10 Best Timberland Hiking Boots in 2021

Paul Ronto
Paul Ronto on

Timberland is among the go-to brands when it comes to serious outdoor footwear. Their hiking boots are built to last and keep you going when the trail gets tougher.

We have tested 10+ incredible Timberland hikers to come up with our top picks. So whether you need the Swiss Army knife of kicks, a super-supportive Timberland boot, or something you can wear on dress-down Fridays, here is the place to be.

How we review Timberland hiking boots

We at RunRepeat always strive to create objective and easy-to-read reviews on the best Timberland hiking boots on the market. The details of our approach are as follows:

  • To ensure that every review is free of bias, we buy Timberland hiking boots with our own funds.
  • We test every Timberland pair in a variety of settings, including diverse terrain and wet conditions.
  • To make our Timbs-centric reviews comprehensive, we take hundreds of opinions from professional testers and regular hikers and blend them with ours.

Having all that in the bag, we eke out a CoreScore. This RunRepeat-exclusive rating system helps us create this list of Timberland’s bests.

Best overall

Beating out a dozen+ astonishing Timberland hiking boots, the Euro Sprint Hiker is our star of the show in virtually every aspect!

Supremely plush on day one, the Euro Sprint Hiker provides comfort like no other. After days of testing on multi-featured terrain, we can say with confidence that this Timbs bad boy needs absolutely no break-in time. Its confines gave us snugness without that squishy feeling.

Despite its rather stout construction, the Euro Sprint Hiker is quite light at 480 g per boot. We believe this lightness comes largely from the shoe’s minimal use of overlays.

Oh, but let’s discuss the Euro Sprint Hiker’s plush collar. While it’s sufficiently padded and flexible, it did an absolute swell job of keeping our ankles secure, even during tricky lateral (sideways) traversals. Yes, it’s a remarkably supportive piece, and we love it!

Are websites calling the Euro Sprint Hiker true to size correct, you might ask? To us, it is. Its sizing was spot-on for all of us, so we were quite pleased with the boot through and through.

Price-wise, the Timberland Euro Sprint Hiker is also amazing. At $110 MSRP, this hiker is without a doubt a steal, so don’t delay and get one now!

See our full review and facts

Do you want something dressy yet powerful? Well, the Timberland Euro Hiker says “hi!”

Coming at 900-ish grams per pair, this leather boot is as trail-serious as it is light. We don’t know how the engineers at Timberland did it, but despite the shoe’s fully randed upper and semi-chunky heel, they managed to keep the Euro Hiker’s weight on the lighter side of the scale.

Equally incredible is the Euro Hiker’s cradling midfoot zone. Its impressive arch support made us go further minus the achy arches. The sole unit responsible for this also gave us enough protection over sharp rocks and the like.

Comfort-wise, the Timberland Euro Hiker is very generous, just like our top pick. That said, we did need to break it in for a couple of days. Its plush and pampering interior could be more breathable, though.

While not a waterproof offering, the Euro Hiker managed to keep our feet nice and dry in light rain (almost drizzle-like). Its randing also barred out wetness through puddles quite well.

And like the Euro Sprint Hiker, this Timberland piece is affordable. Yes, at $110, the Euro Hiker is simply irresistible!

See our full review and facts

Best support

Let’s not beat around the bush with this one. Yes, the Mt. Maddsen Mid Waterproof is our most supportive pick from among Timberland’s finest!

If you got wobbly ankles and arches that need extra hold, the Mt. Maddsen Mid Waterproof is the solution you need. After our week-long testing period with this hiker was over, we didn’t feel any pain anywhere underfoot, and none of us sustained ankle-related injuries.

Now, we were told that the Mt. Maddsen Mid Waterproof would be comfortable from the box. We shouldn’t have doubted them, as the boot in question needed no honeymoon phase. Yes, this Timberland kick, on day one, welcomed our feet with coziness all over!

Its glove-like fit also needed no break-in. Its interior was quite snug from the get-go without slippage anywhere. The Mt. Maddsen Mid Waterproof felt custom-made just for us!

While brawny in appearance, the Mt. Maddsen Mid Waterproof stunned us with its 480-gram weight. Never did we feel like we were dragging our feet in this boot.

The Mt. Maddsen Mid Waterproof also gives its name justice by being fully watertight. Armed with Timber-Dry, this hiking boot made our encounters with all things wet completely moisture-free.

See our full review and facts

Are you looking for a Timberland boot that can keep you going both on and off the trail? Then the Flume Mid Waterproof it is!

We were quite thrilled to test the Flume Mid Waterproof, especially its promise of support. The springiness of its sole unit made us hop around rocky terrain without too much effort. The boot boosted our momentum and kept us at a brisk pace, but without giving our arches a hard time.

