Trail/Pleasure Saddles
Long miles demand comfort—for you and your horse. Shop trail saddles at Teskey’s for western saddles designed to keep you comfortable over hours in the saddle, with secure feel and practical design for everyday trail riding. Whether you ride short loops or all-day adventures, the right trail saddle makes the ride more enjoyable.
When choosing a trail saddle, prioritize comfort and stability: a seat you can stay in, fenders that feel natural, and a saddle that stays put without creating pressure points. Many trail riders also like practical add-ons and compatibility with saddle bags. Fit for the horse matters even more on long rides—small fit issues can become big soreness over time. Use filters to narrow by brand and budget, and if you’re not sure what will be comfortable for your body type and ride style, we can help.
17" HIGH HORSE DAISETTA CORDURA TRAIL SADDLE
High HorseThis new 17" High Horse Daisetta Cordura trail saddle comes in a walnut geometric border tooling with a padded seat. For more information call a sa...
View full details16" DEMO CIRCLE Y GILLETTE TRAIL SADDLE
Circle Y SaddleryThis demo 16" Circle Y Gillette trail saddle comes in a heavy oil rope border tooling with a padded seat. For more information call a saddle salesm...
View full details17" HIGH HORSE EL DORADO CORDURA TRAIL SADDLE
High HorseThis new 17" High Horse El Dorado trail saddle comes in a walnut finish with a padded seat. For more information call a saddle salesman today at ...
View full details15" USED CLINT MORTENSON MULE SADDLE
Clint MortensonThis used 15" Clint Mortenson Mule saddle comes in a heavy oil border tooling with a hard seat. For more information call a saddle salesman today a...
View full details15" USED BIG HORN TRAIL SADDLE
Big HornThis used 15" Big Horn Trail saddle comes in a heavy oil basket and trophy tooling with a padded seat. For more information call a saddle salesma...
View full details17" USED MARTIN CLINTON ANDERSON AUSTRALIAN SADDLE
Martin SaddleryThis used 17" Martin Clinton Anderson Australian saddle comes in a heavy oil barb wire border with a padded seat. For more information call a saddl...
View full details15" CIRCLE Y SNOWY RIVER FLEX2 TRAIL SADDLE
Circle Y SaddleryThis new 15" Circle Y Snowy River Flex2 Trail saddle comes in a walnut border tooling with a padded seat. For more information call a saddle salesm...
View full details13.5" USED CIRCLE Y EQUITATION TRAIL SADDLE
Circle Y SaddleryThis used 13.5"Circle Y Equitation Trail saddle comes in a heavy oil basket and trophy tooling with a padded seat. For more information call a sad...
View full details16" CIRCLE Y OAK GROVE TRAIL SADDLE
Circle Y SaddleryThis new 16" Circle Y Oak Grove Trail saddle comes in a chestnut barb wire border tooling with padded seat. For more information call a saddle sale...
View full details15" CIRCLE Y SNOWY RIVER FLEX2 TRAIL SADDLE
Circle Y SaddleryThis new 15" Circle Y Snowy River Flex2 Trail saddle comes in a walnut border tooling with a padded seat. For more information call a saddle salesm...
View full details15" CIRCLE Y SUNFLOWER FLEX2 TRAIL SADDLE
Circle Y SaddleryThis new 15" Circle Y Sunflower Flex2 Trail saddle comes in a vintage 1/2 sunflower tooling with a padded seat. For more information call a saddle ...
View full details15" CIRCLE Y SUNFLOWER FLEX2 TRAIL SADDLE
Circle Y SaddleryThis new 15" Circle Y Sunflower Flex2 Trail saddle comes in a vintage 1/2 sunflower tooling with a padded seat. For more information call a saddle ...
View full details18.5" TUCKER BIG BEND HERITAGE TRAIL SADDLE
TuckerThis new 18.5" Tucker Big Bend Heritage Trail saddle comes in a black slickout with a padded seat. For more information call a saddle salesman toda...
View full details17.5" TUCKER BIG BEND HERITAGE TRAIL SADDLE
TuckerThis new 17.5" Tucker Big Bend Heritage Trail saddle comes in a heavy oil slickout with a padded seat. For more information call a saddle salesman ...
View full details17.5" TUCKER HIGH PLAINS HERITAGE TRAIL SADDLE
TuckerThis new 17.5" Tucker High Plains Heritage Trail saddle comes in a heavy oiI border tooling with a padded seat. For more information call a saddle ...
View full details15" CIRCLE Y OMAHA FLEX2 TRAIL
Circle Y SaddleryThis new 15" Circle Y Omaha Flex2 Trail saddle comes in a chestnut slickout with a padded seat. For more information call a saddle salesman today a...
View full details16" CIRCLE Y WALNUT GROVE FLEX2 TRAIL SADDLE
Circle Y SaddleryThis new 16" Circle Y Walnut Grove Flex2 trail saddle comes in a medium floral border tooling with a padded seat. For more information call a saddl...
View full details17.5" TUCKER ENDURANCE HERITAGE TRAIL SADDLE
TuckerThis new 17.5" Tucker Endurance Heritage Trail saddle comes in a heavy oil slickout with a padded seat. For more information call a saddle salesman...
View full details17.5" TUCKER CHEYENNE HERITAGE TRAIL SADDLE
TuckerThis new 17.5" Tucker Cheyenne Heritage Trail saddle comes in a heavy oil 1/2 border tooling with a padded seat. For more information call a saddle...
View full details17" HIGH HORSE DAISETTA CORDURA TRAIL SADDLE
High HorseThis new 17" High Horse Daisetta Cordura Trail saddle comes in a walnut border tooling with a padded seat. For more information call a saddle sales...
