Best Trailheads in 2026

4-WAY STRETCH FABRIC features a smooth, durable outer layer that is wind and abrasion resistant. The super soft, brushed inner layer wicks moisture away from your skin for maximum thermal efficiency.

TOUCHSCREEN COMPATIBLE- conductive fabric on tips of thumb and forefinger enables use of touchscreen devices.

SILICONE PALM GRIPS in a snowflake-shaped pattern enhance dexterity. These women’s running gloves have an attractive metallic swirl print on back of hand.

INNOVATIVE AND VERSATILE -This winter hat features a drop down fleece design for protecting your ears and neck from the cold and wind. As your body warms up, simply flip the ear wamer up to help regulate body temperature.

PONYTAIL HAT - The subtle ponytail opening accommodates most ponytails or braids and features reflective stitching for enhanced visibility in low light situations.

SUPER SOFT AND LUXURIOUS - The stretchy polyester / spandex fleece is comfortable, cozy and delivers a fabulous fit. Interior elastic band stretches to fit MOST head sizes; measures 22 1/2".

INNOVATIVE AND VERSATILE -This winter hat features a drop down fleece design for protecting your ears and neck from the cold and wind. As your body warms up, simply flip the ear wamer up to help regulate body temperature.

PONYTAIL HAT - The subtle ponytail opening accommodates most ponytails or braids and features reflective stitching for enhanced visibility in low light situations.

SUPER SOFT AND LUXURIOUS - The stretchy polyester / spandex fleece is comfortable, cozy and delivers a fabulous fit. Interior elastic band stretches to fit MOST head sizes; measures 22 1/2".

4-WAY STRETCH - The polyester/spandex with 4-way stretch, premium quality fabric of this sweat wicking headband is highly breathable and is water resistant. The brushed fleece interior feels soft and cozy against the skin.

CONTOUR FIT – The contoured shape provides full ear coverage, keeping you warm and delivering protection where it’s needed most. This running headband is warm enough for chilly winter days but also lightweight enough for cool fall and spring workouts. Measures 3” at the front and 4” over the ears; one size fits most.

PONYTAIL COMPATIBLE - The slit opening allows you to easily slip your hair through and provides a “snug solution” for your workout. It’s the perfect long hair headband, but can also work well for non-ponytail wearers. The form fitting styling is a great choice for extra warmth under a helmet.

4-WAY STRETCH - The polyester/spandex with 4-way stretch, premium quality fabric of this sweat wicking headband is highly breathable and is water resistant. The brushed fleece interior feels soft and cozy against the skin.

CONTOUR FIT – The contoured shape provides full ear coverage, keeping you warm and delivering protection where it’s needed most. This running headband is warm enough for chilly winter days but also lightweight enough for cool fall and spring workouts. Measures 3” at the front and 4” over the ears; one size fits most.

PONYTAIL COMPATIBLE - The slit opening allows you to easily slip your hair through and provides a “snug solution” for your workout. It’s the perfect long hair headband, but can also work well for non-ponytail wearers. The form fitting styling is a great choice for extra warmth under a helmet.

4-WAY STRETCH - The polyester/spandex with 4-way stretch, premium quality fabric of this sweat wicking headband is highly breathable and is water resistant. The brushed fleece interior feels soft and cozy against the skin.

CONTOUR FIT – The contoured shape provides full ear coverage, keeping you warm and delivering protection where it’s needed most. This running headband is warm enough for chilly winter days but also lightweight enough for cool fall and spring workouts. Measures 3” at the front and 4” over the ears; one size fits most.

PONYTAIL COMPATIBLE - The slit opening allows you to easily slip your hair through and provides a “snug solution” for your workout. It’s the perfect long hair headband, but can also work well for non-ponytail wearers. The form fitting styling is a great choice for extra warmth under a helmet.

4-WAY STRETCH - The polyester/spandex with 4-way stretch, premium quality fabric of this sweat wicking headband is highly breathable and is water resistant. The brushed fleece interior feels soft and cozy against the skin.

CONTOUR FIT – The contoured shape provides full ear coverage, keeping you warm and delivering protection where it’s needed most. This running headband is warm enough for chilly winter days but also lightweight enough for cool fall and spring workouts. Measures 3” at the front and 4” over the ears; one size fits most.

