“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.
- 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!
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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