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West Chester Chili Cook-Off, Halloween Parade and More October 2022 Events Near Chestnut Square

September 19, 2022

Hoping to catch the fall vibes this October? Look no further than right in our own neighborhood!

From the West Chester Halloween Parade to the Chili Cook-Off, there’s lots to do this October near Chestnut Square in West Chester, Pa.

West Chester Halloween Parade – Wednesday, Oct. 26

The West Chester Halloween Parade returns from a long hiatus Wednesday, Oct. 26 beginning at 7 p.m.  The parade will kick off at Church and Market Street, making a loop around downtown through 9 p.m.. To apply to be in the parade, visit here. Follow West Chester Parks and Recreation on Facebook for more information about the West Chester Halloween Parade.

West Chester Chili Cook-Off – Sunday, Oct. 9

On Sunday, Oct. 9, head to Downtown West Chester for a day of fun, and a whole lot of chili as more than 50 chili teams, composed of businesses, hometown cooks, and non-profit organizations set up on the street to cook chili. Each team is vying for none other than the People’s Choice Award for the absolute best chili in town. 

The cook-off is more than just the food, of course, there will also be a kid zone, artisan vendors, drinks from local breweries and winners. Learn more about West Chester Chili Cook-Off.

Fall Foliage Express – Sunday, Oct. 9 & 16

If you’re hoping to truly take in the fall vibes this October, might we recommend hopping on the Fall Foliage Express.

Tickets are $20 for adults, $18 for children ages 2-12, and under 2 rides free!  One ticket takes you on an immersive picturesque 90 minute train ride experience through the Chester Creek Valley to Glen Mills and back. Learn more about West Chester Railroad’s Fall Foliage Express.