Verdict from 9 experts and 100+ user reviews

6 reasons to buy

  • An overwhelming number of Timberland Chocorua Trail Mid Waterproof reviews speak of its unbelievable comfort.
  • Many hikers love these boots for giving them great arch and ankle support.
  • It's an extremely lightweight hiker, as several expert reviews point out.
  • Plenty of wearers have talked about the wide toe box that gives them more freedom of movement.
  • A significant number of users say it has helped them overcome slush, snow, and rain thanks to the Timberland Chocorua Trail Mid Waterproof Goretex construction.
  • It's a sturdy all-purpose boot that can endure months and years of use and abuse, many people claim.

2 reasons not to buy

  • The soles are quite thin for tougher terrain, according to several expert reviews.
  • Some wish the boot has a toe bumper for added protection against sharp hazards.

Bottom line

Known for making high-quality hikers, Timberland has again impressed many outdoorsy folks with the Chocorua Trail Mid. It's an all-around hiking shoe that is touted for being amazingly comfortable, supportive, and waterproof. Even more impressive is its lightness, which means you can use it for walking long hours without feeling tired.

Undoubtedly, this hiker from Timberland has everything one will need from an all-purpose boot. Use it for work, on the trail, or when traveling. It won't disappoint.

Tip: see the best hiking boots.

Good to know

-This premium waterproof leather boot has an internal Goretex membrane that keeps the foot warm and dry in wet conditions. It's also equipped with additional waterproof features, including a seam-sealed full-grain leather upper.

-It has a solid lug outsole that offers good grip and traction on varying terrain. Meanwhile, the EVA midsole is lightweight, durable, and soft enough to provide comfort and support.

The Chocorua Trail WP is a mid-top hiker with a full leather upper that conforms to the shape of the foot, creating a snug fit after the break-in period. Its tongue and collar are padded for support, and the forefoot is quite flexible. The under arch design allows the foot to lean inward instead of neutralizing the stance. Lastly, it features a speed lacing system for a personalized fit. 

This boot comes with a solid rubber sole that is designed for most types of terrain, such as sand, mud, and even granite. Timberland soles are known not only for their performance but also for their durability. Since it's made with a quality rubber compound, it can withstand wear and tear for a considerable amount of time.

Like other premium boots, the Chocorua Trail Mid WP uses an EVA midsole. It's a synthetic foam that has several desirable qualities, such as responsiveness, lightness, softness, and a high bounce rate. While it isn't as durable as a polyurethane midsole, EVA offers significant resistance against wear and tear.

This boot contains a nylon shank - a semi-rigid insert between the insole and outsole that protects the foot from sharp objects and provides stability on rough terrain.

The shoe upper is constructed using premium full-grain leather. It features a classic design with an ankle shaft height of 4.5". Inside the boot is the Goretex membrane that seals water out. While it isn't insulated, the waterproof barrier is warm enough to keep the feet feeling comfortable in moderately cold weather. Completing the upper is the rust-proof speed-lacing hardware that lets you achieve a customized fit whenever needed.

-Given its structure and features, the Timberland Chocorua Trail Mid Waterproof is best used for day hiking in well-established trails. 


How Timberland Chocorua Trail Mid Waterproof ranks compared to all other shoes
Top 39% hiking boots
All hiking boots
Top 44% Timberland hiking boots
All Timberland hiking boots
Top 37% day hiking hiking boots
All day hiking hiking boots


The current trend of Timberland Chocorua Trail Mid Waterproof.
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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.