Set your goals.
The best way to make sure you get out for that big trip? Plan it yourself. Start by deciding what kind of trip you want. Is this a leisurely escape, with lots of lakeside naptime, or a hard-charging quest to maximize miles? Look for routes that fit your criteria, rather than zeroing in on the highest rated hikes.
Choose a location.
How far you can travel and how long you can be away. Search trail sites, of course, but also try googling images for destination + season. You’ll get inspiration with a bit of reality. (Sierra passes can still be snow-covered even in July.)
Scout a route.
Look at trip reports, online maps, aerial photos, and elevation profiles. Are there any seasonal hazards, like river crossings or snowy passes? Identify prime campsites, tricky trail junctions, resupply points if necessary, and bailout options for emergencies. Add key points to your paper map and/or GPS.
Some hard-to-score permits require early application. Research the rules for your trip so they're no surprises. Tip: Some parks have built-in loopholes, like starting at an alternate trailhead, that makes it possible to do your desired hike even if you don’t get your desired permit.
Don’t count on signing people up at the last minute. That might work for weekends, but not for the big trip you’re planning. Aim for at least three months’ notice for a weeklong trip, and provide a detailed description of your plan (difficulty, distances, weather concerns, etc.).
Arrange a shuttle.
Unless you’re doing a loop, most big trips require a shuttle. Options: Get a friend, hire a shuttle, or bring two cars. For the DIY option, leave the larger car at the end point, and stock it with water (and snacks if bears are not a special concern). For long DIY shuttles with big groups, consider splitting into two parties and exchanging keys when you cross paths midway.
Do a gear shakedown.
Does your route require special equipment? Make sure your boots are broken in? Does your shell need a treatment? Make sure your gear—and others’—is checked well before your trip. Let companions know what personal gear they’ll need and what group gear (tent, cookware, water filter, first aid) you’ll be sharing to save weight.
Plan a menu.
Check with others concerning dietary needs, tastes, and appetite (the only thing worse than too much food is too little). Have each hiker pack personal snacks, and split the group food into bags to divide the weight.
Buy non-perishable ingredients.
Order dehydrated foods well in advance so you can get the best deal on bulk meals.
Shop for perishable groceries.
Cheese, tortillas, meat, and fresh produce on the menu? Get this stuff right before the trip.
Just before departure, make sure you have it all: maps, permits, gear, food. Use a list and cross it off.
Till we meet through the smoke of the campfire.
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