Play in the City: Exciting October Events in Wilmington, DE
October in Wilmington is special. The air turns crisp, the trees show off, and the city buzzes with energy from the Riverfront to Market Street. Looking to unwind after work, plan a weekend outing, or celebrate spooky season in style? Discover these October Events in Wilmington DE that make it easy to live and play in the city.
From fall festivals and live music to family fun and Halloween thrills, here’s a look at some of the best October events in Wilmington.
October 4
INshop Tasting, Frank’s Wine
Sip, swirl, and discover South African gems for the most historic wine estate in South Africa, Babylonstoren, at Franks Wine. Join Brand Ambassador, Nadine, as she shares the stories behind each remarkable pour. The tasting starts at 12PM and no RSVP is needed — just curiosity and taste buds.
Christina Cultural Arts Center 80th Anniversary Concert, The Baby Grand
The Christina Cultural Arts Center is celebrating 80 years of creativity. The 88Time: Christina Cultural Arts Center's 80th Anniversary Benefit Concert blends music and storytelling around powerful themes like Black maternal health, caregiving, book banning, and autism. The event starts at 4PM.
October 5
Yoga & Wellness Retreat, Siegel JCC
Recharge your body and mind with a full day of yoga, mindfulness, and creativity on the JCC’s 32-acre campus. Escape the noise and gift yourself a day of deep self-care, reflection, and renewal. On Sunday, October 5, from 10 AM to 3:30 PM, the JCC invites you to nourish your body and free your mind.
SwifTea Showgirl Soirée, HOTEL DU PONT, 7PM
Swifties, celebrate the Taylor's new album with a glamorous afternoon of tea, treats, and sparkle as the “showgirl era” comes to life. Delight in delicate pastries, themed bites, and enchanting ambiance inspired by Taylor’s Life of a Showgirl. Hosted in the Gold Ballroom with costumes and flair encouraged! Doors open at 6PM with the show starting at 7PM.
October 7
Movie Quizzo with Mack!, The Nomad Bar
Bring your thinking caps and trivia buddies for brain-teasing challenges, laughter, and friendly competition for trivia at 7PM. The Nomad Bar features live music, hand-crafted drinks, and an atmosphere unlike anywhere else in Wilmington.
October 7–12
Wilmington International Film Festival, Multiple Venues
This vibrant celebration brings together filmmakers, enthusiasts, artists, non-profits, and businesses for connection and creativity. Enjoy independent films, live performances, local art, and global flavors, creating an experience that goes far beyond the screen. More than a film festival, it’s a cultural gathering that highlights the best of film, arts, and community in Wilmington.
October 10
City on the Pitch, Chase Fieldhouse
Young athletes ages 6–14 are invited to City on the Pitch, a free soccer clinic at The Chase Fieldhouse. Sharpen skills, play age-appropriate games, get plenty of ball touches, and make new friends — all while enjoying an evening of soccer, smiles, and community! The event runs from 5PM to 6:30PM.
Virtuosity Unleashed, Delaware Symphony Orchestra
Experience Rachmaninoff’s Third Piano Concerto and Tchaikovsky’s Fourth Symphony in an electrifying performance. Visit The Grand Opera house at 7:30PM for this event. Don’t miss this chance to enjoy soaring melodies, dramatic moments, and a finale full of triumph!
October 11
Black & Brewers Fest, Makers Alley
Celebrate National Black Brewers Day with Black & Brewed Delaware at 2PM, at Makers Alley. Enjoy tastings from Black-owned breweries, live music by Devon Aaron, and a $20 tasting mug that supports Black & Brewed DE. Free parking for 3 hours at Midtown Park Garage with AirGarage registration.
Hocus Pocus Drag Brunch, The Queen
Get ready for a wickedly fun brunch filled with dazzling performances, spooky vibes, and plenty of laughs. This Hocus Pocus–themed drag brunch promises over-the-top entertainment, delicious bites, and festive cocktails that will put a spell on you. Gather your crew and join the magic for a brunch like no other. Brunch starts at 11:30AM.
October 17
The Rocky Horror Picture Show 50th Anniversary Tour, The Queen
Celebrate five decades of outrageous fun with this iconic cult classic brought to life in a spectacular anniversary tour. Starting 8PM, expect dazzling costumes, audience participation, unforgettable performances, and an atmosphere filled with wild energy that guarantees an experience unlike any other.
