Those are nice areas- we got married at the Colonial Inn last year, it was great fun. I'm not sure I could handle 40 miles- maybe if they were flat. I'm currently at 15-20 miles, tho it's rather hilly where we go by Dover, Natick. I'm willing to try for longer of course, just not sure how pretty it'll be! I'm averaging around 13mph including snailing my way up the hills and zooming like a crazy fool (25mph) down. I also don't draft yet because I'm worried about touching wheels (and my hubby sets the pace too high when he leads anyway). This would be my first group ride, so I might need a quick crash course on what's expected of me- signaling slowing, etc.