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Timberland Men's Mt Maddsen Mid Waterproof Hiking Boots

Timberland Men's Mt Maddsen Mid Waterproof Hiking Boots

4.5· 3,100 ratings

Best price now

$43.98at Level UpObserved at 6:07 AM
Deal: 63% off at Level Up →

Compared across 6 stores. Prices are checked against each store and labelled with when.

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Our take on the Timberland Men's Mt Maddsen Mid Waterproof Hiking Boots

The Timberland Mt Maddsen Mid is a men's mid-cut hiking boot with a waterproof membrane, a removable anti-fatigue footbed and a rubber lug outsole. An internal TPU shank adds torsional rigidity for uneven ground. The best new price is $43.98 at Level Up as of November 5, 2026, well below what this boot usually sells for at full retail.

Best forDay hikers and casual trail walkersWet-weather commuters and dog walkersShoppers who want a budget leather hiking bootPeople who use custom orthotics
Pros
  • Waterproof membrane keeps feet dry in rain and shallow puddles
  • Removable footbed fits custom orthotics
  • Rubber lug outsole grips dirt and gravel trails
  • Internal TPU shank adds stability underfoot
  • Leather-and-mesh upper is supportive without being stiff
Cons
  • Mid-cut height gives less ankle support than a full backpacking boot
  • EVA midsole compresses over time with heavy use
  • Warm in hot weather because of the waterproof liner
  • Not built for multi-day loads or technical scrambling

Timberland Men's Mt Maddsen Mid Waterproof Hiking Boots prices at every store

  • Level UpNew

    In stock

    $43.98Observed at 6:07 AM
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  • TargetNew

    In stock

    $119.99Observed at 7:06 AM
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  • Shoe SensationNew

    In stock

    $129.99Observed at 7:06 AM
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  • REINew

    In stock

    $130.00Observed at 6:07 AM
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  • DICK'S Sporting GoodsNew

    Availability unknown

    $129.99Observed at 7:06 AM
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  • Academy Sports + OutdoorsNew

    Availability unknown

    $129.99Observed at 7:06 AM
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Also available at

  • DSWCheck price at DSW
  • DTLRCheck price at DTLR
  • Shoe StationCheck price at Shoe Station
  • TimberlandCheck price at Timberland
  • Finish LineCheck price at Finish Line
  • JD SportsCheck price at JD Sports

Timberland Men's Mt Maddsen Mid Waterproof Hiking Boots price history

Lowest price we've seen: $43.98 on Nov 5 at Level Up. Tracked across 12 stores since Nov 5.

What reviewers say

With 4.5 out of 5 from about 3,100 ratings, owners mostly treat these as comfortable, dry everyday hikers. Complaints center on durability under hard use and on fit for wide feet.

Pros
  • Comfortable out of the box with little break-in
  • Keeps feet dry in wet grass and rain
  • Good value at sale prices
  • Light enough for long walks
Cons
  • Soles and seams wear faster with frequent hard hiking
  • Runs narrow for some wearers
  • Can feel warm in summer

Specifications

Gender
Men's
Boot Style
Hiking boots
Type
Boots
Closure Style
Lace-up
Water Resistant
Yes
Safety Features
Internal TPU shank for torsional rigidity
Age Group
Adult
Insulation
Yes (effective waterproof liner insulates from the elements)
Occasion
Hiking
Theme
Outdoor
Sole Material
EVA (midsole), Rubber
Sole Support
Arch support
Sole Style
Lug sole
Sports
Hiking
Traction Features
Rubber lug outsole for traction
Weather Highlights
Waterproof
Weather Proofing
Waterproof
Arch Support
Yes
Orthotics Compatible
Yes
Footbed Features
Removable, Anti-fatigue
Outsole Material
Rubber
Outsole Style
Lug sole
Department
Men's

Questions and answers

Are the Timberland Mt Maddsen Mid boots actually waterproof?
Yes. They use a waterproof membrane inside a leather and mesh upper, which handles rain, wet grass and shallow puddles. They are not wading boots, so deep stream crossings will still soak through.
Is $43.98 a good price for these boots?
It is a strong price. Level Up lists them at $43.98 as of November 5, 2026, far below the usual retail of around $100 to $120 for this model. Check that the listing is the men's waterproof mid version before buying.
Do they fit true to size?
Most owners say they run true to size, but the fit is on the narrow side. If you wear wide shoes or thick hiking socks, consider going up a half size.
Can I use my own insoles in them?
Yes. The anti-fatigue footbed is removable, so custom orthotics or aftermarket insoles drop in easily. The boot also has arch support built in.
Are they good for serious backpacking?
No. They suit day hikes and light loads. For multi-day trips with a heavy pack, a stiffer, higher-cut boot gives more ankle support and underfoot protection.
What is the difference between the Mt Maddsen Mid and Timberland's other hiking boots?
The Mt Maddsen Mid is the mid-cut waterproof leather option in Timberland's hiking line, positioned below the stiffer White Ledge and Mt. Maddsen low versions. It trades some support for lighter weight and a lower price.
Where is the Timberland Men's Mt Maddsen Mid Waterproof Hiking Boots cheapest?
At Level Up, for $43.98, 63% off, as of our latest check.
What do buyers say about the Timberland Men's Mt Maddsen Mid Waterproof Hiking Boots?
Rated 4.5 out of 5 from 3,100 ratings.
Where can I buy the Timberland Men's Mt Maddsen Mid Waterproof Hiking Boots?
12 stores we checked sell it, including DICK'S Sporting Goods, Target, Shoe Sensation, Academy Sports + Outdoors, Level Up.

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