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Writer's pictureBen Easley

Trail Leadership 101: Best Practices for Hosting Overlanding and Off-Road Events

So you've been on a few overlanding trips and think you're ready to lead a group yourself. Awesome! Leading groups to exciting new places can be a lot of fun, but like most things in life, a successful event will depend heavily on your preparation. While being an experienced off-roader doesn’t hurt, it’s not essential for leading a successful overland journey (unless there’s an abundance of technical terrain). In fact, preparation and communication skills are the most important qualities of a trip leader. This guide will cover the essential tasks, skills, and considerations you need to make your trip enjoyable for both the group and yourself. If the group enjoys themselves, chances are you will too!


As trip leader, bring a smile and positive can-do attitude to your event.

Be Yourself

In most cases, people are just excited to be out in the wilderness, and chances are you are too. If you show the group you’re enthusiastic about the event, they’ll mirror your energy. Whether you’re out with friends or people you’ve just met, you want them to be excited about the experience and confident in your leadership skills—this is where planning, communication, and leadership come into play.


Planning Your Event

As the trip leader, it’s your responsibility to come up with a game plan—a trip route and itinerary. Depending on where you’ll be exploring, acquaint yourself with the local rules and regulations (fire restrictions are a big one out west) and ensure your planned route is open and accessible to vehicles. We understand this can be difficult in remote, lesser-traveled areas, but at least have a Plan B in place.


Some common rules and regulations to check include:

  • Fire restrictions

  • Vehicle access (some areas have seasonal closures)

  • Dispersed camping regulations

  • Permits and/or fees

  • Pets (typically applies at certain National Parks)

  • Vehicle length and/or trailer restrictions


Beyond rules and regulations, there are practical considerations to research. Depending on the length of your trip, not all of these may apply:


Practical considerations:

  • Refueling opportunities

  • Opportunities to buy food/water

  • Communications (GMRS, FRS, HAM, etc.)

  • Group size

  • Expected weather

  • Trip distance/daily driving distance

  • Vehicle requirements (Are you soft-roading or tackling technical trails that require a high-clearance 4x4?)


A few notes regarding group size and daily driving distance: Remember, you’re only as strong as your weakest link. The larger your group, the greater the possibility of vehicle-related issues, which can slow the pace. If traveling through a busier or more popular area, we recommend limiting your group size to 6-8 vehicles. If the group is larger, consider breaking it into smaller groups and staggering start times to avoid unnecessary trail congestion.


Many new leaders assume “more is better,” but trying to cover too much ground can create an exhausting, unenjoyable experience. Be sure to allow plenty of time for snack and lunch breaks, as well as opportunities to explore outside the vehicles. Most people enjoy traveling at a leisurely pace and breaking up the time spent behind the wheel.


A final note on event attendance: Folks will inevitably drop out or no-show, especially for free events. Stay in communication with your group, and if you have a message board, group chat, or email thread, check in with attendees 2-3 weeks before the event, then again a week before to confirm attendance. While not always true, we’ve noticed a correlation between people who don’t communicate and their likelihood of not attending.


Communication & Leadership

As a leader, it’s important to bring a positive, can-do attitude once you hit the trail. But even before your event begins, first impressions matter, often starting when someone reads or finds out about your event. This is where planning and communication play a big role.


Your planning should result in a clear and appropriately detailed itinerary. Just as a coach creates a game plan for their team, your itinerary is the game plan for the group and will act as your guiding star. Generally, your itinerary may include daily mileage, points of interest, refueling opportunities, fees/permits, and possible camp locations. We’ve included a sample itinerary at the bottom of this article to show the items we typically include for our events.


We'll cover this in greater detail in the next section, but repetition is key to ensuring everyone in your group understands the plan. In addition to your morning briefing, it doesn’t hurt to share details the night before while gathered around the campfire.


Always designated a sweeper so no one is left behind.


Running the Event

Set the tone each day by gathering the group to review the day's itinerary. These daily meetings are also an opportunity for Q&A. Ensure everyone is using the same communication channel, and designate a sweeper (the last vehicle in the convoy) each day to ensure no one is left behind.


It’s easier than you think to lose someone on the trail. If there’s a turn or intersection, require that a vehicle waits until the next vehicle in line reaches the intersection and has a clear line of sight of the vehicle behind them. We recommend waiting until the next vehicle is within 50 feet of yours.


Create an enjoyable environment for the group by allowing time for snacks, lunch, bathroom breaks, and chances to get out of the vehicle. Just as a coach monitors their team’s morale, you should pay attention to the group’s mood. If your itinerary is leading to more time behind the wheel than expected, be flexible and adjust as needed.


