Gift Cards
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 Horse
Original price
$1,499.00
-
Original price
$1,499.00
Original price
$1,499.00
$1,499.00
-
$1,499.00
Current price
$1,499.00
This 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 details
Original price
$1,499.00
-
Original price
$1,499.00
Original price
$1,499.00
$1,499.00
-
$1,499.00
Current price
$1,499.00
16" DEMO CIRCLE Y GILLETTE TRAIL SADDLE
Circle Y Saddlery
Original price
$2,199.00
-
Original price
$2,199.00
Original price
$2,199.00
$2,199.00
-
$2,199.00
Current price
$2,199.00
This 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...
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Original price
$2,199.00
-
Original price
$2,199.00
Original price
$2,199.00
$2,199.00
-
$2,199.00
Current price
$2,199.00
17" HIGH HORSE EL DORADO CORDURA TRAIL SADDLE
High Horse
Original price
$1,499.00
-
Original price
$1,499.00
Original price
$1,499.00
$1,499.00
-
$1,499.00
Current price
$1,499.00
This 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 ...
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Original price
$1,499.00
-
Original price
$1,499.00
Original price
$1,499.00
$1,499.00
-
$1,499.00
Current price
$1,499.00
15" USED CLINT MORTENSON MULE SADDLE
Clint Mortenson
Original price
$2,850.00
-
Original price
$2,850.00
Original price
$2,850.00
$2,850.00
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$2,850.00
Current price
$2,850.00
This 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...
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Original price
$2,850.00
-
Original price
$2,850.00
Original price
$2,850.00
$2,850.00
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$2,850.00
Current price
$2,850.00
15" USED BIG HORN TRAIL SADDLE
Big Horn
Original price
$595.00
-
Original price
$595.00
Original price
$595.00
$595.00
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$595.00
Current price
$595.00
This 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...
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Original price
$595.00
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Original price
$595.00
Original price
$595.00
$595.00
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$595.00
Current price
$595.00
17" USED MARTIN CLINTON ANDERSON AUSTRALIAN SADDLE
Martin Saddlery
Original price
$3,550.00
-
Original price
$3,550.00
Original price
$3,550.00
$3,550.00
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$3,550.00
Current price
$3,550.00
This 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...
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Original price
$3,550.00
-
Original price
$3,550.00
Original price
$3,550.00
$3,550.00
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$3,550.00
Current price
$3,550.00
15" CIRCLE Y SNOWY RIVER FLEX2 TRAIL SADDLE
Circle Y Saddlery
Original price
$2,799.00
-
Original price
$2,799.00
Original price
$2,799.00
$2,799.00
-
$2,799.00
Current price
$2,799.00
This 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 details
Original price
$2,799.00
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Original price
$2,799.00
Original price
$2,799.00
$2,799.00
-
$2,799.00
Current price
$2,799.00
13.5" USED CIRCLE Y EQUITATION TRAIL SADDLE
Circle Y Saddlery
Original price
$595.00
-
Original price
$595.00
Original price
$595.00
$595.00
-
$595.00
Current price
$595.00
This 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...
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Original price
$595.00
-
Original price
$595.00
Original price
$595.00
$595.00
-
$595.00
Current price
$595.00
16" CIRCLE Y OAK GROVE TRAIL SADDLE
Circle Y Saddlery
Original price
$2,999.00
-
Original price
$2,999.00
Original price
$2,999.00
$2,999.00
-
$2,999.00
Current price
$2,999.00
This 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...
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Original price
$2,999.00
-
Original price
$2,999.00
Original price
$2,999.00
$2,999.00
-
$2,999.00
Current price
$2,999.00
15" CIRCLE Y SNOWY RIVER FLEX2 TRAIL SADDLE
Circle Y Saddlery
Original price
$2,799.00
-
Original price
$2,799.00
Original price
$2,799.00
$2,799.00
-
$2,799.00
Current price
$2,799.00
This 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 details
Original price
$2,799.00
-
Original price
$2,799.00
Original price
$2,799.00
$2,799.00
-
$2,799.00
Current price
$2,799.00
15" CIRCLE Y SUNFLOWER FLEX2 TRAIL SADDLE
Circle Y Saddlery
Original price
$3,499.00
-
Original price
$3,499.00
Original price
$3,499.00
$3,499.00
-
$3,499.00
Current price
$3,499.00
This 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 ...
