webinar

Wed, Nov 18 • 11:00 AM

Sand Creek Country Club

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The Cigar Maker Experience

Sat, Jan 9 • 12:00 PM + 24 more

3093 Village Point

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Online Events

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SAMHAIN SÉANCE: Ancestral Collaboration with Pam Grossman & Janaka Stucky

Sunday • 6:00 PM EST

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Humanitarian Water Engineering Fall 2026

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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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The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

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REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

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The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 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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SAMHAIN SÉANCE: Ancestral Collaboration with Pam Grossman & Janaka Stucky

Sunday • 6:00 PM EST

Check ticket price on event

Humanitarian Water Engineering Fall 2026

Check ticket price on event

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

Check ticket price on event

The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

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REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

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The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 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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Free events

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Coffee Creek Center Trunk or Treat

Today • 5:00 PM

Allen Law Group / Coffee Creek Professional Center

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RISE Around the Region

Thu, Nov 5 • 5:30 PM

Just Breathe

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Don't Let the Flu Catch You - Essential Steps for a Healthy Season

Fri, Nov 13 • 12:00 PM

Duneland Family YMCA

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C12 Executive Luncheon with Patrick Lencioni Webinar

Wed, Nov 18 • 11:00 AM

Sand Creek Country Club

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Coffee Creek Center Trunk or Treat

Today • 5:00 PM

Allen Law Group / Coffee Creek Professional Center

Check ticket price on event

RISE Around the Region

Thu, Nov 5 • 5:30 PM

Just Breathe

Check ticket price on event

Don't Let the Flu Catch You - Essential Steps for a Healthy Season

Fri, Nov 13 • 12:00 PM

Duneland Family YMCA

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C12 Executive Luncheon with Patrick Lencioni Webinar

Wed, Nov 18 • 11:00 AM

Sand Creek Country Club

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From nearby cities

Divine Vines Comedy + Costumes at Anderson's

Tomorrow • 5:30 PM

Anderson's Winery and Vineyard

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The Porter County haunted terror tour by Bus October 30th!

Tomorrow • 7:00 PM

100 east Indiana Ave St, Valparaiso, IN 46383, United States

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Halloween Bash '26 NWI | Open Bar Costume Party + $1,000 Contest

Saturday • 8:00 PM

Duneland Falls All-Inclusive Event Venue

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Italian Cooking Class

Thu, Nov 5 • 5:30 PM

Blue Moon Vintage Barn

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Dig the Dunes Artisan Market

Sat, Nov 7 • 10:00 AM

Lubeznik Center for the Arts

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Rescued Metal Art - Beginner friendly welding and metal arts

Sat, Nov 14 • 1:00 PM

The HUB NWI

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TalkativeChic Presents Chicagoland Stand-up Comedy Show

Sat, Nov 21 • 7:30 PM

Art Theater

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Jump: America's Van Halen Experience

Sat, Nov 28 • 8:00 PM

Blue Chip Casino Hotel Spa

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Divine Vines Comedy + Costumes at Anderson's

Tomorrow • 5:30 PM

Anderson's Winery and Vineyard

Check ticket price on event

The Porter County haunted terror tour by Bus October 30th!

Tomorrow • 7:00 PM

100 east Indiana Ave St, Valparaiso, IN 46383, United States

Check ticket price on event

Halloween Bash '26 NWI | Open Bar Costume Party + $1,000 Contest

Saturday • 8:00 PM

Duneland Falls All-Inclusive Event Venue

Check ticket price on event

Italian Cooking Class

Thu, Nov 5 • 5:30 PM

Blue Moon Vintage Barn

Check ticket price on event

Dig the Dunes Artisan Market

Sat, Nov 7 • 10:00 AM

Lubeznik Center for the Arts

Check ticket price on event

Rescued Metal Art - Beginner friendly welding and metal arts

Sat, Nov 14 • 1:00 PM

The HUB NWI

Check ticket price on event

TalkativeChic Presents Chicagoland Stand-up Comedy Show

Sat, Nov 21 • 7:30 PM

Art Theater

Check ticket price on event

Jump: America's Van Halen Experience

Sat, Nov 28 • 8:00 PM

Blue Chip Casino Hotel Spa

Check ticket price on event

Frequently asked questions about Chesterton

What are some top spots for art events in Chesterton?

The Chesterton Art Center is the main hub for visual arts. It features rotating gallery exhibitions and organizes the annual Chesterton Art Fair in Dogwood Park. For performing arts, 4th Street Theater stages community productions, including an annual 10-minute play festival.

Are there family-friendly events in Chesterton?

Yes, Chesterton offers many events perfect for families. The annual Downtown Trick-or-Treat is a seasonal highlight, and the weekly European Market in Thomas Centennial Park provides a lively atmosphere. Dogwood Park also hosts several family-oriented festivals and runs.

How can I find free things to do in downtown Chesterton?

Exploring downtown during the monthly Third Fridays event is a great free activity. Galleries like the Chesterton Art Center have open doors, and the atmosphere is festive. Many community gatherings in Thomas Centennial Park, like attending the European Market, are also free to enjoy.

What is the nightlife scene like in Chesterton?

Chesterton's nightlife is relaxed and centered on local pubs and community events. Many spots host weekly trivia nights, such as Gastro 49 Pub. For a low-key evening, Cheers offers a family-friendly pub environment that includes a weekly open mic night.

Where can I find live music events in Chesterton?

Live music is a key part of Chesterton's community gatherings. The European Market, held in Thomas Centennial Park from May through October, regularly features local musicians. For a more intimate setting, the pub Cheers is known for its weekly open mic night.

Is there a comedy scene in Chesterton?

The local comedy scene is driven by groups like the Disposable Theatre. This improvisational troupe performs in various local spaces and also offers improv classes for those interested in learning. Their shows pop up in unconventional and community-oriented venues around town.

What are some good date night ideas in Chesterton?

A great date night could involve a stroll through downtown during a Monthly event. Start by visiting the Chesterton Art Center, enjoy dinner at a local restaurant with outdoor dining, and then catch a performance at the 4th Street Theater for a complete evening.

What kind of outdoor events does Chesterton host?

Chesterton's parks are central to its major outdoor events. Thomas Centennial Park hosts the bustling European Market every Saturday from spring through fall, while the larger Dogwood Park is the venue for the annual juried Chesterton Art Fair.