Girl About Town

An urban-exploration guide.

Illustration by Hattie

It’s really nice to stare at a map and fantasize about all the places you’ll visit someday, but sometimes the best adventures can be found close to where you are. Over the past five years, due to lack of money and time, I’ve become an accidental expert at uncovering cool stuff in unexpected places. Here’s my guide to planning (or not planning) an awesome day of urban exploration, anywhere in the world, or right in your backyard:


Obviously, you don’t want to weigh your adventure down with a ton of baggage, but bringing along a few well-chosen tools will increase your potential for fun. A backpack is the best bag for exploring, because you can carry a bunch of stuff and still have both hands free. Here’s what I fill mine with for a day of intensive exploration:

  • A notebook and pen for writing down train times and food recommendations and any other tidbits of intelligence I might acquire.
  • A refillable water bottle and a little snack so that hunger- and thirst-related crankiness doesn’t interfere with my day.
  • A fully charged cell phone. I usually keep my phone turned off on days like these, but knowing you have a lifeline can provide peace of mind.
  • Enough cash to get public transit home, plus a little extra. Sometimes I split this up between my pocket and my backpack in the event that we get separated.
  • A sweater. But I just have that neurotic-Jewish-grandma-take-a-sweater-thing. You might not.

Obviously, you should add to this list to meet your needs. A raincoat when it calls for rain. Band-Aids if you think your shoes might rub. People argue over whether or not bringing a camera is a good idea. I probably bring one with me about half the time. Sometimes I get too caught up with documenting the day, though, and the camera actually detracts from my fun. Having pictures is nice, but I’ve learned that sometimes your brain is the best recorder.

Getting There

My best urban adventures start and end with public transit. People on trains are friendlier, and a long bus ride is a nice set of brackets for psyching yourself up or letting yourself decompress after a long day of exploration. Also, public transit is one of the cheapest ways to get around.

Lots of things about city exploration should be left to chance, but transit is not one of them. The night before your adventure, decide how you’ll be getting to and from the city. Print out the train or bus schedule and highlight the second-to-last ride home. This will be your getaway car. Spontaneity is good, but missing the last ride out of the city will take your day from great to stressful. Bank on the second-to-last departure and you’ll have a nice time buffer in case your adventure ends up running a bit longer than expected.

Getting Somewhere

When you get to the city, the first thing you’ll want to do is get a lay of the land. There are a handful of ways to go about doing this. Visitor’s centers, train station information desks, historical societies, and cool-, friendly-looking strangers (other teenage girls are probably your best bet) on the street are all great sources of info about interesting neighborhoods and sights worth seeing.

If you are at all like me, you are probably thinking, I can just look this stuff up on the internet. It doesn’t hurt to go online and read a little bit about a new city, but honestly, talking to people is the best way to find cool places. The internet can tell you what time things open and close, but it probably won’t share with you a wild anecdote about that one guy who hangs out at the newsstand on the corner, or an insider tip about where to get the best chai. Push yourself to talk to people, even if it feels a little awkward at first. Here are some good questions for starting conversations about local geography:

  • What’s your favorite bookstore in the city?
  • Where’s a nice place to sit down and drink a cup of coffee?
  • Are there any cool events going on right now that I should know about?
  • Do you know of any good thrift shops around here?
  • Where’s your favorite place to people watch?
  • What does this city have that other cities don’t?

Adventure Time

Once you’ve accumulated a nice list of recommendations, start your adventure. Your actual destination doesn’t matter so much as the neighborhood you’re headed toward does. Check out that bookstore the girl in the train station told you about, but don’t forget to keep an eye out for random stuff nearby. It’s really rare that one good place will exist in a wasteland of boredom. Most of the time, that bookstore will be situated near a rad vintage shop or a well-curated art space. Have an open mind about changing plans and checking out mysterious places. Especially look for signs directing you towards basement entryways and side doors. Smaller, weirder endeavors often thrive in crappier real estate.

Every place you uncover is a potential link to newer and cooler places. Ask store clerks and coffee shop patrons for their advice on where to visit. When I visit a city, I’m usually able to build an agenda by asking people at each consecutive place I visit where I should go next. Hand-drawn maps often make the best guides. Use your notebook for these.