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Original price
$3,499.00
-
Original price
$3,499.00
Original price
$3,499.00
$3,499.00
-
$3,499.00
Current price
$3,499.00
15" CIRCLE Y SUNFLOWER FLEX2 TRAIL SADDLE
Circle Y Saddlery
Original price
$3,499.00
-
Original price
$3,499.00
Original price
$3,499.00
$3,499.00
-
$3,499.00
Current price
$3,499.00
This 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 details
Original price
$3,499.00
-
Original price
$3,499.00
Original price
$3,499.00
$3,499.00
-
$3,499.00
Current price
$3,499.00
18.5" TUCKER BIG BEND HERITAGE TRAIL SADDLE
Tucker
Original price
$3,699.00
-
Original price
$3,699.00
Original price
$3,699.00
$3,699.00
-
$3,699.00
Current price
$3,699.00
This 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...
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Original price
$3,699.00
-
Original price
$3,699.00
Original price
$3,699.00
$3,699.00
-
$3,699.00
Current price
$3,699.00
17.5" TUCKER BIG BEND HERITAGE TRAIL SADDLE
Tucker
Original price
$3,690.00
-
Original price
$3,690.00
Original price
$3,690.00
$3,690.00
-
$3,690.00
Current price
$3,690.00
This 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 details
Original price
$3,690.00
-
Original price
$3,690.00
Original price
$3,690.00
$3,690.00
-
$3,690.00
Current price
$3,690.00
17.5" TUCKER HIGH PLAINS HERITAGE TRAIL SADDLE
Tucker
Original price
$3,899.00
-
Original price
$3,899.00
Original price
$3,899.00
$3,899.00
-
$3,899.00
Current price
$3,899.00
This 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 details
Original price
$3,899.00
-
Original price
$3,899.00
Original price
$3,899.00
$3,899.00
-
$3,899.00
Current price
$3,899.00
15" CIRCLE Y OMAHA FLEX2 TRAIL
Circle Y Saddlery
Original price
$2,799.00
-
Original price
$2,799.00
Original price
$2,799.00
$2,799.00
-
$2,799.00
Current price
$2,799.00
This 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 details
Original price
$2,799.00
-
Original price
$2,799.00
Original price
$2,799.00
$2,799.00
-
$2,799.00
Current price
$2,799.00
16" CIRCLE Y WALNUT GROVE FLEX2 TRAIL SADDLE
Circle Y Saddlery
Original price
$2,999.00
-
Original price
$2,999.00
Original price
$2,999.00
$2,999.00
-
$2,999.00
Current price
$2,999.00
This 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 details
Original price
$2,999.00
-
Original price
$2,999.00
Original price
$2,999.00
$2,999.00
-
$2,999.00
Current price
$2,999.00
17.5" TUCKER ENDURANCE HERITAGE TRAIL SADDLE
Tucker
Original price
$3,699.00
-
Original price
$3,699.00
Original price
$3,699.00
$3,699.00
-
$3,699.00
Current price
$3,699.00
This 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 details
Original price
$3,699.00
-
Original price
$3,699.00
Original price
$3,699.00
$3,699.00
-
$3,699.00
Current price
$3,699.00
17.5" TUCKER CHEYENNE HERITAGE TRAIL SADDLE
Tucker
Original price
$3,899.00
-
Original price
$3,899.00
Original price
$3,899.00
$3,899.00
-
$3,899.00
Current price
$3,899.00
This 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 details
Original price
$3,899.00
-
Original price
$3,899.00
Original price
$3,899.00
$3,899.00
-
$3,899.00
Current price
$3,899.00
17" HIGH HORSE DAISETTA CORDURA TRAIL SADDLE
High Horse
Original price
$1,499.00
-
Original price
$1,499.00
Original price
$1,499.00
$1,499.00
-
$1,499.00
Current price
$1,499.00
This 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 details
Original price
$1,499.00
-
Original price
$1,499.00
Original price
$1,499.00
$1,499.00
-
$1,499.00
Current price
$1,499.00
16" CIRCLE Y OAK GROVE TRAIL SADDLE
Circle Y Saddlery
Original price
$2,999.00
-
Original price
$2,999.00
Original price
$2,999.00
$2,999.00
-
$2,999.00
Current price
$2,999.00
