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A Guide to Over 35 Things to Do in Delaware This May



Wilmington Flower Market Rockford Park

The Wilmington Flower Market takes place May 10-12 in Rockford Park.//photo by Joe Del Tufo


Week of May 1-7

Live for Chocolate
5/3 • Seaford
Nanticoke Health Services presents a night of fun, laughter and support to promote women’s health. The city of Seaford hosts a scavenger hunt with 13 clue stops (each stop gets you a piece of chocolate, so you do that math!), a Race for a Cure (dudes in stilettos running an obstacle course—seriously), music, food, wine tasting and more. If you’re looking for something different, you can’t do much better.

Nascar Spring Races
5/3–5/5 • Dover
Welcome spring in a zoom-zoom way: Dover International Speedway hosts the Gander Outdoors Truck Series, the NASCAR XFINITY Dash 4 Cash Series and the Monster Energy NASCAR Cup Series. Fuel up—this weekend is gonna go fast.

5/3-5/30 • Wilmington
It won’t take long for you to sense that the artists exhibiting in this joint venture between the Delaware Contemporary and the University of Delaware are on the cusp of making a splash in the world of contemporary art. Get on the ground level of some fresh, innovative, raw talent at the 2019 MFA Thesis exhibition in Wilmington.

Anything Goes
5/3-6/1 • Greenville
Artist Helena Van Emmerik-Finn exhibits her vivid, impressionistic new oil paintings and pastels.

Dover Days
5/4 • Dover
Celebrate First State heritage, tradition and modern attractions in a free-admission festival for the whole family in—you guessed it—beautiful Dover. The Maypole turns 86 years young this year, so you better gather round and boogie on the green.

Milton Town-Wide Yard Sale
5/4 • Milton
The people of Milton are doing a heck of a spring-cleaning job, and you get to reap the benefits: Hunt for new treasures or just come hang during this yard sale extravaganza, sponsored by the Milton Chamber of Commerce. If de-cluttering pains you, don’t worry, your stuff is getting a really loving new home—perhaps even right next door.

White Clay Creek Fest
5/4 • Newark
It’s not Dawson’s, but it’s way better (and with a lot less teen angst): White Clay Creek is one of the area’s most precious natural resources. Celebrate the creek—and learn how to protect it—at Creek Fest. Live music, family entertainment, food, animal education, giveaways, hikes and activities for all.

British Car Show
5/4 • Lewes
The British are coming … but this time, they’re trading horses for horsepower. This year when the British Motorcar Show rolls into Lewes, the Nash Metropolitan gets the spotlight. Check out sleek, gorgeous British imports at the Cape May-Lewes Ferry Terminal—just don’t expect tea and crumpets or the Dowager Countess.

Wheels for Meals
5/4 • Milton
We’ll do just about anything for a good beer and a good cause, so get your bike the spring tune up it deserves and meet us at Dogfish Head in Milton for a 12-, 25- or 50-mile ride to benefit Meals on Wheels. Once you unclip, get those gloves off to receive an ice-cold Dogfish Head brew and enjoy lunch on the grounds. Pretty perfect Saturday, if you ask us.

Wilmington Garden Day
5/4 • Wilmington
WGD celebrates more than 70 years of benefiting underserved children with this self-guided tour of Brandywine Valley homes, gardens and landscapes. Green thumbs not required, but stamina is—the tour is from 10 a.m. to 4 p.m.

A Year With Frog and Toad
5/4-5/19 • Wilmington
Step aside, Meredith and Christina—when it comes to BFFs, it’s pretty hard to one-up lookalike pals Frog and Toad. With a jazzy accompanying score, you’ll spend time adventuring with these #squadgoal friends, learning life lessons along the way. All shows are curtains up at 2 p.m. in Wilmington. 

Teal Ribbon 5k
5/5 • Wilmington
Laces up for a good cause: the fight against ovarian cancer. The 10th annual race kicks off at Tubman-Garrett Park at the Wilmington Riverfront.

5/5 • Wilmington
The ultimate Sunday indulgence, this event is what resort wear was made for: Delaware’s must-do steeplechase racing/people-watching spectacular springtime classic is back. Get out your spreads and your Sunday best to mint julep the day away on the grounds at Winterthur. We can’t think of a better way to usher in the spring, can you? Gates open at 10:30 a.m.

Week of May 8-14

Walt Jones Memorial Golf Outing
5/10 • Lewes
Say “fore” for a good cause: the Walt Jones Memorial Golf Outing in Lewes benefits Sussex County Habitat for Humanity. Get your tee time at Midway Par 3, between 10 a.m. and 2 p.m.

