Walking New York: All the Way Around

image“Walking New York” is my post-series on sights that you can enjoy in New York for cheap of free, just by walking. There is so much to see and do in this massive and culturally inspiring city. If you have a suggestion for a place for me to walk, feel free to let me know through my contact page.

For the past three years, my friends and I have walked the entire perimeter of Manhattan in a single day. We named our adventure “The Side Walk” (as we were walking along the side of the island). There is also a fully organized and open walk around Manhattan run by a great group called the Shorewalkers. They call their walk “The Great Saunter” and if your friends aren’t interested in this crazy activity, I would definitely recommend joining forces with the Shorewalkers. The whole trek is about 32 miles and every year has been grueling, awful, and so very rewarding.

Note: My 60-year-old mother, who thought she would join us for 10 miles or so, ended up completing the full trek one year. You can do this!

Now, for those of you who don’t live in NYC or don’t plan on visiting just to spend an entire day tearing up your body, take a moment to figure out another route you can take that is local to you. In San Francisco, for instance, perhaps Oakland Airport to San Fran Airport? Or in Boston, the Prudential Center to the New Hampshire state line is a similar distance and sounds like a fun challenge. In any case, many of the tips below should apply to long walks no matter where you are.


Before you head out on this trip, you need to do a few things to prepare.  The checklist below should help you get started:

Pick a Date (And a Makeup Date) – The best time to go is Spring or Fall when it isn’t too hot, but comfortable.

  • Scout Your Route – In Manhattan, The Great Saunter provides a GREAT map with all of the pitfalls and areas you have to navigate around. However, for people in other areas, you may want to drive your route first to make sure there are sidewalks or trails the entire way. It is also extremely important to make sure there are accessible bathrooms along the route!

The Packing List

  • Moleskin – This is the most important item. Even more important than water since this is an urban excursion and you will probably be able to buy water if you need it. Wrap this ALL around your feet, between your toes, on your heels, anywhere friction might occur. For those of you who don’t have issues with joint pain, blisters are the biggest concern on a walk this distance.


  • Extra Socks (maybe two or three pairs) – Again, as your socks get sweaty, you want to avoid blisters. Plus fresh socks feel SO good later in the trip.
  • Water – Though you will likely be able to buy water if you need it, bringing at least two refillable water bottles is a great idea. For our walk, Manhattan parks often had water fountains we could use to refill.
  • Map – Do not rely on a smartphone. The batteries will probably not last and you need it for emergencies.
  • Comfortable Clothing (don’t actually pack this – wear it) – Athletic shorts and a shirt made from a good sweat-wicking material are your best bets.
  • Food – Our first year, we decided to find a local place and grab food in a part of town we had never been before. Although it was a great experience, it was a mistake. When we stood up after an hour-long lunch, we were extremely stiff. Don’t make this mistake. Pack sandwiches, trail mix, granola bars, and other food that you can eat on the move or on a 10-15 minute break and keep moving! Plus, this way is less expensive.
  • Baby Powder/Gold Bond – Optional, but I find it VERY helpful for preventing – ehem – chafing.
  • Jacket (Optional) – Depending on the date you decide to go, you may need a jacket for the early morning/evening portions of the trip.

The Walk

  • Start Time – Get started early. If you are going 32 miles, expect it to take 12-15 hours. A 7am start is a good idea because at worst, it isn’t safe to be walking in certain places at night and at best it is deflating that it is dark and you haven’t finished.
  • Start/End Location – If you are making a giant loop, make sure that you are starting somewhere that you will want to end up. We started at Pier I, an outdoor cafe/bar on the Hudson because we knew we would want some beers after our trek. Either way though, make sure to have a convenient meeting place for your start and finish locations. And make sure your route won’t take you through any places you don’t want to be at night.
  • Friends – I would recommend inviting at least 4-6 people on this trip (the more the merrier, but if you have too many, having them all arrive on time can be tough). On the other hand, 12-15 hours is a LONG time to make conversation with just one or two other people.
  • Breaks – Be sure to take breaks along the way as you need them, but keep them very short! Continuous movement will make the trip a lot easier at the end.
  • Sightseeing – You will get to see sights you have never seen before from a walking perspective. Take pictures! Take note of interesting/strange landmarks to look up later. Sure, there is a lot of planning involved, but don’t forget to have fun!

Before this trip, I had no idea there was so much green space in Manhattan, why there are pillars in along the Hudson, or that the northern tip of Manhattan has a wigwam!



That’s it! You just went on an EPIC journey that costs very little. I will say one more thing. The best beer I have EVER had in my life, was just a simple Sam Adams Lager, consumed at the very end of the Side Walk. I am convinced that Sam Adams or any other beer has never tasted as good as that first one did to me.

So what do you think? Would you ever do an epic urban walk like this one?

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22 thoughts on “Walking New York: All the Way Around

  1. Danny March 13, 2014 at 9:22 am

    What a great idea this is! I’ve always thought that some of the best views in the city are on the piers/edges. Also, Inwood Park is gorgeous all year round. Highly underrated, in my opinion, and greatly overshadowed by another famous Manhattan park 😉 Hope the side walk goes well for you all this year!

    • Mr NYBudget March 13, 2014 at 9:56 am

      I had no idea Inwood Park was so gorgeous until I did this. And, I found out you can grill in that park (unlike that other famous Manhattan park!) That is definitely on my list to do this summer!

