Design 
Quality of Materials 
Craftsmanship 
Fit & Sizing 
Value for Money Since we started BootSpy this year, I’ve spent a lot of time cooped up in a room staring at a computer screen.
If you’re anything like me, a lack of fresh air and outdoor time can feel draining.
But you get a good early morning hike together and it’s like a refresher for the soul.
You understand, right?
Well, I saw one inspirational Instagram feed too many and decided it was time to get out and hit the trails. And hit the trails I did. I was so pumped up, I figured hiking had to become my new hobby, so I did my research and came across the Timberland Mt. Maddsen hiking boot.
I picked up a pair for myself and put together this review so you can decide whether it’s the right boot for you.
My verdict is in, so keep reading to get all the nitty-gritty details on this classic Timberland hiker.
Timberland Mt. Maddsen Overview
The Mt. Maddsen is one of Timberland’s more popular hiking boots. Built to be waterproof and secure on uneven terrain, this boot has a lot of the hallmarks of a classic hiker, like d-rings and full grain leather, but brings in a dose of new technology like the EVA comfort-first midsole.
Timberland continues their commitment to the environment with this design, including features like the TimberDry lining made with 50% recycled PET plastic bottles and a sole made with 15% recycled rubber.
While more and more brands are moving toward eco-conscious production, Timberland has taken things to the next level, promising to make a net-positive impact on the environment by 2030.
That’s right—when most companies are struggling to make their products environment neutral (which is awesome), Timberland seeks to give back more than they take.
Things to Consider Before Buying
Timberland Mt. Maddsen boots are a solid value at under $100. That said, there are some construction issues you’ll face in most boots at this price point. I’ll discuss what those details are further down in the review, but it’ll suffice to say that avid hikers who spend every weekend on the trail may want a more beefy boot.
For me, I needed something cost effective that could offer arch and ankle support, plus waterproofing and extra grip on trails for about 20+ hikes a year.
I’m not a big-time hiker, but I love to head outside once or twice a month for a 5+ mile hike.
I figured with that much trail-time, I needed something specialized, but didn’t want to invest a ton of money into the best hiking boot on the market.
If that sounds like you, keep on reading.
The Timberland Mt. Maddsen is light and nimble considering how decked out it is with comfort features. Hikers who need extra arch support will enjoy the insole and shank combination this boot offers---something rare for hiking boots under $100.
My Hands-On Review
If you get more from watching than reading check out our YouTube review of the Mt. Maddsen boots below:
First Impression
The Timberland Mt. Maddsen is a handsome boot. I love the natural look, and I’m always skeptical of hiking boots that look super techy.
Really, what I was looking for was a solid leather boot with a few hiking-specific features that would help keep my feet dry and offer more traction and support on the trails.
A few things that stood out to me after my first hike is that the Mt. Maddsen is waterproof as advertised. That may not sound like glowing praise, but I’ve been duped before and picked up faulty boots that leaked like a rusty pirate ship.
It also impressed me that these boots have a TPU shank in the midsole. Timberland claims that this helps with “torsional rigidity,” which is a fancy way of saying that it offers more arch support.
The TPU shank is especially helpful if you’re hiking on crumbly rocks. It creates a stiffer platform for your foot, so uneven terrain doesn’t cause your ankle to roll.
Overall, this makes the boot a little more rigid, but made me feel like I was more in control on unpredictable steps.
The gusseted tongue also kept dirt and water away from my socks which I always appreciate, and I loved that my boots came with two pairs of laces.
Leather Quality and Care
The upper for the Mt. Maddsen is waterproof treated full grain leather. I’m surprised that Timberland is using full-grain leather (as opposed to genuine) for such a value-driven boot, but I’m not complaining.
The full-grain leather will help with durability and care in the long run, so that’s a big bonus for me.
As for the waterproofing, look for yourself:
Water just rolls right off this leather no problem.
I’ll probably re-up the waterproofing on these boots every six months, depending on how often I hike.
To keep them in tip-top shape, I’ll be applying Timberland’s Waximum waterproofing and leather protector.
