Are Timberlands Good For Hiking?

Back in the 70s, Timberlands were synonymous with the rugged outdoors. Some folks had a pair of hardworking Timberlands that withstood three decades of abuse. But at the end of the 70s, Timberland began to pivot towards becoming a fashion brand. Thus, they are no longer the go-to for hiking boots.

So, are Timberlands good for hiking?

The classic Timberlands are now a fashion shoe and not suitable for hiking. However, Timberland does have a real hiking boot range using traditional materials. For instance, Mt. Maddsen Valley is excellent value for money. But the old-school materials do come with some drawbacks.

There’s nothing wrong with wanting to look cute while enjoying the great outdoors. But the classic Timberlands are for strolling along paved tourist hiking paths of 5 miles or less or simple jaunts. However, if you are looking for affordable hiking boots, Timberland does have some options

4 Timberland Boots You Can Hike In

Dressing for hiking has become more complicated as our options have increased, including footwear. However, even the true old-school Timberlands, which were the footwear equivalent of a cast iron stove, still wouldn’t be the first go-to for hiking boots in our modern times.

Modern materials have introduced breathability keeping our feet dryer, even in waterproof varieties. They are also lighter to wear. But the problem with high tech is that it comes with eyewatering prices. In addition, quality leather lasts.

Thus, we’ve found leather boots an excellent option in temperate climates, such as the Southern Oregon Coast and the UK, especially in spring and late fall. Of course, they’re not our first choice for long, thru-hikes. But they can be very reassuring when stomping for the day on muddy trails.

So if you are a casual hiker on a budget with no desire to take on the Pacific Crest Trail, Timberland does have a few pairs of leather hiking boots worth a look at. But be warned; as people who have been stuck in leather boots in hot climates, these are not ideal summer hiking footwear.

Lastly, while we have our clear favorites of the Timberland hiking boot range, feet come in different shapes, and so do Timberlands. The toe boxes and heel shape of the boots vary between styles. So just because we love one boot more than the other doesn’t mean it’s the best shape for your foot.

Timberland Men’s Mt. Maddsen Valley Mid Waterproof Hiking Boots

The men’s Timberland Mt. Maddsen Valley Mid Waterproof Hiking Boots look like they were designed back when hiking in jeans was still common. Thus, these are not taking advantage of modern hiking technology. But just as there are a few advantages to hiking in jeans, there are pros to wearing an all-leather boot.

Pros Of Timberland Mt. Maddsen Valley

Timberland uses leather, a classic material that is rugged, tough to puncture, conforms to the shape of the foot (eventually), and is water-resistant pre-treatment and waterproof (mostly) when treated.

Timberland has treated the Mt. Maddsen Valley boots, making these as waterproof as you can get without synthetics. Many leather shoes will still leak, but these have a membrane that prevents water from sneaking in.

Timberland also uses recycled materials for its synthetic materials. They still provide grip, cushion, stability, and protection. However, it is not the standard of high-end hiking shoes, especially regarding cushioning. But for what you are paying, it would be difficult to find better.

Pros summary:

  • Durable
  • Waterproof
  • Good soles for the price

Cons Of Timberland Mt. Maddsen Valley

The Mt. Maddsen’s, like any leather boot, has a long break-in period, which frustrates some wearers. In addition, impatience will earn blisters. Leather is also heavy, hot, and isn’t a breathable material. Wear these in hot climates, and your toes will be swampy.

In addition, the midsoles and soles are less than what’s found in high-end shoes. The grip could be gripper, the cushion could be a whole lot cushier, and the ankle support is rather meh. But are you going to find better in this price range? Highly doubtful.

Cons summary:

  • Long break-in period
  • Heavy
  • Hot
  • The sole and support don’t meet high-end standards

Verdict On Timberland Mt. Maddsen Valley

The men’s Timberland Mt. Maddsen Valley is one of the best hiking boots a person could find in this price range. So if you are a casual hiker that isn’t tromping around the desert, these will serve you well, so long as you patiently break them in. Nor will you have to be replacing them anytime soon.

But if you are a serious hiker, perhaps save up to get a lighter, more breathable boot. Again, you’re going to struggle to find anything better in this price range. But the heat and weight will get old if you frequently pound the trail.

