Picturing yourself strolling down the street, authentic stromboli in one hand, local craft beer in the other, listening to a live band and the enthusiastic giggles of children as they ride carnival rides? You’re not alone. Welcome to Delaware’s summer festival season. Follow along as we go through some of the major events happening this summer.
Holy Trinity Greek Festival
June 1 – June 6, Wilmington
808 N. Broom Street Wilmington, DE 19806
Photo of the Holy Trinity Greek Festival, courtesy of www.facebook.com/wilmgreekfest/photos
Kicking off the festivities is the annual Greek Festival at Holy Trinity. As the largest Greek Festival in the Mid-Atlantic region and the only Greek festival in Delaware, this yearly favorite event provides the perfect opportunity to dine and dance in the Greek fashion. Snag some baklava from the balcony, browse the vendors lining the grounds, and dance to live Greek music every night. The Terpsichorean Dancers will perform traditional Greek dances nightly beginning around 6:00pm. Collect a dinner of souvlaki, kalamari, loukoumades, and top it off with a gyro before settling in to watch the festivities.
The Festival runs daily, Monday June 1st through Saturday June 6th from 11:00am to 11:00pm. Don’t have time to wander the festival, but craving spanakopita and baklava? Order takeout goodies at this link. The Take-Out Booth is located in the south parking lot adjoining Broom Street. The Dining Room operates from 11:00a to 8:00p daily with a curbside drive-up/pickup option from 11:00a-3:00p along Broom Street.
Delaware Pride Festival
Saturday, June 6th, 10 AM – 5 PM
Dover Legislative Green, Dover
A photo of Delaware Pride, courtesy of www.delawarepride.org.
Celebrate Pride Month with Delaware’s own Pride Festival, celebrating diversity, acceptance, and the strength and beauty of our LCBTQIA+ community. Enjoy live music, panels, food trucks, and tons of vendors! Organized by Zach Workman, who will also be performing in drag as Scarlet Masters, this year’s event is sure to be a day of camaraderie, community, and advocacy. For more information, visit www.delawarepride.org/delawarepridefestival2026-1.
St. Anthony Italian Festival
June 7 – June 13
901 N. DuPont St. Wilmington, DE 19805
A photo of the St. Anthony’s Italian Festival, courtesy of Leslie W. Kipp.
Grab your family and get ready to eat, St. Anthony’s Italian Festival is up next. Held every year at the church, this festival features food and fun for everyone. Ride the carnival rides, dance to the Italian music, and eat as many cannoli as you can stomach at this state favorite event.
A variety of traditional Italian and contemporary music will play at various venues on site, including the stylings of Opera Delaware with a selection of Italian Arias. The Brandywine Center for Dance will present a dance tribute to Italian Music on Monday 6/8 at 6:30 PM! Check out the Cultural Activities tent next to the church for more activities.
It wouldn’t be an Italian event without mountains of delicious food! Taste handcrafted Italian specialties from vendors like Ristorante Attilio, Cafe Riveria, La Pizzeria Metro, La Casa Pasta, Luigi and Giovanni’s, and Trattoria di Napoli! Top off your meal of pizza and pasta with a cannoli from Serpe’s Bakery and a gelato from Gotta Lotta Gelata.
If you’d like to participate in the parish’s celebration of mass, there is a new celebration for this year’s festival. On opening Sunday, the 7th, the parish will mark their devotion to their patron St. Anthony of Padua by celebrating his Feast Day with a Mass at 12:30 PM and a Procession of Saints at 2:00 PM.
This event serves as the primary fundraiser for St. Anthony of Padua Grade School. Come on out to support and eat some delicious food while you’re at it. Tickets cost $5, with free admission for children under 14 and adults over 61. For more information, visit sapde.org/italianfestival/
Delaware State Fair
July 23rd – August 1st
Delaware State Parks 18500 S DuPont Hwy Harrington, DE 19952
A photo of a girl exhibiting her goat, courtesy of www.delawarestatefair.com/livestock/.
Celebrate all things Delaware at this year’s State Fair! View exhibitions of agricultural achievement, or just coo over how cute the kids and the baby goats are. Cheer on the horse and car races with a funnel cake in hand, or kick back and enjoy the country stylings of the Summer Concert Series. Ride the rides, shop for homemade goods, and celebrate the rural achievements of our fantastic state.
Parking is free. Tickets range from $5 for kids to $10 for adults, with free admission for children under 5. For more information visit www.delawarestatefair.com/.
Rehoboth’s Outdoor Show
August 1st, 2nd, 8th, and 9th
12 Dodds Lane, Henlopen Acres Rehoboth Beach, DE 19971
A photo of the Rehoboth Art League Outdoor Show, courtesy of rehobothartleague.org/events/.
The Rehoboth Art League’s hallmark Outdoor Show will return to the historic Henlopen Acres for its 53rd year. Over 125 artists and artisans will showcase and sell their fine wares amidst great food, live music, artist demonstrations, gallery exhibits, beautiful gardens, the historic Peter Marsh Homestead, and a Dogfish Head Beer Garden. Explore their offerings for a new art piece to spruce up that corner of your home, or come to simply enjoy the ambience of shopping outdoors.
A weekend entry pass costs $5 for adults, and children under 12 attend for free. Purchase tickets at the gate. For more information visit www.rehobothartleague.org/events/outdoor-show/.
Middletown Olde-Tyme Peach Festival
August 15th. 8:45 AM to 4:00 PM
Main Street, Middletown, DE 19709
A photo of peach-enjoyers, courtesy of middletownpeachfestival.com/.
Calling all peach lovers! Time to get your yearly fix of all things peaches at the annual festival in Middletown. Sample cobblers, pies, and tarts while sending your kids off to do crafts and meandering over to investigate a historical exhibit or an local artist’s display. No matter what you get up to, rest assured peaches will be involved. For more information visit middletownpeachfestival.com/.