PONYTAIL COMPATIBLE - The slit opening allows you to easily slip your hair through and provides a “snug solution” for your workout. It’s the perfect long hair headband, but can also work well for non-ponytail wearers. The form fitting styling is a great choice for extra warmth under a helmet.

LIGHTWEIGHT – A lightweight, sports cap, it weighs only 2 ounces and is available in a variety of colors. The dark under bill keeps your face shaded and reduces glare. It’s a hiking and running essential that keeps you comfy without weighing you down.

MOISTURE WICKING PERFORMANCE - Quick drying polyester mesh fabric works to keep you dry and comfortable during every workout. The light polyester mesh construction means air flows freely and allows your skin to breathe.

ENHANCED VISIBILITY – This reflective running hat features silver accents on the back closure and on the ‘sandwich trim’ across the brim in addition to a reflective TrailHeads logo on the side. Be safe and be seen while working out!

Versatility & innovation - This winter hat features an innovative drop down fleece design for protecting your ears and neck from the cold and wind. As your body warms, simply flip up the ear covers to help regulate your body temperature.

Superior comfort - the plush polyester / spandex fleece of our men’s running cap is incredibly comfortable and delivers a secure fit.

Be safe, be seen - the curved 3” visor of our outdoor hat features a reflective accent along the brim for enhanced visibility. The TrailHeads logo is embroidered on the side.

Lightweight – This super lightweight performance sports cap weighs only 2 ounces. The dark underbill keeps your face shaded and reduces glare making it a hiking and running essential that won’t weigh you down!

Polyester mesh construction – Moisture wicking fabric works to help keep you dry and comfortable. The mesh construction of this quick drying cap delivers exceptional breathability and allows air to flow freely through the fabric.

Improved visibility – This cool sports cap for women features a stylish, reflective ‘sandwich’ trim that enhances visibility during those early morning and late afternoon running workouts.

THE ULTIMATE IN PONYTAIL COMPATIBILITY - the stylish, innovative, integrated loop design of this running headband for women provides a “snug solution” for ponytail wearers by holding your hair securely in place.

CHOOSE YOUR COLOR(S) - We offer a wide variety of fleece and binding colors to complement your winter wardrobe; from mild to wild, we’ve got you covered.

CONTOUR FIT - The contoured shape provides full ear coverage, keeping you warm and delivering added protection where it’s needed most. This fleece ear band for women measures 2.5” at the front and widens to 4” over the ears. The poly / spandex binding stretches and recovers to ensure the ear warmers provide a snug, comfortable fit. One size fits most.

LIGHTWEIGHT – A lightweight, sports cap, it weighs only 2 ounces and is available in a variety of colors. The dark under bill keeps your face shaded and reduces glare. It’s a hiking and running essential that keeps you comfy without weighing you down.

MOISTURE WICKING PERFORMANCE - Quick drying polyester mesh fabric works to keep you dry and comfortable during every workout. The light polyester mesh construction means air flows freely and allows your skin to breathe.

ENHANCED VISIBILITY – This reflective running hat features silver accents on the back closure and on the ‘sandwich trim’ across the brim in addition to a reflective TrailHeads logo on the side. Be safe and be seen while working out!

4-WAY STRETCH FABRIC - features a smooth, durable outer layer that is wind resistant. Our lightweight gloves have a soft, brushed, moisture wicking, inner layer providing maximum thermal efficiency.

TOUCHSCREEN GLOVES- conductive fabric on tips of thumb and forefinger enables use of touchscreen devices. Use our running gloves to adjust your workout playlist or text your running buddy without freezing your fingers.

SILICONE PALM GRIPS - The diamond shaped grips enhance dexterity and these black gloves have a terry cloth brow wipe on the back of the hand.

4-WAY STRETCH FABRIC - features a smooth, durable outer layer that is wind resistant. Our lightweight gloves have a soft, brushed, moisture wicking, inner layer providing maximum thermal efficiency.

TOUCHSCREEN GLOVES- conductive fabric on tips of thumb and forefinger enables use of touchscreen devices. Use our running gloves to adjust your workout playlist or text your running buddy without freezing your fingers.

SILICONE PALM GRIPS - The diamond shaped grips enhance dexterity and these black gloves have a terry cloth brow wipe on the back of the hand.

