The Triangle, Wilmington
Think of the Triangle as an urban oasis, offering the energy and convenience of the city with the friendly vibe of a small village. When Allison Symonds moved here in 2014 with her husband David and their first child, she quickly learned why so many families stay for generations.
“Immediately people were coming over to say hello and they really never stopped,” she says. “If you need a cup of flour, someone will run it over to you.”

That sense of community makes the Triangle a great place to bring up children. Gov. John Carney and First Lady Tracey Quillen Carney raised their family in the neighborhood.
“People who grew up in the Triangle bring up their kids here. There are aunts and uncles and grandparents all around,” Symonds says.
She was raised in the rural Midwest and sometimes felt isolated. But the neighborhood offers a sense of camaraderie among parents as their kids come home from school. “The bus stop is one of my favorite times of day,” she says. “My neighbors are my extended family.”

The Symondses, who now have two children, enjoy walking to Brandywine Park and stopping to smell the roses at Josephine Gardens. They make frequent use of their membership to Brandywine Zoo.
“The amenities and parks make up for the small yards you find in the city,” she says. (However, a handful of residents do have sizable backyards, and to their neighbors’ delight will host frequent gatherings.)
Symonds appreciates the beauty of the Arts and Crafts architecture and mature shade trees in her neighborhood. Often, homes are snapped up before a For Sale sign is planted. When the couple started looking for a larger place, they didn’t have to search far to find their dream house.
“Right around the corner, 177 steps from our old house,” she says.
Arden
The village of Arden was founded in 1900 as an Arts and Crafts colony that included people from all walks of life and embraced green space. Jeffrey and Pam Politis first visited in 1999, arriving from Michigan.

“We were right out of grad school and the azaleas were in bloom,” Jeffrey Politis recalls. “We stopped to ask for directions and wound up in a 15-minute conversation.”
Soon after, they rented a house in the enclave, sight unseen. A year later, they bought a house a few blocks away. They had two sons, Jackson, now 20, and Jacob, 16. “We’re now in our fourth house in Arden,” Pam Politis says.

With only 229 households, the village is a close-knit community. The volunteer-run Arden Club, founded in 1908, is the hub for community interests. Both of the Politis sons participated in the village’s young actors Shakespeare workshop and volunteer at the annual Arden Fair, an eagerly anticipated crafts and games festival held the first Saturday in September.
“That sense of community makes the triangle a great place to bring up children. Gov. John Carney and First Lady Tracey Quillen Carney raised their family in the neighborhood.”
The Arden Community Recreation Association (ACRA) operates a summer co-op for children and grandchildren of residents of Arden, and sister villages Ardentown and Ardencroft. “It’s like having summer camp in your backyard where people share their art or teach a dance,” Pam Politis says.
Families enjoy hiking through the woods that wind through the village. The Politis boys grew up playing hop rock, Jeffrey Politis says, “where we go out on the creek and jump around on the rocks.”

The community organizes a Fourth of July celebration, a Halloween Party and Breakfast in the Woods, held each fall. “On snow days, we do a pop-up hot chocolate stand for kids and parents at the sledding hill,” Pam Politis says.
That neighborly vibe creates a sense of extended family throughout the village. “We don’t have family here, so it’s great to live in a place where there are other adults who take an interest in the kids, like grandparents,” she says.
Hockessin
Nothing warms Lisa Driban’s heart more than seeing moms and dads cuddled together with their little ones reading books.
“It’s my favorite thing in the whole world,” she says.
Driban’s heart goes pitter-patter on a daily basis, thanks to her job at Hockessin BookShelf, the 856-square-foot literary jewel box where generations gather to read, buy and talk about books.
She and her husband David raised three daughters in Hockessin, a sweet slice of suburbia known for good schools, low crime and the most popular Fourth of July parade in Delaware. “[It’s] adorable, with that small-town feel,” she says.
Throughout the summer, the bookstore partners with Woodside Farm Creamery, the site of Story Time Under the Big Tree, where volunteer teachers, business owners and authors read to children. Jen Blab, who bought the bookstore in 2023, took her own kids there for years. “Parents come with brand-new babies and their siblings,” Driban says.
With 130 acres of woodland, meadows and marshes, nearby Ashland Nature Center offers families a wonder-filled place to hike and enjoy a picnic lunch. Kids can celebrate growing another year older at birthday parties with such themes as butterflies, maple sugaring, campfires and s’mores, and scavenger hunts.
“It’s the kind of small town where parents dream their kids will grow up.…The sense of community is remarkable.” —Lewes resident Mike DePaolo
It’s easy to get into the fitness swim at 11.6-acre Hockessin Athletic Club (HAC), one of the largest health clubs in America. Amenities include five pools, exercise classes, nutrition coaching, yoga and massage, and more than 100 weekly youth activities. Kids can dance away an afternoon, learn martial arts or develop a fitness routine designed for growing bodies.
Lewes
Mike DePaolo and his wife Jill moved to Lewes more than 20 years ago, before they had children. They knew right away that it would be a great place to raise a family.
“It’s the kind of small town where parents dream their kids will grow up,” he recalls. “The sense of community is remarkable.”

