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Cushioned Trail Shoes

Find cushioned trail shoes that suit your fit and style preferences. Compare available styles and sizes, then check each pair’s product details for cushioning information and fit guidance to help narrow your choices.

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Women's HOKA Challenger 8 Trail Shoes, GORE-TEX
HOKA Women's HOKA Challenger 8 Trail Shoes, GORE-TEX
A gray trail running shoe with GORE-TEX waterproofing, cushioned EVA midsole, and reflective safety details.
(0)
$165 $165
SALE
$165 $165
SALE
Women's HOKA Challenger 8 Trail Shoes
HOKA Women's HOKA Challenger 8 Trail Shoes
A lightweight blue trail shoe featuring cushioned EVA midsole, recycled mesh upper, and multi-directional traction lugs.
(0)
$150 $150
SALE
$150 $150
SALE
Men's HOKA Challenger 8 Trail Shoes, GORE-TEX
HOKA Men's HOKA Challenger 8 Trail Shoes, GORE-TEX
A black trail running shoe with GORE-TEX waterproofing, EVA midsole, and 4mm lugs for all-terrain traction.
(0)
$165 $165
SALE
$165 $165
SALE
Men's HOKA Challenger 8 Trail Shoes
HOKA Men's HOKA Challenger 8 Trail Shoes
A lightweight blue trail running shoe with cushioned EVA midsole and durable, recycled mesh upper.
(0)
$150 $150
SALE
$150 $150
SALE
Men's On Cloudsurfer Trail 2 Running Shoes
On Men's On Cloudsurfer Trail 2 Running Shoes
A lightweight gray trail running shoe featuring a cushioned Helion™ midsole and durable Missiongrip™ rubber outsole.
(0)
$170 $170
SALE
$170 $170
SALE
Men's Access Hiking Shoes, Waterproof
L.L.Bean Men's Access Hiking Shoes, Waterproof
A waterproof hiking shoe with a leather/rubber upper and superior cushioning for all-day comfort.
(0)
$140 $119.99
SALE
$140 $119.99
SALE
Men's NextVenture Hiking Shoes, Waterproof
L.L.Bean Men's NextVenture Hiking Shoes, Waterproof
A waterproof tan hiking shoe with cushioned EVA midsole, Vibram® outsole, and breathable mixed-material upper.
(0)
$150 $150
SALE
$150 $150
SALE
Men's On Cloudvista 3 Trail Running Shoes
On Men's On Cloudvista 3 Trail Running Shoes
A lightweight white trail shoe with breathable mesh, soft foam cushioning, rebound, and grippy mixed-terrain traction.
(0)
$160 $160
SALE
$160 $160
SALE
Women's On Cloudvista 3 Trail Running Shoes
On Women's On Cloudvista 3 Trail Running Shoes
A white, lightweight trail shoe with breathable upper, Helion™ cushioning, and Missiongrip™ traction for mixed terrain.
(0)
$160 $160
SALE
$160 $160
SALE
Men's Oboz Bridger Low B-Dry Hiking Shoes
Oboz Men's Oboz Bridger Low B-Dry Hiking Shoes
A versatile, waterproof hiking shoe with advanced cushioning and superior arch support in dark shadow.
(279)
$160 $160
SALE
What customers like:
Well-designed
Durable construction
Advanced cushioning
Superior support
Comfortable fit
$160 $160
SALE
Women's Trail Model X Waterproof Hiking Shoes, Leather
L.L.Bean Women's Trail Model X Waterproof Hiking Shoes, Leather
A waterproof gray leather hiking shoe with enhanced traction, recycled materials, and thermoregulating comfort lining.
(0)
$120 $120
SALE
$120 $120
SALE
Men's Heritage Hiking Shoes, Waterproof
L.L.Bean Men's Heritage Hiking Shoes, Waterproof
A waterproof tan hiking shoe with suede-and-nylon upper, grippy rubber outsole, and recycled mesh lining.
(0)
$140 $99.99
SALE
$140 $99.99
SALE
Men's On Cloudvista Trail Running Shoes
On Men's On Cloudvista Trail Running Shoes
A lightweight gray trail running shoe featuring breathable mesh, Helion™ superfoam cushioning, and Missiongrip™ rubber traction.
(0)
$150 $150
SALE
$150 $150
SALE
Women's NextVenture Hiking Shoes, Waterproof
L.L.Bean Women's NextVenture Hiking Shoes, Waterproof
A waterproof brown hiking shoe with mesh, rubber, and leather for comfort, traction, and durability.
(0)
$150 $150
SALE
$150 $150
SALE
Men's Trail Model X Waterproof Hiking Shoes
L.L.Bean Men's Trail Model X Waterproof Hiking Shoes
A waterproof hiking shoe with brown suede leather, offering enhanced traction and comfort for outdoor adventures.
(0)
$110 $110
SALE
$110 $110
SALE
Women's Trail Model X Ventilated Hiking Shoes
L.L.Bean Women's Trail Model X Ventilated Hiking Shoes
A purple hiking shoe with water-resistant suede, offering enhanced traction and comfort for outdoor adventures.
(0)
$99.95 $99.95
SALE
$99.95 $99.95
SALE
Men's Trail Model X Waterproof Hiking Shoes, Camo
L.L.Bean Men's Trail Model X Waterproof Hiking Shoes, Camo
A waterproof hiking shoe featuring water-resistant suede, TEK2.5® membrane, and enhanced traction for wet trails.
(0)
$110 $92.99
SALE
$110 $92.99
SALE
Men's Oboz Sawtooth X B-DRY Hikers, Low
Oboz Men's Oboz Sawtooth X B-DRY Hikers, Low
A rugged brown leather trail shoe with waterproof lining, cushioned midsole, and reliable traction for wet conditions.
(0)
$165 $165
SALE
$165 $165
SALE
Men's Trail Model X Ventilated Hiking Shoes
L.L.Bean Men's Trail Model X Ventilated Hiking Shoes
A gray suede and rubber hiking shoe featuring breathable mesh panels and enhanced wet-surface traction.
(0)
$99.95 $99.95
SALE
$99.95 $99.95
SALE
Women's Access Hiking Shoes, Waterproof
L.L.Bean Women's Access Hiking Shoes, Waterproof
A waterproof hiking shoe featuring recycled mesh, nubuck leather, and grippy rubber for all-day comfort.
(0)
$140 $140
SALE
$140 $140
SALE
Women's On Cloudvista Trail Running Shoes
On Women's On Cloudvista Trail Running Shoes
A lightweight green trail running shoe with breathable recycled mesh and ultra-sticky rubber outsoles for traction.
(0)
$160 $160
SALE
$160 $160
SALE
Men's Trail Model X Waterproof Hiking Shoes, Leather
L.L.Bean Men's Trail Model X Waterproof Hiking Shoes, Leather
A brown waterproof leather hiking shoe with enhanced traction, breathable mesh panels, and recycled polyester details.
(0)
$120 $120
SALE
$120 $120
SALE
Women's Elevation Trail Shoes, Waterproof
L.L.Bean Women's Elevation Trail Shoes, Waterproof
A lightweight blue trail shoe with waterproof mesh upper, grippy rubber outsole, and thermoregulating lining.
(0)
$130 $130
SALE
$130 $130
SALE
Men's Elevation Trail Shoes, Waterproof
L.L.Bean Men's Elevation Trail Shoes, Waterproof
A brown, waterproof trail shoe with recycled mesh, rock protection, cushioned comfort, and grippy rubber traction.
(0)
$130 $130
SALE
$130 $130
SALE

