Review: the Timberland Mt. Maddsen Mid Leather hiking boots are made to excel in rain or shine

These hiking boots make climbing mountains more comfortable.

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Years ago, a near disaster during a poorly-planned hike beneath the South Rim of the Grand Canyon beat into me the need for quality hiking boots. I was an Air Force Butter Bar, on leave with some friends before reporting to my next duty station (which was Alaska, so you could say I was taking the scenic route). I was also a miser, and at the time I wore these horrible, no-support, ugly-as-hell blue hiking boots. I don’t remember the brand, but they were literally the cheapest thing I could find. We descended into the canyon, and after a few hours in 100-plus degree temperatures, made it to the Colorado River. To mark the occasion, we waded into the waters and basked in triumph. After a little rest, my group started the return trek, prepared to climb the 4,800 feet in elevation spread over seven miles or so to get out. That was when it happened: The cheap glue on my boots disintegrated, and the bottom of my right boot started to literally peel off, exposing my cotton socks (don’t judge; remember, I was a lieutenant). In order to make it out of the canyon before sunset, I had to cannibalize my first aid kit and mummy wrap my boot with gauze and medical tape. Thusly shod, I limped my way out of the Grand Canyon, swearing to never skimp on boots again.

Editors note: the Timberland Mt. Maddsen Mid Leather hiking boots also made Task & Purpose’s guide to the best hiking boots of the year.

I currently have a five-year-old pair of Chaco Jaeger hiking boots which have started allowing water to seep in, so I feel it’s time for an upgrade. In the years following the “Grand Canyon event,” I’ve owned several pairs of high-quality boots, including some from Timberland. Yet for some reason, I’ve been of the opinion that Timberland’s boots are more for looks and less for rigorous hiking. After reviewing their current selections, however, I decided I needed to test that assumption. I wanted something that not only looked decent (no more hideous blue boots) but could also soak up the punishment from real hiking. That’s why I picked the Timberland Mt. Maddsen Mid Leather hiking boots. They cost about $100, making them relatively inexpensive for hiking boots, and promise to “[keep] feet dry in any weather.” It turned out that I’d have just the opportunity to test this.

Timberland Mt. Maddsen Mid Leather hiking boots


The folks at Timberland know how to ship their products. The Mt. Maddsen boots arrived in a solid, forest-green box with their logo printed on the top, and the company’s promise that they are “guaranteed waterproof” printed on a large sticker on the inside. The dark brown boots (which is one of several color options) were separated by plastic and a thin sheet of posterboard, presumably to keep the boots from scuffing one another in transit. Each boot had a cardboard shoe tree inserted to protect the boot’s shape and keep the leather from creasing. All in all, very nice. I’d expect a company like Timberland to know how to safely ship their products, and sure enough, they delivered.

Timberland Mt. Maddsen Mid Leather hiking boots (W.E. Linde)

The Mt. Maddsen hiking boots are some fine-looking footwear. The exterior is made of waterproofed leather that feels surprisingly supple right out of the box. The only outer part not made of leather is the back of the padded collar and the tongue. The outsoles are black, partially recycled rubber that looks really sharp under a grey midsole. And the deep tread on the bottom looks ready for action, meaning the lug pattern (the knobby things on the bottom of your boot) are prominent, multi-directional, and spaced apart for optimal grip. Yet for all this, the boots are surprisingly light, with each boot weighing just over a pound. I wore them around the house for a couple of days, and I was surprised at how comfortable they were for casual use. That’s not at all what I expect from a new boot, especially one made of leather. Right off the bat, the Mt. Maddsen hiking boots were off to a good start. 

Timberland Mt. Maddsen Mid Leather hiking boots

How we tested the Timberland Mt. Maddsen Mid Leather hiking boots 

There are a couple of ways to break in a new pair of hiking boots. First, there’s the water submersion method popular with many hikers and some military folks, where you soak the boots for a few hours before wearing them around to work the leather and then letting them dry thoroughly. There’s a bit more to it than this, but the purpose is to make them more pliable and less likely to cause blisters out on the trail. 

