Questions to Ask About a City
For travelers, newcomers, students and writers who want to know what a city is really like, whether you are asking someone who lives there or researching it yourself. The questions follow the order a good conversation takes: first impressions, neighborhoods and getting around, food and fun, history, people and pace, then what outsiders miss.
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The questions
Each question, and why to ask it
First impressions
How would you describe the city to someone who has never been here?
Why ask it
A resident's own summary shows what they think defines the place: the water, the work, the weather or the people. If it comes out like a brochure, ask how they would put it to a friend who was thinking of visiting.
What is the city best known for, and does it deserve the reputation?
Why ask it
Most cities are famous for a single thing, and residents have heard about it all their lives. A local who defends the reputation with detail is telling you it is real, and a sigh is your cue to ask what they wish the place were known for instead.
What is the best thing about living here, and what is the worst?
Why ask it
The telling answers are small and daily, like a walk to work along the river or the noise under the window every Friday night. Be a little wary when the best thing about the city is how easy it is to leave for somewhere else.
How big is the city, and does it feel that size?
Why ask it
A population figure depends on where the boundary is drawn, and a city of two million can still run as a string of villages. Ask how often they bump into someone they know, which measures the scale of daily life better than any number.
If I had one free day here, where would you send me first?
Why ask it
The first stop a local picks is seldom the top of the guidebook. Ask why that place, since the reason is their idea of what the city is about, and then ask what they would do with the afternoon.
How long does a first visit need: a day, a weekend, a week?
Why ask it
Residents nearly always name more days than you have, so follow up with what they would cut. If the answer is that an afternoon is plenty, ask what a second day would be spent on, because slow cities get undersold this way.
Does the city have a nickname, and do the people who live here use it?
Why ask it
Some nicknames belong to the tourist office and some to the residents, and a local can tell you which kind this is in a second. The story behind the name makes an easy first fact for a class report, provided you check it somewhere other than a souvenir mug.
What does an ordinary morning here look, sound and smell like?
Why ask it
This one is for writers and for language classes practicing description. A strong answer has a detail no other city could supply, such as gulls over the bus station or coffee roasting on one particular street. When you only get sights, pick a corner they know and ask what they would hear there at eight.
Which season shows the city at its best, and what happens to daily life in the others?
Why ask it
You are after behavior more than temperatures: when the tables come out onto the sidewalk, when the streets empty, which month people simply endure. If you are visiting, hold the answer up against your dates before you book anything.
What surrounds the city: sea, mountains, farmland, another city?
Why ask it
The edge of a city explains its weekends, its produce and often its weather. Follow up with how long it takes to get out and whether people really go, because a mountain an hour away that nobody visits is only scenery.
Around town
How is the city laid out: one center, or several?
Why ask it
Draw a rough map while they talk and let them correct it. Whatever they add first, whether a river, a hill or a ring road, is the thing that organizes the city in a resident's head, and it is the map a fictional character would carry too.
Which neighborhoods have the most character, and what is each one like?
Why ask it
Ask for three and a sentence on each. When the descriptions come as kinds of people (students, old families, new money), you are being given the social map along with the street map, so write down both.
Which area would you tell a first-time visitor to stay in?
Why ask it
Listen for the reason as well as the name, because 'central' and 'quiet at night' are seldom the same street. Locals rarely book a hotel in their own city, so the best answers come from where their visiting relatives stayed and how that went.
Which part of the city are you from, and what does the rest of the city say about it?
Why ask it
Everyone knows the joke about their own area and most people enjoy telling it. The answer also shows which side of town their other opinions come from, which is worth remembering when they describe places they rarely go.
Is there a dividing line people talk about, such as a river, a rail line or a hill?
Why ask it
Plenty of cities have a north and south or an east and west that carry real feeling about money, history or who belongs. If one side is described with contempt, do not repeat the view elsewhere; find someone from across the line and put the same question to them.
Which area do visitors crowd into, and where do locals go for the same thing?
Why ask it
The pairing is what you want: the famous square and the quieter one two streets back that does the same job. If the local admits they still go to the famous one, it has earned its crowds.
What is the easiest way to get around: on foot, by bike, by public transit or by car?
Why ask it
Listen for where the easy answer stops, such as a hill, a river with one bridge or a last train. Tickets, passes and ride apps differ from city to city, so ask how paying works here and check the operator's own site before you rely on it.
