How to Plan a Great Outdoor Trip

From choosing the right adventure to knowing what to pack, a little preparation goes a long way.

Planning an outdoor trip is part of the fun. You start looking at destinations, researching trails, watching videos, and imagining what it might be like to actually be there. But somewhere between finding an exciting route and figuring out what you need to bring, things can get a little overwhelming. How difficult is the terrain? What kind of gear do you need? Are you physically prepared? And what happens if something doesn't go according to plan?

As an outdoor guide, I've seen how much of a difference good preparation can make.

You don't need to have every detail figured out or own the most expensive equipment. But understanding a few important things before you go can make your experience a whole lot more enjoyable. Here are four things I'd recommend thinking about when planning your next outdoor adventure:

1. Look beyond the difficulty rating

One of the first things people look for when researching a trip is its difficulty rating. Easy. Moderate. Challenging. Those descriptions can be helpful, but they don't always tell the whole story. A 10-mile hike on a relatively flat trail is very different from a 10-mile hike with steep climbs and rocky terrain. The same goes for cycling. Riding 30 miles on pavement isn't the same as riding 30 miles on loose gravel through the mountains.

Before choosing a trip, take a closer look at the distance, elevation gain, terrain, and expected pace. And think about what you've actually been doing lately, not just what you know you're capable of on your best day. There's nothing wrong with choosing an adventure that challenges you. The goal is to understand what that challenge involves.

2. Figure out what you actually need to bring

Outdoor gear can be a rabbit hole. There are endless opinions about the best boots, backpacks, jackets, bikes, and equipment. And if you're new to an activity, it can be difficult to figure out what's necessary and what's just nice to have. Start with the basics. What will the weather be like? How long will you be outside? Will you need to carry your own equipment? Is there anything specific to the activity or terrain? If you're booking a guided trip, check what equipment is included and what you're responsible for bringing. And if something isn't clear, ask before buying new gear. One of my biggest recommendations is to test what you already own. Wear your hiking shoes before a multi-day trip. Take your bike out with the setup you plan to use. Practice packing your bag. A little familiarity with your equipment can save you a lot of frustration later.

Intro to Backpacking in the Appalachian Mountains

3. Know what support is available

Not every outdoor adventure works the same way. Some trips are fully self-supported, meaning you carry your own gear and manage much of the logistics yourself. Others include guides, transportation, equipment, meals, or additional support. Neither approach is necessarily better. They're just different experiences. If you're booking a guided adventure, find out what's included. Will you carry your own luggage? Are meals provided? Is transportation arranged? What happens if you can't complete a section of the route? For cycling trips, you might also want to ask about mechanical assistance or vehicle support.

The important thing is understanding how the trip operates before you arrive. That way, you're not making assumptions about services that may or may not be included.

4. Get to know the people you're going with

If you're joining a guided trip, spend a little time learning about the people leading it. Where do they guide? What kind of experience do they have? What do they enjoy about the places they explore?

I think this part of planning is often overlooked. A good guide brings more than navigation and logistics to an adventure. They bring knowledge, stories, and a perspective on a place that you might not have experienced otherwise. And when you're spending several days outdoors with someone, it's nice to know a little about them beforehand.

It's one of the reasons we put so much emphasis on the people behind the adventures at Lost Terrain. Our marketplace features independent guides and small guiding companies who create and operate their own trips. We help travelers discover their experiences, learn about the people leading them, and book through our platform.

Lea & George, founders and Trip Leaders for Chilco Bike

Leave a little room for the unexpected

Here's the thing about outdoor adventures: you can't plan for absolutely everything. Weather changes. Trails get muddy. Sometimes the best moments are the ones you didn't see coming. Good preparation isn't about eliminating every surprise. It's about understanding the important details so you can spend less time worrying about what you forgot and more time enjoying where you are.

Do your research. Ask questions. Bring what you need. And choose an experience that feels right for you.

Then leave a little room for the adventure itself.

— Eli Adams

Founder & Outdoor Guide, Lost Terrain Tours