This month’s dare is to walk from Boston to Northampton (~100 miles) without any money or food. Well, I’m not allowed to bring any food but I can “obtain” it on the way through my industrialness. I will also have to find places to sleep at night.

Since I’ve decided to take on this dare, a number of friends and family have tried to talk me out of it. It’s potentially very dangerous, they said. Well, I couldn’t agree more. I’ve lived a pretty sheltered life and have not been exposed to much physical danger (thankfully), either of the natural or man-made variety. Sure, I’ve travelled, but only to tourist-friendly countries. And yes I’ve camped, but only in groups and at campgrounds with coin-operated hot showers.

Since this dare was born, every now and then as I’m drifting off to sleep at night, I would startle awake with a bit of panic at the realization that, oh shit, I will be sleeping in the woods, in the dark, by myself, starving. As I lay awake, I’ve fought off imaginary rapists, hungry bears, and rabid raccoons. You laugh, but there are bears in Western Massachusetts. I remember a friend telling me that black bears regularly visit his back yard, digging through his trash. And he lives just a mile from downtown Northampton.

Now, you might ask with all these potential risks, why do I want to undertake this journey in the first place? Well, this challenge excites me, even after thinking through the risks. I guess that’s all the affirmation I needed, considering I’m normally not anywhere near being a reckless person. I want to go for it because I don’t want to look back at my life some day and regret not having experienced things because I was worried about some imaginary worst-case scenario.

With all this talk of danger and risk, you’d think I’m preparing for a post-apocalyptical journey through zombie land rather than a walk through picturesque New England towns. Let’s get back to reality here. As far as logistics, here is what I’m taking with me (besides the clothes on my back).

Equipment: ultra lite sleeping bag, mosquito net, emergency space blanket/tarp, water bottle & an empty Spring water bottle for extra capacity, mini Swiss army knife, mini flash light, 3 safety pins, marker, pen, paper, 1 large garbage bag, Ziplock bags, 20′ of thin but strong cord from REI, 4 aluminum tent stakes (for the mosquito net setup)

Clothing: 1 long sleeve T, 1 short sleeve T, 1 ultra-lite rain jacket, 1 shorts, 4 pairs of socks, 4 underwear, Toms shoes, hat

Medical: Advil, blister care, allergy medications, 3 cough drops, electrolyte pills

Beauty & hygiene: sun screen, lotion, toothbrush, toothpaste, floss, Clearasil, 6 packs of Kleenex tissues, mini face towel, eye brow pencil, foundation, blush (gotta look good when I panhandle…)

Other: iPhone, credit-card-sized iPhone tripod (for taking pictures and videos), iPod Nano (so I don’t run down the battery on my phone) phone charger, gum, library card, driver’s license, business cards (free from Vista Print that has my walk challenge mission printed on them), marker, pen, paper

The one thing that I decided to do without is a tent. The lightest tent that’s reasonably priced is about 3 lbs. Now, it may not sound like much, but those 3 lbs over 100 miles will indeed add up. Instead, I opted for a 3.2 oz mosquito net that cost $15.37. I also brought an emergency space blanket that will not only keep me extra warm but can also dub as a tarp if it rains, weighing in at 12 oz.

At the last minute, I also decided to ditch the sleeping pad. It weighs around a pound and I think I’d rather have a lighter pack then cushier sleep.

I’m leaving tomorrow morning and I will try to do some live updates on the road. Wish me luck!

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