Men’s Timberland Mt Maddsen WP Hiking Boot Review

Bottom Line

If you’re looking for classic leather hiking boots but don’t want to pay an arm and a leg for them, we recommend the Timberland Mt. Maddsen WPs. The Mt Maddsens stand out on our Best Hiking Boots for Men guide as a stellar value when it comes to a secure feel, weather readiness, and durability on a budget. 

Senior Gear Analyst Ian Krammer put these boots through their paces on more than 80 miles of rough Colorado backcountry in winter, spring, and summer conditions. They proved their value on chilly and muddy hikes thanks to the solid leather uppers, sturdy midsoles, and reliable traction that performed well on flat and moderate terrain. The gusseted tongue and waterproofing work well to keep feet dry in wet conditions, and the cushioned ankle cuffs and soft footbeds add comfort. 

From week-long backpacking trips to weekend hikes and tackling outdoor chores, these boots will check all the boxes – and at an affordable price, too.

However, the Mt Maddsen’s lower price comes with a few comfort trade-offs. Their stiff leather uppers and outsoles take time to break in and can be a bit uncomfortable along the way, including hot spots and blisters. So you may want to keep your first few adventures short until they begin to soften. The all-leather uppers are not especially breathable, making them less ideal for hot summer days – but they work well for cooler weather and shorter hikes to keep you comfortable and moving. 

At nearly 3 pounds, they’re some of the heavier boots in their class, and the narrow toe box may not suit everyone’s foot shape or size. But for this price, you could outfit two hikers with new Mt Maddsens for the price of one pair of several boots in our men’s hiking boot guide.

Comfort

If you’re hiking groomed, rocky trails in spring and fall, the Mt. Maddsens’ rugged, classic design will keep you feeling steady. With full-grain leather uppers, they offer burly ankle support and a secure feel, ideal for folks who want additional protection on trail. Our testing found these boots have a substantial break-in period of 25 to 35 miles – but that’s normal for all-leather boots, and the payoff is worth it. Once the creases in the leather are started and they soften around your foot shape, the Mt Maddsens offer a cozy, malleable feel. The combination of flat, highly adjustable laces are easy to tie and adjust, and they stay put once tied. Inside, the footbed offers a supportive, soft feel, and the wide heel loop makes these boots easy to slip on and adjust snugly. They’re definitely heavier than other hiking boots, but the extra weight directly translates to robust support and a stable ride, perfect for carrying a heavy pack or hiking in challenging environments.

That said, you’ll need to employ a bit of patience and work to make the Mt Maddsens truly comfy. The leather uppers and rubber soles are stiff out of the box, so these boots require a longer break-in period to avoid major rubbing or blisters and reach peak comfort. We highly recommend wearing these Timberlands at home, well before you’ve committed to a longer hike – consider rocking them during errands and dog walks to start the process. However, our testers found it’s worth the effort: the materials soften and adapt to your feet over time. Also, the Mt Maddsen has a narrower toe box compared to other hiking boots we’ve tested, so you’ll want to order the wide version if you have wider feet or like natural toe splay. We find these boots are best in cooler weather below 70°F since the leather tends to trap heat and feels too warm for hot climates, lower-elevation hikes, and summer weather.

Ankle Support

The Timberland Mt. Maddsens are well-suited for day hikers and weekend adventurers who want solid ankle protection. Due to their mid-cut design, outstanding lacing system, and leather construction, these boots are a great choice for protecting your ankles. Their beefy leather uppers wrap securely around the leg to prevent twisting on funky angles and rocky trails, but that doesn’t mean Timberland sacrificed comfort. These boots’ padded foam and nylon collar feels surprisingly soft and pliable, so you’re not fighting against the boots for your natural gait. Whether pushing through thin slot canyons in the Utah desert or trudging over high rocky passes in Colorado, the substantial height of these boots and a thick, gusseted tongue add to a snug fit that keeps the ankle stable on uneven terrain. 

One of our favorite things about the Mt Maddsens is the lacing system. With metal eyelets for secure, customizable lacing configurations and double lacing hooks at the ankle, these boots can be locked firmly in position and reduce the risk of slipping or sliding. The weight of the boot combined with edge lugs that flare slightly outwards contributes to a grounded, stable feel. 