First settled in 1631, Lewes is known as the First Town in the First State. The DePaolos’ children—Will, 15, and Amelia, 11—have grown up in the village with a sense of history, visiting the Zwaanendael Museum, a showcase for maritime history, and Shipcarpenter Square, an enclave of restored 18th- and 19th-century structures. Families gather at Puzzles, a store that specializes in games and brain teasers.
Living in a small town means most destinations are accessible by walking or biking. The family routinely pedals to Dairy Queen to buy ice cream and watch the waves roll in on a nearby beach. It’s also an ideal place for kids to take on responsibilities as they grow. Will often rides his bike to Lloyd’s Market to pick up a rotisserie chicken.
“He goes to the farmers market to buy milk and veggies, and neighbors report back to my wife and me on how polite and well-behaved he is,” DePaolo says.
On Halloween, the town closes Kings Highway so families can trick or treat. Throughout the fall, DePaolo hears the marching band practice at Cape Henlopen High School.
All year round, the family visits Cape Henlopen State Park, gathering shells on the beach and hiking and biking through the woods.
“There are days when we just pinch ourselves and say we can’t believe we live in this wonderful town,” he says.
Magnolia
Named for the lovely trees that line the street at the north end of the village, Magnolia is home to fewer than 350 residents. There’s ample evidence the locals think this peaceful Kent County town is someplace special. A sign in the center of town proclaims Magnolia “the center of the universe around which the world revolves.”
Incorporated in 1885, the town’s circular boundary represents brotherhood. Twenty-five years ago, when Danielle Lundin and her husband relocated to Delaware from New York, they bought a house in Hunters Ridge, a small development just outside the historic town center.
“We have four children and we loved the country atmosphere. It’s a place where everyone watches out for one another and kids regularly visit their friends’ houses for dinner,” says Lundin, an agent with the Bryan Realty Group. “You also get a little bit more land out here when you buy a house and we liked that. Our lot was 3/4 of an acre.”

Fishing is a favorite activity for kids and parents at Scotton Landing, a boat ramp on the St. Jones River, just northeast of town. The fishing pier is accessible to people of all abilities. The verdant countryside is dotted with numerous ponds and Lundin kayaks at least once a week. Her local favorite is McGiniss Pond.
“Blue herons are all over the place. Magnolia is a great place for families who love nature,” she says.
Downtown Middletown
More than 20 years ago, the Rokosz family moved to downtown Middletown with two young daughters, a 4-year-old preschooler and an 8-month-old baby.
Kate Rokosz and her husband Randy were intent on raising their girls in a community with a warm, close-knit feeling. Little Chelsea and Karli walked to church with their parents. They enjoyed summer theater at the Everett, originally built as a movie house in 1922 and now a cultural center for films, theater lovers and art exhibits.
“They didn’t ride a bus until high school,” she recalls.
Rokosz, who now directs the Main Street Middletown development agency, established a family tradition of giving back to the community with the Big Ball Marathon, a 24-hour fundraiser in which groups form teams and play to raise money for charities in the Middletown–Odessa–Townsend community.
Over the years, Middletown grew dramatically as the town annexed land for booming housing developments and the population grew to 25,000. Today, Middletown’s attractions include the award-winning Appoquinimink School District and a new 56,000-square-foot YMCA on Cochran Street with a splash park adjacent to the Silver Lake Pool. Kids can play sports and learn to swim, as well as receive instruction in STEM classes. The Fit Kids program, for children ages 7 to 12, teaches youths to work together and embrace a healthy lifestyle.
In the historic town center, Middletown retains its charm with Victorian–era homes, boutique shopping and restaurants. Each August, Main Street blossoms with vendors, crafts, a parade and pie contest as Middletown celebrates its annual Olde-Tyme Peach Festival.
“It’s a warm and safe community, family-friendly with great schools,” Rokosz says. “Even as much as we’ve grown, there’s still an intimate small-town feel. I can’t imagine not living in Middletown.”
Milton
MJ Ostinato discovered Milton 16 years ago when she was housesitting for friends.
“Everywhere we went, people were super nice and helpful,” she says. “I had always wanted to live in a town where you can walk everywhere and Milton is it, a friendly small town with a little funkiness to it. People want to make you glad you moved here. They want you to like it.”
“Even as much as we’ve grown, there’s still an intimate small-town feel. I can’t imagine not living in Middletown.”
—Kate Rokosz
Ostinato soon bought a home built in 1874 located in the historic district. “If you want to teach kids to appreciate history, come to Milton,” she says. “The historical society has a number of walks with different themes, like folklore and cemetery strolls.”
During local festivals, many kids opt to take a small train—“totally adorable”—that chugs through town during special events. The Holly Festival, celebrated on the second Saturday in December, features wreath making, boutique shopping, and crafts and games for children. Throughout the summer, families enjoy live music every Wednesday at Milton Memorial Park.
Built in 1910, Milton Theater has been restored to serve as the artistic hub of the community, with films, concerts, comedy, art classes and summer camps for ascendant thespians. “The theater is wonderful, with lots of programs for children,” she says.
Downtown Milton also offers an updated public playground. Kids enjoy walks with parents and grandparents on the Mispillion Riverwalk near the Milton Public Library. East of town, Prime Hook National Wildlife Refuge, a 10,000-acre sanctuary for migrating birds, offers 7.5 miles of family-friendly hiking trails. Older children can gain experience there as volunteers.
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