The Life of a Backroads Trip Leader

Preview Leaders Laughing in California's Wine Country

I've been a Backroads Trip Leader for seven years and one of the most frequent questions I'm asked by my guests is, "What's the life of a Backroads Trip Leader like?" It's a simple question, but not an easy one to answer. When I applied for a leader position at Backroads, I had no idea of the complexity of this job and how much it goes beyond any regular work environment.

A Day in the Life of a Backroads Trip Leader

As I had imagined, we're up early! We're staging bikes, filling water bottles, putting out a snack table, doing food preparation for picnics, pumping tires, hitching our trailer, and sneaking in a quick breakfast where we talk through our logistics and support plan for the day. Then we're greeting our guests, answering questions and giving a "route rap" - our daily briefing about the cultural highlights of the day as well as route options, safety tips, points of interests and our favorite places to stop along the way.


Preview Backroads Leaders giving a Route-Rap

As a team, we take turns each day - one of us driving the van and one of us biking with the guests (or on a hiking trip, likely two of us on the trail and our support leader driving). On the road or trail, we're offering guests route support, doing bike adjustments and, answering the question "what's that?", sharing local insights and offering support stops along the way. One of us may also be preparing a gourmet picnic full of our local treats then shuttling guests to the next luxury hotel, where their luggage awaits because we've already transported it there.

Preview Backroads Leader Presents a Picnic

Once all of our guests have safely finished the day's activity and are at the hotel, we're hurrying to get ourselves and all the equipment cleaned-up and organized. We're putting on evening attire for a camp cookout, a meal at a local restaurant or a seven-course Michelin-starred dinner. During dinner, leaders are making sure our guests are happy, translating menus and daily specials, and giving information for the next day. Then we're off to retire to bed - but only after conferring with our co-leaders to ensure everything is organized, thoroughly planned and ready for tomorrow.

Preview Backroads Trip Leaders in Action

Phew! There are so many hats that we wear as a Backroads Trip Leader in any single day - cyclist, hiker, cultural interpreter, bike mechanic, chef, public speaker, motivator, professional driver, snack-master, chalk-board artist, translator, problem-solver, teacher, cheerleader, nature guide... and the list could go on. So, while our days might start with pumping tires under olive trees in the Tuscan countryside, it's filled with solving problems, being flexible and resourceful, and doing everything we can to make our guests happy.

The most important part of our job is making sure that all our guests are having a great experience, even if that means different things to different guests. While Trip Leaders are certainly active travel guides, we're also very much customer service providers that just happen to work outside in beautiful and amazing places.

Travel Perks

A huge perk of the Backroads Trip Leader lifestyle is travel - whether it's getting intimately familiar with our National Parks or traveling abroad, we get to work in everyone's bucket list locations all over the world! While sometimes we're traveling frequently, other times we are immersed in one incredible region for the bulk of a season, getting to know it intimately and learning to call it our second home. Or third. Or fourth... As leaders, we're outside every day, and it's one of the few jobs where you regularly think to yourself, "Am I really getting paid right now?!"

Preview Backroads Leaders in Biking Gear

While travel comes with some challenges (more on that below), it's also one of the most rewarding parts of the job. In my time at Backroads, I've had the pleasure of ringing in the New Year in Cambodia while watching the sunrise over Angkor Wat, cycling the lavender-laden island of Hvar in Croatia, and spending many beautiful days under the Tuscan sun watching the seasons change: from green wheat fields dappled with red poppies in the spring to sunflower-filled valleys in the summer to hay bales and yellow rolling hills in the fall. What a gift!


Our Days Off

With so many on-the-job perks and the gift of traveling to the most beautiful locations in the world, what do we do on our days off? Guests always want to know where we live and what we do once a trip is over. When we've said farewell to our guests, we head back to our regional field staff house. The field staff house is our little hub - a place to do our laundry, cook a meal, connect with our friends and re-boot before the next trip. In some smaller Backroads regions, this might be an apartment with 4 or 5 field staff living together, and in some bigger regions it might be 25 of us living communally.

Preview Backroads Leaders on their day off

On days off we're usually playing just as hard as we work. A normal day off might include big group hike or bike ride, exploring a part of the region we don't see on a trip or making a big group dinner. This is our time for personal adventures, but also our time to jump on Skype and reconnect with our friends and family back home, put our feet up and recover. While field staff house living is a blast, it can also be one of the biggest challenges of the leader lifestyle - it takes a lot of energy to be "on" all week and come back to such a social living situation during your downtime. There's finesse in learning how to make it work. Going for a run, doing yoga or escaping to a local café with a book are all ways to take a solo break after being around so many social, outgoing, interesting, creative and fun people.

The Challenges

The job of a Backroads leader and other field staff is a lot of fun and a lot of work, all mixed together. It's not for everyone - it takes a lot of self-awareness, grit (and being okay with constantly having bike grease under your fingernails), and the ability to take care of both other people and yourself for a whole season on the road. When we're leading trips, we're not on a personal adventure - we are doing a customer service job and taking care of each of our guests so that they have the best trip possible. If it sounds intense, it is! From about May to October, most of us live out of one or two carefully curated bags so that we're able to move around easily, be prepared for different climates and weather, lead different types of trips, and don the perfect mix of outdoor apparel and fine-dining attire.

Preview Backroads Leaders Gathering

During our time off, while surrounded by all the new friends we make in the season, we also must prioritize ways to stay connected to our friends and family back home, which also takes work!

The Backroads Community

The biggest highlight of this job is being part of the Backroads community. Most of us will tell you that our best friends are the colleagues we met working for Backroads.

Preview Backroads Leaders and Guests

In addition to the incredible life-long friendships we make with each other as Backroads colleagues, another deeply satisfying part of the job is connecting with our guests and learning their diverse backgrounds and inspiring stories. Recently, I had an 81-year-old guest on a challenging Tuscany biking trip (her 85-year-old husband rode an e-bike, but not her!), who was one of the most inspiring and interesting guests I've ever had. In addition to appearing in a bike commercial as "Grandma Joan," she's done voice-overs for NPR, run for political office, narrated walking tours and raised a family. When I asked her what she was most proud of, she answered "All the marathons I ran in under three hours." Wow! It's incredible to get the chance to meet so many interesting people with so many stories to share. And in this case, the real gift for me is that we don't live far from each other, so "Grandma Joan" and I already have a biking date set up for when I'm back home this winter.

Honestly, I can't think of any other job that compares to being a Backroads Trip Leader - it's a job, a lifestyle, and a huge opportunity to challenge yourself and grow in ways that make you more capable, kind and aware. On top of that, year after year, you continue to meet incredible guests and incredible co-leaders. It's not for everyone - you have to be grounded, flexible and resourceful; you have to like working hard making people happy. As a leader, I've pumped many a bike tire and poured countless bags of peanut M&M's before 7:00 in the morning, but working hard, playing hard and making meaningful connections on Backroads trips continues to be an immensely satisfying experience.

Preview Backroads Group in Cambodia
Do you or someone you know have what it takes to be a Backroads Trip Leader or Field Staff? We want to hear from you! ! Apply at
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