I expect many of those who would have questions have drifted into the discussion groups like "Manly Hunters," "Riflemen," and "Traditional Archery"
--Vendetta, I suggest you dig through a few years worth of the early autumn/autumn months editions of Field & Stream and Outdoor Life magazines. Lots of stuff for the neophyte or just anyone who wants basic information on deer hunting.
Your local DNR will have a lot of recommendations on where to hunt legally, and what the local regulations are regarding guns (some places have specific restrictions on caliber, as well as when you can hunt). Distance and terrain will be a factor in what weapon makes sense.
Youtube, honestly, has some very good tutorial videos on dressing various animals - to get a general familiarity.
I also really like Theodore Van Dyke's book "Still Hunter" on tracking, and hunting deer (I much prefer this method over sitting in a tree stand).
Vendetta, I'm glad you have an interest in hunting!
So as for how to get into deer hunting, The first thing I would do is visit your states DNR or Game and fish website. They are usually categorized and fairly easy to navigate. Look at the deer regulations (usually downloadable as a pdf) and review them and the accompanying hunt area maps. also check to see if they have public access programs to allow hunters to utilize private properties. There are also outside sources such as On X Maps which show area boundaries, private and state owned property.
Appropriate weaponry... I would start with a light to medium caliber in a good bolt action rifle. I am talking about .243 Winchester up to a maximum of 7mm Remington magnum. There are some .30 Caliber firearms that fall in this category as well like the .308 Winchester and the infamous 30-30 WCF. Personally I have been challenging myself this year and hunting exclusively with my Marlin 336 lever action 30-30 and been enjoying it immensely, in fact I just killed a deer this morning with it.
The brand of rifle really doesn't matter that much these days, Most all manufacturers produce a product that is adequate in the field, however i would recommend against semi automatic rifles in the field as they are more prone to failure at critical times. Overall my recommendation would probably have to be a Remington 700 in .243 Winchester with a 3-9x adjustable scope from a reputable manufacturer. This should provide a packable rifle on a platform that can easily be upgraded later on.
Liam Strain pointed out YouTube as an excellent place to find information on field dressing. I would encourage searching there. Personally I don't field dress animals in the traditional fashion any more but I use a method known to me as "Indian Quartering" in which you essentially remove all four quarters, back straps and tender loins from the carcass. This is an excellent way to go if you are hunting on foot and have to pack the meat out.
As I am unfamiliar with your state, always check local laws.
The nice thing about living in Mass, is you are not a very long drive from other states.
In a moment of temporary insanity I asked a former show guest who I knew hunted (Rodale had challenged him to live off only his garden for a month, which he could supplement with his frozen deer meat) if I could accompany him on a hunting outing.
I had hooked him up into a local land trust I am trustee of, as a hunter to control the deer population, so I didn't think the request was too forward as I had done him that favor. As a meat eater I wanted to face the reality of animal destruction my eating habits enforce.
He replied via email that I'd have to make sure all my clothes were washed scent free, as the deer would smell me, and he would let me know next time he went. An interesting insight this smell thing, but it ended there. He never got back to me with a specific invitation, which I took as a sign I should not bother hunters.