🍂West Chester Fall 2025 Event Guide

Pumpkins, beer, festivals, and, oh so many, ghosts

Author

Cara Corridoni
September 03, 2025

From festivals to tours to Gay Street hangs, there are at least 54 ways to celebrate this fall.

Welcome to your guide to all your favorite West Chester fall activities. That beloved time of year, where temperatures start to cool, and pumpkins, festivals, beer, and ghosts, oh so many ghosts, take over. 

To help you with the seasonal transition, here’s a roundup of the can't miss West Chester events happening over the next couple of months, sorted by date. Plus a couple highlights each month, that deserve a little extra attention!

Seasonal Series: Multiple Events Under the Same Theme

From art walks to history tours, West Chester has plenty of ways to lure you outdoors this fall. Image: CCHC Facebook

While there are plenty of one off events that happen over the course of the fall, there are some themes that you’ll find repeated. From 5K races to history walks, here are some events you’ll see on rotation this year. 

Movies by the light of the moon. Each year, West Goshen shows new release movies at the amphitheater in West Goshen Community Park. Movies run weekly from Sept. 20 through Oct. 18. All movies start at 7 p.m. (assuming technical difficulties don’t hold them up.)  

Creepy walking tours. It wouldn’t be fall in the Borough without a series of creepy walking tours. This season, the Chester County History Center is bringing back Plagues and Pestilence, a look at the impact of disease on the nineteenth century, as well as Dark History, West Chester’s ghost tour. Also, Chesco Tours will be on the streets with its haunted history tour. As they say, every house in West Chester is haunted. Wonder who’s in yours? All tours have plenty of dates and times to choose from.  

Races for good. With cooling temps comes the return of West Chester races. Ready to pick up your pace? Here are a few ways to get in your steps while benefiting a good cause: 

Image: Unite For Her

  • Dr. Mary’s Legacy 5K Run takes place on Sept. 6 at West Goshen Community Park. Registration is open now. The proceeds go to support Community Volunteers in Medicine. 

  • The 9/11 Heroes Run is the only local race, I know, that offers a rucksack option. This year’s event will take place Sept. 7 at Rustin High School. Register here. 

  • On Sept. 21, West Chester University is holding its seventh annual Rams Let’s Walk 5K. Racers will meet on S. Church St. in support of student-athlete mental health. 

  • West Chester’s biggest race of the fall season, the 13th Annual Unite For HER 5K, is on Oct. 18. Sign up now and help paint the town pink and teal in support of those affected by breast and ovarian cancer.

Art outside. Lately, there has been a real push to get art outside the confines of the gallery walls and into the natural world. On September 27, East Goshen Township will hold its annual Chester County Art Walk. The exhibit features the work of more than 75 local artists lined along the trails or East Goshen Park. There will also be music and food trucks at this day-long celebration of community, creativity, and connection. Then in October, the Chester County Art Association bringing back Art in the Woods, a 2D and 3D art trail ending with s’mores by the fire, and Downtown West Chester hosts its twice-annual Gallery Walk. This time, however, the artworks stay inside local shops and galleries while attendees exit into the crisp fall air.  

On September 28, the Chester County Art Association is holding its annual Chester County Art Walk event. Head to East Goshen Park to view the work of more than 100 artists, along with trucks and live music. Art can be viewed from 10 a.m. through 4 p.m. Then, less than a week later, it will be Downtown West Chester’s turn to highlight local artists with its twice-annual Gallery Walk. The fall version will be held on October 4 from 4 to 8 p.m. Light refreshments will be provided. Visit the Downtown West Chester website for a map of participating locations.

September

West Chester's Secret Garden Tour returns in September after a five-year hiatus.

September Highlights

West Chester Children’s Business Fair. Now in its fourth year, the West Chester Children’s Business Fair is making the move from May to September, but the inspiring junior entrepreneurs remain the same. Featuring more than 40 different kid-run businesses, the Children’s Business Fair will take place at 44 W. Plaza at the corner of Gay and Church Streets. Each budding entrepreneur is encouraged to work through all the pieces of starting a small business from inception to production. Booths open at 9 a.m. and will run until noon.

West Chester’s Secret Garden Tour. After a multi-year hiatus, the beloved Secret Gardens of West Chester Tour is making a much-anticipated return. This self-guided tour takes visitors through a curated selection of private gardens of West Chester’s northeast quadrant. From meticulously manicured formal gardens to lush, naturalistic landscapes, get ready to be inspired. Tour takes place Sept. 6 from 10 a.m. to 2 p.m. Tickets required.

