June Events

Kick off the summer with our list of one time events happening throughout the month of June.

June 1

Up on the Roof Party

Join the West Chester Downtown Foundation for an unforgettable night up on the roof of the Chestnut Street Garage for the 17th year in a row. From 7-11pm, take in the beautiful panorama of downtown as you enjoy dinner, cocktails, and appetizers from West Chester’s best restaurants. Dance under the summer night sky with live music by Josh K and the Sons of Thunder. Tickets are $105 in advance and $120 at the door. All proceeds benefit the ongoing beautification of downtown West Chester.

Strawberry Harvest Celebration

Kick off the summer picking season picking delicious strawberries at Highland Orchards. Shuttle rides to the strawberry field will be available as well as: local vendors, food trucks, face painters, beer, and wine. The bakery will have their famous apple cider donuts and fresh baked fruit pies. The event goes from 12-5pm, and is free to attend.

June 2

Bark in the Park

A new event for our furry friends, where dogs are welcomed to Hoopes Park. Enjoy K9 demonstrations, vendors, contests, activities, food, and even on site dog adoptions. This event goes from 12-4pm, free to the public.

West Chester History Train

Back by popular demand, the West Chester Railroad is hosting their Summer Picnic Special starting June 2. Two-hour train rides start at noon and cover eight scenic miles around West Chester, including a picnic. As you eat, enjoy an interactive presentation about trains from the 19th and 20th centuries. Tickets are $15 for adults, $13 for children ages two to 12, and free for children under.

June 3

Quest for the Chamber Cup Golf Outing

This annual Radley Run Country Club golf outing starts at 10:30am and is a great opportunity to play a round with the business leaders who make West Chester and Chester County amazing. Proceeds benefit the Chamber’s Education Foundation Scholarship Program! Enjoy a lunch, a cocktail hour, a free umbrella and swag bag, and more. Registration costs $215 for an individual and $860 for a foursome, with options to add more players. Sponsorship opportunities start at $100.

Peach and Corn Harvest Celebration

It’s prime picking season, at Highland Orchards at this time of year. Take pleasure in picking delicious corn and peaches, while also sipping on some local craft beers. Foodtrucks and apple cider donuts will be available as well. Festivities go from 12-5pm.

June 5

24th Annual Poetry Conference

The West Chester Poetry Conference is the nation’s only all-poetry conference dedicated to formal verse. During, the conference offers workshops in traditional poetic craft. It is a national platform for many who attend, to discuss major trends and concepts of contemporary poetry. The event runs from June 5-8 starting at 5pm. Tickets and registrations online.

June 7

Steely Jam: Countdown to Ecstasy at Uptown!

Named for Steely Dan’s 1973 sophomore album, Countdown to Ecstasy has dedicated themselves to this music and to their audience of hipsters, old-heads and youthful seekers of truth. Tickets available online for $30. All include a $3 service fee.

Dub C 5K

Kick off your summer running in the 10th downtown race, supporting Chester County Down Syndrome Interest Group and Parkinson Council. Awards will be given to the overall top male and female runners, along with the top masters. A quarter mile kids fun-run for ages 1-13, will start at 6:45pm, costing $5. Both 5K and 2K walks start at 7pm costing $25. Register online.

Malena’s Anniversary Party

Malena’s Boutique is turning 16, and is hosting a two-day event to celebrate. They will be opening the private showroom space to the public both days and offering 16% off all inventory (excluding fine jewelry and consigned items) to honor the community that has supported her through all the years. The party starts at 11am both days!

June 8

The First Ladies of Rock & Soul at Uptown!

Back at Uptown! For their third appearance, are these top notch professional musicians.The First Ladies of Rock and Soul will perform music from the girl groups of the 1960’s, that have captivated audiences for generations. The show starts at 7:30pm, tickets found online.

Brews for Bassetts at Levante Brewing Company

Tri-state Basset Hound Rescue is hosting their second annual fundraiser. This fun event includes games, raffle prizes, food trucks, craft beer, a “Smooch a Pooch” kissing booth, and hounds available for adoption. The event goes from 2-5pm, and is free to attend.

June 9

Dog Walk and Brunch

Looking for something special to do with your dog? Enjoy a day, dedicated just for him/her hosted by Canine Creature Comforts. Starting at 9:30am, take a beautiful 2.5 mile hike through Stroud Preserve. Afterwards, take your pup out to brunch on the patio at Four Dogs Tavern from 11:30am-1pm. To reserve a seat, give them a call or fill out the sign-up sheet in their office in Malvern.

