Except to hardcore hikers, not every day is great for hitting the trail. This is especially true for casual hikers and families with children. Dry, pleasantly warm days with limited wind always are best for hiking but are rare indeed.
The weather probably is the most important factor to consider. Always check the forecast for the area you plan to visit. If thunderstorms or snow are predicted, skip the hike. Wind and a sprinkle here or there probably are fine for most adults but know that many children will find it pure misery.
Whenever high winds, precipitation and cold temperatures are forecast at lower elevations, they will be worse in the mountains. Winter, early spring and late autumn are dangerous times to hike high mountains. Lower elevations and hilly country are best hiked on pleasant spring days; late summer is best for high mountains.
The season also is significant. Spring through autumn are the best seasons wherever snow falls and at high altitudes; fall through spring tend to be best in southern climes. This ensures you miss the north’s and a mountain’s bitter cold or snowfall in winter and a desert’s or subtropical area’s blistering heat in summer.
That being said, hiking in winter is quite popular in northern regions and mountain areas where outdoor activities are common year around. Not being able to hike in winter would limit the activity to a few months out of the year. Winter hiking has its advantages, as well, such as no bugs and smaller (and often no) crowds. If a family, however, remember that cold weather is a no-no for infants.
Also, avoid deserts during the wet seasons as flash floods can occur, sweeping down sandy washes and canyons, leaving you stranded, wet, or worse drowned. Outside of the wet season, avoid any days in which rain, high wind, and hot temperatures are forecast.
Another consideration is what the trail’s condition will be. If it’s open, as would be one in the desert or a prairie, you can expect a lot of sun and probably wind. The sunshine may be just fine on cooler days. During the hot days of summer, though, look for tree-lined, shaded trails. In cold climates, winter and spring, the ground often will be muddy.
For coastlines, always check local tide tables if walking along beaches and coastlines, as you don’t want to get stranded in the ocean or a large lake by rising water.
Lastly, consider what events might be going in the area where your trail is located. If in high tourist season or if a local festival is going on, expect busy trails and heavy traffic.
One high tourist season you probably won’t be able to avoid is flower and foliage displays, though. Often the main reason to go on some trails is for their wildflower displays.
Also, don’t hike during high hunting seasons. There’s really no sane reason, for example, to hit a Wisconsin trail during Thanksgiving week’s deer hunting season, when more than nearly a quarter million armed hunters with buck fever comb virtually every woods and field.