Your Truck Is More Trouble Than It's Worth
Pickup trucks are on practically every street…but should they be? Though the average American gets a lot of use out of them, trying to navigate congested streets or literal uphill battles in one isn’t always easy. From strict parking regulations to historic neighborhoods that weren't designed for oversized vehicles, these 20 cities can make pickup ownership look way less appealing.
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1. New York City, New York
Finding somewhere to park a full-size pickup in Manhattan? Right, good luck to you! Parking garages in and around the city also have height restrictions, and crowded streets leave little room for maneuvering. New York also has additional parking restrictions for commercially registered vehicles, meaning you need to do some serious homework about how your vehicle’s actually classified.
2. San Francisco, California
San Francisco's famously steep hills can make driving a large pickup something of a nightmare, especially in tight intersections or parking along an incline. Parking doesn’t make things any easier. The city's rules also require drivers to curb their wheels on sufficiently steep grades, adding another consideration when leaving your vehicle unattended.
3. Boston, Massachusetts
Boston's historic layout might be fun on the outside, but when you’re driving a truck inside, you’ll run into nothing but problems. Navigating narrow roads requires more than a little patience, too, particularly when delivery vehicles occupy valuable street space. Residential parking restrictions and limited curbside availability also make finding a place to leave your baby difficult.
4. Chicago, Illinois
Chicago has an unusual complication for pickup owners—the city maintains specific regulations governing where certain trucks can even park (without getting slapped with a ticket). Noncommercial pickups under the applicable 8,000-pound threshold can qualify for residential street parking under city rules, but heavier vehicles face even more restrictions. Combine that with congested downtown streets and harsh winters, and suddenly the bus doesn’t seem so bad.
5. Philadelphia, Pennsylvania
Philadelphia's older neighborhoods weren't made with modern crew-cab pickups in mind. If you’ve ever tried to drive a pickup through one now, you know exactly what we’re talking about. The city's own guidance recommends parallel parking spaces approximately 19 to 20 feet long, which can be a tight fit for certain full-size trucks. Anyone living around South Philadelphia's closely packed rowhouses might just consider a sedan.
6. Washington, D.C.
Washington has a nasty combination of restricted parking zones, busy intersections, and heavy commuter traffic. If you couldn’t guess, none of that is welcoming to oversized vehicles. Although a pickup might prove useful for weekend projects, finding convenient parking is another matter entirely.
7. Seattle, Washington
Between its steep hills and crowded neighborhoods, Seattle never fails to make life hard on a truck driver. Even the city's transportation department has addressed restricted vehicle access on narrow roads, so it’s worth considering before you bring your behemoth to the city. All that infamous rain won’t make your day any better, either.
8. Los Angeles, California
Have you ever tried to sit through LA traffic? That’s just step one. Now try doing it in a pickup! Dealing with congestion or navigating crowded parking lots can make a full-size truck seem like the most foolish thing you ever did. Fuel consumption during frequent stop-and-go driving also becomes difficult to ignore, especially if you own a thirsty V8 model.
9. Miami, Florida
Miami's dense coastal neighborhoods make parking a headache waiting to happen, and curbside spaces are often difficult to secure. Driving a pickup through busy streets filled with pedestrians, cyclists, and tourists is also a constant game of vigilance and patience. Don’t forget that coastal exposure also means owners who regularly park outdoors should take corrosion prevention seriously.
10. New Orleans, Louisiana
New Orleans has plenty of streets where historic architecture and limited parking space make oversized vehicles inconvenient. Driving a pickup demands extra care around pedestrians and closely spaced intersections, too. Don’t forget about that heavy rainfall and recurring street flooding.
11. Charleston, South Carolina
When Charleston's picturesque historic district first emerged, no one had modern pickup trucks on the brain, particularly those with huge beds. That’s exactly why some streets feel restrictive when you're navigating closely parked vehicles and trying to avoid all that traffic. Hopefully a downtown trip isn’t in the cards, because if so, parking is a whole other hurdle.
12. Savannah, Georgia
Savannah's historic squares make the city distinctive, but they also introduce additional turns and intersections that require attention from drivers of larger vehicles. Maneuvering through the historic district can be uncomfortable when tourists and even literal horse-drawn carriages share the streets. Put parking near popular destinations out of your mind, too.
13. Portland, Oregon
Portland's central neighborhoods have all sorts of bike lanes, pedestrian crossings, and busy commercial streets where large pickups require a delicate touch. Though it might not seem like it at first glance, drivers who primarily use their trucks for short urban trips will undoubtedly struggle to justify the fuel expenses associated with moving such a heavy vehicle around town.
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14. Pittsburgh, Pennsylvania
Pittsburgh throws a lot of things at pickup drivers: steep hills, winding roads, and complicated intersections. If you don’t know where you’re going, maneuvering through all those obstacles gets old pretty quickly. Not to mention, winter conditions add another problem to your plate.
15. Honolulu, Hawaii
Honolulu seems like it’s nothing but idyllic, open space—but not so fast! It’s less about the traffic and actually more about the maintenance. Vehicles, replacement components, and certain accessories can be expensive to transport to Hawaii. If you get stranded, you won’t find quick help there, either. Everyday island driving often involves relatively short distances, so owners may find themselves paying for towing and hauling capabilities they rarely need.
16. Jersey City, New Jersey
Jersey City's densely populated neighborhoods create plenty of difficulties for anyone hoping to park a full-size pickup near home. Narrower streets are practically a Tetris match, particularly when both sides are lined with parked cars already. If you’re commuting toward Manhattan, there’s nothing but more congestion in your future.
17. Hoboken, New Jersey
Hoboken's compact layout makes owning an oversized pickup especially inconvenient! We’re talking limited curbside space and residential blocks packed with vehicles, which makes finding a spot long enough for your truck nearly impossible. Even everyday errands become an issue.
18. Cambridge, Massachusetts
Cambridge is no stranger to residential streets, and when you stack heavy pedestrian activity and busy intersections on top of them, drivers need to fight for their lives on those streets! Residential parking regulations further complicate ownership for anyone without access to a private driveway or garage.
19. Providence, Rhode Island
Providence combines older neighborhood streets with hills and closely spaced buildings, which obviously don’t mesh well with what a pickup needs. Tight corners and vehicles parked along both curbs happen all the time, too. All that cargo space will have nowhere to go in this town.
20. San Diego, California
Don’t fall for San Diego's generally pleasant weather—it’ll trick you into thinking pickup ownership is easy! In reality, finding appropriate parking just won’t happen on busy weekends, and if you mostly drive between restaurants and downtown offices, a large truck may provide considerably more capability than your daily routine actually needs.