Cushioned Trail Shoes

Cushioned Trail Shoes bring together two things worth considering as you choose your next pair: the feel you prefer underfoot and a style made for the trail. Cushioning is a personal preference, and more isn’t automatically better for every person. Some people enjoy a noticeably cushioned feel, while others prefer something less pronounced. Think about what you like in the shoes you already own, including where they feel roomy, where they feel snug, and what you would change. Those familiar details make a useful starting point when comparing options. Whether your favorite trail winds through a neighborhood woodland or leads to a spot you visit with family every fall, choosing shoes begins with your own preferences—not someone else’s idea of the perfect pair.

Fit deserves just as much attention as cushioning. As you browse, compare the available sizes and widths, check each pair’s fit notes, and use the size chart rather than relying on size alone. Leave room for your toes to move without choosing a fit that lets your foot slide around, and pay attention to how the heel and midfoot feel. When trying shoes on, wear the socks you expect to wear with them and take time to notice any pressure points. A pair that looks right on the screen still needs to feel right on your feet. If you’re deciding between two options, details such as the shape of the toe area, the way the shoes fasten, and your preferred amount of cushioning can help narrow the choice. Color and overall style matter, too; there’s nothing wrong with choosing a pair you enjoy looking at once the fit feels right.

For someone who looks forward to time on the trail, cushioned trail shoes can also make a thoughtful gift—especially when you know their size, preferred fit, and taste. Picture the family member who always suggests the wooded loop after a weekend get-together, or the friend who stops to point out the first turning leaves. Their enthusiasm gives the gift meaning, but their footwear preferences should guide the selection. If you’re unsure, choosing together can be part of the experience, with a shared trail outing to look forward to afterward. This collection offers a place to compare options at your own pace, keeping the decision centered on the details that matter to the person wearing them. Start with fit, consider the cushioning you prefer, and choose a style that feels like your own.

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