Timberland Mt. Maddsen Hiking Waterproof Boots - Trail Ready
Timberland Mt. Maddsen Hiking Waterproof Boots - Trail Ready
Price subject to change. Tap below for current.
Couldn't load pickup availability
In this review of the Timberland Mt. Maddsen Hiking Waterproof Boots the bottom line is simple: these are leather hikers built for people who want dependable waterproofing and day-long comfort on mixed trails. The review finds the boots most compelling for walkers who value a true wide fit and lightweight feel without sacrificing a rugged look. With a waterproof Premium Timberland Leather upper and TimberDry eco-conscious membrane, these boots keep feet dry while the anti-fatigue removable footbed and compression-molded EVA midsole reduce fatigue on long outings.
Key Features
- Waterproof leather upper: Premium 100 percent waterproof leather from an LWG Silver-rated tannery keeps moisture out while offering the durability expected of a leather hiker.
- TimberDry membrane: The eco-conscious waterproof membrane protects feet in wet conditions without adding bulk so the boots stay comfortable on all-day walks.
- Gusseted tongue: The fully gusseted tongue helps block debris and further seals out water for better on-trail protection.
- Anti-fatigue footbed: The removable anti-fatigue footbed provides cushioning and support for long periods of standing or hiking and can be swapped for orthotics if needed.
- Recycled outsole and lining: The lining uses ReBOTL fabric and the outsole contains 15 percent recycled rubber, offering an eco-conscious touch to the construction.
Who It's For
The Mt. Maddsen is best for outdoor enthusiasts who need a waterproof, leather hiking boot that doubles as a casual everyday shoe. Hikers who value a wider last and a lightweight feel will appreciate how these boots perform on day hikes, light trails, and around town.
Those who need aggressive mountaineering traction, a very high ankle cuff, or heavy-duty soles for backpacking multi-day treks should look elsewhere; these are aimed at moderate trail use and comfort rather than technical alpine climbing.
Pros & Cons
Pros
- Exceptional comfort from the anti-fatigue removable footbed and compression-molded EVA midsole.
- Reliable waterproofing thanks to premium waterproof leather and the TimberDry membrane.
- True wide fit and relatively lightweight construction make them easy to wear for long periods.
- Durable appearance that transitions well from trail to casual wear.
Cons
- Some customers have reported long-term sole separation on a minority of pairs, so durability of the outsole may vary.
- Not intended for technical mountaineering or heavy backpack loads.
Specifications
| Brand | Timberland |
| Upper | Premium 100 percent waterproof leather |
| Waterproof system | TimberDry eco-conscious membrane |
| Lining | ReBOTL fabric lining |
| Footbed | Removable anti-fatigue footbed |
| Outsole | 15 percent recycled rubber |
| Shaft height | Approximately 5 in from arch |
Our Verdict
The Timberland Mt. Maddsen Hiking Waterproof Boots are an excellent choice for hikers and everyday wearers who want dependable waterproofing, a forgiving wide fit, and long-wear comfort. They deliver clear value for moderate trail use and daily wear, though users seeking extreme durability under heavy backpacking loads should consider a purpose-built backpacking boot.
Frequently Asked Questions
Are these boots fully waterproof?
Yes; the boots use premium waterproof leather and a TimberDry waterproof membrane to keep feet dry in wet conditions.
Can the footbed be removed for custom orthotics?
Yes; the anti-fatigue footbed is removable and can be replaced with custom insoles if needed.
How high is the shaft and heel?
The shaft measures approximately 5 in from the arch and the heel measures approximately 1.5 in.
Editor's Take
The Mt. Maddsen boots offer dependable waterproof leather, a comfortable anti-fatigue footbed, and a true wide fit, making them a strong value for day hikers and everyday wearers.

Recently viewed
Recently viewed products will appear here as customers browse the store.