This rigidity may feel restrictive for those who prefer more freedom of movement around the ankle. However, they’re suited for hikers who make  ankle stability  a priority.

Weight

For hikes where ankle support, sure footing, and warmth matter most, the sturdy build of the Mt Maddsens is preferable. Built with full-grain leather uppers and burly outsoles, these are one of the more durable and aesthetic hiking boots we’ve tested – but also one of the heaviest. They weigh just shy of 3 pounds per pair. Thick leather paneling helps with weather resistance and durability, rugged rubber outsoles provide decent traction, and a supportive midsole adds support – but each of these elements add heft to every step. The good thing about heavier boots is they perform especially well in rugged environments, so the Mt Maddsens are an awesome choice for keeping stable with heavy backpacking loads and navigating softer ground like mud, gravel, and snow, and rocky, uneven trails, too. We also recommend these boots for colder hikes between 25°F and 65°F, since the heavier materials, combined with an effective waterproof liner, insulates from the elements well. 

But their weight is a con on treks with steep ascents and descents and hikes over large distances, where their weight can feel cumbersome and can lead to fatigue and tired legs faster than boots that weigh half as much. These boots are best suited for folks who prioritize durability over agility on the trail – if you’re looking for a light, versatile option, this model might be less appealing.

Traction

With a rubber outsole that grips well on everything from packed dirt to rocks and mud, the Timberland Mt. Maddsen has reliable traction on flat and moderate slopes. The tread pattern features wide, angular lugs on the edges of the boot that flare out and slightly away from the uppers, delivering a ridiculously stable-feeling ride that effectively bites the ground especially well on shallower angles. Rounded, shallow lugs through the center of the foot give additional stability on uneven surfaces, making them ideal for shorter adventures and mixed trails. This unique lug pattern sheds debris, so you won’t deal with stuck gravel or mud, and this design is fast and easy to clean. 

The Mt Maddsens’ soles are fairly stiff, which inspires maximum confidence on most trails, but as they break-in the boots offer more flexibility when going uphill and downhill. Gear Analyst Ian Krammer likes these boots for spring and fall hikes with lots of rolling terrain and mixed conditions, since they also perform well in damp conditions and wet leaves, so they’re one of our favorite choices for shoulder-season hiking, too.

You’ll want to watch your step depending on where you’re headed, though. While they do well on moderate angles and established routes, our testing shows the Mt. Maddsen’s traction falls short on really steep and slick terrain because of their shallower lug depth and tread design. We’ve climbed several peaks over 13,000’ with these boots, and they aren’t our first pick when it comes to traction in off-trail terrain.

The lugs through the center of the boot are fairly low and round, which limits grip on smooth, wet surfaces like rocks, ice, and roots because they don’t penetrate deeply enough to reduce stability. The toe and heel areas are nearly smooth and are missing the aggressive ridges needed for braking power on descents, and the biting power needed for intense inclines. While the rubber is fairly dense, it’s not the stickiest blend out there.

For serious mountain treks, the traction design may leave you feeling less secure than other boots with deeper, more aggressive lugs. That said, these traction issues are really only apparent on technical trails with lots of up and downs, and on routes with ice and mud – so if you’re mostly hiking on moderate trails and decent weather days, the traction definitely gets the job done.

Weather Resistance

The Timberland Mt. Maddsen is reliably water and weather resistant – they’re made of naturally full-grain leather after all. We’ve pushed the limits of these boots through mud, rain, and snowy conditions, where they easily block water thanks to leather construction, a waterproof membrane and a gusseted tongue. We like the fast-drying, flat laces on muddy trails because they dry quickly and don’t stretch – even when your boots are soaked, these boots are easy to adjust and relace. Testing in all seasons reveals they’re just tall enough to avoid splashback from shallow puddles and you don’t need to worry about soaked socks crossing shallow streams and creeks – these boots will prevent water from seeping in. Paired with quality waterproof pants, they’re reliable for most wet conditions without compromising comfort on cool, wet adventures.

