West Chester Fall Event Guide 2024

Welcome to West Chester fall activities where pumpkins, festivals, beer, and ghosts, oh so many ghosts, take over. To help you get ahead of the game, here’s a roundup of events happening in the area over the next couple of months sorted by date. 

September Highlights

Chester County Restaurant Festival heats up Gay St. 

Full of local food vendors, artisans, and entertainers, the Chester County Restaurant Festival returns on Sunday, September 15. With more than 50 food trucks and restaurants represented plus dozens more crafters and artisans, this is one of the area’s biggest events of the season. Expect a wide range of food selections from ethnic entries to festival favorites. Vendors will be located on Gay Street from Matlack St. to Darlington St. as well as on Church and High Sts.

There will also be a Beer and Wine Garden and live musical performances throughout the day. The event starts at noon and runs to 5 p.m. Entrance is free. 

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 house and walk. If you can’t, your best option is to grab space in one of the garages. Event parking will be available – $10 for the day. 

• Scan this QR code for a block-by-block lineup. 

West Chester Oktoberfest just can’t wait for October 

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. For the third year in a row, Downtown West Chester is offering its own take on the now ubiquitous fall tradition. On Sept. 28, head to Gay St for live music and $6 fall beers and ciders. Music begins at 1 p.m. on Gay St and runs until 8 p.m. Drink specials last all day. 

The arts get an outdoor focus

On September 28, the Chester County Art Association is holding its annual Chester County Art Walk. Head to East Goshen Park to view the work of more than 100 artists along with food 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.

Then if that wasn’t enough, on Oct. 12 the Chester County Art Association is hosting a one-day “Art in the Woods” pop-up event. In addition to the works of more than 50 artists, the CCAA will also unveil its brand new walking trail. A permanent property addition, the trail will feature 2D and 3D masterpieces alongside a pathway through the woods. 

September events:

• Sept. 14 – Halfway to St. Patrick’s Day Party, Knights of Columbus Social Club, 110 W. Market St., 1-5 p.m. 

• Sept. 15 – West Chester Restaurant Festival, Gay St., 12 – 5:30 p.m.

• Sept. 18 – Safe Harbor Cornhole for Charity event, Locust Lane Brewery, 50 Three Tun Rd., 5 – 8 p.m. 

• Sept. 18, 19, 25, 26 – Plagues and Pestilence: A Walking Tour, Chester County History Center, 6 – 7:30 p.m.

• Sept. 21 - Fall Movie Series - Inside Out 2, West Goshen Park, 7 p.m. 

• Sept. 28 – Unite for HER 5K, Downtown West Chester, 7:30 a.m. registration; 9 a.m. race start. 

• Sept. 28 – 2024 Chester County Art Walk, East Goshen Park, 10 a.m. – 4 p.m. 

• Sept. 28 – Oktoberfest 2024, Gay St., 1 – 8 p.m. 

• Sept. 28 - Community Fall Yard Sale, various locations, 9 a.m. to 2 p.m. 

• Sept. 28 - Fall Movie Series - The Garfield Movie, West Goshen Park, 7 p.m. 

• Sept. 29 – Craft Beer Festival 2024, Melton Center, 501 E. Miner St. 

October and November Highlights

The West Chester Chili Cook-off returns on Oct. 6

After 21 years hosted by the West Chester Rotary Club, the West Chester Chili Cook-off has new leadership this year. Fiorenza’s Food for Friends, a nonprofit food brokerage firm, is looking to use the event to help raise awareness around its efforts to end hunger in America, but like in previous years, there will be plenty of yummy chili. Competitors will line up along W. Gay St. ready to dish out samples to everyone with a wristband. In addition to dozens of recipes to taste, there will be a new high school competition, a nonprofit showcase, and a beer tent. Yes, a beer tent, and not just any beer tent, a Levante beer tent. So not only will you be able to enjoy beer and chili on Gay St, you’ll be able to enjoy Levante beer and chili on Gay St. Festival runs from noon to 4 p.m. Wristbands are $10 and can be purchased here.     

Look Around Festival adds a fall concert event

Three years ago, West Chester musician Nikki DiGiorgio started the Look Around Festival as a way to showcase original local talent. Now she and her team are adding a second day of music. The first-ever Look Around Fall Fest will take place at the Elks Lodge at 401 W. Washington St. on Oct. 19 from 3 p.m. to 8 p.m. This is an all-ages event. Expect a lot of great local and fall-themed activities. Tickets are $15.    

Food Truck and Music Festival set to rock East Goshen park

The East Goshen Food Truck and Music Festival returns for its seventh year on Oct. 12. Attracting more than 4000 attendees, this is East Goshen Park’s biggest event of the year. This year’s bands include Rick’s Office Band, which will play from 2:30 to 3:30 p.m., and Arcade Anthem which closes the festival with a 4 to 6 p.m. set. There will also be beer and wine available from Locust Lane Brewery and Chadsford Winery and a dozen or so food and treat trucks to choose from.