The other way is for people like me, who just want to hike. This process is to give the boots shorter break-in hikes, and then gradually increase the distance. This naturally softens the leather, and the shorter hikes will give you a sense of potential trouble with the fit before you find yourself 10 miles from civilization and something unexpected happens, like blisters or maybe the glue on your boots dissolving in the middle of a desert. Yes, I’m still a little scarred by this. 

I started my testing by wearing the Mt. Maddsen boots on a few simple hikes in a couple of the many trail-packed parks scattered across southwest Ohio. I kept the hikes to around three miles each and no more than 250 feet elevation change. These first trails were also fairly non-technical, although there were a number of streams and creek beds to traverse. I didn’t carry gear on my first two hikes, but on my third I brought a lightly-filled daypack. I have to say that even though these excursions were not overly taxing, the boots still impressed me. I never once felt like I was wearing rigid leather, and I didn’t experience any real discomfort that I normally expect from new boots. My feet stayed comfortable, and although occasionally I was aware of the tongue of one boot rubbing the bottom of my shin, the sensation always disappeared. On these initial outings, the Mt. Maddsen boots aced the tests.

Timberland Mt. Maddsen Mid Leather hiking boots (W.E. Linde)

After clocking about 10 miles or so in this manner, I started phase two of my testing: I brought these on a hiking weekend trip to Chattanooga, Tennessee. I figured traipsing around Lookout Mountain would be a great way to test the limits of these boots. Even Mother Nature helped me up the ante. Over the four days I was there, it rained. A lot. This really got me excited, because I not only got to test the comfort and tread, but I was able to really give the waterproofing a run for its money.

I put about another 10 miles on the Maddsen boots, crisscrossing the north and west sides of  the same mountainside that Union Maj. Gen. Joseph Hooker’s forces travelled during the Battle of Lookout Mountain in November 1863.  My load wasn’t quite as much as those soldiers carried, though: I only had about 15 pounds of water, snacks, and sundry other items in a tactical daypack. The trails ranged from flat to challenging, with about 800 feet in elevation change. And then there was the rain. At times I thought about turning back from one longer hike because I was afraid a thunderstorm was about to roll in. I lucked out. The lightning never came, just sheets and sheets of rain. And yet the boots performed amazingly well. Let me break down some specifics.

Traction: The Maddsen boots were fantastic. The water-logged trails of Lookout Mountain were at times slippery, slimy, and muddy. As an experienced hiker, I looked for any change in the trail composition so I could evaluate how well these puppies gripped the ground. It didn’t matter if it was packed dirt, loose gravel, tree roots, clay, or wet rock — I never really had any kind of slip. This remained true on significant inclines and declines in the trail. The rubber outsoles not only held the earth well, but they also showed little evidence of wear even after slogging up some pretty jagged creek beds. 

Water resistance: Timberland is clearly confident in the Mt. Maddsen boots’ waterproofing. “Waterproof” is not only included in the name of the product, but the word is also literally stamped on the side of the heel beneath the company logo. And I have to admit, they have every reason for this confidence: It was nearly flawless. On days with no precipitation when I walked in streams and creeks, the boots remained completely dry on the inside. And although it was very hot (85 degrees and higher) every day I took to the trails, the boots breathed well enough that my feet felt almost completely dry at the end of each hike. Timberland achieves this by using what they describe as a “breathable membrane” on the inside of the boot.

This breathable membrane really proved its worth in heavy rain. Although the boot is made so the tongue is fully gusseted (meaning the tongue is connected to the boot shaft, which helps keep water out when you’re walking in it), it’s not magic. When lots of rain falls from above, some will eventually seep down into the boot. But whether it’s this breathable membrane or just witchcraft, I never had a problem caused by moisture. By the time I finished my hike and removed the boots, there was some dampness, but my feet were perfectly happy. These boots were carefully designed, and it shows.

