Scouring the internet last year I found mention of 4 club meetings for Jeeps.
BAJA meets in Brampton every week. I've never attended a meeting but assume they are still happening as BAJA seems to be one of the more active clubs.
The Newmarket Jeepers meet for coffee every week. I last attended late summer 2014, they had between 6-16 people turning out across several meetings. Every Tuesday around 8pm at Tim Horton's parking lot, 855 Murlock Dr., Newmarket. It's about a 30 min drive from 401 & DVP.
Central Ontario 4x4 Club meets monthly at the Falcon & Firkin Pub, 10300 Yonge St., Richmond Hill. I've never attended a meeting so can't tell you if this is still on. The first Wednesday of each month at 8pm.
TMR Club Jeep Night meets monthly at The Works Gourmet Burger Bistro, 18075 Yonge St., Newmarket. I've never attended a meeting so can't tell you if this is still on. The first Thursday of each month at 8pm.
There was an attempt to meet in North York at a Tim Horton's around 650 Sheppard West a few year's back, but I've seen confirmation that the guy cancelled the meets because no one was showing up.
If anyone attends the meetings above, do post on here confirming they are still on and what type of turn-outs are typical.