Only wander as far as things feel safe or interesting. Unless you have explicit information otherwise, a poorly lit residential street probably isn’t going to yield some awesome attraction. People are a good sign that a place is safe and worth visiting. If you see a crowd, push your way in. If you’re walking and you suddenly find yourself alone, it’s probably time to turn around.


Feeding yourself on your urban adventure is a complicated thing, because it is the only element of the day (besides maybe transit) that requires money. If you’re trying to spend as little cash as possible, make some sandwiches at home and throw them in your backpack. Parks make the best free restaurants.

If you have some cash to burn, look for places with cheap prices and lots of people. It isn’t hard to eat great food on the cheap, but the best way to make sure you won’t be vomiting on the train ride home is to look for restaurants that are moving through a lot of food quickly. If you can, avoid eating at chains. I love Chipotle as much as the next person (probably more), but an adventure isn’t really an adventure unless you push yourself to try someplace new. Thai food, falafel, food trucks, and soup are all great, cheap options to look into, depending on the city you’re visiting. If you aren’t sure where to try, ask more strangers!


Walking dozens of blocks and talking to as many strangers can be tiring; you might want to take a little bit of time out from your excursion to relax. Coffee shops, libraries, parks, and benches are all great places to people watch and decompress. If you are going to sit in a place that sells something, buy something cheap like a cookie off the menu. Throw your change in the tip jar and you probably won’t be rushed out of the establishment as soon as you finish eating.

Common Sense

I’m not going to insult your intelligence by telling you to look both ways before crossing the street, but I do feel obligated to pass on some the wisdom I’ve gathered through my own mistakes. You don’t have to take any of this advice, but here are some things I’ve learned in my adventures:

  • Don’t follow strangers back to their houses.
  • Don’t follow strangers anywhere that isn’t a public space.
  • Don’t get in someone’s car!
  • Stay aware of your surroundings.
  • Stay out of abandoned buildings.
  • Go to the bathroom when you have the chance to.
  • Don’t jaywalk unless you have a spare $200 you are looking to donate to the City of Houston.
  • Don’t jump subway turnstiles unless you really think $2.25 is worth ruining your day over.
  • Always assume your fake ID is less good than you think it is.
  • Be friendly to cops, service employees, babies, and old people.
  • Be friendly to everyone you meet until you have a reason not to be.
  • Any kind of person can be dangerous, no matter what age or gender, but as an extra measure of safety don’t approach solo grown men, OK? It would just make us feel better.

Most of all, be open-minded. Use good judgment, but keep in mind that great things rarely happen in your comfort zone. Be aware. Peek around corners and down alleys. Trust your intuition. Don’t write something off as boring until you’ve given it a shot.

Godspeed! ♦


  • Naomi Morris March 19th, 2012 3:08 PM

    i love you jaime

  • starcollector March 19th, 2012 3:14 PM

    Yeahhh adventure! :) This was really helpful! I feel like you don’t really understand or appreciate your home-town until you’re a teenager with nothing to do… because that’s when you have the motivation to really explore some weird places!

    For example, there was this giant area behind one of the libraries by my house, and if you went far enough into the forest, there was a giant creepy field which was used for beekeeping. Unfortunately, my friends and I found that out the hard way! It was still a lot of fun though, and I feel like I know a little “secret place” that I didn’t know before.

  • Marguerite March 19th, 2012 3:18 PM

    I wish i could do that, but my city is 0.3 square miles and i can assure you, i’ve seen every bit of it…

  • eralc March 19th, 2012 3:21 PM

    add dont go into cafes that few or no people are in

  • Narita March 19th, 2012 3:21 PM

    Jamie, you inspired me. I guess I’ll be on a trip to Amsterdam in a few weeks because this sounds awesome. Are there any Dutch Rookie readers that would like to join the fun?

    • Stellalune March 19th, 2012 4:33 PM

      I’m not Dutch but my mom lives in Amsterdam so here are some ideas:
      Visit the Negen straaten, awesome vintage boutiques etc but some shops are quite expensive..
      If you’re interested in museums, art whatever go to the van gogh museum, the Anne frank house or the national gallery they are all great,
      Places to chill: definitely vondel park all the students hang there, have bbqs etc. Or do a boat ride on the Grachten, the city is beautiful from the water :)
      Have fun!!

