West Chester Holiday Events

Lights Up! Holiday Weekends in West Chester

137 N High St 27 Nov 2026

2026 West Chester Hometown Christmas Parade

Downtown West Chester, PA 4 Dec 2026

West Chester Christmas Parade & Tree Lighting

137 S High St 4 Dec 2026

Christkindlmarkt 2026

Downtown West Chester, PA 12 Dec 2026

West Chester Turkey Trot 2026

Downtown West Chester, PA 26 Nov 2026

Singles Holiday Party at Penn Oaks | 55+

Penn Oaks Golf Club 20 Nov 2026

2nd Annual West Chester Holiday Shop & Stroll

Downtown West Chester PA 15 Nov 2026

Westtown Township Bus Trip to American Music Theatre and Kitchen Kettle Village

1014 S Concord Rd, West Chester, PA 19382-7407, United States 2 Dec 2026

Irving Berlin’s White Christmas

226 N High St., West Chester, PA, United States, Pennsylvania 19380 5 Dec 2026

Merry & Bright: A Holiday Chalkboard Class

Stove and Tap West Chester 11 Nov 2026

Milk and Cookies Storytime with Santa and Buddy the Elf

1014 S Concord Rd, West Chester, PA 19382-7407, United States 13 Dec 2026

Comfort & Joy

Fugett Middle School Auditorium 11 Dec 2026

10 Years of Christmas Magic: Opening Weekend

895 S Concord Rd, West Chester, PA 19382-5562, United States 28 Nov 2026

Holiday Cookie Decorating Class - FRIDAY 12/11

426 W Gay St 11 Dec 2026

The "Jolly Jawn" formerly "Sleigh Bar" in West Chester update..

30 N Church St, West Chester, PA 19380-3022, United States 29 Nov 2026

The Parade AFTER PARTY @ Kildare's

West Chester Kildare's Irish Pub 4 Dec 2026

Santa Band Stroll Fundraiser

Borough of West Chester 23 Dec 2026

Die Hard

226 N High St., West Chester, PA, United States, Pennsylvania 19380 14 Dec 2026

Uptown Studio Annual Holiday Cheer Concert

226 N High St., West Chester, PA, United States, Pennsylvania 19380 4 Dec 2026

It’s A Wonderful Life

226 N High St., West Chester, PA, United States, Pennsylvania 19380 21 Dec 2026

How The Grinch Stole Christmas (2000)

226 N High St., West Chester, PA, United States, Pennsylvania 19380 28 Dec 2026

Emerald Strings: A Winter Journey

226 N High St., West Chester, PA, United States, Pennsylvania 19380 9 Dec 2026

Brunchalong West Chester Holiday Party

Station 142 27 Dec 2026

The Polar Express

226 N High St., West Chester, PA, United States, Pennsylvania 19380 7 Dec 2026

Screen to Stage: A Holiday Dance Celebration

Stetson
Middle School 12 Dec 2026

December Gallery Openings

100 N Bradford Ave, West Chester, PA, United States, Pennsylvania 19382 9 Dec 2026

A Crooner’s Christmas

226 N High St., West Chester, PA, United States, Pennsylvania 19380 17 Dec 2026

West Chester Historic Downtown Hunt

2 N High St 7 Nov 2026

Craftapalooza!

100 N Bradford Ave, West Chester, PA, United States, Pennsylvania 19382 15 Nov 2026

Holiday Cookie Decorating Class - SATURDAY 12/12

426 W Gay St 12 Dec 2026

Santa, Sweets & Christmas Lights

895 S Concord Rd, West Chester, PA 19382-5562, United States 12 Dec 2026

Singles Mistletoe and Martinis | 38-55

Penn Oaks Golf Club 13 Nov 2026

Toys for Tots Collection at CCAA

100 N Bradford Ave, West Chester, PA, United States, Pennsylvania 19382 2 Dec 2026

FREE Photos with Santa

VRA Realty 14 Nov 2026

Charity Ball 2026 - Back To The 80's

111 W Ashbridge St, West Chester, PA 19380-2301, United States 5 Dec 2026