This 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 details
Original price
$2,999.00
-
Original price
$2,999.00
Original price
$2,999.00
$2,999.00
-
$2,999.00
Current price
$2,999.00
17" HIGH HORSE SKY MEADOW TRAIL SADDLE
High Horse
Original price
$1,599.00
-
Original price
$1,599.00
Original price
$1,599.00
$1,599.00
-
$1,599.00
Current price
$1,599.00
This 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 details
Original price
$1,599.00
-
Original price
$1,599.00
Original price
$1,599.00
$1,599.00
-
$1,599.00
Current price
$1,599.00
16" CIRCLE Y WALNUT GROVE FLEX2 TRAIL SADDLE
Circle Y Saddlery
Original price
$2,999.00
-
Original price
$2,999.00
Original price
$2,999.00
$2,999.00
-
$2,999.00
Current price
$2,999.00
This 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 details
Original price
$2,999.00
-
Original price
$2,999.00
Original price
$2,999.00
$2,999.00
-
$2,999.00
Current price
$2,999.00
16" CIRCLE Y JACKSON FLEX2 TRAIL SADDLE
Circle Y Saddlery
Original price
$3,399.00
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Original price
$3,399.00
Original price
$3,399.00
$3,399.00
-
$3,399.00
Current price
$3,399.00
This 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 details
Original price
$3,399.00
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Original price
$3,399.00
Original price
$3,399.00
$3,399.00
-
$3,399.00
Current price
$3,399.00
17" HIGH HORSE BEAR BROOK TRAIL SADDLE
High Horse
Original price
$1,499.00
-
Original price
$1,499.00
Original price
$1,499.00
$1,499.00
-
$1,499.00
Current price
$1,499.00
This 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 details
Original price
$1,499.00
-
Original price
$1,499.00
Original price
$1,499.00
$1,499.00
-
$1,499.00
Current price
$1,499.00
16.5" TUCKER ENDURANCE HERITAGE TRAIL SADDLE
Tucker
Original price
$3,699.00
-
Original price
$3,699.00
Original price
$3,699.00
$3,699.00
-
$3,699.00
Current price
$3,699.00
This 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 details
Original price
$3,699.00
-
Original price
$3,699.00
Original price
$3,699.00
$3,699.00
-
$3,699.00
Current price
$3,699.00
16.5" TUCKER EQUITATION TRAIL SADDLE
Tucker
Original price
$3,399.00
-
Original price
$3,399.00
Original price
$3,399.00
$3,399.00
-
$3,399.00
Current price
$3,399.00
This 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 details
Original price
$3,399.00
-
Original price
$3,399.00
Original price
$3,399.00
$3,399.00
-
$3,399.00
Current price
$3,399.00
15.5" TUCKER ENDURANCE TRAIL SADDLE
Tucker
Original price
$3,699.00
-
Original price
$3,699.00
Original price
$3,699.00
$3,699.00
-
$3,699.00
Current price
$3,699.00
This 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 details
Original price
$3,699.00
-
Original price
$3,699.00
Original price
$3,699.00
$3,699.00
-
$3,699.00
Current price
$3,699.00
17.5" TUCKER CHEYENNE HERITAGE TRAIL SADDLE
Tucker
Original price
$3,899.00
-
Original price
$3,899.00
Original price
$3,899.00
$3,899.00
-
$3,899.00
Current price
$3,899.00
This 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 details
Original price
$3,899.00
-
Original price
$3,899.00
Original price
$3,899.00
$3,899.00
-
$3,899.00
Current price
$3,899.00
16" CIRCLE Y GREY FOREST ENDURANCE FLEX TRAIL SADDLE
Circle Y Saddlery
Original price
$2,799.00
-
Original price
$2,799.00
Original price
$2,799.00
$2,799.00
-
$2,799.00
Current price
$2,799.00
This 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 details
Original price
$2,799.00
-
Original price
$2,799.00
Original price
$2,799.00
$2,799.00
-
$2,799.00
Current price
$2,799.00
17" HIGH HORSE IRON WEED CORDURA TRAIL SADDLE
High Horse
Original price
$1,499.00
-
Original price
$1,499.00
Original price
$1,499.00
$1,499.00