    • Eva March 19th, 2012 5:20 PM

      I’m not Dutch but I live in the Netherlands ( 3hrs from Amsterdam ) .
      Sounds cool =D

      • Narita March 20th, 2012 11:19 AM

        How can you not be Dutch and live in the Netherlands nonetheless? :P Anyway it would be great to meet up with some fellow Rookie readers so maybe we could organize something! (Dear staff people reading this, I’m sorry if you guys don’t like us organizing meeting – we’ll do it all save, ok?)

      • Stellalune March 20th, 2012 3:47 PM

        Narita you can not be Dutch and live anywhere you want ;)
        When are you in Adam? I’m actually going last weekend of march ;)

    • MissKnowItAll March 20th, 2012 6:51 PM

      Family road trip!!!

      • Eva March 21st, 2012 7:36 AM

        Haha , i’m studying here that’s why .

  • Ida March 19th, 2012 3:23 PM

    Great tips, thank you!
    Me and one of my friends often go on what we call “adventures”. We both live in a suburb outside of Stockholm (Yes, Sweden) so on our adventures we go in to town, and then just take the train to a random place that has a nice name or something like that.
    When we get there we often just walk around, imagining what it would be like if we lived there. This has taken us to a lot of cool places and I think it’s a great way of exploring your hometown.
    Fellow Rookies -adventure is out there!

  • ellaronnie March 19th, 2012 3:25 PM

    I once found an abandoned railroad in some kind of industrial area. It was the coolest thing ever. Surrounded of big factories and storage lots but overgrown by bushes and flowers.

  • Abby March 19th, 2012 3:29 PM

    This makes me so sad I don’t live even remotely close to a city… and where I live, you need a car to get anywhere… and my area doesn’t have public transit… *grumpface.* On the plus side, I’ll soon be going to college in a town where you can walk places!

  • KinuKinu March 19th, 2012 3:31 PM

    this is very cool.I’m going to go exploring today :) I LOVE THIS SOOO MUCH!!!!

  • puffytoad March 19th, 2012 3:37 PM

    I nearly bored myself to death in Chicago last summer. That’s impressive, right?

  • youngfridays March 19th, 2012 3:45 PM

    As soon as I saw the title “Adventure Time”
    I was like

    ‘Adventure time,
    come on grab your friends,
    we’ll go to very distant lands,
    with Jake the dog
    and Finn the human.
    The fun will never end,
    it’s Adventure Time’

    so anyway,
    if you have seen or heard of or watched the cartoon show Adventure Time you probably should as it is possibly the best show aside from Doctor Who.

    Peace out <3

    • glitter and gold March 19th, 2012 5:36 PM

      Adventure Time makes me happier than cotton candy and Disney World combined.

      • KinuKinu March 22nd, 2012 12:18 PM

        I missed out on Adventure Time,so yesterday I found the episodes online…..I heard laughing for 15 seconds makes your life last for two more minutes or something..I laughed for ,like,an hour(no joke) on one part.IM IMMORTAL

  • Hazel March 19th, 2012 3:45 PM

    “But I just have that neurotic-Jewish-grandma-take-a-sweater-thing.”

    MmmmHMMMM. Totally. Me.

    Also I always head to public parks whenever I’m in a city on a beautiful day because I love to people watch. I’ve spent almost entire days lounging in Rittenhouse Square by accident because of just getting lost in watching people/dogs/mostly dogs. Just don’t go at night and make sure there are other people in the park. That would be creepers.

    • Narita March 19th, 2012 5:00 PM

      So sure you would love it here. In sumner we’ve got LOADS of tourists and they all BRING THEIR DOGS. I usually ask if I can pet them. I’m doing that since I was like, 4.

    • Amy Rose March 19th, 2012 5:43 PM

      Haha, I have the opposite thing where I’m always in Daisy Dukes in the rain. Can someone please always bug me to take a sweaterrrrrrrr

      • Anaheed March 19th, 2012 5:57 PM

        Being your mom, I will do this.

      • MissKnowItAll March 19th, 2012 7:53 PM

        Mom, can I have an allowance????

  • moonflower March 19th, 2012 3:53 PM

    This is so me! Thankyou so much for this, me and my friend are planning to take a bus to the city this summer and have a day of roller-blading through the streets and thrifting. This made it even more exciting, praise the lord for Rookie/my bible

  • mariaantoniavs March 19th, 2012 4:30 PM

    This is awesome!!! Now I’m dying to go out and explore!!! I just need to ask my mom for permission…

  • nattwenty March 19th, 2012 4:37 PM

    Thank you for this inspiring article! I can’t wait to explore my future college town :] I’m usually apprehensive to venture out without friends but finding secret nooks can be way more fun alone.