Is there a walk, a tram line or a ferry ride that shows off the city in one go?
Why ask it
Many cities have one ordinary route that works as a tour for the price of a ticket. Find out which end to start from and which side to sit on. For a story, it is a journey a character could make every day and stop seeing.
Where is the best view over the city, and what time should I go?
Why ask it
The hour matters as much as the place, since the same hill can be hazy at noon and worth the climb at dusk. If the local names a paid viewing deck and then mentions where they go themselves, take the second one.
Where do people go when they want grass, trees or water?
Why ask it
Parks and riverbanks show how a city rests and who shares space with whom. An answer of 'we drive out of town' means the outdoor life happens beyond the city limits, and a visitor without a car should plan around that.
Where would you tell a visitor to take more care, and at what time of day?
Why ask it
A useful answer names a place, an hour and a kind of trouble, such as pickpockets around the station in the evening. Vague warnings about whole districts often repeat an old reputation, so treat any single answer as one person's map and compare it with a second.
Food and fun
What food is the city known for, and where do you actually eat it?
Why ask it
The word 'actually' does the work. If they name a counter, a stall or a relative's kitchen, the dish is alive. If they have not eaten it in years, it survives for visitors, and the better question is what people here really line up for.
Where would you take a friend from out of town for dinner?
Why ask it
People choose the place they are proud of, which is seldom the most expensive one. Ask what to order and whether you need to book, and notice which neighborhood it is in: that is a second recommendation hidden inside the first.
What does breakfast look like here, and where do people have it?
Why ask it
Breakfast is the meal least staged for visitors. Three minutes standing at a counter and an hour sitting over a newspaper describe two different cities, and either answer tells you where to be when the day starts.
Is there a market, a food street or a late stall that everybody knows?
Why ask it
Get the day and the hour, because a market that is over by noon is no use to someone who arrives at two. Then ask what to buy there that you could not find in a supermarket.
What do people do on a weeknight, and how late does the city stay awake?
Why ask it
Some cities stroll after dark, some go home and shut the door, and some are only getting started at eleven. Ask about a Tuesday and not a Saturday, because nearly every city can manage a Saturday.
Where does the music, art or theater happen, and who goes?
Why ask it
A named venue is a better sign than a general claim that the scene is great. Big touring shows and a small room where local bands play are different kinds of city life, so ask which one they went to last.
Which team does the city follow, and what does a game day do to the streets?
Why ask it
Even people who do not care for sports can answer this, which makes it a safe opener with a stranger. Learn which side they are on before you joke about a rivalry, and ask which parts of town fill up when there is a home game.
Which festival or yearly event takes over the city, and is it worth coming for?
Why ask it
Ask what it does to crowds, prices and finding a room, and whether locals join in or leave town for the week. Both habits are informative. Dates move from year to year, so confirm them with the organizers and not from anyone's memory.
Is it an expensive city to visit, and what costs more than I would expect?
Why ask it
'Expensive' depends on where the speaker is comparing from, so ask for the price of something ordinary, like a lunch or a bus fare, and judge for yourself. The surprise is the useful half: one city is cheap to eat in and dear to sleep in, and another is the reverse. Prices move, so look up current ones before you budget.
What is worth doing here that costs nothing?
Why ask it
Students and anyone traveling on a tight budget should ask this early. A long answer (a beach, a free museum day, a hill, a concert in a park) describes a city generous with its public space. Free days and hours vary, so ask how they work at each place.
Which famous sight would you still take a visitor to?
Why ask it
Locals get tired of their own landmarks, so one that survives this question is worth your morning. Follow with the hour when it is emptiest, and with what they would cross off the list to make room.
History
How did the city begin, and why in this spot?
Why ask it
The founding reason, whether a harbor, a river crossing or a mine, often still shows in where the old streets run. If the person you ask does not know, the city museum or the local history shelf of the library will, which makes this a good first research task for a class.
What is the oldest part of the city, and how much of it is left?
Why ask it
Whether the old quarter survives says as much as what it looks like. Fire, war, flood and redevelopment each leave a different kind of gap, so when the answer is 'not much', ask what happened to it.
What happened here that everyone who grew up in the city knows about?
