Middletown sits in southern New Castle County, below the Chesapeake and Delaware Canal, in country that was mostly farmland a generation ago and is now filled with new neighborhoods. Route 1, a toll highway, runs north-south east of town, crossing the canal on a tall bridge toward Wilmington and heading south toward Dover. US 301, a newer toll road, runs from Route 1 southwest toward Maryland. Route 299 is Main Street through town and continues east to Odessa, while Route 71 and Route 896 lead north toward the canal crossings at St. Georges and Summit.
Route 1 and the canal bridge carry a heavy weekday commute north toward Wilmington, and summer beach traffic piles on top of it on Fridays and Sundays. Route 299 through downtown and the shopping areas near US 301 back up at rush hour as the town's growth outpaces its older two-lane roads. Many subdivisions sit off country roads with narrow shoulders and no sidewalks. A breakdown on the canal bridge or the Route 1 shoulder is dangerous, so the priority is always getting the car to a safe spot first.
DART buses offer limited service, and nearly every household drives, often commuting long distances to Wilmington, Newark or Dover. Flights mean a long drive north to Philadelphia or west to Baltimore. Large distribution centers and industrial parks near US 301 run around the clock, adding truck traffic to local roads and bringing shift workers in and out at all hours. For a mobile mechanic, the newer neighborhoods are easy to reach, while the farm addresses beyond town take a bit more time and clearer directions.