    On another note, I love Rookie editors’ and readers’ style choices…I just bought a pair of Biba platforms and don’t know what to wear with them. Advice? I don’t really have a personal style yet…,r:11,s:0

    • starcollector March 19th, 2012 7:36 PM

      I’m feeling a white lacy/eyelet dress, round sunglasses, maybe a thin belt that matches the tan of the platforms (or highlight one of the colors of the flowers!!!), and maybe a delicate pendant necklace or two!

      Also if you’re feeling daring, a pair of white socks!

  • Stellalune March 19th, 2012 4:39 PM

    I don’t know of its the same in the states but here in Europe you should always take a student ID with you cause you can get free stuff, entrance fees and public transport!
    I love exploring cities, this was awesome :)

    • marimba_girl March 19th, 2012 9:55 PM

      That’s so true! I always ask regardless of if it is posted and depending upon the person working at the desk, I can sometimes finagle my way into a 10% discount. Try it! Especially if you chat it up and bemoan the fact that you had gym the period before and your hair is all frizzy in the picture, it will earn you sympathy points.

  • AnguaMarten March 19th, 2012 4:39 PM

    this is great. unfortunately, i’m stuck in suburbia. i have done some exploring–i can bike to 2 of my friends’ houses, the awesomest bagel shop outside of new york, the pizza parlor, the freaky asian food market, the library, the local coffee shop, and the church. but nobody else really explores and everything is just so far away… ugh. i hate my town.

    • MissGorgeous March 19th, 2012 7:23 PM

      These girls had an amazing adventure, and they were living in the suburbs! All you have to do now is find a celebrity’s cell phone! Haha x) I apologize I couldn’t find a good YouTube video, you could try renting it on Netflix. :) Besides renting this movie, you could also watch some National Geographic films. National Geographic has made a film in almost every country, with amazing views and information in them. It’s like exploring, except you don’t have to leave your couch! ^_^ If you not up to world-traveling, try drawing, painting, collaging, etc. of your “dream town”, or how you would improve your town. :) I hope hope I helped you stay adventurous, even if you’re stuck somewhere boring. ^_^ <3

  • mayaautumn March 19th, 2012 4:44 PM

    Ooh, i love this<3
    I used to go exploring in the woods and fields by my house with friends (always worrying whether we'd be chased by cows!!!)
    I love finding hidden little shops that no one knows about which sell one off vintage clothes and jewellery and everything! Charity shops are amazing for exploring because you never know what you're gonna find – a few weeks back, i got a Chanel (yes, Chanel) cardigan for £9! So im obsessed with charity shops at the mo…..YAY-this is an amazing article:)

  • Krista March 19th, 2012 4:56 PM

    I love this, Jamie!!

    Also: “Go to the bathroom when you have the chance to” FTW!!

    • Stellalune March 20th, 2012 3:49 PM

      But it’s the most important! :)

  • Susann March 19th, 2012 5:03 PM

    Haha, great tips and ideas! Activating common sense is the best idea!

  • gloomyflamingo March 19th, 2012 5:20 PM

    I guess I’ll just have to go somewhere tomorrow, thanks for the inspiration! I live in Prague and I always think I’ve seen every bit of it, but then I accidentally miss my destination by a tram stop or two and I suddenly find myself somewhere in the wilderness.

  • rainysister March 19th, 2012 5:21 PM

    I love this!

  • MissKnowItAll March 19th, 2012 5:31 PM

    Sometimes I just get on the train and get off on the last stop. It’s quite an adventure figuring out where I am and how to get home.

    • KinuKinu March 22nd, 2012 12:21 PM

      that made laugh me laugh SOO hard….♥♥

  • Kathryn March 19th, 2012 5:52 PM

    I wish I could do this! My town doesn’t even have public transportation… lame rural minnesota… :(

  • Lily March 19th, 2012 5:58 PM

    oh wow. now i have a sudden urge to go out exploring

  • poppunkgurrrlx March 19th, 2012 6:13 PM

    I’m from Central IL and was wondering if anyone had any suggestions for cities to explore aside from Chicago? I’m not at all familiar with public transportation so any advice is handy :)

  • queserasera March 19th, 2012 7:00 PM

    I love the article, so helpful,
    and the illustration is beautiful!