Timberland Mt. Maddsen Mid Leather hiking boots (W.E. Linde)

Comfort: Once again, these boots rocked. They’re more comfortable than they deserve to be. These boots include what Timberland calls “removable anti-fatigue footbeds” as well as a compression-molded EVA (ethylene vinyl acetate, basically a foam injection that provides support) midsole. I’m not sure how this “anti-fatigue” thing works, but Timberland sells replacement insoles and says that they are “shock-absorbing, geometrical technology that returns energy back to the foot.” I normally roll my eyes at this kind of marketing gibberish, but I have to conclude that it’s either that or, again, witchcraft, because these boots are very easy on the feet.

What we like about the Timberland Mt. Maddsen Mid Leather hiking boots 

Almost everything about the Mt. Maddsen boots is impressive. They’re practically mission-ready as soon as you get them, although I still recommend you break them in appropriately. If it weren’t for the fact that I was deliberately evaluating these boots, I likely would have not thought about them much at all because they performed so well. I could confidently hike well-maintained trails as well as more challenging slopes with little concern about a surprise slip.

What we don’t like about the Timberland Mt. Maddsen Mid Leather hiking boots 

This is a tough one because I think it’s clear how impressed I am with these boots. The one thing I’ll note is a personal concern born out of the previously mentioned boot failure at the beginning of this article. The fact that these boots are so comfortable and relatively pliable out of the box makes me wonder about how durable they’ll be over the years. I hike a lot, and I’m used to getting several years out of the boots I buy these days. Despite the clear quality I’ve experienced so far with these, I can’t help but wonder about how long these will hold up under constant use and abuse. 


The Mt. Maddsen boots are great. Put simply, they perform amazingly well on the essentials for a hiking boot. I’d recommend them based on the waterproofing and grip alone, but the comfort afforded by these are the real clincher. Add to this the fact that they look rugged and well-made, and there’s not much more one can ask for. If you’re looking for a mid-range, high-quality boot that you can rely on during beautiful days as well as in poor weather, the Mt. Maddsen boots deserve your attention.  

Saved rounds

I failed to mention what kind of socks I used during my testing, and socks can be just as important as the boots in preventing injury and blisters on long hikes. Lately, I’ve been using Weatherproof Wool Blend All-Purpose Outdoor crew socks, which are reliable, comfortable, but not too fancy or expensive. I use them for both summer and winter and never have an issue. It’s important that you choose a good sock that helps your feet breathe and stay dry.

FAQs about Timberland Mt. Maddsen Mid Leather hiking boots 

More questions? Here’s Task & Purpose’s additional brief. 

Q. How much does the Timberland Mt. Maddsen Mid Leather hiking boots cost? 

A. Amazon has these for as low as $99.95..

Q. Are the Timberland Mt. Maddsen Mid Leather hiking boots all leather? 

A. The exterior is made of 100 percent waterproof leather. The interior is made of Timerland’s “waterproof membrane.” The outsole is composed of 15 percent recycled rubber, which so far I’ve found to be quite durable.

Q. Do the Timberland Mt. Maddsen Mid Leather hiking boots come in women’s sizes? 

A. Why yes, they do. Amazon sells the Women’s Mt. Maddsen Mid Leather Waterproof boot for the same price as the men’s. 

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W.E. Linde spent 12 years in the Air Force as an intelligence guy and loved both his enlisted and commissioned time. Now a civilian, he toils away as a healthcare business analyst by day and wannabe writer by night because who needs sleep when you have coffee? His time in the military made him appreciate just how funny the term “military grade” can be. He currently writes for Duffel Blog and for the humor site


W.E. Linde Avatar

W.E. Linde

Contributing Writer

W.E. Linde spent 12 years in the Air Force as an intelligence guy and loved both his enlisted and commissioned time. Now a civilian, he toils away as a healthcare business analyst by day and wannabe writer by night. He currently writes for Duffel Blog and for the humor site