View full details16" CIRCLE Y OAK GROVE TRAIL SADDLE
Circle Y SaddleryThis new 16" Circle Y Oak Grove Trail saddle comes in a chestnut barb wire border tooling with a padded seat. For more information call a saddle sa...
View full details17" HIGH HORSE SKY MEADOW TRAIL SADDLE
High HorseThis new 17" High Horse Sky Meadow trail saddle comes in a heavy oil border tooling with a padded seat. For more information call a saddle salesman...
View full details16" CIRCLE Y WALNUT GROVE FLEX2 TRAIL SADDLE
Circle Y SaddleryThis new 16" Circle Y Walnut Grove Flex2 Trail saddle comes in a walnut floral border tooling with a padded seat. For more information call a saddl...
View full details16" CIRCLE Y JACKSON FLEX2 TRAIL SADDLE
Circle Y SaddleryThis new 16" Circle Y Jackson Flex2 Trail saddle comes in a chestnut geometric border tooling with a hard seat. For more information call a saddle ...
View full details17" HIGH HORSE BEAR BROOK TRAIL SADDLE
High HorseThis new 17" High Horse Bear Brook Trail saddle comes in a walnut slickout with a padded seat. For more information call a saddle salesman today at...
View full details16.5" TUCKER ENDURANCE HERITAGE TRAIL SADDLE
TuckerThis new 16.5" Tucker Endurance Heritage Trail saddle comes in a heavy oil slickout with a padded seat. For more information call a saddle salesman...
View full details16.5" TUCKER EQUITATION TRAIL SADDLE
TuckerThis new 16.5" Tucker Equitation Trail saddle comes in a black slickout with a padded seat. For more information call a saddle salesman today at 88...
View full details15.5" TUCKER ENDURANCE TRAIL SADDLE
TuckerThis new 15.5" Tucker Endurance Trail saddle comes in a black slickout with a padded seat. For more information call a saddle salesman today at 888...
View full details17.5" TUCKER CHEYENNE HERITAGE TRAIL SADDLE
TuckerThis new 17.5" Tucker Cheyenne Heritage Trail saddle comes in a heavy oil geometric border tooling with a padded seat. For more information call a ...
View full details16" CIRCLE Y GREY FOREST ENDURANCE FLEX TRAIL SADDLE
Circle Y SaddleryThis new 16" Circle Y Grey Forest Endurance Flex Trail saddle comes in a chestnut border tooling with a padded seat. For more information call a sa...
View full details17" HIGH HORSE IRON WEED CORDURA TRAIL SADDLE
High HorseThis new 17" High Horse Iron Weed Cordura Trail saddle comes in a heavy oil barbwire border tooling with a padded seat. For more information call a...
View full details17" CIRCLE Y OMAHA FLEX2 TRAIL SADDLE
Circle Y SaddleryThis new 17" Circle Y Omaha Flex2 Trail saddle comes in a chestnut border tooling with a padded seat. For more information call a saddle salesman t...
View full details15" ABETTA ORIGINAL ROUND SKIRT SADDLE
Abetta Saddle CoThis new 15" Abetta original round skirt saddle comes in a black synthetic nylon with a padded seat. For more information call a saddle salesman to...
View full details17" ABETTA BRUSHPOPPER TRAIL SADDLE
Abetta Saddle CoThis new 17" Abetta Brushpopper Trail saddle comes in a black synthetic nylon with a padded seat. For more information call a saddle salesman today...
View full details16" CIRCLE Y SALT RIVER FLEX 2 TRAIL SADDLE
Circle Y SaddleryThis new 16" Circle Y Salt River Flex 2 trail saddle comes in a chestnut barbed wire border tooling with a padded seat. For more information call a...
View full details15" CIRCLE Y ALABAMA TRAIL GAITER SADDLE
Circle Y SaddleryThis new 15" Circle Y Alabama Trail Gaiter saddle comes in a walnut barbed wire border tooling with a padded seat. For more information call a sadd...
View full details16" CIRCLE Y JULIE GOODNIGHT PEAK PERFORMANCE TRAIL SADDLE
Circle Y SaddleryThis new 16" Circle Y Julie Goodman Peak Performance trail saddle comes in a walnut 7/8 floral tooling with a padded seat. For more information c...
View full details16" CIRCLE Y WRANGLER FLEX 2 TRAIL SADDLE
Circle Y SaddleryThis new 16" Circle Y Wrangler Flex 2 trail saddle comes in a heavy oil 1/4 floral tooling with a hard seat. For more information call a saddle sa...
View full details14.5" CIRCLE Y OMAHA FLEX2 TRAIL SADDLE
Circle Y SaddleryThis new 14.5" Circle Y Omaha Flex2 Trail saddle comes in a chocolate shell border tooling with a padded seat. For more information call a saddle s...
View full detailsTrail/Pleasure Saddles
Long miles demand comfort—for you and your horse. Shop trail saddles at Teskey’s for western saddles designed to keep you comfortable over hours in the saddle, with secure feel and practical design for everyday trail riding. Whether you ride short loops or all-day adventures, the right trail saddle makes the ride more enjoyable.
When choosing a trail saddle, prioritize comfort and stability: a seat you can stay in, fenders that feel natural, and a saddle that stays put without creating pressure points. Many trail riders also like practical add-ons and compatibility with saddle bags. Fit for the horse matters even more on long rides—small fit issues can become big soreness over time. Use filters to narrow by brand and budget, and if you’re not sure what will be comfortable for your body type and ride style, we can help.