The Mt Maddsens take a long time to dry out if the boots get soaked, so step very carefully on really wet multi-day hikes. And since the thick leather can trap heat, we don’t recommend these boots in weather above 70°F or in humid places where they can feel overly warm and heavy. Overall, though, weather resistance is a plus. 

Durability

The Timberland Mt. Maddsen boots are burly boots that are built to last, with a sturdy construction designed for tough conditions. The full-grain leather uppers are tough and resist abrasions, providing solid protection against rough terrain. Double stitching adds strength to the leather panels, and their tall, gusseted tongue and waterproof liners further reinforce durability, keeping the interior dry in most wet conditions.

We appreciate the small components like strong all-metal eyelets and flat laces that add to the lifespan of the boots. The rubber outsoles are resilient enough to handle hundreds of miles of rough trail. These boots are also equipped with a thick midsole that offers a bit of flexibility while maintaining strength. With regular care, including waterproofing and maintenance, they can withstand hundreds of miles of wear, even in cooler and wetter environments.

However, the solid durability of the Mt. Maddsens has some pitfalls. The leather is tough, but it needs to be properly maintained or it can crack or absorb water, compromising its waterproofing.  For maximum longevity, you’ll need to be vigilant about cleaning, treating, and maintaining them regularly. Luckily, caring for leather hiking boots is occasional and fairly fast – pop over to our How To Clean Hiking Boots and Shoes guide to learn more.

And durability like this means these boots are heavier than other options, adding strain over long-distance hikes. But if you want burly, long-lasting boots for a stellar price, these could last for years with consistent care.

Should You Buy the Timberland Mt Maddsen WP?

The Timberland Mt. Maddsen WPs is a great match for budget-conscious hikers and outdoor enthusiasts who want solid durability and ankle support more than lightweight mobility. With full-grain leather uppers and a classic hiking boot aesthetic, these Timberlands offer reliable protection on rough and muddy terrain and are a warm and cozy choice for cooler conditions. Owing to their hefty build, they’re especially suited for day hikers, weekend adventurers, and anyone tackling short to mid-range trails. Their waterproof design and sturdy construction make them a dependable choice for shoulder season outings when trails are wet or chilly, and they’ll last for multiple seasons of regular use with some timely maintenance.

However, these boots may not be ideal for everyone. Their heavier weight and stiff leather uppers require a sizable break-in period, and they can be a bit uncomfortable before they soften. The narrower toe box may not suit wider feet, and they run warmer than other options, making them less suitable for summer hikes and longer, more intense excursions. If you’re looking for lightweight flexibility or immediate comfort, the Mt. Maddsen might not be the best fit. If you’re on a budget and want a boot that will last for multiple seasons of outdoor adventuring, these might be the perfect middle ground.

What Other hiking boots Should You Consider?

Head over to our list of the Best Hiking Boots for Men to check out the full list of recommendations.

Columbia Newton Ridge Plus 2 WP Review: Similar to the Timberland Mt. Maddsens, these Columbias deliver solid ankle support and reliable weatherproofing thanks to their all-leather construction. However, we prefer these as a budget option – although they cost more, they’re also lighter by a full pound per pair and have improved traction. If you’re a budget-conscious hiker who wants a lighter feel on longer hikes, these boots deliver both affordability and ease on the trail.

Merrell Moab 3 WP Review: The Moab 3s offer a similar level of weather resistance and traction as the Mt. Maddsens, although you’ll sacrifice durability and ankle support. But where do they truly shine? Comfort. Unlike the Timberlands, these boots need basically no break-in time, so you can hit the trail right out of the box. The Moab 3s are also a great budget option, making them a comfy choice for occasional and beginner day hikers and shorter backpacking trips.

LOWA Renegade GTX Review: The LOWA Renegade GTX boot shares the Mt. Maddsens’ secure lacing and full-leather build. But the Renegades earn top marks when it comes to superior comfort, top-notch weather resistance, and excellent traction, outclassing the Mt. Maddsens in all-weather performance and durability. Although Renegades cost twice as much as Mt Maddens, they’re a great choice for serious hikers who want exceptional durability without sacrificing comfort.