High Trailers
High Trailers Take on the Annapolis 10 Mile Run
Congratulations to High Trailers David Foust and Tyler Shaw, who took on the Annapolis 10 Mile Run this weekend! The annual race takes runners on a challenging 10-mile course through historic Annapolis and across the Severn River. David is also busy preparing for Ironman Maryland in Cambridge and had a big weekend of training, completing…
Read MoreHigh Trail Annual Golf Scramble 2026
Yesterday, our team got together in Annapolis for our annual High Trail golf scramble! It was a brilliant morning and a great chance to spend time together outside of the office. High Trailers take competition pretty seriously, so there was plenty at stake on the course! We always enjoy having the team together in person,…
Read MoreHigh Trailer Amanda Schafer Runs the Boston Marathon and Raises Over $10,000 for a Great Cause
At High Trail, we love celebrating the people behind our business and the things that matter to them outside of work. This month, we’re proud to recognize our teammate Amanda Schafer, who completed the iconic Boston Marathon. Alongside months of training, she also raised more than $10,000 for Good Sports, helping provide sports equipment to…
Read MoreReflecting on IWD: Supporting Women in the Workplace and Beyond
On International Women‘s Day, I want to express my gratitude to the women on our High Trail team, and the many women who have inspired me, supported me and developed me throughout my career. The theme of this International Women’s Day is “Give to Gain”, encouraging us to support the many non-profits that advance gender equality…
Read MoreFurther Together: Team Building Through Improv
As a team, you’ll often find High Trailers out on the golf course or the pickleball court, focusing on collaboration through sport. But this week, during our team meet-up in Annapolis, we opted for a different kind of challenge: an improv class! It was a refreshing change of pace to step into a completely different…
Read MoreAppreciating the People Who Make Our Work Possible
With Thanksgiving approaching, we want to take a moment to recognize the people who make our work possible. To our clients, members, family and friends, thank you for your support, your trust and the part you play in our journey each year. Wishing you a Happy Thanksgiving from all of us at High…
Read MoreShaping Our Future Together as a Team
This week, High Trailers gathered in Annapolis to talk about the future and spend time together as a team. On day one, we focused on who we want to be, how we’ll continue to elevate the work of our members and clients, and what it means to keep our customers at the center of…
Read MoreFurther Together: Building a Stronger Team to Elevate Client and Member Success
Our mission is to elevate the work of our members and clients and that starts with building a stronger, more self-aware team. Last week, High Trailers took part in an Insights Discovery workshop to better understand ourselves and each other. One of the biggest takeaways was gaining a better understanding of how people…
Read MoreFurther Together: High Trailers in Annapolis, MD
This week, High Trailers came together in beautiful Annapolis, MD, to reflect on 2024 and plan for the year ahead. In true High Trail fashion, we added some energy and fun with a team pickleball tournament – huge congratulations to Drew Evans and Pat Morrison for taking home the championship! These moments remind…
Read MoreWhat outdoor activities keep you feeling your best?
We believe a healthy team is a happy team, and that’s why we prioritize getting outside. High Trailer Amanda Schafer has her routine down, taking her dog Koda to Chesapeake Beach for some fresh air and a reset in nature. This is your reminder to use your time outside the office to get…
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