Hi Folks! The Royal Astronomical Association of Canada have done a superb job of collating a list of objects that are generally thought to be the most interesting to view at various times of the year for beginners and intermediates, and they form a great start to planning an observation session; pick your season, and start at the top of the list and see what you can find. The beginner set are relatively easy even with little experience and they provide good instruction.
I'd suggest a planisphere or star atlas of some sort to help locate them. Once you've tried these, take a look at the other Messier objects (search around the site for a Messier list to find them - again the RASC provides a wealth of info).
Slightly more advanced are the RASC "Finest NGC" lists. These provide a set of objects organised into seasons that you can challenge yourself with - you will definitely need a star atlas, Stellarium or SkySafari to find these (unless you cheat and have a computerised goto scope!)
In fact, if you have Sky Safari or Stellarium (both with the Messier and NGC catalogues installed) you can import an observing list directly into the program and navigate through them directly.
You can find the lists at the bottom of the Finest NGC Objects page.
Highly recommended!
Colin