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Holiday Window Decorating Contest 2023

Downtown West Chester 2 N High Street, West Chester, PA

To celebrate the holidays and make the season brighter, dozens of businesses in Downtown West Chester will be creating special holiday displays in their storefront windows! The best part is…you get a chance to decide who wins!

Free
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Gingerbread House Competition 2023

Downtown West Chester 2 N High Street, West Chester, PA

The Professional Gingerbread House Competition, sponsored by Delphi Wealth Management, returns to West Chester! Professional bakers from the area are competing to create the best Gingerbread House. Houses are scattered around downtown and you get to vote!

Free
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Kildare’s Music Trivia

Kildare's Irish Pub 18 W Gay Street, West Chester, PA

Music trivia night is back is back at Kildare’s Irish Pub every Thursday at 8pm!

Free
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Ryan’s Pub Quizzo

Ryan's Pub 124 W Gay Street, West Chester, PA

Visit Ryan's Pub for Quizzo at 8:30pm every Thursday night! There's a gift card prize for the winner, plus drink prizes and giveaways!

Free

December First Friday 2023

Downtown West Chester 2 N High Street, West Chester, PA

Head to Downtown West Chester for First Friday! To celebrate, the Greater West Chester Chamber of Commerce is hosting the West Chester Christmas Parade!

Free
Recurring

Holiday Window Decorating Contest 2023

Downtown West Chester 2 N High Street, West Chester, PA

To celebrate the holidays and make the season brighter, dozens of businesses in Downtown West Chester will be creating special holiday displays in their storefront windows! The best part is…you get a chance to decide who wins!

Free
Recurring

Gingerbread House Competition 2023

Downtown West Chester 2 N High Street, West Chester, PA

The Professional Gingerbread House Competition, sponsored by Delphi Wealth Management, returns to West Chester! Professional bakers from the area are competing to create the best Gingerbread House. Houses are scattered around downtown and you get to vote!

Free
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Caroling in Downtown West Chester

Downtown West Chester 2 N High Street, West Chester, PA

Dressed in Victorian attire, The West Chester Borough Balladeer Carolers will roam around Downtown West Chester and perform throughout the holiday season!

Free
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Dungeons and Dragons Club

Chester County Art Association 100 N Bradford Ave, West Chester, PA

Have you wanted to learn how to play in the fun and imaginative world of Dungeons and Dragons? Join in the fun and we will go over all things D&D related.

The Holiday Cheer Show

Uptown! Knauer Performing Arts Center 226 N High Street, West Chester, PA

Start the Holiday Season off with a bang and enjoy Uptown Studio’s annual Holiday Cheer Concert!

$12 – $23

Little Lincolns Gettysburg Address Contest 2023

Chester County Community Foundation 28 W Market Street, West Chester, PA

Come out to support the annual "Little Lincolns" at the Gettysburg Address Competition taking place on the balcony of the Historic Lincoln Building, located at 28 West Market Street in Downtown West Chester. This event encourages youth to become more involved in their community and more deeply appreciate local history.

Free
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Bring Your Own Vinyl Night

Hop Fidelity 121 W Market Street, West Chester, PA

You bring it, we spin it! Every Friday from 6pm-10pm, come to Hop Fidelity for Bring Your Own Vinyl Night.

Free