October 18
Halloween Ghost Ship, Kalmar Nyckel
The 7th annual family-friendly Halloween Ghost Ship returns with indoor tours, outdoor pumpkin painting, a costume parade, crafts, face painting, food trucks, and free tours of Kalmar Nyckel, Delaware’s Tall Ship. From 12PM, get free admission and parking; some activities may have a fee. It's set to be one of the top October events in Wilmington for the whole family!
10th Anniversary Celebration, LaFate Gallery
LaFate Gallery invites you to its 10th Anniversary Celebration at 3PM! For a decade, the gallery has been a pillar of Wilmington’s art scene — hosting classes, exhibitions, and community events that bring people together. Join in honoring this cultural staple and celebrating the theme: Reflection & Vision Forward.
The Broadway Rave, The Queen
A night where stage meets dance floor. An all-out party celebrating the biggest show tunes and theater anthems, remixed with a high-energy twist. Sing, dance, and lose yourself in the magic of Broadway like never before at this one-of-a-kind rave experience. Doors open at 8PM with the show to follow at 9PM.
October 19
Art Battle Wilmington, The Queen
It's like Battle of the Bands but on a canvas. Art Battle Wilmington brings together 12 local artists to compete in three 20-minute rounds, with one champion crowned at the end. It's an exciting and innovative way to experience live art. The battle begins at 4PM.
October 23
Halloween Trivia Night, Makers Alley, 6PM
Sip spooky spirits, test your smarts, and compete for prizes including a $50 Maker’s gift card. Come in costume for 10% off and enjoy 25% off wings and burgers while you play. Free parking for 3 hours at Midtown Park Garage with AirGarage registration. Trivia starts at 6PM.
October 24
Spirits at the Zoo, Brandywine Zoo
Celebrate Halloween under the stars at Brandywine Zoo with spooky cocktails, live music, light bites, and entertaining performances. Costumes are welcomed as guests stroll the grounds, enjoy the ambiance, and sip libations (drink & food sold separately). Strictly 21+ — admission includes the entertainment. Gates open at 5:30PM.
October 25
Fearless Improv, City Theater Company
Experience fast-paced, unscripted comedy with Wilmington's own improv pros. Audience suggestions fuel each unique show—no script, no safety net, just pure spontaneity. Perfect for a night out with friends or a fun date night.
The Return of Dub Step, The Queen
Get ready as the bass takes over and the energy surges with an explosive return of dubstep at The Queen. Featuring relentless drops, immersive visuals, and top-tier DJs, this high-voltage experience will keep the crowd moving all night. Ages 18+. Doors open at 7PM with the show starting at 8PM.
October 26
First State Ballet Presents: Dracula, The Grand
Experience a gothic tale of love and shadows at The Grand. Choreographed by Viktor Plotnikov and based on Bram Stoker’s classic novel, this haunting performance will stay with audiences long after the final curtain. The show starts at 4PM. Be sure to grab your tickets early if this is on the list of October events in Wilmington that you can't miss!
Fred Reed X Tanqueray Hayward, The Queen
Experience an unforgettable evening of soul as Wilmington’s own Fred Reed joins forces with Philadelphia powerhouse Tanqueray Hayward. Two extraordinary voices share the stage for a night filled with passion, rhythm, and timeless R&B vibes at The Queen. Doors open at 7PM with the show starting at 8PM.
October 29
The Price Is Right Live, The Playhouse
“Come on down” to experience the classic game show brought to life on stage, with audience members playing fan-favorite games. Fabulous prizes, surprise giveaways, and interactive fun await — your chance to play could come right from your seat.
Bounce Spooktacular Halloween Party, Bounce Pickleball, 6PM
Grab your paddle and join for a devilishly good time on the courts! Leveled open play welcomes all skill levels — novice, intermediate, and advanced. Space is limited, so rally your friends and get ready for a fun-filled, spooky twist on everyone’s favorite game.
October 31
October 31 – Masquerade on 11th, Tonic Seafood & Steak, 9PM
Get ready for chills, charm, and killer tunes at Tonic Seafood & Steak with a high-energy performance by Special Delivery, a festive photobooth, and a costume contest with prizes. Costumes encouraged, so dress to impress.
Make the Most of October Events in Wilmington, DE
From yoga retreats to late-night concerts, October is packed with ways to explore, connect, and celebrate the season. Check out the full schedule, plan your outings, and experience everything Wilmington has to offer.
See the full events calendar here.