Lavishly comfy, the Flume Mid Waterproof spoiled our feet with its nicely padded confines. Yes, the inside of the shoe was just delicious, particularly around the collar and instep. We also didn’t feel any rubbing around our Achilles’ heels. Superb!

Engineered with a seam-sealed, treated leather upper and gusseted tongue, the Timberland Flume Mid Waterproof held its own in creeks and puddles. No moisture got inside the boot’s confines, giving our tootsies enduring dryness as a result.

We also tested the Flume Mid Waterproof in the cold. We are happy to report that, while not insulated, this Timberland piece warmed our feet just right.

It might not be the best tool for traversals on super-muddy terrain, though.

Still, the Flume Mid Waterproof is a must-buy for those looking for a kick with extraordinary arch support!

See our full review and facts

Best rugged

Here is a tough one for you. The White Ledge Mid Waterproof from Timberland will decimate anything on its path, whether you’re ready or not!

With its thicker-than-usual outsole and shock-absorbing midsole, the White Ledge Mid Waterproof didn’t fail to impress us on rock- and root-filled sections. You can say that this rugged-ready gem eats rough terrain for breakfast, lunch, and dinner!

Now, let’s not forget to give its mighty upper the credit it deserves. Those sharp rocks and aged roots didn’t leave major dents or scratches on it. And since it has minimal seams, we’re confident that the White Ledge Mid Waterproof will last us (and you) years.

But is this brilliantly brawny piece soft on the inside? If by “soft” you mean comfy from the get-go, our answer is yes! Our heels, ankles, and arches got all the plushness they deserved. We had no encounters with rubbing or hotspots with the boot, either!

The White Ledge Mid Waterproof is also the defender you need in rainy weather. Its seam-sealed design locked out moisture where wetness was present (think streams and puddles of muddy water).

So, if you want to keep it simple where the trails aren’t as, the White Ledge Mid Waterproof should be your “it” boot!

See our full review and facts

If you think you’re ready to level up your game from simple hikes to more treacherous adventures (off the beaten path and rocks everywhere), don the Chocorua Trail 2.0 Waterproof!

Yes, this Timberland hiker is a workhorse, despite its casual, ready-to-hit-the-pub appearance. Its intimidating sole unit is capable of cutting through all things rugged without being too clunky.

Built with a Gore-Tex membrane, the Chocorua Trail 2.0 Waterproof kept everything on the inside moisture-free. Our extended hike was met by moderate rain, yet not one drop found its way into the shoe’s dreamy interior!

And let’s not be coy about the boot’s level of comfort. The Timberland Chocorua Trail 2.0 Waterproof has that premium feel on the inside, particularly around the forefoot and instep. No one from us got blisters in the boot, either.

As for protection, we give the Chocorua Trail 2.0 Waterproof’s shield-like toe guard props. Our kicking encounters with semi-buried rocks (which were bigger than our fists) didn’t cause us to cower, thanks to this rubberized bumper!

While not as affordable as our top pick for rugged traversals, the Timberland Chocorua Trail 2.0 Waterproof is bound to prove its worth where the going gets tough!

See our full review and facts

Best casual

Who’s got the biggest swagger among Timberland’s must-buys? The Field Trekker Mid, who else!!

Dressed up in layers of premium leather, this chic boot will earn you style points with every step you make in it. That said, don’t let the Field Trekker Mid’s almost retro look fool you. This offering is as beastly on the trail as it is an eyecatcher in the city!

Engineered with a grippy outsole and low-rise lugs, the Timberland Field Trekker Mid offers versatile adhesive prowess. On hardpacked soil and dusty tracks, the boot carried us through with high tenacity. On pavements and concrete walkways (wet or dry), it was the same narrative—we got to our destination slip-free.

The Field Trekker Mid is cotton-soft inside. Our feet got their much-needed escape from the initial stiffness that many hiking boots have. Thanks to its almost non-existent break-in period, we were able to enjoy our test hikes right from day one!

Support-wise, we have no complaints with the Field Trekker Mid. Quite the contrary, in fact, because its rearfoot zone kept our heels in place, not giving us a single instance of lift.

At $130 MSRP, the Timberland Field Trekker Mid is hard to ignore. Make sure you don’t!

See our full review and facts
Paul Ronto
Paul Ronto

Over the past 20 years, Paul has climbed, hiked, and ran all over the world. He has summited peaks throughout the Americas, trekked through Africa, and tested his endurance in 24-hour trail races as well as 6 marathons. On average, he runs 30-50 miles a week in the foothills of Northern Colorado. His research is regularly cited in The New York Times, Washington Post, National Geographic, etc. On top of this, Paul is leading the running shoe lab where he cuts shoes apart and analyses every detail of the shoes that you might buy.