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

West Chester Christmas Parade 2023

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

Voted “Best Local Parade” and “Best Family-Friendly Event” by readers of Main Line Today, the parade delights more than 20,000 fans of all ages. Parade night kicks off December 1st at 6:30 p.m. with the official lighting of West Chester’s stunning 25-foot-tall Christmas tree on the lawn of the Historic Chester County Courthouse. The spectacle continues at 7 p.m. with the West Chester Christmas Parade!

Free

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
Recurring

West Chester Growers Market

Chestnut & Church Streets 201 N Church Street, West Chester, PA

As the first producer-only market in Southeastern PA, the West Chester Growers Market continues celebrating the direct connection between discriminating customers and local farmers and artisans.

Free

Holiday Home Tour 2023

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

The perennially popular Holiday Home Tour will take place on Saturday, December 2 from 10:00 am to 3:00 pm and will showcase eight homes in the Northwest and Southwest quadrants of the Borough decked out for the holidays. Ranging from petite to grand, the homes blend original details with modern updates and display the homeowners’ art, collectibles, and antiques.

$40 – $50
Recurring

Making Spirits Bright Holiday Music Series 2023

Chester County Historic Courthouse 21 W Market Street, West Chester, PA

The “Making Spirits Bright Holiday Music Series” will feature local choirs and performers as they sing your favorite holiday songs on the steps of the Historic Chester County Courthouse on High Street!

Free
Recurring

Santa on the Firetruck 2023

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

Bring the family downtown and see Santa on the Firetruck! Sponsored by Tolsdorf Oil Lube Express, Santa on the Fire Truck is happening every Saturday at 3pm from November 25th - December 16th! Santa will be escorted through the streets of Downtown West Chester by First WC Fire Co.

Free

Bourbon Street Jam 2023

Unitarian Congregation of West Chester 501 S High Street, West Chester, PA

The West Chester Green Team and the Unitarian Congregation of West Chester invite you on Dec. 2nd for our local jazz fest to get in the mood for, and raise money for, West Chester Porchfest 2024! Bourbon Street Jam will offer live music, raffles, a fashion show, tastings, and more!

$20
Recurring

Christmas Tree Train

West Chester Railroad 230 E Market Street, West Chester, PA

West Chester Railroad is again hosting it's popular Christmas Tree train this holiday season! We have partnered with Wiggins Tree Farm in West Chester, PA. Don't miss this classic holiday tradition!

Free – $30

Santa’s Express 2023

West Chester Railroad 230 E Market Street, West Chester, PA

All aboard Santa's Express! Join Santa for a 75-minute journey on our heated & decorated train through the Chester Creek Valley. We'll have multiple train rides for each date listed. Make sure you bring your holiday lists with you, so Santa can check them twice!

Free – $35

Brian’s Run 2023

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

Brian’s Run began in 1978 as a one-time fund raising event to benefit Brian Bratcher, a West Chester Henderson High School football player who sustained a life-challenging spinal cord injury at the age of 15 during a scrimmage. Brian was paralyzed that year, and his friends, their parents and the community as a whole wanted to help. Brian’s Run will be in Downtown West Chester on Sunday, December 3rd starting at 1pm. It will have a 5k and a 5 mile option this year!

$30