While many people worry about finding good places for new companions to go on nature outings, the reality is that the hardest part is anticipating and avoiding the small failures that so easily turn a nice walk in the woods into a grueling test of endurance. That difficult trail, sore and uncomfortable shoes, inability to easily turn back, and worst of all, failure to have a thoughtful conversation about expectations before you head out the door – all of these are easily avoided by good nature outing planning. The trip does not have to be long or go far into the country. In fact, just the opposite.
Start with the person, not the destination
The first step in planning a good nature outing is to ask some basic questions about your companion such as how much walking they think they can do, are they used to being on uneven ground, do they have any fears such as of heights, of dogs, of insects, etc. and what they consider to be problems such as weather, distance from car etc.
This is a good time to explore with your companion what the purpose of the trip will be. A quiet wildlife walk, a photography excursion, a nature walk to identify plants and trees, and a beginner's hike are all best done at different speeds. For example, someone interested in examining the habitat of animals will probably get frustrated on a fast-paced, long distance hike. Someone else who wants to start to gain confidence on the trails might get frustrated on a trip with many stops to adjust equipment.
Treat the least experienced person on the trip as the planning limit for the trip. That does not have to mean you are treating them in a patronizing manner. Rather, you are ensuring that the trip will remain an experience in nature for all parties involved and not an endurance contest.
Choose an easy route with exit options
An easy trail is not necessarily a short one. Surface, degree of slope, exposure, degree of difficulty to navigate, amount of shade, and whether or not there is an easy place to turn around all need to be considered when planning a trip for a beginner. A short trail with loose rock and many steep sections can be much more difficult than a longer, relatively flat trail.
Before you leave for your trip check the route description and map for your chosen location from a reliable local source. Check access, and any specific parking requirements for your trip. Check for any current closures on public land, and verify hunting seasons and restricted areas with the relevant local land manager or official website.
An out-and-back route is usually better for a first time companion as they can always see where you are going and turn back when ever they want. Bring an offline map and let someone at home know where you will be.
Set a pace that leaves room for noticing
A slow pace for a first time companion's first nature outing is usually better than a fast one, even for an experienced outdoorsperson. Time should be allowed for shoe changes, for water drinking, for examination of animal and bird tracks and for lots of other things. Conversations can also be time filled by a leisurely pace of travel.
Using natural way points on the trail such as a view point, bend in the trail or a spot to sit is also a good way to look at the way you are traveling. You can decide as a group whether you continue on or not.
It may become obvious halfway down the trail whether or not someone is managing. Be able to recognize signs of fatigue, such as providing shorter responses to queries, stumbling over their own feet, reluctance to take a break, or falling far behind but stating that they're fine.
Pack for comfort, not for a gear demonstration
The useful items are items that will solve problems for you on the way and not add to your burden. Water, a small amount of food, bandages, a fully charged phone, a map, rain wear and a light weight layer or two will cover most of the needs for a short day out. Additionally, you may want to bring personal items, such as medications, or items that will assist with your companion's disability or needs.
Sole care is possibly the most important part of gear choice – give your companions a try-out for a short local trip before heading out on the longer trip in order to test for any signs of rubbing or hotspots. A single unpleasantly placed blister on a long trip could dominate the rest of the day.
Don't lend equipment that you aren't familiar with to use, such as trekking poles, binoculars, a rain shell and a pack. Explain to your partner what he or she is doing with each piece of equipment before you set out. Make sure to pack lightly so that you can easily take off any layer of clothing. A number of layers with light clothing will provide better protection in unpredictable weather than one bulky item.
Build hiking safety into the conversation
Plan for safety, but share your plans with your companion so they know what to do in case of separation or loss of phone service. Discuss the possibility that one of you might want to head back in different directions, and agree that either of you can call for a return to the car at any time.
Pay attention to your footsteps as well as the weather. Keep a safe distance from wildlife, be sure to pack out all your food and be sure to follow all posted rules and regulations. This includes knowing the current hunting seasons and wearing the proper visibility gear when hunting. And don't assume that just because you know a certain route that it is open to public access the entire year. Requirements for public access can vary greatly from season to season and even from year to year.
A short check list before leaving the car: water, layers, charged phone, known route, return time and way shared.
Leave the door open for the next outing
Keep your first outing small enough to end it before your companion is completely exhausted. Turn back while it is still good weather or fail to reach the end of the spur of the last leg of the trip.
Consider feedback from your companion on how the trip went. How did they feel along the way? Were there places where it felt too hard or where it felt too easy? Look to their feedback for what aspects of the trip were favorites and how you might change up subsequent trips in order to include aspects that your companion especially loved.
There is one measure by which to judge your success: did your companion have such a good time that they want to go out again? Choose a relatively short route and travel lightly, with plenty of opportunity to change your plans should you need to.