Verdict from 100+ user reviews

7 reasons to buy

  • The Timberland Chocorua Trail 2.0 Waterproof is a comfortable hiking boot, based on numerous customer reviews.
  • Its lightness has left a lot of users happy.
  • A bunch of outdoor enthusiasts commends its great ankle support.
  • Many owners admire its Gore-Tex liner for giving sufficient protection against wet elements.
  • According to a handful of buyers, this Timberland product runs true to size.
  • There is virtually no break-in period, as testified by some purchasers.
  • Its grippy outsole has left the minority satisfied.

1 reason not to buy

  • Several consumers were upset to discover that the Chocorua Trail 2.0 Waterproof’s sole separated from the upper after a year or two.

Bottom line

Those who value comfort and lightness may like what they see in the Timberland Chocorua Trail 2.0 Waterproof. The boot also got good marks for its ankle support, traction, and waterproofness. On the other hand, it failed to deliver in terms of durability because of some sole delamination issues. All in all, the Chocorua Trail 2.0 Waterproof can give satisfactory results with its strengths but might disappoint some after a year of use.

Tip: see the best hiking boots.

Good to know

  • Timberland has updated the Chocorua Trail 2.0 Waterproof with features that promote protection and support. From the brand’s patented Timber Dry liner, it now sports a Gore-Tex membrane for water protection. The designers also supplied the collar with more padding and lowered the height of the cuff. The pull tab exits this version.
  • Its footbed now comes with Timberland’s trademarked Anti-Fatigue technology to deliver dynamic arch support and underfoot comfort. It’s paired with an ethylene-vinyl acetate (EVA) midsole to create a cushioned and stabilized ride for the user. The boot’s solid rubber outsole offers traction on different ground conditions.

Timberland’s Chocorua Trail 2.0 Waterproof is a hiking boot crafted for male hikers. Its length selection is made up of whole and half sizes. It’s available only in standard width. It runs The gear’s lace closure system allows wearers to achieve a secure and personalized lockdown. Also, this Timberland product fairly runs true to size.

Keeping users steady on uneven ground conditions is the Timberland Chocorua Trail 2.0 Waterproof’s solid rubber outsole. Its profile is filled with multi-directional lugs which grants grip on challenging terrain, including slippery surfaces. This component is made of 34% recycled rubber, making it eco-friendly. It also has a heel brake integrated into its design for added control on downhill slopes.

This hiking boot from Timberland uses a midsole made of EVA foam. Its construction provides lightweight cushioning, rebound, and shock absorbency over rugged terrain.

The footgear’s Anti-Fatigue footbed uses an inverted cone design to render support. It has an Ortholite top layer which manages moisture and grants underfoot comfort. Moreover, the dynamic arch construction of this component helps adapt to the user’s foot shape.

The Timberland Chocorua Trail 2.0 Waterproof’s upper is made of full-grain leather and mesh fabric, a combination that brings durability and breathability. A Gore-Tex membrane is also embedded within the upper to protect the foot from wet trail conditions.

This Timberland product’s lace closure system uses a combination of metal hooks and eyelets for fit personalization. These components are also rustproof to preserve their quality. The tongue is fully gusseted to prevent debris from entering the boot.

Both of these Timberland products sport full-grain leather uppers, EVA midsoles, and sturdy rubber outsoles. They are also built for male adventurers with standard width feet.

As for their features, the Timberland Euro Hiker is more rigid and delivers more arch support, thanks to a steel shank found within its midsole component. It’s also tougher against abrasion because of a rubber rand wrapping around the upper’s base portion.

Those who are looking for a pair that offers more in terms of durability and support might want to consider getting the Euro Hiker. On the other hand, outdoor enthusiasts who value water protection may gain more from this boot-type Gore-Tex hiker from Timberland.


How Timberland Chocorua Trail 2.0 Waterproof ranks compared to all other shoes
Bottom 27% hiking boots
All hiking boots
Bottom 12% Timberland hiking boots
All Timberland hiking boots
Bottom 30% day hiking hiking boots
All day hiking hiking boots


The current trend of Timberland Chocorua Trail 2.0 Waterproof.
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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.