Why ask it
Most cities have one, and it is as likely to be a championship as a flood. Notice the tone: some events are told with pride and some with care, and with the careful ones you should listen more than you ask.
What work built the city, and what replaced it?
Why ask it
The trade that paid for the grand buildings often named the streets as well, so ask what it left standing and what those buildings are used for now. If nothing replaced it, you are hearing the main fact of the city's last few decades, and the answer deserves room.
How has the city changed since you first knew it?
Why ask it
Find out how long they have been here, because a five-year answer and a fifty-year answer describe different cities. When they say it is better or worse, ask for whom, which usually opens the more honest version.
Which area is changing fastest, and how do the people who have long lived there feel about it?
Why ask it
New cafes and rising prices look like good news or bad depending on who is talking, and a fair answer gives both views. For a visitor it explains why a fashionable street can offer a cool welcome.
Is there a building, a statue or a street name that people argue about?
Why ask it
How a city fights over its past shows what it has not settled. As a guest, ask what each side says and keep your own verdict to yourself. For a class this is a debate topic with two real positions to research.
Who from here became famous, and which of them does the city claim proudly?
Why ask it
Murals, airport names and statues show who was chosen. A city that puts forward a poet has a different picture of itself from one that puts forward a striker or an inventor, and the person left off the wall can be the more interesting story.
What legends, ghost stories or old jokes do people tell about the place?
Why ask it
Whether any of it is true matters less than the fact that it gets retold, so ask who first told it to them. Writers can take these as free material, and for a visitor they turn an ordinary bridge or tower into somewhere worth stopping.
People and pace
How would you describe the people here, and is the usual stereotype fair?
Why ask it
Most cities carry a one-word label such as blunt or reserved, and locals will usually accept half of it. The half they reject, and the example they give, tells you how they would like to be read.
What time do people eat lunch and dinner, and does anything close in the middle of the day?
Why ask it
The daily timetable is the easiest thing for a visitor to get wrong and for a writer to get right. Ask what a Sunday is like too, since in many places the hours shift again. Hours change, so check the specific place before you set out.
Do strangers chat in line and on the bus, or keep to themselves?
Why ask it
Reserve can be good manners and not coldness, and easy talk may not mean friendship. The answer tells you how to read a silence here, and whether starting a conversation will seem welcome or strange.
What accents or languages will I hear, and is there a local word I should know?
Why ask it
Ask for one word, what it means and how to say it, along with the right way to pronounce the city's own name. Then ask if an outsider should use the slang at all, since the kind answer is often no.
Is this a city of people born here, or of people who arrived?
Why ask it
Ports, capitals and university towns tend to be full of arrivals, and that shapes how quickly a newcomer is absorbed. A warm answer names the communities and what each brought, down to the bakery and the festival. A cold one talks about 'them', and tells you about the speaker.
What are people here proud of that a visitor might walk straight past?
Why ask it
It could be the tap water, a bridge, a dialect or the fact that the city rebuilt itself. This is the question that makes a guarded local open up, so ask it early if the conversation is stiff.
Which nearby city is the rival, and what do people here say about it?
Why ask it
Cities define themselves against a neighbor: friendlier than there, more serious than there, older than there. The jokes are usually affectionate, but let the local make them, and enjoy how the list of the rival's faults doubles as a self-portrait.
Where would I find teenagers, families and older people on a Sunday afternoon?
Why ask it
Three different answers describe a city where the generations live apart, and one square or park named three times describes a shared one. It also tells a writer where a character of any age would plausibly be.
What outsiders miss
What do visitors most often get wrong about the city?
Why ask it
Ask it late, once you have enough of a picture to be corrected. The answer usually knocks down a stereotype or a film version of the place, and it is fair to ask next what fed the wrong idea.
What gives someone away as a tourist within a minute?
Why ask it
Expect small things, like a mispronounced district or standing on the wrong side of the escalator. Collect them lightly: the aim is to stop annoying people, and you will be spotted as a visitor anyway.
Where do you go that the guidebooks leave out?
Why ask it
Some people guard these places and are right to. If they hesitate, ask for the kind of place and not the address: a swimming spot, a lunch counter, a bench. If they do tell you, think twice before posting it.
What would you change about the city if you could?
