Middletown, Delaware

On the list for the second year in a row, Middletown used to be a tavern spot midway along a historic trade route that ran between the Atlantic Ocean and Chesapeake Bay in the 17th century. Today, it’s the midpoint between Dover and Wilmington, 27 miles to the south and north, respectively.  

The small town, with a population of just under 25,000, has blended historical charm with residential growth. Its downtown features a selection of boutiques, eateries, and breweries. One of the most popular venues is Crooked Hammock Brewery, featuring live music, craft beer, and lawn games like cornhole for the kids. On weekends, Middletown hosts a farmers’ market, and culture seekers can delight in concerts and films at the Everett Theatre, which dates back to the early 20th century.

The area has a big family-friendly appeal. Charles E. Price Memorial Park offers two playgrounds where kids can release their energy, a fishing pier, a long path for strolling, and a dog park. Every summer, Middletown hosts the Olde-Tyme Peach Festival in honor of its first cash crop that helped kick off the town’s population boom in the 19th century. The festival delivers everything from a peach parade to a peach pie contest.

Middletown has some of the best public high schools in Delaware, as part of the highly rated Appoquinimink School District. The high school graduation rate is 95%.