Skip to main content

It's time to upgrade your browser

Your current browser is no longer supported on llbean.com. Please upgrade to one of the following for a smoother, safer shopping experience with us:

Comfortable Trail Running Shoes

Find comfortable trail running shoes that suit your fit preferences and running routine. Browse the selection and compare each pair’s fit information, sizing guidance and product details to help narrow down your options for time on the trail.

Read More
Men's HOKA Challenger 8 Trail Shoes, GORE-TEX
HOKA Men's HOKA Challenger 8 Trail Shoes, GORE-TEX
A waterproof black trail shoe featuring a GORE-TEX membrane, EVA midsole, and 4mm multi-directional lugs.
(0)
$165 $165
SALE
$165 $165
SALE
Men's On Cloudvista Trail Running Shoes
On Men's On Cloudvista Trail Running Shoes
A lightweight gray trail running shoe with breathable recycled mesh, Helion™ superfoam cushioning, and Missiongrip™ rubber traction.
(0)
$150 $150
SALE
$150 $150
SALE
Men's On Cloudmonster 3 Running Shoes
On Men's On Cloudmonster 3 Running Shoes
A gray running shoe featuring a cushioned Helion™ midsole, engineered mesh upper, and durable rubber outsole.
(0)
$190 $190
SALE
$190 $190
SALE
Men's HOKA Bondi 9 Running Shoes
HOKA Men's HOKA Bondi 9 Running Shoes
A black running shoe with unmatched cushioning, reflective details, and eco-friendly mesh for everyday comfort.
(0)
$174.95 $174.95
SALE
$174.95 $174.95
SALE
Men's Elevation Trail Shoes, Waterproof
L.L.Bean Men's Elevation Trail Shoes, Waterproof
A lightweight blue trail shoe with waterproof mesh upper, thermoregulating lining, and grippy rubber outsole.
(0)
$130 $130
SALE
$130 $130
SALE
Men's HOKA Gaviota 6 Running Shoes
HOKA Men's HOKA Gaviota 6 Running Shoes
A blue running shoe with breathable mesh upper, exceptional cushioning, and enhanced support for daily miles.
(0)
$175 $175
SALE
$175 $175
SALE
Men's On Cloudrunner 3 Running Shoes
On Men's On Cloudrunner 3 Running Shoes
A cushioned, multi-color running shoe with breathable mesh, Helion™ superfoam, and durable rubber outsole.
(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 HOKA Challenger 8 Trail Shoes
HOKA Men's HOKA Challenger 8 Trail Shoes
A blue trail running shoe featuring a lightweight mesh upper, cushioned EVA midsole, and grippy 4mm lugs.
(0)
$150 $150
SALE
$150 $150
SALE
Men's HOKA Clifton 11 Running Shoes
HOKA Men's HOKA Clifton 11 Running Shoes
A lightweight gray running shoe featuring breathable mesh, plush EVA foam cushioning, and a durable rubber outsole.
(0)
$155 $155
SALE
$155 $155
SALE
Women's Oboz Sawtooth X B-DRY Hikers, Low
Oboz Women's Oboz Sawtooth X B-DRY Hikers, Low
A rugged, waterproof trail shoe with reliable traction and a breathable nubuck leather upper in hazy gray.
(158)
$165 $165
SALE
$165 $165
SALE
Men's Trail Model X Waterproof Hiking Shoes
L.L.Bean Men's Trail Model X Waterproof Hiking Shoes
A brown suede leather hiking shoe with waterproof features and enhanced traction for wet surfaces.
(0)
$110 $110
SALE
$110 $110
SALE
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 membrane, EVA midsole, and 100% recycled mesh upper.
(0)
$165 $165
SALE
$165 $165
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, breathable mesh panels, 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 trail shoe with waterproof nubuck leather, breathable lining, and multi-directional traction lugs.
(0)
$165 $165
SALE
$165 $165
SALE
Men's Access Hiking Shoes, Waterproof
L.L.Bean Men's Access Hiking Shoes, Waterproof
A waterproof hiking shoe with blue leather and rubber, offering all-day comfort and superior traction.
(0)
$140 $140
SALE
$140 $140
SALE
Men's On Cloud 6 Shoes
On Men's On Cloud 6 Shoes
A lightweight blue sneaker with a recycled mesh upper, cushioned CloudTec® midsole, and durable rubber outsole.
(0)
$150 $150
SALE
$150 $150
SALE
Men's NextVenture Hiking Shoes, Waterproof
L.L.Bean Men's NextVenture Hiking Shoes, Waterproof
A tan waterproof hiking shoe with a cushioned EVA midsole, Vibram outsole, and breathable TEK2.5 membrane.
(0)
$150 $150
SALE
$150 $150
SALE
Men's HOKA Transport 2 Shoes
HOKA Men's HOKA Transport 2 Shoes
An ultra-comfortable gray athleisure shoe with recycled polyester, water-repellent finish, and eco-friendly Vibram outsole.
(0)
$150 $150
SALE
$150 $150
SALE
Women's On Cloudvista Trail Running Shoes
On Women's On Cloudvista Trail Running Shoes
A lightweight green trail running shoe with breathable mesh upper, Helion™ superfoam cushioning, and Missiongrip™ rubber outsole.
(0)
$160 $160
SALE
$160 $160
SALE
Men's Elevation H2O Shoes
L.L.Bean Men's Elevation H2O Shoes
A lightweight green water-friendly shoe with breathable nylon/neoprene, cushioned EVA midsole, and VertiGrip outsole.
(0)
$99.95 $64.99
SALE
$99.95 $64.99
SALE
Men's 1985 Mountain Classic Sneakers
L.L.Bean Men's 1985 Mountain Classic Sneakers
A versatile gray sneaker featuring water-resistant suede, recycled mesh, and grippy VertiGrip rubber outsole for outdoor adventures.
(0)
$110 $79.99
SALE
$110 $79.99
SALE
Men's Trail Model X Ventilated Hiking Shoes
L.L.Bean Men's Trail Model X Ventilated Hiking Shoes
A water-resistant suede hiking shoe with enhanced traction, comfort, and recycled materials for outdoor adventures.
(0)
$99.95 $99.95
SALE
$99.95 $99.95
SALE
Men's New Balance 990V6 Running Shoes
New Balance Men's New Balance 990V6 Running Shoes
A classic sneaker with breathable mesh, pigskin leather, and all-day cushioning for comfort and stability.
(0)
$199.95 $199.95
SALE
$199.95 $199.95
SALE