Sole
The sole components are probably what impress me most on the Mt. Maddsen.
The outsole is made with 15% recycled rubber and has a firm grip on uneven terrain. My recent hikes have been in North Carolina, where the ground is damp and there aren’t too many rocks. It’s different from the super rough terrain of Utah, Arizona, or California, where I’ve done most of my hiking.
I wouldn’t say I’ve put the Mt. Maddsen to the absolute toughest test, but for my needs, the rubber lug sole has plenty of sticking power.
This boot also features an EVA midsole (the grey strip along the side). This really helps add a lot of cushion when walking and standing and introduces more flex. I’d say this sizable EVA addition helps a lot in making the Mt. Maddsen comfortable right out of the box.
Timberland also slips in a removable Anti-Fatigue insole. There’s a decent amount of cushion in the heel and a minor improvement in arch support from your standard insole.
For most people, the Mt. Maddsen will offer an excellent amount of arch support. If you have flat feet or plantar fasciitis, you’re no stranger to orthotics. You’ll probably still need to take out this Anti-Fatigue insole and add your own orthotics if you’re flat footed. But otherwise, I’m happy with the level of support.
Fit and Sizing
I picked up my true size (10.5) and I’m happy with the fit. Other Timberland boots run big, so I felt it was a gamble to go with my true-size, but it’s the best choice.
If anything, the Mt. Maddsen runs a little narrow.
I like the slight extra snugness because it offers more ankle support, but many reviewers mentioned the Mt. Maddsen was just too narrow for them. Most of the reviewers normally ordered wide E and EE boots anyway, but it’s an important note.
If you have standard width feet, you can expect some snug fit around the sides of your foot, but nothing uncomfortable. If you border between standard and wide feet, look into the wider E width.
Break-in Period
I didn’t experience much of a break-in period on my Mt. Maddsens. My feet were a little sore the following day after my first hike with them, but that was also after a six-mile hike with brand new boots.
The full grain leather is stiff out of the box, so the soreness I felt was most likely from breaking that leather in and getting my creases.
Otherwise, I didn’t get any blisters along my heel or the ball of my foot.
Overall, the Mt. Maddsen is comfortable out of the box, but if you want to avoid all soreness, maybe do a quick two or three-mile hike to work the leather before doing anything over five miles.
What Do Other Reviewers Say?
Looking at reviews from around the web, the consensus is that the Timberland Mt. Maddsen hiking boot is lightweight, comfortable, and offers plenty of weather resistance to make for a great trail partner.
On the downside, many guys felt they were narrow. With no EE width available, this is an issue for gents with wider feet.
The Mt. Maddsen is one of the few Timberland boots that fit true to size, so my recommendation for guys with wide feet is to move up a half-size. I picked up my true size and I have standard width-feet and I didn’t feel the Mt. Maddsen was too narrow.
The Timberland Mt. Maddsen is light and nimble considering how decked out it is with comfort features. Hikers who need extra arch support will enjoy the insole and shank combination this boot offers---something rare for hiking boots under $100.
Timberland Mt. Maddsen Hiking Boots Alternatives
Timberland White Ledge
The Timberland White Ledge has a few key differences that make it a viable alternative to the Mt. Maddsen.
There’s more ankle support and it’s generally $10-20 less expensive. After scouring reviews from the web, it looks like their durability is comparable, so there’s no point awarded either way there.
But the Mt. Maddsen has the White Ledge beat in the sole department because of its added TPU shank.
While the White Ledge may have a higher ankle, the TPU shank in the Mt. Maddsen offers a sturdier base, and therefore more support.
If you’ve got a lot of light hiking planned and prefer the look of the White Ledge over the Mt. Maddsen, I say go for it.
The Timberland White Ledge is a versatile hiking boot, robust enough for outdoor activity, while still lightweight and stylish enough as a casual urban shoe. Its slip-resistant and agile rubber sole, velvety nubuck upper, and supportive padded collar offer great value for money, especially since these are one of Timberland’s lower-priced offerings in the category.