East Bradford breaks out the pumpkins for its Fall Festival

East Bradford gets into the fall spirit on Sunday, Oct. 20 with its family-friendly Fall Festival. Stop by the park between noon and 4 p.m. and enjoy live music, food trucks, and a tree giveaway. For the kids, there will be a pumpkin patch and a petting zoo. 

West Chester Preservation Awards go on a charm offensive

West Chester’s rich history, vibrant parks, tree-lined roads, and charming streetscapes are all part of what makes it special – yes, even those sometimes uneven brick sidewalks. To keep that from slipping away, the West Chester Preservation Awards work to recognize the builders and homeowners who go above and beyond to keep that history alive. This year’s awards are scheduled for October 17 at 5:30 p.m. at the Chester County History Center. 

West Chester Public Library Halloween Door Tour

New this year, the West Chester Public Library is bringing its popular Holiday Door Tour concept to Halloween. This self-guided tour will take you through some of the best West Chester has to offer by way of Halloween decorations. A map of locations will be available for a small donation. Tour homes anytime between Oct. 18 and 31. 

West Chester Halloween Parade

The West Chester Halloween Parade returns to downtown West Chester on October 23 at 7 p.m. This popular event gives kids another opportunity to don their costumes while festive floats make their way around a downtown loop that starts at Church and Market. Candy is not distributed during the parade but kids can pick up treats at candy stations set up along the parade route. 

West Goshen Police nail Trunk or Treat 

A couple of years ago, West Chester tried to host a community Trunk or Treat event and while it was fine, it turns out no one quite does Trunk or Treat like the West Goshen Police Department. The event is on Oct. 18 from 6:30 to 8:30 p.m. at 918 Old Fern Hill Rd. If you have not yet been to a trunk or treat event, bring your kiddo in costume with an appropriate candy-carrying device and wander through a series of decorated cars gathering various gizmos and treats. 

Golden Rams celebrate Homecoming 

This year, West Chester University’s Homecoming weekend is Oct. 25 -27. Last year, the university combined its Family and Homecoming events into one tradition-laden weekend that’s got something for everyone - and it looks like they will do it again. Visit their Homecoming and Family Weekend website for a complete list of weekend activities including Rams After Hours Family event, a pickleball tournament, and Planetarium events.  Some events are for students and alumni only but many are open to the public. If you are planning on going to the game, it’s 2 p.m. against Millersville.  

Spreading the word about the Veteran’s Parade

West Chester has long held a Veteran’s Parade but in recent years it had gotten overshadowed by the season's other numerous events. So this year, the American Legion is upping its marketing efforts and getting the word out early. Parade is Nov. 10 at 2 p.m. The route runs from Henderson High School down Gay St. to the Old Court House. Bring your American flags and be prepared to cheer.

October and November events: 

• Oct. 4, 5, 11, 12, 18, 19, 25, 26- West Chester Haunted History Walking Tour, Historic Chester County Courthouse, 7 p.m. Additional dates available by request.

• Oct. 5 - Fall Movie Series - Despicable Me, West Goshen Park, 7 p.m. 

• Oct. 6 - West Chester Chili Cook-Off, Gay St, noon - 4 p.m. 

• Oct. 12 - Art in the Woods, Chester County Art Association, 12 - 5:30 p.m. 

• Oct. 12 - Food Truck and Music Festival, East Goshen Park, 2 p.m. 2024 

• Oct. 12 - Fall Movie Series - Barbie, West Goshen Park, 7 p.m. 

• Oct. 12 - OutFest, Bierhaul Townhouse, 15 N. Walnut St.

• Oct. 14 - Safe Harbor Golftoberfest 2024, Radley Run Country Club, 11 a.m. to 7 p.m. 

• Oct. 18 - Trunk or Treat, 918 Old Fern Hill Rd, 6:30-8:30 p.m. 

• Oct. 19 - Look Around Fall Fest, Elks Lodge, 401 W. Washington, 3-8 p.m. 

• Oct. 19 - Fall Movie Series - IF, West Goshen Park, 7 p.m. 

• Oct. 20 - East Bradford Fall Festival, East Bradford Park, 12 - 4 p.m.

• Oct. 23 - The West Chester Halloween Parade, downtown West Chester, 7 p.m. 

• Oct. 25 - 27 - West Chester University Family and Homecoming weekend, various events.

• Oct. 26 - WCU Homecoming Game against Millersville, Ferrell Stadium, 2 p.m. 

• Nov. 10 - West Chester Veteran's Day Parade, Henderson HS to the Old Courthouse, 2 p.m. Help honor all those who have served with a parade through downtown West Chester.

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 supported includes Restaurant Fest, the Music at Marshall series, Porchfest, the Children’s Business Fair, the West Chester 225 Birthday Parade, the West Chester Christmas Parade, and Santa at the Square.