Your goal isn’t to stick rigidly to the itinerary but to create an enjoyable experience. If a significant delay arises due to vehicle issues, let the group know that no one will be left behind (this should be communicated on day one). Adjustments to the planned itinerary and route may be necessary, so keep the group updated on any changes.


Recoveries and Spotting

Most vehicle damage and injuries occur during recoveries and spotting. The best recoveries are those that never happen—do your best to avoid situations where vehicles get stuck. If recovery is needed, create a plan. If someone is more experienced in recoveries, you can cede authority to them. Once the recovery begins, ensure everyone knows the plan and stays in safe locations.


Spotting can also be dangerous. When a spotter is required, designate one person to communicate with the driver. If multiple people are shouting instructions, interject and remind the group that only one person should spot. You can work with a team of spotters, but only the primary spotter communicates with the driver.


Safety and Group Management

During your day one briefing, cover safety protocols. Emphasize safe driving behavior, adherence to regulations, and no tolerance for driving under the influence. Stress the importance of T.R.E.A.D. Lightly and Leave No Trace principles. If someone drives unsafely, address it immediately.


Also, carry at least some basic recovery gear: a shovel, kinetic rope, tow rope, and shackles (soft or bow). While winches and traction boards aren’t essential, they do offer extra security. A satellite communication device like a Garmin InReach or Zoleo is useful if you need emergency services or can’t reach loved ones. Many modern smartphones also send S.O.S. alerts to first responders.


Remember, the main objective is to have fun!

Conclusion

Leading an overlanding trip is a rewarding experience that goes beyond handling a vehicle on rugged terrain. It’s about preparation, clear communication, and thoughtful leadership. By setting the tone with proper planning, safety protocols, and flexibility, you can ensure your group has a memorable and enjoyable experience.


Success as a leader isn’t just about reaching the destination—it’s about guiding your group through the journey. Keep participants informed, energized, and engaged with strong communication and a positive attitude. Adapt to the group’s needs, and prioritize their enjoyment over rigidly following the plan.


Ultimately, leading is about creating experiences that inspire others to come back for more. The preparation, effort, and leadership you bring will set the standard for future adventures, ensuring everyone walks away with great memories and a stronger desire to return to the trail.


------------------------------------------- Sample Itinerary

Dates: Oct 1-3

Trip duration: 3 days/2 nights (meetup Friday AM, head home Sunday AM)

Vehicle Requirements: 4x4, AWD (high clearance), and Sprinter 4x4s

GPX File: [download link]


Trip Lead: Joe Schmoe


Meeting Location [date]

Upper Lake @ 9am

775 CA-20, Upper Lake, CA 95485 (Chevron)


Please make sure you arrive with a full tank of fuel and all of the necessities required for the duration of the trip. Cheapest gas in the vicinity is at Coyote Valley Casino in Redwood Valley about 5 minutes north of Ukiah and the highway 20 exit.


Documents/Fees

n/a


Camping

We'll be camping at all dispersed locations. With that in mind, bring appropriate gear for packing out your trash, and a portable toilet.


Pets

Please let me know how you guys feel about pets on this trip!


Gear & Fuel

Bring appropriate hiking/outdoor gear. [this should be updated with expected weather based on time of year ]. Please have a GMRS radio either handheld or mounted in your rig as this will be our form of communication on the trip.


Medical Info / Emergency Contact

Please print a copy of pertinent medical info and emergency contact info (at least two persons) on a card/piece of paper, and have this attached to your visor.


Comms: GMRS channel 15, freq 462.550

Firewood: please bring firewood if you can!



Day 1 | Upper Lake to Hull Mountain

Camp: Grizzly Flats or Skunk Rock

Mileage: 66 miles (mostly pavement with some dirt)

Day 1 starts with pavement, then the duration of of the trip is all dirt (except a few short miles around Lake Pillsbury)

  • Lake Pillsbury

  • Eel River

  • Hull Mountain Lookout

  • Drive to top of Bald Mountain

  • Find camp!


Day 2 | Hull Mountain to Board Tree Campground

Camp: Board Tree Campground vicinity

Mileage: 80 miles (95% dirt)


  • Stop at Black Butte River Ranch

  • Visit the Eel River

  • Visit Howard Lake (great lunch stop)

  • Anthony Peak fire lookout

  • Hike to top of Black Butte

  • Visit Ocean Viewpoint

  • Find camp!


Day 3 | Drive Home!

Take FH7 / Hwy 162 down to the mountain to I-5 near Willows.

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