-
$1,499.00
Current price
$1,499.00
This 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 details
Original price
$1,499.00
-
Original price
$1,499.00
Original price
$1,499.00
$1,499.00
-
$1,499.00
Current price
$1,499.00
17" CIRCLE Y OMAHA FLEX2 TRAIL SADDLE
Circle Y Saddlery
Original price
$2,699.00
-
Original price
$2,699.00
Original price
$2,699.00
$2,699.00
-
$2,699.00
Current price
$2,699.00
This 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 details
Original price
$2,699.00
-
Original price
$2,699.00
Original price
$2,699.00
$2,699.00
-
$2,699.00
Current price
$2,699.00
15" ABETTA ORIGINAL ROUND SKIRT SADDLE
Abetta Saddle Co
Original price
$759.00
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Original price
$759.00
Original price
$759.00
$759.00
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$759.00
Current price
$759.00
This 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...
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Original price
$759.00
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Original price
$759.00
Original price
$759.00
$759.00
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$759.00
Current price
$759.00
17" ABETTA BRUSHPOPPER TRAIL SADDLE
Abetta Saddle Co
Original price
$799.00
-
Original price
$799.00
Original price
$799.00
$799.00
-
$799.00
Current price
$799.00
This 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 details
Original price
$799.00
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Original price
$799.00
Original price
$799.00
$799.00
-
$799.00
Current price
$799.00
16" CIRCLE Y SALT RIVER FLEX 2 TRAIL SADDLE
Circle Y Saddlery
Original price
$2,799.00
-
Original price
$2,799.00
Original price
$2,799.00
$2,799.00
-
$2,799.00
Current price
$2,799.00
This 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 details
Original price
$2,799.00
-
Original price
$2,799.00
Original price
$2,799.00
$2,799.00
-
$2,799.00
Current price
$2,799.00
15" CIRCLE Y ALABAMA TRAIL GAITER SADDLE
Circle Y Saddlery
Original price
$2,699.00
-
Original price
$2,699.00
Original price
$2,699.00
$2,699.00
-
$2,699.00
Current price
$2,699.00
This 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 details
Original price
$2,699.00
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Original price
$2,699.00
Original price
$2,699.00
$2,699.00
-
$2,699.00
Current price
$2,699.00
16" CIRCLE Y JULIE GOODNIGHT PEAK PERFORMANCE TRAIL SADDLE
Circle Y Saddlery
Original price
$3,299.00
-
Original price
$3,299.00
Original price
$3,299.00
$3,299.00
-
$3,299.00
Current price
$3,299.00
This 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 details
Original price
$3,299.00
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Original price
$3,299.00
Original price
$3,299.00
$3,299.00
-
$3,299.00
Current price
$3,299.00
16" CIRCLE Y WRANGLER FLEX 2 TRAIL SADDLE
Circle Y Saddlery
Original price
$3,299.00
-
Original price
$3,299.00
Original price
$3,299.00
$3,299.00
-
$3,299.00
Current price
$3,299.00
This 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 details
Original price
$3,299.00
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Original price
$3,299.00
Original price
$3,299.00
$3,299.00
-
$3,299.00
Current price
$3,299.00
14.5" CIRCLE Y OMAHA FLEX2 TRAIL SADDLE
Circle Y Saddlery
Original price
$2,699.00
-
Original price
$2,699.00
Original price
$2,699.00
$2,699.00
-
$2,699.00
Current price
$2,699.00
This 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...
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Original price
$2,699.00
-
Original price
$2,699.00
Original price
$2,699.00
$2,699.00
-
$2,699.00
Current price
$2,699.00
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.