  • lorobird March 19th, 2012 7:37 PM

    Haha “be nice to babies” I agree, this one is very important! Babies are awesome :3

    My boyfriend is away for the next couple weeks, so to distract myself I will do this on friday :) thanks Rookie!

  • Nomi March 19th, 2012 7:52 PM

    I live in NYC, but NYC is huuuuge, even if I stay in manhattan. So you’ve just given me a great idea for something to do on a boring Sunday.

  • toizelle March 19th, 2012 8:16 PM

    This made my heart warm and hungry for more adventures.

    Thank you! :)

    It’s true, it does not take a lot of money or some exotic location to fulfill your wanderlust.

    This speaks to that part of my being that seeks to enjoy my surroundings and does not take pleasure solely in material things, but in rich experiences.

  • megpear March 19th, 2012 8:47 PM

    Ahhhh thank you for posting this!! I moved to Chicago this past year and have yet to legitimately explore the city and its neighborhoods because I’ve been pretty intimidated by the sheer size of it… But this is super helpful for knowing how to at least start going about it. :)

  • nataliehern March 19th, 2012 9:14 PM

    does anyone live in miami and have some good suggestions?

  • marimba_girl March 19th, 2012 9:57 PM

    This is so great, I will totally be exploring more of Philly during the summer. I live in the suburbs and tend to only go to the city for concerts and then to grab a coffee before coming home. I now have inspiration!!

  • merdina March 19th, 2012 11:52 PM

    omg, this is perfect timing. i’m staying in seattle for a couple of days and though i’m having fun, i feel kind of lost on how to do things and what to do about it (i’m on my own and i don’t really know where to start). so this is very helpful. <3 thank you so much.

  • Astoria March 20th, 2012 10:41 AM

    I honestly love you for this! You definitely inspired me to go visit the cities close to where I live. Because even though I live in the biggest city in my country, it gets boring here. It’s all the same!
    So thank you very, very much. I’m planning trips to places I’ve never been before already :)

    • MissKnowItAll March 21st, 2012 4:02 PM

      By any chance do you live in Queens?

  • all-art-is-quite-useless March 20th, 2012 1:00 PM

    The only adventuring I’ve ever done with my friends is going to find an old air-raid shelter from WW2 (I think its an Anderson Shelter) in a field near my friends house… now I’ve read this article I’ll have to do some more exploring!

  • RockHatesMiriam March 21st, 2012 2:07 PM

    Uhrm, sorry to be awkwardly British here, but what’s jaywalking?
    Awesome article btw! I’ll be using sone of theese tips when me and my friends explore London in the summer, it’s only a 30min train ride away!

    • MissKnowItAll March 21st, 2012 4:03 PM

      It’s when the policemen are being jerks and decide to fine you for crossing at the wrong part of the street.

  • Yasemin March 21st, 2012 8:46 PM

    The note about handwritten maps reminded me of when I was in Tokyo this past summer. I picked up a book, Tokyo on Foot, in a bookstore near my hotel. It was honestly the best decision ever! It’s a fat book written by a French man who stayed in Tokyo for 6 months or something, and he has all these hand drawn maps of every neighborhood, all the people he saw, all the places he went, and it’s quite awesome!

  • Ben March 21st, 2012 10:26 PM

    I really want to go exploring the city with a friend now! My parents said i have to wait till i’m 18 to go explore without an adult. =( But i’d probably be to scared to anyways! LOL I went on a fun adventure in chinatown last year with my family. It was really cool and we found this random thing on the sidewalk called the church of elvis! It was so crazy! I documented it here:

  • Shutterbug1998 March 21st, 2012 10:37 PM

    If only I had seen this earlier! I just got back from Naples, FL and I would’ve loved these tips to guide me around the city :)

  • Clarissa March 22nd, 2012 8:41 PM

    Um, I live in the middle of Alaska……”Sigh”

  • ShakespeareRules March 24th, 2012 1:54 PM

    You may not read this Jamie, but today was one of the best days ever and it’s thanks to you. Me and my friend got a bus into town with about £10 between us ($15 to most of you I think) and it was just a really awesome day out. We went to art galleries, to the canals,we people watched, shared ice-cream and it was great. So, thanks. xxx

  • clady April 4th, 2012 4:55 AM

    really make me wanna go exploring my town w/ friends xD
    thnk u!