Wilmington Flower Market
5/10-5/12 • Wilmington
She may look fresh as a spring daisy, but the Wilmington Flower Market has been blooming since 1921. Browse through a large selection of plants and flowers and enjoy crafts, merchants, food, carnival rides, games and entertainment during this ultimate Delaware tradition at Rockford Park. Did you forget a Mother’s Day gift? Well, we can’t give you a bigger hint than this—TAKE MOM HERE. Three fun-filled days await at Rockford Park. 

Artisans Fair
5/12 • Ocean View
Fans of unique, handcrafted art will gather at Lord Baltimore Elementary School in Ocean View for the 12th annual Artisans Fair. Find intriguing art exhibits inside and outside, featuring textiles, fine art, glass, jewelry, photography, woodworking, pottery, metalwork and sculpture. Local foodies, don’t miss the Farmers Market with all kinds of specialty goodies. The best thing about this day of unique shopping? Proceeds go to college scholarships for local students.

Mother’s Day Buffet on the Wilmington & Western Railroad
5/12 • Wilmington
Guys. Don’t make mom cook tonight. Instead, all-aboard for a gorgeous two-hour dinner trip around Ashland. With Appleton Catering putting it down in the kitchen, you can’t miss. Just don’t throw momma from the train—it is her day, after all.

Week of May 15-21

Grand Prix
5/17-5/19 • Wilmington
For the cyclists in the area, it’s basically the Super Bowl: Wilmington’s three-day cycling event includes plenty of pro racing action along with the Governor’s Ride, a parade, a street festival, and, for the Quadzillas in attendance, lots of climbing action on the Gran Fondo. Even if you’re not a bike geek, come on out to the Monkey Hill time trial, where you might see a neighbor or two conquer the cobbles. It’s a terrific party in the park that just happens to have cycling on the side. The only rule? More cowbell, please.

An Affair With the Arts
5/18 • Dover
Help the Biggs Museum put the “art-y” in “party” and this year’s An Affair with The Arts gala fete. Cocktails, gourmet food, a silent auction, live music, dancing under the outdoor tent and museums tours.

Buddy Walk
5/18 • Middletown
Take a one-mile walk to promote the understanding, inclusion and acceptance of those with Down syndrome. Following the walk are free activities and entertainment for toddlers to teens at Silver Lake park in Middletown.

A Day in Old New Castle
5/18 • New Castle
Take old school to a whole new level in Old New Castle for this lovely Spring day on the water. Plundering pirates, Colonial crafters, beer garden in the wharf, tours of private homes and gardens, historical reenactments—what’s not to love? P.S.: Our friends from New Jersey (who have since forgiven us for that whole loud-music-emanating-from-the-riverfront thing) are kind enough to send over a few tall ships for the occasion. The fun starts at 10 a.m.

Strawberry Festival
5/18 • Wyoming
Check out Fifer Orchards in Wyoming for food, music, kids’ activities, a farm animal meet-and-greet, tractor rides and all kinds of yummy strawberry treats—we’re talking smoothies, ice cream, funnel cakes and the chocolate-covered variety. This lip-smackin’ sweet day starts at 10 a.m.

Radnor Hunt Races
5/18 • Chadds Ford, Pa.
May in Delaware and (slightly) beyond offers not one, but three chances to pretend you’re at a steeplechase event when you are, in fact, at a spring fashion spectacle. Let’s see the fancy hat, ladies—but please don’t wore the same one you wore to Point-to-Point. And gentlemen, the dapper-er, the better. While you may be in it for the fashion, the people-watching, the innovative tailgating and the endless Instagram fodder, please remember the horses are doing some hard work—let’s give them the same props you do the lady with the ah-maze peacock hat. The 89th Radnor Hunt race kicks off at 9 a.m.

Fair Hill Scottish Games
5/18 • Fair Hill
Hope those kilts are freshly laundered because you’re gonna need ‘em for this festival in Fair Hill, Md., which features competitions in music, dancing and athletics along with demonstrations, exhibitions, food and entertainment.  Elke Baker, the 1995 U.S. National Fiddle Champion (yes, that’s a thing) will be on hand to judge the fiddling competition. Too high-brow? Well, there’ll be folks throwing hammers and rocks, too. The Celtic culture game is strong. It’s Scottish black pudding for breakfast—doors open at 8 a.m.

Spring Concert
5/19 • Newark
The Newark Symphony Orchestra takes on Antonin DvoÅ™ák’s Symphony No. 7 and Hector Berlioz’s Overture to “Le Corsaire,” with an assist from youth competition winner Juliana Castillo. The afternoon of music starts at 3 p.m. at the Independence School in Newark.

Newark Memorial Day Parade
5/19 • Newark
Newark offers a memorial ceremony on the UD Green, along with a parade on Main Street.

