Start to Finish Canadian DRIP & SPP Walkthrough
Chose a Company or Trust that offers a Dividend Reinvestment Plan (DRIP). Companies that offer these plans generally offer a regular dividend or distribution, making the plan attractive. Be sure to look for a Share Purchase Plan (SPP) that will allow you to BUY more shares in the future. CDN DRIP & SPP List lists all Canadian plans and details.
 Research every aspect of the company. Beyond all their financials, some topics of interest for DRIPpers are: Dividend increase frequency, how long dividend has been paid, SPP availability, discount on reinvested dividends, plan fees if any, minimum purchase amount for the Share Purchase Plan, etc. These details should be explained in the DRIP Circular, available online on the company's website.
 In Canada, investors are required to buy their initial common shares on the open market (through a discount broker) OR through a private transfer. One (1) Share is enough if a Share Purchase Plan is available since you can buy more later, but if the Company ONLY has a DRIP and no SPP, many more shares are needed to be realistic.  So BE 100% SURE you know what kind of plan the company is offering.  You MUST get at least 1 Share of EACH company you want to DRIP/SPP.
 1st Method "Broker": Buy your share(s) on the open market. This requires a brokerage account like E-Trade, QTrade, TD Waterhouse, Etc.. A fee would be charged to buy your share(s), see the Canadian Discount Brokers page for a list of fees.  Organize a Group Buy to spread the fees evenly amongst participants.  1-3 days to settle.
2nd Method "Exchange": Find someone to transfer 1 share to you. If you don't know someone, try the Share Exchange Board at the DRIP Resource Center. You would pay them the share value and a small fee for the effort and postage. Since only 1 share is required for Canadian DRIPs, that's most often what's offered. Either seller mails the certificate to the buyer, or seller transfers 1 share from their DRIP holdings (Using a Transfer Form) to the buyer. 1-2 weeks.
Broker purchases: Call & Request a Share Certificate in your name, a fee of $30-$50 is common, see brokers page for comparison. 1-2 weeks.
Private transfers: Mail the certificate to the Transfer Agent to make the transfer official.  Sometimes the seller will mail it in for you.
 In both cases a new certificate will be issued with YOUR NAME on it.   Sometimes for private transfers the Transfer Agent mails the certificate to the Seller and not the Buyer, so don't be alarmed if there's a delay.   Keep this certificate in a SAFE PLACE.  1-4 weeks.
 DRIP enrolment forms and Circulars are can be found on the company's website, on the Transfer Agent's website or links for each company on the CDN DRIP & SPP LIST.
Complete and mail it to the Transfer Agent.  This must be done ONCE for EACH COMPANY. If you are interested in buying additional shares through the SPP (if applicable), be sure to complete an Anti-Money Laundering Form.  Computershare forms are specific to each Company and sometimes are mailed later, or you can call to request one.
 That's it! You're done! You're now investing Fee Free! When your first dividend is reinvested, or your cheque is cashed and shares purchased, you will receive a statement from the Transfer Agent with purchase details (purchase price, # of shares, etc). You can use the DRIP Log to keep track of this information. Statement will also include a Stub or Form to use for future Optional Cash Purchases (OCP). Keep all records for tax purposes. DRIP/SPP schedules can be monthly, quarterly or yearly.

Have more questions? Check out the DRIP Faq.