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.

All Travel Tech Clothes Shoes Jewelry Home Beauty Outdoors Toys

This hour's deals

Timberland Men's Mt Maddsen Mid Waterproof Hiking Boots

−63%

Shoes · Level Up

Timberland hiking boots built for the trail

Name: Timberland Men's Mt Maddsen Mid Waterproof Hiking Boots
Brand: Timberland
Rating: 4.5 (3100 reviews)

Timberland Men's Mt Maddsen Mid Waterproof Hiking Boots

Men's Mt Maddsen mid waterproof hiking boots from Timberland, for anyone who wants dry feet on the trail.

Deal score 8.0 · Steal

$43.98$120.00 usual price

You save $76.02 at Level Up

This deal was in an earlier drop. The store may have changed its price since.

Why it's a great deal

Elsewhere right now: Timberland $119.99, DICK'S Sporting Goods $129.99, DSW $129.99, and 2 more (typical $129.99 across 5 stores)
Cheaper than all 5 other stores selling it right now
Google Shopping says it usually sells for $120.00
Rated 4.5 out of 5 by 3,100 buyers
Timberland says cushioning comes from an anti-fatigue removable footbed and compression-molded EVA midsole Timberland

Visit Level Up

Every store we checked

Level UpNew
In stock
$43.98Observed at 6:07 AM
Visit store
TargetNew
In stock
$119.99Observed at 7:06 AM
Visit store
Shoe SensationNew
In stock
$129.99Observed at 7:06 AM
Visit store
REINew
In stock
$130.00Observed at 6:07 AM
Visit store
DICK'S Sporting GoodsNew
Availability unknown
$129.99Observed at 7:06 AM
Visit store
Academy Sports + OutdoorsNew
Availability unknown
$129.99Observed at 7:06 AM
Visit store

Price history and every store's price →

Reading Level Up’s product page for the details…

Specs

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

About 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

More deals like this

More from Timberland

All Travel Tech Clothes Shoes Jewelry Home Beauty Outdoors Toys

This hour's deals

−63%

Shoes · Level Up

Timberland hiking boots built for the trail

Timberland Men's Mt Maddsen Mid Waterproof Hiking Boots

Men's Mt Maddsen mid waterproof hiking boots from Timberland, for anyone who wants dry feet on the trail.

Deal score 8.0 · Steal

$43.98$120.00 usual price

You save $76.02 at Level Up

This deal was in an earlier drop. The store may have changed its price since.

Why it's a great deal

Elsewhere right now: Timberland $119.99, DICK'S Sporting Goods $129.99, DSW $129.99, and 2 more (typical $129.99 across 5 stores)
Cheaper than all 5 other stores selling it right now
Google Shopping says it usually sells for $120.00
Rated 4.5 out of 5 by 3,100 buyers
Timberland says cushioning comes from an anti-fatigue removable footbed and compression-molded EVA midsole Timberland

Visit Level Up

Every store we checked

Level UpNew
In stock
$43.98Observed at 6:07 AM
Visit store
TargetNew
In stock
$119.99Observed at 7:06 AM
Visit store
Shoe SensationNew
In stock
$129.99Observed at 7:06 AM
Visit store
REINew
In stock
$130.00Observed at 6:07 AM
Visit store
DICK'S Sporting GoodsNew
Availability unknown
$129.99Observed at 7:06 AM
Visit store
Academy Sports + OutdoorsNew
Availability unknown
$129.99Observed at 7:06 AM
Visit store

Price history and every store's price →

Reading Level Up’s product page for the details…

Specs

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

About the Timberland Men's Mt Maddsen Mid Waterproof Hiking Boots

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

More deals like this

Ask our agent about this deal

It checks today's price at every store, compares the alternatives and answers in about a minute.

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

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.