Above: Colonial-era reenactors at the annual Separation Day parade in Historic New Castle. Photo by Lindsay Rudney duPhily.

By Amy Watson Bish

We do like our festivals, whether they’re celebrating ethnicity or the contributions of a jazz legend such as Clifford Brown. Following is a look at this year’s festival season. As usual, things get off to a galloping start with the annual Point-to-Point. Enjoy!


47th Annual Winterthur Point-to-Point
Sunday, May 4 | Winterthur Museum, Garden & Library, Wilmington

Delaware’s springtime tradition has it all — steeplechase racing, antique carriage parade, festive tailgates, fancy hats, and fun for the entire family.

— Visit Winterthur.org


Train Day at Auburn Heights
Sunday, May 4 | Marshall Steam Museum, Yorklyn

All aboard! Whether you’re a lifelong railfan or just looking for a family-friendly day out, Train Day has something for everyone: from rides on the Auburn Valley Railroad and Museum tours to model train displays and hands-on activities.

— Visit AuburnHeights.org/Train-Day


Wilmington Flower Market
May 8 – May 10 | Rockford Park, Wilmington

This time-honored, three-day event has been a rite of spring for more than 100 years. Explore a wide selection of plants and flowers for your garden, shop for gifts from craft vendors, and delight in carnival rides, games, and live entertainment.

— Visit WilmingtonFlowerMarket.org


Bellefonte Arts Festival
Saturday, May 17 | Brandywine Blvd, Wilmington

Discover the tiny, bohemian town of Bellefonte, just off Philadelphia Pike, at this fun-filled annual outdoor festival highlighting more than 50 local artisans, live music, food trucks, kids’ activities and more. Rain date Sunday, May 18.

— Visit BellefonteArts.com


A Day in Old New Castle
Saturday, May 17 | Historic New Castle

Celebrate heritage and history at the 100th anniversary of A Day in Old New Castle, the country’s oldest open house and garden tour event. This festive day includes tours of museums and historic homes, family-friendly activities, demonstrations, costumed reenactors, and more.

— Visit HistoricNewCastle.com


Wilmington Street Food Festival
Saturday, May 17 | Tubman-Garrett Park, Wilmington Riverfront

The Wilmington Street Food Festival returns to the Riverfront offering $5 bites from area restaurants and food trucks. Enjoy live entertainment, family activities, axe throwing, mechanical bull riding, a breakdancing competition and more. Proceeds support the Trauma Survivors Foundation.

— Visit StreetFoodFests.com


5th Annual Brandywine River ShadFest
Sunday, May 18 | Brandywine Park, Wilmington

Celebrate the Brandywine River and the return of the American Shad. This free, family-friendly event raises awareness of environmental issues and includes live music, food vendors, fishing lessons, and more.

— Visit BRRT.org


Summer Kick-Off Celebration
Saturday, May 24 | Hagley Museum & Library, Greenville

Get a taste of Hagley’s summer programs during this special preview day featuring hands-on activities, tours, food trucks, and more. Activities are from 10am to 4pm, with regular museum operations until 5pm.

— Visit Hagley.org


The Ladybug Music Festival
Friday, May 30 | Market Street, Wilmington

Wilmington’s 100% female-fronted, multi-genre music festival returns to Market Street for its 15th year. The country’s largest celebration of women in music is open to all ages and is free to attend. This year features Margaret Glaspy, Martha Wash, Koser, and more.

— Visit TheLadybugFestival.com


Holy Trinity Greek Festival
June 2 – June 7 | 808 N. Broom Street, Wilmington

Transport yourself to Greece at this annual week-long celebration of culture, cuisine, and tradition. Enjoy authentic dishes, folk dancing, and live Greek music from Philadelphia’s Atlantis, all in a festive village-style atmosphere. Opa!

— Visit Holy-Trinity-Greek-Festival-Wilmington-De.Square.Site


Separation Day
June 6 & 7 | Historic New Castle

One of the state’s longest-running traditions returns, recognizing Delaware’s declaration of independence from Pennsylvania and the British crown. Festivities begin on Friday evening with an outdoor block party at The Wharf, featuring live music, food trucks and a beer/wine garden. On Saturday, a Colonial-inspired parade kicks-off at noon followed by an afternoon of activities in Battery Park featuring a vintage market, kids’ rides, food & drink, live music, and a grand fireworks finale over the Delaware River in the evening.

— Visit SeparationDayDe.com


St. Anthony’s Italian Festival
June 8 – June 15 | 901 N. Dupont Street, Wilmington

Hosted by St. Anthony of Padua Church, this festival is one of the largest Italian American cultural events in the region and brings the spirit of Italy to Wilmington with authentic cuisine, live music, traditional dances, carnival rides and games for all ages.

— Visit SAPDE.org/ItalianFestival


31st Annual Juneteenth Parade & Festival
Saturday, June 14 | Rodney Square and Tubman-Garrett Riverfront Park, Wilmington

Hosted by the Delaware Juneteenth Association, this celebration of freedom and resilience begins with a parade down King Street, followed by a free family-friendly festival at Tubman-Garrett Riverfront Park featuring live music, entertainment, food trucks, and more.

— Visit DelawareJuneteenth.org


38th Annual Clifford Brown Jazz Fest
June 18 – June 21 | Rodney Square, Downtown Wilmington

The Clifford Brown Jazz Fest, the largest free jazz festival on the east coast, features a star-studded line-up of jazz artists. Each night the main stage performances are followed by late light jam sessions hosted by local establishments throughout downtown Wilmington.

— Visit CliffordBrownJazzFest.org


Old-Fashioned Ice Cream Festival
Saturday, June 28 | Rockwood Park, Wilmington

You scream, I scream, we all scream for ice cream! And there’s plenty of the sweet treat to enjoy at this quintessential summer event that also includes live music, family entertainment, free museum tours, a beer garden, fireworks at dusk, and more.

— Visit NCCDE.org/ICF