PONYTAIL HAT - our new winter hat for women features a high ponytail opening that allows you to comfortably wear your hair up when you choose.

WINTER TRUCKER- our women’s ponytail hat features a stylish wool blend plaid on the front panel of the trucker cap.

VERSATILE - perfect for changeable winter weather, our plaid ponytail hat features a drop down fleece. Wear the fleece down when your ears and neck need protection from the cold and wind; as you warm up fold the fleece up.

PONYTAIL HAT - our winter hat for women features a high ponytail opening that allows you to comfortably wear your hair up when you choose.

INSULATED WINTER TRUCKER- our women’s ponytail hat features a stylish, quilted trucker front panel with 200g Polatrec Powerfill Insulation. 100% of the insulation is recycled post consumer content.

VERSATILE - perfect for changeable winter weather, our quilted ponytail hat features a drop down fleece. Wear the fleece down when your ears and neck need protection from the cold and wind; as you warm up, fold the fleece up.

FOLDABLE BILL - This unstructured running cap is the perfect travel companion; it fits easily into a pocket or daypack. One size fits most; however, we realize we won't meet everyone's needs.

ATTRACTIVE FLORAL SCREENPRINT - A floral design appears in tonal colors on the sides of this pretty charcoal grey cap.

SUPER LIGHTWEIGHT (2oz. ) - As a low-profile hat this running cap is quick-drying and has a moisture-wicking sweatband for all day comfort.

EXCEPTIONAL BREATHABILITY AND COMFORT – The Women’s Print Ponytail Headband is highly breathable, wicks moisture and feels soft against your head. The contoured styling provides full ear protection.

PONYTAIL COMPATIBLE – The ponytail-compatible opening securely holds your hair in place during cool weather running workouts. This style also performs well for non-ponytail wearers. This one-size-fits-most headband measures 3” in front and 4.5” over the ears

MADE IN USA – Since 2002, TrailHeads has been passionately crafting performance headwear in New England. Designed and trail tested in Connecticut. Made in Massachusetts. Enjoyed worldwide.

LIGHTWEIGHT FABRIC - Our blend of polyester spandex has moisture-wicking technology. This spandex glove dries quickly to prevent your sweat from soaking the material and freezing your hands. NOTE: This lightweight glove is PERFECT for SPRING and FALL temperatures; NOT intended for winter's coldest days.

TOUCHSCREEN GLOVES - Conductive fabric on thumb and forefinger enables use of touchscreen devices.

TOPO GRIP - silicon in a fun topographical pattern on the palm enables better grip whether you’re holding your smartphone, your keys or your steering wheel. (not available on the black/grey option)

BLOCK THE BURN - our Men’s UV Hat will help you enjoy the outdoors longer. Our running hat offers 50+ UPF protection, the highest rating available for fabric.

DARK UNDERBILL - the 2 ¾” brim shades your eyes and the dark underbill reduces glare which will improve your sightline in a game of golf or tennis.

QUICK DRY HAT - the poly spandex fabric wicks away sweat and dries quickly to keep you comfortable during a run.

BLOCK THE BURN - our women’s running hat offers excellent UV protection with a 50+ UPF rating.

QUICK DRY HAT - this women’s running hat will keep you comfy all run long. Our women’s running hat is 97% polyester, 3% spandex.

DARK UNDERBILL - the 2 ½” dark underbill shades your eyes and reduces glare from the sun.

BLOCK THE BURN - our women’s running hat offers excellent UV protection with a 50+ UPF rating.

QUICK DRY HAT - this women’s running hat will keep you comfy all run long. Our women’s running hat is 97% polyester, 3% spandex.

DARK UNDERBILL - the 2 ½” dark underbill shades your eyes and reduces glare from the sun.

LIGHTWEIGHT FABRIC - Our blend of polyester spandex has moisture-wicking technology. This spandex glove dries quickly to prevent your sweat from soaking the material and freezing your hands. NOTE: This lightweight glove is PERFECT for SPRING and FALL temperatures; NOT intended for winter's coldest days.

TOUCHSCREEN GLOVES - Conductive fabric on thumb and forefinger enables use of touchscreen devices.