Comfortable Trail Running Shoes

Comfortable Trail Running Shoes belong on the short list for anyone who enjoys taking a run beyond the pavement, whether that means a familiar loop through the trees or a trail shared with a friend on Saturday morning. There’s something inviting about that change of scenery: the bend where the woods open up, the quiet stretch before the next turn, the conversation that picks up again when the pace eases. Choosing shoes for those miles is personal, and comfort is a good place to start. Rather than choosing by appearance or size alone, take time to compare the fit information for each pair. A familiar size is a useful starting point, but the way a shoe fits your individual foot matters more than the number on the box. This selection brings together trail running styles to consider at your own pace, with room to find a pair that feels right for you.

When comparing options, think about what you appreciate in your current running shoes and what you’d like to change. Perhaps your toes feel crowded, your heel shifts, or you find yourself adjusting the laces more often than you’d like. Those everyday details give you a more useful shopping checklist than looks alone. Read the sizing notes and available width information, and try shoes with the socks you expect to wear for trail running. Give your toes room to move, pay attention to how the heel sits, and notice any pressure across the top or sides of your feet. Try both shoes and spend a little time moving around rather than deciding from a seated fitting. Comfort shouldn’t depend on overlooking a spot that already bothers you. If you wear an insert, check the individual shoe’s details for compatibility instead of assuming every style will accommodate it.

Trail running shoes can be a thoughtful gift for someone who looks forward to a weekly trail outing, is getting acquainted with local routes, or enjoys making time outside part of a shared routine. Because fit is so individual, a little groundwork makes the choice more personal: find out their usual size and width, ask what they like about their current pair, and check exchange options before purchasing. Letting them help choose can be part of the gift, too—an afternoon comparing favorites, followed by plans for a run together. Whether you’re shopping for yourself or someone close to you, start with personal preferences, compare the details, and keep a comfortable fit at the center of the decision. The right choice is the one that makes sense for the person wearing it, not simply the pair that catches your eye first.

Read More

FAQs