Holiday Happenings Guide

Find out what festive activities are happening in West Chester this holiday season!

The holidays are a bustling time in West Chester. There is so much to see and do in our community to get into the holiday spirit, which is why we put together the West Chester Holiday Happenings Guide. We hope this guide helps you find the perfect activities to ring in the holiday season in our amazing town! 

West Chester Hometown Christmas Parade and Tree Lighting 

Friday, December 1st

6:30 pm Tree Lighting at the Lawn of the Historic Courthouse

7:00 pm Parade 

Location: Downtown West Chester 

Even Santa himself can’t stay away from this annual tradition. The Hometown Christmas Parade and Tree Lighting is back for another year to usher in the holiday season with more marching bands, award-winning floats, a wide array of community group performances, and capped off with the big guy himself waving a hearty “Ho Ho Ho” to everyone along the parade route. It’s a great way to get into the Christmas spirit with your community.  

West Chester Railroad 

Santa’s Express: Dec 2, 3, 9, 10, 16, 17 

Times: 11 am, 1 pm,  3 pm, 5 pm 

Christmas Tree Train: Dec 3, 10 

Times: 8 am Only 

Location: Market St. Station in West Chester 

All Aboard! The West Chester Railroad is full-steam ahead for this holiday season offering both the popular Santa’s Express and Christmas Tree Train! 

Guests of all ages can join Santa on a 75-minute holiday journey through the Chester Creek Valley en route to the Glen Mills station. The heated and decorated train will feature live entertainment, refreshments for purchase on board, and of course, Santa himself. This popular event is sure to sell out, so make sure to get your tickets early! 

The popular Christmas Tree Train takes passengers to the Wiggins Tree Farm to pick out their holiday tree. All passengers will depart the Market St. location at 8 a.m. When they arrive at the tree farm, they will be provided with a hand saw as they embark on their mission to find the perfect tree. Passengers will board the train to return to West Chester at 9:45 a.m. Seating is very limited for this event, so order your tickets early. The trip is approximately 2 hours in length. 

Visit www.wcrailroad.com for more information.

Christkindlmarkt at the Chester County Art Association 

Saturday, December 9 from 1 pm - 8 pm 

Sunday, December 10 from 11 am - 4 pm

Location: Gay St. in Downtown West Chester 

Join the Chester County Art Association for its 4th annual Christkindlmarkt. This free holiday market will feature over 60 stall holders offering individually handcrafted and locally designed products including art, ceramics, jewelry, homewares, food, and much more on Gay Street in Downtown West Chester. This is a great way to support our local artisans as well as find the perfect holiday gifts for your loved ones! Visit the Chester County Art Association website at www.chestercountyarts.org for more information. 

Professional Gingerbread House Competition

Now Through January 2nd 

Location: Throughout Downtown West Chester

Professional bakers from the area compete in this annual competition to see who can create the best Gingerbread House in West Chester. The competition takes place throughout Downtown West Chester now through January 2nd. Visit www.greaterwestchester.com for more information on participants and how to vote! Past participants include Kilwins of West Chester, The Master’s Baker, Carlino’s Market, John Serock Catering, Cakes & Candies by Mary Ellen, and Yori’s Bakery. While you’re visiting these amazing creations, make sure to pick up a delicious treat from their shops. 

Holiday Shows - Uptown! At Knauer Performing Arts Center  

Throughout December

Location: 226 N. High St. in West Chester

To help you get into the holiday spirit, the Uptown! has great holiday shows happening throughout December. 

Starting with the Holiday Cheer Concert on Dec 1st, the Uptown Studio singers will sing a mix of holiday favorites and current pop and R&B hits. Come out and support our area youth, also known as our future stars of Broadway!  

On Wednesday, December 6th,  Accent, the international acappella hit group will dazzle the audience with their smooth jazz overlays to classic holiday hits. This is a concert you won’t want to miss! 

Other shows throughout the month include Holidays in Hollywood,  The Cartoon Christmas Trio, The Last Big Band, Twelve Twenty-Four, A Dream is a Wish, and Ballet with a Twist. For more information and to purchase tickets for a show, head to uptownwestchester.org. 

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