Updated November 1, 2025 – Finding things to do in West Chester, PA is never a challenge. The borough has its many perks. From the incredible restaurants and nightlife to the fantastic university, it truly is a special place. But it would be hard to argue that a few places on Earth are more charming than West Chester, PA, during the holidays. The decorations downtown are hung by local volunteers and usher in a holiday spirit that feels like small-town heaven.
With that being said, in no particular order, here are our top picks for things to do in West Chester PA during the Holidays in 2025.
Holiday Home Tour
This year’s 14th Annual Holiday Home Tour presented by the West Chester Public Library is set for Saturday, December 6, 2025, from 10:00 am to 3:00 pm, featuring eight homes in the Borough’s Northeast and Southwest neighborhoods adorned for the season. These residences, spanning from cozy to spacious, showcase historic charm and modern enhancements, as well as homeowners’ unique collections of art, antiques, and other treasures. Attendees can also visit the Chester County History Center and gain complimentary access as part of the tour experience. If you’re looking for fun things to do in West Chester, PA, this event is a top pick.
Think Shop, Buy Local
No list of fun things to do in West Chester, PA, would be complete without highlighting a full day in downtown West Chester during the holidays — and local businesses have never needed more support. The Greater West Chester Chamber of Commerce “Think Shop Buy Local” initiative joins the West Chester Business Improvement District’s “Shop Small West Chester” weekend, which will take place Friday, November 28, through Sunday, November 30, 2025. Start with brunch at one of the many excellent local restaurants, grab coffee and fresh pastries at a local café, wander the holiday-decked streets, pick up unique gifts, and consider treating yourself to a stay at a boutique hotel. This is truly one of the best things to do in West Chester, PA, if you love a festive shopping day.
West Chester Holiday Films
This year, one of the best things to do in West Chester, PA, is to bundle up and head to the Uptown for holiday‑film nights. The Uptown’s holiday lineup includes a screening of Elf on Friday, November 28, 2025, at 7:00 pm, followed by White Christmas on Monday, December 8, at 7:00 pm, then Holiday Inn on Monday, December 15, at 7:00 pm, and finally The Man Who Invented Christmas on Monday, December 22, at 7:00 pm at the Uptown – Knauer Performing Arts Center.
Whether you’re looking for fun things to do in West Chester, PA, with family or friends, catching one of these films in the Uptown’s charming historic theatre is a festive and cozy way to embrace the season.
All Aboard! – the West Chester Railroad Santa Express
Hop aboard one of the most magical fun things to do in West Chester PA this season — the Santa Express train ride. Running on select weekends from Saturday, November 22 through Sunday, December 21, 2025, this 75‑minute journey departs from the Market Street Station in downtown West Chester and winds through the scenic Chester Creek Valley, arriving at Glen Mills before returning.
As you settle into the warmed and festively decorated train cars, you’ll be greeted by Santa himself at the station and accompanied by live onboard entertainment and holiday treats. This special ride ranks among the best things to do in West Chester PA for families or anyone wanting to embrace that seasonal charm — be sure to reserve tickets early, as the excursion tends to sell out.
Show Your Love and Support
West Chester is truly a gem. It didn’t become this beloved town by chance—it took dreaming, planning, and hard work. During this holiday season, let’s rally behind the local businesses, restaurants, and cultural institutions that make this place unique. Before you click “Buy Now” on a big-box site, remember that the small businesses of West Chester depend on our support. Commit to shopping locally in 2025 and beyond. You’ll be doing something meaningful for our community and discovering some of the very best things to do in West Chester, PA.
From all of us at Zukin Realty, we wish you a happy holiday season.