TOPO GRIP - silicon in a fun topographical pattern on the palm enables better grip whether you’re holding your smartphone, your keys or your steering wheel. (not available on the black/grey option)

TWO IN ONE VERSATILITY - Switch between fingerless gloves and cozy mittens. The mitten top can stow away in a pocket on the back of your hand - freeing your fingers for texting or taking photos.

SEPARATE THUMB TOPS W/ MAGNETS- Hidden magnets hold the thumb flaps in place when not in use. The separate thumb flaps ensure that these winter mittens have a snug, secure fit.

4-WAY STRETCH - Polartec Power Stretch Pro Fabric provides protection in cooler weather, making these feature packed men’s mittens great for active use. Note: designed for aerobic activity, not suitable for standalone use in extreme cold weather. The Men’s S/M are 3 ¾ inches in width, 8 ¼ -8 ¾ in length, the M/L are 4 ¼ in width and 8 ¾ - 9 ¼ in length.

BLOCK THE BURN - our women’s running hat offers excellent UV protection with a 50+ UPF rating.

QUICK DRY HAT - this women’s running hat will keep you comfy all run long. Our women’s running hat is 97% polyester, 3% spandex.

DARK UNDERBILL - the 2 ½” dark underbill shades your eyes and reduces glare from the sun.

IMPRESSIVE UV PROTECTION: Our men's running hat boasts a 50+ UPF rating, providing maximum protection against harmful UV rays. UPF-rated clothing benefits everyone but is particularly important for sun-sensitive individuals & those with fine hair or shaved heads. Stay protected and enjoy the outdoors with our advanced, high-quality fabric running hat.

ULTRA LIGHTWEIGHT: This lightweight performance cap gives you protection without sacrificing comfort or impeding your movements when running, hiking, biking, playing golf, or training. Made of 97% polyester, 3% spandex.

QUICK DRYING: Poly-spandex blend wicks away sweat and dries quickly to keep you comfortable during sweaty workouts. Lightweight fabric ensures breathability and allows air to flow freely through the cap.

LIGHTWEIGHT FABRIC - Our blend of polyester spandex has moisture-wicking technology. This spandex glove dries quickly to prevent your sweat from soaking the material and freezing your hands. NOTE: This lightweight glove is PERFECT for SPRING and FALL temperatures; NOT intended for winter's coldest days.

TOUCHSCREEN GLOVES - Conductive fabric on thumb and forefinger enables use of touchscreen devices.

TOPO GRIP - silicon in a fun topographical pattern on the palm enables better grip whether you’re holding your smartphone, your keys or your steering wheel.

PONYTAIL COMPATIBLE - The subtle, 4 ¼” slot opening is wide and stretchy so it accommodates most ponytails; this women’s headband style also works well for days when you choose not to wear a ponytail.

LUXURIOUSLY SOFT BRUSHED FABRIC - the unmatched softness of the brushed fabric makes this wide earband a favorite of TrailHeads’ popular ponytail headband collection.

LIGHTWEIGHT COMFORT - The moisture-wicking fabric is lightweight, but warm. Our headband can be used as under helmet ear protection for skiing or biking.

TWO SLOT PONYTAIL HAT - Designed to let you express yourself even when you are exercising, our women’s beanie has TWO ponytail openings. The discrete slot styling also allows you to wear our soft black skullcap with a high, low or no ponytail.

SUPERIOR STRETCH – our ponytail beanie has exceptional 4-way stretch and recovery. The circumference of this hat is 18.5" with a lot of stretch. With insulating properties, our winter hat is perfect as a helmet liner for winter biking. One size fits MOST.

STYLISH REFLECTIVE DETAILS – This ponytail hat features a reflective logo and cover stitching that accentuate its solid black fabric. These accents give you enhanced visibility on the road during dark winter runs.

PONYTAIL COMPATIBLE - This winter beanie is the perfect addition to your cold weather wardrobe - set your ponytail free as you snowshoe, skate, or run errands. The 2 ½” ponytail opening is large enough to accommodate most ponytails.

EXCEPTIONAL STYLE - This ponytail beanie made of luxuriously soft acrylic knit in a classic cable pattern creates an attractive look for all your cold weather outdoor activities.

SUPERIOR COMFORT - The incredibly soft high pile polyester fleece ear band provides another element of comfort, luxury and warmth where you need it most. This women’s ponytail beanie is one size fits most.