Danner Trail 2650 GTX Mid
The Danner Trail 2650 is roughly double the price of the Mt. Maddsen, but it’s in a different league.
Danner made the unusual move to place the heel counter on the outside of the boot which makes this hiking boot super secure and comfortable.
If you’re planning on doing a lot of hiking over the next few years, I recommend investing in an excellent pair of boots. While the Mt. Maddsen is a solid value, the extra lightweight security and durability of the Danner Trail 2650 is worthwhile if you consider how the boots will perform over several years.
This boot is loaded with features like an external heel counter, 100% waterproof Gore Tex lining, and Vibram’s irregular tread soles, which can tackle any terrain with ease. Plus, it's super light. If hiking is your hobby, you’ll love the Danner Trail 2650.
Ariat Terrain
Playing at the same price point, the Ariat Terrain boot has many of the same features as the Mt. Maddsen.
The biggest difference is the insole. Ariat’s ATS insole system is more comfortable and supportive than Timberland’s.
On the flip side, the Terrain doesn’t have nearly the same grip as the Mt. Maddsen.
So the verdict between these two boots is simple. If your hikes are mild—no elevation, relatively clear paths: the Ariat Terrain is the comfortable choice. But if you’re encountering any uneven ground, stick with the Timberland Mt. Maddsen.
With its thick but not bulky silhouette, and sleek multi-surface topography, the Ariat Terrain offers plenty of ventilation and ergonomics in one stylish hiking boot package.
My Thoughts Overall
What I Like
The combination of the insole and TPU shank offers excellent arch support.
Great materials considering the price, including waterproof full grain leather and the 50% recycled PET lining.
The green rubber sole has substantial grip.
The d-rings and speed hooks have that classic hiker look and make changing laces a breeze.
What I Don’t Like
Many folks mentioned the boots felt too narrow. I don’t mind the snugness, but if you have wide feet, check other options for an EE width boot.
The Mt. Maddsen has a cemented sole, which isn’t the most reliable over years of wear.
Who is Timberland Mt. Maddsen for?
The Timberland Mt. Maddsen is the perfect hiking boot for people who want to get out into nature a few times a month and don’t want to drop a lot of cash on footwear. If you just need something to offer extra support and water protection, but you don’t need a beast-boot for decades of outdoor adventure, the Mt. Maddsen is your choice.
The Verdict
Coming in at just under $100, the Mt. Maddsen is a solid value pick for those looking to hit the trails with a lightweight boot with plenty of arch support.
I need a boot that offers a lot of traction on uneven ground and keeps my ankle supported. Oh, and it has to be waterproof. The Mt. Maddsen checks these boxes.
But that’s because I don’t plan on going hiking every weekend, or even every other weekend. I’m a “once a month” kind of guy. So getting a value pick was perfect for me.
Because of the cemented construction, I recommend going with something more substantial like the Danner Trail 2650 if you plan on doing a lot of hiking in the next five years.
But if you’re like me and you just want some extra stability, comfort, and protection on the trails and don’t want to spend a lot, the Timberland Mt. Maddsen is a fantastic choice.
The Timberland Mt. Maddsen is light and nimble considering how decked out it is with comfort features. Hikers who need extra arch support will enjoy the insole and shank combination this boot offers---something rare for hiking boots under $100.
FAQs
How do Timberland Mt. Maddsen Boots Fit?
Timberland Mt. Maddsen boots fit a little narrow, but otherwise true to size. If you need a wide boot, check to see if an EE width is available.
Can Hiking boots be used as winter boots?
Hiking boots like the Timberland Mt. Maddsen don’t have a lot of insulation, but they are waterproof. In most cases, keeping your feet warm is simply a matter of keeping them dry. If your hiking boots are waterproof, they’ll do a fine job as winter boots in most scenarios. But if the weather is heavy or you live in a really cold area, a dedicated pair of insulated waterproof boots is a better choice.
Is it ok to wear Timberlands in the rain?
Yes, you can wear Timberlands in the rain. Most Timberland boots have been treated with weatherproofing on the leather and they feature storm sealed welts so you don’t have to worry about ruining your boots.
