TrailHeads is a Kent-based business that markets a distinct collection of headbands, gloves, hats, and accessories for runners and outdoor enthusiasts. We visited the team and took some gear out to the Appalachian Trail for a test hike!

Post sponsored by TrailHeads

TrailHeads, the story so far…

Stephanie and Ed Raftery started TrailHeads back in 2002 while working out of their small, one-bedroom apartment in New York City. The two worked tirelessly to develop their initial products starting with the original ponytail hat.

Stephanie and Ed working on their next design, with the help of brand ambassador Winnie!

The brand is known for its use of premium fabrics and innovative styles. Think ponytail compatible headbands and convertible running mittens!

In 2006, Stephanie, Ed and their two daughters relocated to Kent. Their growing business began a steady transition from focusing on selling to “brick & mortar” retailers to also selling directly to customers online.

Between the demands of a growing family and a growing business, the Raftery’s house in Kent filled up and at times overflowed. They had inventory and cardboard boxes in almost every room, and a seasonal storage trailer parked in the driveway.

Eventually, it was time to move beyond the “kitchen table” fulfillment model. TrailHeads now resides in a beautifully renovated workspace just down the road from their home.

It takes a micro multinational crew

In addition to the Connecticut based team of six, TrailHeads has grown into what Stephanie and Ed like to call a “micro multinational”. They employ a “global mix” of employees. A Vietnam-based production manager and a Philippines based customer service representative. A South Carolina based graphic artist, a website developer based in India, and a digital advertising consultant based in Minnesota. 

Whether it’s hiking, skiing, snowshoeing or participating in local running events throughout the year, the TrailHeads team is passionate about their outdoor adventures.

Katie Burns recently took a mini-sabbatical from TrailHeads to hike the 272 mile Long Trail in Vermont.

Appalachian trail ready

Twice a week, the TrailHeads Run Club takes a midday break and heads to the Appalachian Trail to get in a quick workout. Inspired, we joined Stephanie, Ed, and Winnie (photobomber extraordinaire) for a short hike to do a spot of TrailHeads gear “blogeling.”

4 reasons convertible mittens rule!

  • They are “snackessible”. Flip the mitten top back and tear open that granola bar wrapper with ease.
  • Enjoy a winter walk with your pooch. Handle a leash, pull out cookies, toss a ball, and stay warm.
  • Change the exposure on your camera without feeling the exposure! Mitten top on while you wait for the right light, fingers free for the quick click.
  • Flip your mit to text your running buddies about the amazing new trail you’ve found.

Work hard, give back

TrailHeads is passionate about giving back and is committed to helping people overcome challenges of all kinds. Co-founder Ed Raftery has a degenerative retinal disease and is legally blind. Ed’s personal experience led TrailHeads to begin working with Guiding Eyes for the Blind

The entire team works to organize the annual Lake Waramaug Polar Bear Run, held in late February each year. In recent years, it has also been a fundraiser for Guiding Eyes for the Blind. Over the last few years, the Polar Bear Run has raised $6,600 for this amazing charity.  The goal for 2020 is to reach the $10,000 mark!

Blaze Your Own Trail Scholarship

In February 2020, TrailHeads will be awarding its first Blaze Your Own Trail scholarship to one exceptional student. They’ll be giving out a $1,000 scholarship to go towards any education-related expense. Applications are open to high school seniors, undergraduate, and graduate students. Applications are open until January 15th of 2020. More instructions on how to apply can be found on

TrailHeads gear can be found on, on Amazon, and at running specialty retailers across the U.S.

Words: Bev/ Pics: Lora

This post has been sponsored

Join the Conversation

  1. I have a couple of Trailheads items and they are the best. Especially love the brimmed hat with the fold down ear flaps.

  2. Lora and Bev – It was so fun to work with you guys! You’ve inspired us to work harder and have more fun at the same time 🙂
    Thank you for telling our story so authentically and taking such great photos. See ya around!
    Stephanie, Ed and everyone here at TrailHeads

    1. Thank you!! ❤️ See you on the trails!

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