For the past two years, my friends and I have walked the entire perimeter of Manhattan in a single day. After some deliberation, we named this event “The Side Walk”. 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”. My friends and I simply wanted to head out on our own, but if I were alone, I would definitely join up with the Great Saunter. The whole trek is about 32 miles and both times have 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 this past 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.

Preparation

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) - Depending on where you live, often the best time to go is Spring or Fall when it isn’t too hot, but comfortable. You never know when it is going to rain, so clearing two weekends in your schedule is a good idea (perhaps plan an indoor event that can flex to whichever weekend you aren’t walking).

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!

- 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! Pack (Night Before) - There are some crucial items that you need to bring with you that you may not think about. I will get to those in a moment.

(Night Before) - There are some crucial items that you need to bring with you that you may not think about. I will get to those in a moment. Eat Healthy (Night Before) - I would suggest some carbs, protein, and plenty of water in preparation. Definitely do not go on a huge bender the night before!

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. Bring extra moleskin in case you need to replace some (or if a friend forgets).

- 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. Bring extra moleskin in case you need to replace some (or if a friend forgets). 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.

(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.

- 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.

- 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.

(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!

- 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! Baby Powder/Gold Bond - Optional, but I find it VERY helpful for preventing - ehem - chafing.

- 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.

- 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.

- 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, you need to let them know that you won’t wait for everyone and that other people should form mini-groups in case they get a later start). On the other hand, 12-15 hours is a LONG time to make conversation with just one or two other people.

- I would recommend inviting at least 4-6 people on this trip (the more the merrier, but if you have too many, you need to let them know that you won’t wait for everyone and that other people should form mini-groups in case they get a later start). 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.

- 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! Enjoy your trip and create a new great story to tell people when you are done. 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.