1. When To Go

Question 1: When are we going?

This might seem like a super obvious question, but the date of your Disneyland trip is so important. There are lots of things to consider; time of year, holidays, whether or not the kids are in school, California temperature, cost... Yes, different times of year can have different costs. 

The first thing I always consider is the size of the Disneyland crowds. There are times of the year that are so crowded you can't take normal-sized steps, and there are times that are so empty you can frolic throughout the land with your eyes closed and you won't bump into anyone for at least 10 steps. If you want to get a fairly detailed crowd index for the exact dates you want to go, head over to TouringPlans for some easy-to-follow stats. You may have to pay for a subscription though. If you just want a general idea of the best and worst times to go, just keep reading.

The not-so-good times to visit Disneyland are as follows:

• All summer. Not only will the park be busy, but it gets extremely hot! I suggest not going in the summer unless it's your only option.
• Update: I just went at the end of July in 2016 and it actually was not very busy at all. I don't know why, it just wasn't. We were even there on the weekend. I would keep an eye on more current crown indexes during the summer to make your decision, but I guess the summer at Disneyland shouldn't be feared anymore. It was still extremely hot though!
• Weekends. Year-round, the weekends get pretty busy at the DLR. However, a lot of the time Annual Passes are blocked out on Saturdays. Click here to go to the calendar on the Disneyland website - you can see annual pass blackouts there. If passes are blocked, it's probably going to be a busy day! However, since many passes are blocked on Saturdays rather than Sundays, I would recommend going on a Saturday if you're going to go on a weekend. 
• Major holidays. If you want to be able to see the ground under your feet, I would recommend staying far away from Disneyland on Thanksgiving Weekend, as well as the week before Christmas up until New Years. If the kids are out of school for the holidays, families will be flocking to the DLR. If you want to visit during a holiday, I'll post more about how to safely do so below.
• Other holidays, namely ones that boast 3-day weekends. I'm talking holidays like Memorial Day, Labor Day, President's Day, Martin Luther King Jr. Day, and Veteran's Day. And even though it doesn't have a long weekend, I would also be wary of visiting around Easter.
• During special events. MouseSavers has a good page about various DLR special events. Not every event will draw a huge crowd, but some will. Be careful.
• Some lesser-known events. Things like Dapper Day, Bats Day, and Gay Days can bring in huge crowds. There are also Grad Nights (mid-May through mid-June) and lots of conventions through February. Do your research and find out what is going on when you're trying to go to the park. 

And now for some good times to visit:

• September-December, but not during holidays. Once those kids go back to school, Disneyland empties out. And this is your way to go during the holidays but not have insane crowds. Starting in mid-september is Halloween Time. Haunted Mansion goes all Nightmare Before Christmas on us at this time, and I can personally tell you that it is a treat. I've been during Halloween Time a few times, and I love it. Mid-November brings the Christmas decorations. The trick is to go after Thanksgiving, but BEFORE winter break. Or you could simply go before Thanksgiving. The kids might miss a little school, but if the Christmas celebrations minus the crowds are worth it to you then I say go for it. 
• Mid-January through March. I mentioned before that there tend to be conventions in February, but don't be too worried; I've been twice in February and it's really not that bad, as long as you go mid-week. But even though the crowds are smaller, it's not always the best option to go at this time of year as there tend to be more rides closed for refurbishment. You can head here to once again check out Disneyland's calendar. This will show you which rides are scheduled for refurbishment. And remember, watch for 3-day weekend holidays in January and February. 
• Rainy days and weekdays. Bad weather seems to deter a lot of crowds, and as long as it's not raining too hard the rides typically stay open. The more exposed rides, such as Dumbo, may close if it starts pouring but will reopen once the rain calms down. And Disneyland typically sees smaller crowds in the middle of the week. Tuesday and Wednesday seem to be the slowest, by my personal observations.

As you may have guessed, it is actually more expensive to go when the parks are expecting big crowds. Hotels are less available, and therefore cost a lot more. Similarly, hotels cost more on weekends as opposed to the middle of the week. Anyone who has tried to fly anywhere during holidays will know that airfare goes way up. Travel tends to be more expensive in general throughout the summer, whether you are flying or driving. Just make sure you look into hotel reservations and prices far, far in advance to make sure you get the best rates, as well as the best ideas in regards to crowd levels. 

Second day of Halloween Time - these crowds aren't so bad!

In summary, there is a lot to consider when planning your DLR trip. You just need to prioritize. For me, the most important thing is crowd levels. For those of you with children, you need to consider school and if you are willing to let your kids miss some of it just so you can have a less crowded trip (in my experience, totally worth it). It can all take a lot of research and planning, but that's what I'm here for! This may seem like a lot of trouble, but I can guarantee you that it is always worth it to experience the magic the way you want to. 

Happy planning!

*UPDATE MARCH 2016*
Disneyland has adopted a tiered ticketing system for the one-day tickets! The "value" tickets are cheapest when the park is slowest, coming in at $95, or $155 for a park hopper. The "regular" tickets, for days that crowds will pick up a little, are $105, or $160 for a hopper. And the "peak" tickets are a whopping $119, or $169 for park hopper. See, I told you it pays to go on slower days! You can find a calendar displaying which days allow you to attend for the different types of tickets on Disneyland's website. However, the tiered system is only for the one-day tickets. The tickets for two consecutive days and up, have consistent prices year round.