Timberland Women’s Chocorua Waterproof Boot (And Men’s)

The Timberland Chocorua is a great buy if you are a woman. Confusingly, the Chocorua, not the Women’s Mt. Maddsen, has a waterproof membrane. In addition, it is the only one in the women’s line with such a high level of waterproofing.

The men’s Chocorua is the only other boot with the membrane in the men’s line. The only technical difference between it and the men’s Mt. Maddsen is that the latter has better cushioning. Which is saying something, given that it is one of Mt. Maddsen’s weaker points.

Pros Timberland Women’s Chocorua

The Women’s

  • Durable
  • Waterproof
  • Good soles for the price

Cons Timberland Women’s Chocorua

The Timberland White Ledge doesn’t have the membrane, which means it has more cons than the St Maddsen:

  • Long break-in period
  • Heavy
  • Hot
  • The sole and support don’t meet high-end standards

Verdict On Timberland’s Chocorua

The women’s Chocorua is one of the best hiking boots a person could hope to find in this price range. It is a quality build that will last. We’d recommend it over the women’s Mt. Maddsen. However, the men will be better off with the St Maddsen should it suit their foot shape.

Timberland Men’s White Ledge Waterproof Boot

The Timberland Men’s White Ledge is probably the most popular of the real hiking boots. It’s essentially a cheaper version of the Mt. Maddsen, although not always sold at a lower price. However, users often prefer the aesthetic.

Pros Timberland White Ledge Waterproof

The Timberland White Ledge has many of the same pros as the Mt. Maddsen:

  • Durable
  • Waterproof (resistant)
  • Good soles for the price

Cons Timberland White Ledge Waterproof

The Timberland White Ledge doesn’t have the membrane, which means it has more cons than the Mt. Maddsen:

  • Hot
  • Only slightly more breathable
  • Prone to leaks
  • Less cushioning

Verdict On White Ledge Waterproof

We’d stick with the Mt. Maddsen, as it is more reliable when it comes to waterproofing and has more cushioning. But if you want more breathability or need to save a few bucks, they’re a good buy for the price.

Timberland Men’s Garrison Trail Waterproof Mid Hiker

The Timberland Garrison Trail Waterproof Mid Hiker is a boot for people who want sneakers. Thus, these are not true hiking boots, although the uppers are made of respectable materials. But the soles feel closer to running shoes or a trail runner.

The advantage to the casual hiker is that they don’t require as much of a break-in period to gain flexibility in the sole. They are also perfect for people who find hiking boots uncomfortable.

Thus, these are not a bad choice if you only hike a few miles here and there but want something more substantial than regular running shoes. But don’t expect the durability from these as the classic Timberland or their more rugged hiking boots. The price of that sneaker-like sole is that it wears out faster.

Nor is the waterproofing up to the standards of the Mt. Maddsen. However, it is on par with their lesser hiking boots. The leather is still quality and treated. So in long damp grass and sticky trails, your feet will probably stay perfectly dry. But if you stomp into a stream, you’ll probably get a little wet.

Pros Timberland Garrison Trail Waterproof

The Timberland Garrison Trail may not be a traditional hiking boot, but it still has some positives:

  • Waterproof (resistant)
  • Feel more like a sneaker
  • More fashionable

Cons Timberland Garrison Trail Waterproof

The Timberland Garrison Trail Waterproof does have some cons:

  • Prone to leaking
  • Sole isn’t as durable as the traditional hiking boot
  • Leather still makes them hot to wear in warm climates
  • Will quickly lose their fashionable edge if worn on proper trails

Our Final Verdict

Timberlands would not be our first choice when it comes to hiking boots. If money were tight, we’d be looking out for sales in brands with more modern materials, such as Merrel, Keen, Salomon, La Sportiva, etc.

That said, if we needed a hiking boot immediately and were on a budget, the Timberland Mt. Maddsen Valley Mid Waterproof Hiking Boots for men and the Timberland Chocorua for women would be solid buys.

In fact, having a pair for soggy springs and damp falls isn’t a bad idea if you’ve got the cash to spare to own more than one pair of hiking boots. But we’d been searching for something else when hiking in the desert or in hot and humid conditions. It’s like wearing jeans in summer: no, thank you.

Author at Wilderness Redefined camping website

James has been escaping to the outdoors for as long as he can remember. This first started in family camping trips but soon turned into adventure camps and hiking through the Scottish Hebrides. Now he has turned towards trying to make camping more comfortable and accessible.