Let Freedom Sing Featuring The Main Liners Men’s A Capella Chorus & Victory Belles

At 2pm the championship Mainliners Men’s Chorus will perform a variety of songs in tribute of WWII and all our veterans. Joining them, will be The Victory Bells a trio performing music from the 1940’s. This event will be at the Uptown! Knauer Performing Arts Center. Purchase tickets online for $20-$35. All include a $3 service fee.

Chester County Hospital Polo Cup

Hosted and sponsored by the Chester County Hospital, the 13th Annual Polo Cup in Toughkenamon is a wonderful day for a derby. Bring your fascinators and fancy hats because you’re part of the party. General admission is $30, but prices vary and range up to $350. All proceeds benefit the Ob/Gyn Clinic and the Women’s Auxiliary’s NICU Pledge.

Brandywine Baseball Club Home Game

Come out to East Goshen Park for an afternoon at the ball game.  The Brandywine Baseball Club formed in 2013 and is modeled after its 1865 West Chester namesake. They will be facing the team Elkton Eclipse starting at 11am.

June 10

Playing a Round for SHINE

Join in on the Side Bar and Restaurant’s annual golf outing — in support of The Chester County Hospital Foundation; SHINE. SHINE continues to strive helping patients with their fight against Cancer. The golfing event will be held at Applebrook Country Club starting at 9am. Single Golfers cost is $130 which includes: greens fees, cart, lunch, kegs on the course and a two hour open bar/buffet at Side Bar & Restaurant afterwards.

June 12

Family Event at Everhart Park

Spend the afternoon outside in beautiful Everhart Park. From 2-4pm, enjoy family-fun time filled with whatever you want, whether that’s sharing a picnic, playing catch, or bringing Fido to run around.

June 13

West Chester Community Concert Band at East Goshen Park

Since 1986, the all-volunteer West Chester Community Concert Band has been performing in and around the West Chester area. Under the direction of Joseph Gehring since 2003, the band plays everything from classical and jazz to marches and contemporary pieces. The concert is free and will be held from 7-8pm.

Faunbrook Open House

Beyond an incredible venue for private parties, weddings and events, Faunbrook B&B is a property rich in West Chester history—it was built in 1860 and purchased in 1867 by the Darlington family (whose name everyone in West Chester will recognize). So, if you’re interested in hosting your next big event there,now’s your chance to get the tour!  The event is from 6-8pm. The event is free, but an RSVP on their Facebook event page is encouraged.

Trailblazer Run

Run through 600 acres of private woods and fields. The Trailblazer Run supports East Bradford Township’s public trails. Participants compete in the five-mile run or opt for the more leisurely 1.5-mile hike (perfect for the family). On-site registration begins at 5pm, and the race begins at 6:30am. All participants receive a free beer from Victory Brewing Company, with root beer for minors and non-drinkers.

Clay With us – Kids Edition

Join in and create your own one of a kind, ceramic project at Highland Orchards. During each session, Julie Pook will share her love of clay and create a unique experience. The class begins at 10am, and registration is required. It costs $18 for kids ages 3-11.

June 14

The Music of Billy Joel

Celebrate one of the world’s best artists, Billy Joel at Uptown! John Grecia and his band will perform some of your favorite hits like, “Piano Man”, Movin Out, or “My life”. Tickets can be purchased online, and start at $15 with a three dollar service fee. The show begins at 7:30pm.

Dead Fest: Brandywine Red Clay Alliance

The 10th Annual Celebration of the popular band, Grateful Dead starts at 6pm. Fifty Musicians around the Brandywine Valley will come together for a night full of fun. Tickets will be $15 in advance, or $25 at the gate. For children ages 12-18, it’s $12 and kids under 12 are free.

June 15


Join the Expanding the Table 5k Run/Walk, and enjoy food, fun, and prizes for the top runners. Registration is found online, ending June 13. Registration for students and kids is $12 and for adults $25. The fun begins at 9am!

The Forces of Nature

Witness the 37th Annual Dance Recital of Diane Matthews School of Dance & Arts,  at West Chester East High School. The first session will start at 10:30am, following with the second session at 3pm. Tickets cost $18 in advance, or $20 at the door.