  2. Stefanie @ The Broke and Beautiful Life March 13, 2014 at 9:48 am

    I did my marathon training around the perimeter of Manhattan. I would start on the east river around 34th (north of there, the waterfront is inaccessible I think), and loop around the bottom all the way up to Harlem on the West Side. Definitely a fun trip, and doable by citibike now.
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    • Mr NYBudget March 13, 2014 at 9:54 am

      The northeast corner is definitely tricky. For part of the time, you are not actually walking along the edge, sadly. I am hoping that an initiative to develop parks in that area is not too far in the future.

      I definitely wouldn’t mind trying it by CitiBike as well!

  3. Leslie Beslie March 13, 2014 at 11:49 am

    I always suggest “walking around” as a cheap and fun activity to do here. It may not seem fun but with all the views and neighborhood changes it really is.

    Tip: Vaseline or bodyglide is also good for anti-chafing
    Leslie Beslie recently posted: Pinata Cake Instructions With Surprise M&M’s InsideMy Profile

    • Mr NYBudget March 13, 2014 at 11:59 am

      Great tip! Yeah, it is much harder on my body than I thought it would be!

  4. Andrew@LivingRichCheaply March 13, 2014 at 12:07 pm

    This sounds very interesting…I’m sure you get to see a lot on that journey. There are definitely great views along the water. Not sure I’d want to make the 12-15 walk…but biking it would be doable.
    Andrew@LivingRichCheaply recently posted: Are Personal Finance Bloggers “Pound Foolish”?My Profile

    • Mr NYBudget March 13, 2014 at 12:17 pm

      A big reason I try to do the whole thing is for the challenge, but there is no reason you couldn’t break this up into 2 or 3 days as well!

  5. Evan March 13, 2014 at 1:17 pm

    I have lived near by my entire life and never thought of doing that! Sounds like a lot of fun. How far north are you going? Like all the way to the Bronx?
    Evan recently posted: We are Expecting Our Second ChildMy Profile

    • Mr NYBudget March 13, 2014 at 1:43 pm

      Just around the edge of Manhattan specifically. You can look across the river and see GREAT views of the Bronx when you are at the northern tip. Fun fact, there is actually a part of Manhattan that is across the river and not physically on the island of Manhattan: the Marble Hill neighborhood.

  6. Ryan @ Impersonal Finance March 13, 2014 at 5:21 pm

    I do miss living in a city (Chicago… I never lived in NY). So many things to see and do that require no more than a little energy.
    Ryan @ Impersonal Finance recently posted: the classics of personal financeMy Profile

  7. Phil March 13, 2014 at 8:56 pm

    Great post! I walk all over the city. On a nice day it’s so easy to walk all around Central Park, along the water, all the way downtown from the UES, etc. There is a lot to see. Also, it’s always easy to take a break with so many spots to grab a bite or cold drink. Also, walking across the Brooklyn Bridge on a sunny day is always a thrill, especially with the ice cream joint right there on the Brooklyn side!
    Phil recently posted: Holy falafel Batman! Mamoun’s Falafel in NYC is the shizz!My Profile

    • Mr NYBudget March 14, 2014 at 8:15 am

      Oh man – I cannot WAIT for warmer weather. It’s almost here!

  8. Mel @ brokeGIRLrich March 14, 2014 at 11:53 am

    Cool wigwam! That walk definitely sounds like a pretty cool accomplishment.
    Mel @ brokeGIRLrich recently posted: #NYCFail – I Lost My Metrocard. Again.My Profile

    • Mr NYBudget March 14, 2014 at 12:48 pm

      Thanks – yeah, I was very surprised by the wigwam as well!

  9. Debby March 15, 2014 at 12:00 pm

    I’ve started doing Monthly NYC adventures: it’s amazing what there is to see in this city! A walk around Manhattan’s perimeter sounds like something that fits that goal. I’d be totally up to see a tipi 🙂
    Debby recently posted: Day 151 – Game Night.My Profile

    • Mr NYBudget March 15, 2014 at 10:17 pm

      NYC Adventures are my fave. Let me know what you plan!

  10. Erin @ My Alternate Life March 15, 2014 at 6:44 pm

    Wow, that’s an awesome walk! I should try something similar in Portland — there will be bridges involved!

    I really need to get back to NYC sometime to see the non-touristy parts.
    Erin @ My Alternate Life recently posted: How Much Do Cats and Dogs Cost?My Profile

    • Mr NYBudget March 15, 2014 at 10:16 pm

      Let me know when you figure out a route in Portland. It’s high on my list of cities I want to visit in the US and I wouldn’t mind exploring it via an epic walk!

  11. Dee @ Color Me Frugal March 19, 2014 at 8:36 pm

    Oh my gosh, the Side Walk sounds a little crazy… but fun! I spent a couple weeks in NYC last fall and I totally agree that it is a fun city to walk around.

    By the way, I nominated you for a Liebster Award today! You can see today’s blog post for details: http://color-me-frugal.com/liebster-award/
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    • Mr NYBudget March 19, 2014 at 11:19 pm

      Thanks Dee! Yeah, us locals get bored of a lot of the tourist traps, but I will never get tired of walking the city!

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