Magic Tree House 
5/19 • Wilmington
It’s about darn time someone penned a hip-hop William Shakespeare show for kids. The entire family can bop with the Bard at the Grand when it stages Magic Tree House: Showtime with Shakespeare. Daring sibling duo Jack and Annie are whisked back in time to Elizabethan England, where they meet the great writer himself. Whip-smart jams set the pace for this singular show, and by the end of the night, you’ll be spittin’ fire in iambic pentameter. The musical matinee starts at 3 p.m. in Wilmington.

Week of May 22-28

Children’s Beach House Golf Classic
5/23 • Lewes
Kick off the summer season at The Peninsula on Indian River Bay Golf Course to support the Children’s Beach House in Lewes. The driving range opens at 11 a.m., tee time is 12:30, followed by a buffet dinner in the new clubhouse—no golf shoes allowed, friends.

Fair Hill Races
5/25 • Fair Hill
And here’s we have it, your third fashion—we mean horse race—event of the month. We suggest you do your spring cleaning in April:  Get your closet nice and clutter-free so you don’t have to argue when you begin hauling in all the new gear for May steeplechases. Enjoy horse racing, a tailgate contest, Jack Russell terrier races, vendors and kids’ activities in Fair Hill, Md. Gates open at 10 a.m.

Horseshoe Crab & Shorebird Festival
5/25 • Milton
Boat rides, canoe trips, scavenger hunts, arts and crafts, train rides, food and music await visitors to Milton Memorial Park and Prime Hook National Wildlife Refuge.

Sounds of Summer
5/25 • Kennett Square
Ice cream and beach weekends and sun-drenched evenings are lovely, but is there any better way to welcome summer then settling in around Longwood’s Main Fountain Garden—the jewel of the most significant fountain collection in the United States—when Fireworks and Fountains makes its summer premiere? Come be inspired by the five-acre masterpiece created in the early 20th century. This show features iconic seasonal anthems from the likes of the Go-Gos, Justin Timberlake, and, naturally, (Delaware’s own) DJ Jazzy Jeff and Will Smith … time to sit back and unwind.

48th Annual Antiques Show
5/24-5/25 • Wilmington
The Brandywine River Museum hosts exceptional antiques from across the nation: American and English furniture, glass, metalware, folk arts, Oriental and European furniture, quilts, rugs—if you can’t find it, you’re not looking hard enough.

May 29-31

Backyard Bash
5/31 • Wilmington
It’s a coolers-and-Copeland kind of summer vibe at the Delaware Art Museum’s backyard shindig. The Copeland Sculpture Garden is the whimsical backdrop for this ushering in of the season community chill. Bring your chair, your flops and your best stargazing blanket. See you at the Delaware Art Museum at 6 p.m.

Ending this month

Fairy Tales to Nursery Rhymes: The Droller Collection of Picture Book Art
Thru. 5/12 • Wilmington
From the Brothers Grimm and Mother Goose to Dinosaur Bob and Bumble-Ardy, engaging stories and captivating images come alive in the art of picture books. Climb into the magical world of children’s literature through this stunning collection of more than 100 original and imaginative illustrations.

American Beauty: Highlights From the Richard M. Scaife Bequest 
Thru. 5/27 • Chadds Ford, Pa.
In a special collabo between the Brandywine River Museum of Art and The Westmoreland Museum of American Art, this exhibition will share the finest works from the Richard M. Scaife Bequest. A long-time trustee of the Brandywine Conservancy & Museum of Art—as well as a newspaper publisher, art collector, and philanthropist—Scaife left a major part of his extensive art collection to both museums after his death in 2014. This exhibition includes 50 paintings that celebrate Scaife’s passion for the rich traditions of American art.

Collecting as Activism: African American Art and the Legacy of Paul R. Jones
Thru. 5/17 • Newark
A collector and philanthropist, Paul R. Jones (1928-2010) began collecting art in the 1960s, focusing on acquiring works by African American and African diaspora artists—artists, at the time, who were often marginalized and excluded from major museum collections. Through artworks from his collection, the exhibition invites visitors to ask questions surrounding diversity, inclusion and visibility in art museums, as well as the role of collectors in supporting underrepresented artists. See it at the University of Delaware’s Mechanic Hall Gallery.

Throughout the month

Spirit Revealed: New Works by Aaron Paskins
Thru. 7/21 • Dover
Aaron Paskins may be a Dover sculptor, but he’s been making some national noise with his African figures and imagery, which utilize unexpected materials to craft complex pieces that speak to the rich narrative of indigenous tribes with a twist of the fantastical. Celebrate his first solo exhibition at the Biggs.

Looking for more things to do? Check out our community calendar here.