Why ask it
A classroom favorite, because every student has to choose one thing and defend it. From a resident the answer tends to name whatever the city is arguing about this year, be it traffic, the river or the old market, and that argument is worth looking up afterward.
What would you miss most if you moved away?
Why ask it
People who have left and come back answer this best. It is rarely a landmark; more often a sound, a snack sold on one corner or the look of the river at dusk, and those small things are the ones a visitor can go and find.
If one place had to stand for the whole city, which would you pick?
Why ask it
Save it for the end. The choice might be a station, a market stall or a stretch of waterfront, and it sums up everything else they have told you. Go there, stay an hour, and see whether you agree.
Getting a local to describe the city they live in
Practical guidance for the conversation itself
Before you start asking
Choose who to ask
A lifelong resident, someone who arrived two years ago and someone who moved away each know a different city. The lifer has the history, the newcomer still notices what is odd, and the one who left can say what they miss. If you can reach two of them, ask the newcomer about daily life and the lifer about change.
Say why you want to know
Tell them whether you are visiting for a weekend, writing a story set there or doing a class project. A local picks different details for each, and people are more generous once they know the answers are going somewhere.
Ask for places and hours
'It is lively' gives you nothing to use. Each time you get an adjective, ask where and when: which street, which evening, which month. The notes under the questions point to the follow-up that turns an opinion into something you can find on a map.
Pick a dozen
Nobody wants to sit through the whole list. Take two or three from each group, start with First impressions and let the answers choose the next question. If the person lights up on food or history, stay there.
Using the list for a trip, a class or a story
Before or during a trip
Lean on the Around town and Food and fun groups, and put them to the people you meet early: a host, a driver, whoever is behind the counter at breakfast. Mark each named place on a map as you hear it. By the second day you will have a version of the city that no guidebook printed.
In a language class
Pair students from different hometowns and have each interview the other, then report on the partner's city in the third person. First impressions and People and pace can be answered in the simple present, while History and What outsiders miss push toward past tenses and opinions. If the whole class shares one hometown, give each pair a different neighborhood to speak for.
For a school project or report
Split the six groups among teams so each owns one, and have every answer say where it came from: a person, the city's own website, a museum, a map. Where two sources disagree, report the disagreement. It is usually the most interesting slide in the presentation.
For a story or a game setting
Put the questions to the real city you are borrowing from, or answer them yourself for one you are inventing. The dividing line, the work that built the place, the rival city and the thing locals are proud of give an invented city a past and a grudge, which do more for a setting than a street plan.
With nobody to ask
Read a week of the local paper, study the transit map, find the city museum's site and look around two neighborhoods on a street-level map. Then list the questions you still cannot answer. Those are the ones to take to an online group for the city, or to the first person you meet there.
Where the conversation goes wrong
Sliding into a moving checklist
Rent, salaries and school places belong to a different conversation with higher stakes. If you are deciding whether to live there, get to know the city with these questions first, and take the relocation questions to people who can give you current figures.
Treating one person as the city
Every resident lives in a small part of the place and judges the rest from there. Put the same three questions to a second person from another neighborhood or another generation, and pay attention to where the two disagree.
Old reputations
Opinions about which areas are rough, dull or overrun can be ten years out of date. When someone warns you off a district, ask when they were last there.
Pressing on a sore subject
Politics, a divided past or a recent disaster may come up through the History questions. Let the local decide how far to go. You are a guest in the conversation as well as in the city, and a change of subject is an answer.
Details that expire
Prices, opening hours, ticket rules and festival dates are the first things a memory gets wrong. Take the place and the idea from the person, then check the practical details with the venue or the operator, because how these things work differs from one city to the next.
After the conversation
Put it on a map
Pin every place that came up while you still remember which answer it belonged to. Clusters appear quickly, and a cluster of pins is an afternoon already planned.
Test one answer on foot
Choose a single recommendation and go: the view at the hour they said, the breakfast counter, the walk across town. One answer checked in person teaches you how far to trust the rest.
Bring something back
If you will see the person again, tell them what you found. Locals like hearing their city described by fresh eyes, and the second conversation is often the one where the guarded places come out.
Keep what did not fit
The answer that contradicted the guidebook, or the point on which two locals disagreed, is what a report, a story or a good trip is made from. Keep those notes apart from the list of sights.