If you want to treat Mom to a special getaway to take in the beauty of the season or the bright lights of our little city, May in Wilmington is truly a sight to see! Enjoy the incredible blooms of the du Pont estates, nights out at the ballpark, and history around every corner with these Wilmington & the Brandywine Valley events.  

May Market in Historic New Castle – May 5-6 

Enjoy a great day exploring Historic New Castle, Delaware during this May event. Check out unique plants in a wide variety, healthful herbs, a bounty of botanical bargains, and beautiful and useful home and garden treasures! 

Kalmar Sailing Season – Begins May 6 

The Kalmar Nyckel Tall Ship is one of Delaware’s best kept secrets! The ship is a full-scale replica of the Swedish flagship from the 1638 expedition that founded the first permanent European settlement in the Delaware Valley. Hop on board and haul lines, set sails and hear tales from the crew while enjoying the views of Historic New Castle or the Christina River. They even have special events like Pirate Day and Superhero Day throughout sailing season! Plan your next adventure with a sail on the Kalmar Nyckel.  

Point to Point – May 7  

For 45 years, the Winterthur Museum, Garden and Library’s Point-to-Point event has brought together horse racing and history. This festive day on the estate grounds has it all—steeplechase racing, pageantry, and fun for the entire family!  

Wilmington Flower Market – May 11-13 

For 101 years, the Wilmington Flower Market has brought food, entertainment and everything you need to start your spring garden off in style to Wilmington’s Rockford Park. This free festival has a reputation for booking nationally touring bands and continues to create an atmosphere perfect for the whole family to enjoy. Rides, flowers, food, and fun...  

Hockessin Flyer – May 13 (more dates available here) 

Relax aboard the Wilmington and Western Railroad and take a 2½-hour round-trip ride along the entire length of the line to the town of Hockessin (a 17-mile round-trip). Enjoy a ½-hour layover in downtown Hockessin to browse the local shops and grab a bite to eat! Along the way, the train will closely follow Red Clay Creek and travel through several large rock cuts (tunnels without a roof)! The ride will take you through the backyards of several neighborhoods along the tracks, and up the steepest grade on the railroad entering downtown Hockessin. Get ready for a wild ride aboard the Wilmington & Western.  

Third Thursdays at Nemours Estate – May 18  

Every third Thursday of the month from May – August, join Nemours Estate after hours as they open the grounds for half-price admission. Enjoy live music in the gardens with food trucks, beer and wine! Explore the grounds of this exquisite estate in a different way.   

Auburn Heights After Hours – May 18  

Once a month from May – September, the Marshall Steam Museum at Auburn Heights invites visitors for an afterhours experience. Relish the beautiful scenic views of the grounds, craft brews, a food truck, and games to amuse all! Limited seating is available so feel free to bring blankets and chairs to set up.  

Twilight on the Terrace – May 19  

Unwind from the week on the terrace of the Mt. Cuba Center. Kick back with some good food, good company and amazing views. Food, beer and wine will be available for purchase.   

Music: Ty Mathis Experience 
Food Trucks: The Box Lunch & Bivoua Pizza 

Grand Prix Weekend – May 19-21  

Are you an avid biker? An amateur cyclist? A spectator? If so, then Wilmington’s Grand Prix Weekend is for you! Delaware, known for its top rank in having bike friendly trails, takes on three days of racing for all levels of competition. Check out time trials on Friday evening at Monkey Hill in Brandywine Park with live music and food trucks, and a street festival with pro and amateur races on Saturday. The weekend concludes on Sunday with the Delaware Gran Fondo, a recreational ride through the area's world class attractions – with race paths made available ONLY for this event!  

This annual event is one of the top races in America and features racers competing for the NRC Points Championship in both team and individual categories.

A Day in Old New Castle – May 20  

A Day in Old New Castle is the country's oldest continuously running house and garden tour. The community of Historic New Castle invites visitors to explore many private homes and gardens as well as historic public buildings. Events and activities include historical reenactments, performing pirates, colonial craftsmen, music performers, open museums, tours of homes and gardens, food trucks and tent seating, a plein air art competition and sale, and an early travel exhibit in The Old Library.  

Bellefonte Arts Festival – May 20  

Enjoy a day of entertainment at the Bellefonte Arts Festival! During this annual event, Brandywine Boulevard will be filled with art from a number of local artisans selling their work, live music, food trucks, and lots of FUN! Admission is free. Rain date – May 21 

Derby at the Vineyard – May 20 and 21  

What do a hunter derby, live music, local shops, food trucks, and Penns Woods Winery have in common? Derby at the Vineyard! 

Blue Rocks Games – Varying Dates May 9-28 

May (select dates) brings the Blue Crew home to compete at Frawley Stadium. Look out for theme nights at the ballpark like 90s-night, game show night, pup nights, and more to fill your evenings (and some afternoons you may have to play hooky for) cheering on the Wilmington Blue Rocks.  

It’s time to plan your next getaway to Wilmington & the Brandywine Valley! These events are only the beginning of what the area has to offer this month. Whether you’re coming in for a quick day trip or taking some time to explore, the history and culture of the area shine in spring. We hope you share your experiences with us! Tag us using #VisitWilm.  

If you’re looking for a way to experience the area but don’t want to break the bank, check out the Brandywine Treasure Tail Passport – visit 12 attractions for just one price.