The Chester County Restaurant Festival. On Sunday, Sept. 21, dozens of restaurants, food trucks, and artisan vendors will bring their tasty wares to the streets of West Chester for the 44th Chester County Restaurant Festival. Most offer trial-size portions of popular dishes, allowing plenty of room for sampling! There is also a beer and wine garden and a large vendor fair. This popular event attracts 25,000 attendees each year.  

Insider tips: 

  • If you have a particular item in mind to taste. Get there early. Many of the most popular dishes can sell out quickly. 

  • Park at a friend’s and walk. If you can’t, your best option is to grab space in one of the garages. Event parking will be available. 

West Chester Octoberfest. Is there a better time for a beer than outside on a beautiful fall day? The Germans didn’t think so. Ok, so Oktoberfest actually started with a royal wedding, but you’ve got to assume it wouldn’t have gained the popularity it has if not for the timing. Now in its fourth year, West Chester Octoberfest will take place on Sept. 27. Come September out and enjoy all-day food and drink specials and a selection of live music. 

September Events

October

Attn: The West Chester Halloween Parade is moving from Wednesday night to Sunday afternoon. Let's hope the bright light of day doesn't diminish those spooky vibes.

October Highlights 

West Chester University Homecoming Weekend. A couple years ago, West Chester Unversity decided to merge family and homecoming weekends into  an action packed couple of days. In additon to the big game which will take place on Saturday, you can expect tailgates, musical performances, and plenty of athletic competitions. 

Westtown Day. Every fall festival has live music and food trucks, not eveyone has a petting zoo, historical reenactors, and tours of Oakborne Mansion. Westtown’s annual community celebration is Oct. 5 at Oakborne Park. 

West Chester Chili Cook Off. On Sunday Oct. 11, dozens of professional and amaetur cooks will line Gay St. ready to earn attendees coveted wooden nickels and emerge as top chef. Come out for a day of chili tasting at this West Chester fall classic. 

East Goshen Pumpkin Festival. I am pretty sure this is something East Goshen Township preferred that was not shared widely, but I am going to tell you anyway. The East Goshen Pumpkin Festival is simply the best way to get your pumpkins in the area. Piled high in East Goshen Park, they are free for the hauling, but hauling you will do. Parking gets tight as the festival, which includes pony rides, turkey bowling, food trucks, and other novelties, is a popular one.  

West Chester Halloween Parade. A childhood tradition dating back decades now, the West Chester Halloween Parade is moving for the first time to Sunday afternoon. Traditionally, it’s been held on Wednesday, but the challenge of closing Gay and Market Street during the busy evening hours became too much so this year they are trying Sunday instead. I have been to a few Sunday parades and they have not been particularly well attended so we shall see how this goes. 

The Rocky Horror Picture Show at Uptown Theater. Started a couple of years ago as part of Uptown’s $5 Monday Movie night, the annual showing of the cult rock ‘n’ roll classic is turning into a bit of a seasonal tradition. Film attendees are encouraged to dress in costume and sing, dance, and shout along! 

October Events

November

After a successful first year, West Chester is committed to making its Turkey Trot a tradition. Image: Downtown West Chester

November Highlights 

Little Women, the Musical. Starting Nov. 21, West Chester University’s Theater Department will present the Louisa May Alcott classic in musical form. This Broadway classic tells the story of March sisters - Jo, Meg, Beth and Amy - as they grow up during the Civil War. 

West Chester Turkey Trot. After a successful, if rainy, inaugural run, West Chester’s Turkey Trot will return Thanksgiving morning. A perfect way, to burn a few extra calories before settling into a day of excess. 

Small Business Weekend. Come to downtown West Chester the day after Thanksgiving and all weekend long for special sales, instore events, and complimentary gift wrapping. With more than 50 retail stores, you’ll have plenty of opportunties to find something for everyone on your gift list.    

November Events

I'm not sure if it's the return of the West Chester University students or cool fall mornings and all our coffee shops, but West Chester comes alive in the fall. Don't believe me? Come out and see for yourself.

For a complete list of seasonal events, visit our event list.

A very special thank you to COCOON for their support of not only this guide but of events in West Chester. Their growing list of events includes the Music at Marshall series, Chester County Restaurant Festival, the West Chester Christmas Parade, and Santa at the Square.

Hello, West Chester! We are COCOON and we also call West Chester home. (You might have driven by our Design Studio on West Chester Pike.) If you didn’t know, we remodel homes – and we do our best to make remodeling as stress-free as possible. If you’re thinking about remodeling, reach out to us! We’d love to help you explore your options!