Cruisin’ 4 Chris – Car Show

Come out and support Chris’ fight against Cancer, by attending the car show and benefit in his honor. There will be food, music, prizes, kids rides, and raffles. The show goes from 9am-2pm, rain or shine located at the
Goshen Fire Company Fairgrounds.

June 16

Father’s Day Express

Treat Dad to a 90-minute ride through the West Chester scenery on the borough’s most historic train. During the brief layover at the Glen Mills train station, you will be able to enjoy a picnic along Chester Creek. Tickets online, $15 for children (2-12), $15 for Adults $15, $5 for Dad, and free for kids under two.

Father’s Fest

Nothing says “thanks for everything, Dad!” quite like a ride in a helicopter. From 10am-3pm enjoy an exciting day with antique cars, motorcycles, food trucks, and more. Festival admission is $10 per person. Helicopter rides are $60 and are first come, first serve.The event is located at the American Helicopter Museum.

Opera tutti! Presents: The Old Maid and the Thief at Uptown!

The Old Maid and the Thief, one of the first operas composed specifically for radio broadcast by Italian-American composer Gian Carlo Menotti. Commissioned by NBC in 1939, the production has become a comic opera classic. The show starts at 2pm, and tickets are available online costing $10-$30 (children under 10 free). All include a $3 service fee.

June 20

Death of the Most Hated Man on Broadway

The Center for Performing and Fine Arts Theater is performing an exciting Broadway show, offering showtimes on June 20-22. They continue their murder mystery comedy theme from years past, by taking a look at inflated ego’s of celebrities. Tickets are $12 for adults and $10 for students or seniors.

Story and Yoga Time at West Chester Public Library

Join Libby Piper author of her newly released book, “Honeysuckle Hugs”, in reading this mother nature themed adventure. After reading, she will do a guided interactive yoga practice. Free meditative coloring pages will be available to take home and create. Ages 4-9 are welcome, and will start in the community room at 12pm.

June 21

Happy Hour on the Terrace: Meet the Pharaohs

Ever wanted to view ancient Egyptian artifacts? Sherin Motawea, former head of the Egyptian Museums Department in the Supreme Council of Antiquities, will bring 100 pieces from her Meet the Pharaohs exhibit. Hosted at the West Chester Public Library, you can enjoy cash wine, beer, and soda bar will be offered as well. Tickets are $10 each, and includes a drink of your choice.

June 22

Doo Wop Explosion Four

Classic Urban Harmony LLC brings street-corner doo wop acappella to Uptown! at 7pm. Enjoy listening to the best of blues and doo wop harmony that was born out of 1940s and 1950s urban America. Tickets found online, for $45 each. All include a $3 service fee.

West Chester Craft Beer Festival

The third annual Craft Beer Festival runs from 12-5pm and features local breweries, vendors, and sponsors, and live music. General admission includes a sampling glass, while VIP tickets also grant you advance admission and a complimentary lanyard. Tickets are online for $40, VIP is $45, and non-drinking tickets are $5.

June 23

Saloon 151 Anniversary

TBD: Check back on their Facebook for updates on the event!

June 24

21st Annual Challenge For Cancer Bike Ride

Want to make a difference in someone’s life? Sign up for this bike tour, created to raise money for patients living with Cancer in Chester County. You can register to ride individually, or you can build your own challenge team. The ride starts bright and early at 7am, and registration starts at $40.

June 26

International Brotherhood of Magicians – Ring 6 at Uptown!

Watch a family friendly magic show featuring award winning acts by “The Core”. The show begins at 7pm and will run for approximately two hours. Tickets cost $12 for kids (ages 12 and younger) and $17 for adults with a $3 service fee.

June 29

New York City On Your Own

Spend the day in New York City on your own (or with your friends)! Take a carriage ride through Times Square, shop at Macy’s, or see a Broadway show — the choice is yours. Cost is $45 per person. The bus leaves West Chester at 9am and returns back at 10pm.

EGT Community Day Celebration

Come out to East Goshen Park and celebrate the community that makes our area amazing. You’ll find moon bounces, live music, a helicopter landing, a petting zoo, and 10 food trucks! Music Lineup includes: The Swing Time Dolls, The Little Red Rooster Band, Not Quitting Our Day Jobs. This event is free, from 4-8pm.

Swinging Through the Ages at Uptown!

Join the Pennsylvania Philharmonic Big Band celebrating the best of the Swing era with all-time favorites. The show begins at 7:30, and tickets can be bought online. Tickets cost $39 in advance and $42 at the door, with a $3 service fee for both.