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I don't know of any centuries in June, but there is a hillclimb race up Whiteface in mid-June http://whitefacerace.com/bikeraceinfo.html (it's not quite in New England but it's close). I did the run last year- it was great!
For challenging rides http://www.northeastcycling.com/NE_Climbs_main.html is a great webside. It compares all the major NE hillclimb races with elevation profiles etc (I did the Equinox race last summer and am planning on going back). The Gap ride section of the website is also really helpful. I can recommend doing part or all of the Vermont 6 gap ride. So far I've only done the App Gap- Middlebury Gap loop but I really enjoyed it and would love to do the 4 gap or 6 gap ride sometime.
Have fun!
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If you're willing to come to New York in September, there is a gruelling century called the Highlander. Its turned into a big event, time trials Friday evening, Mtb bike race and the road event is on Sat. and they've incorporated a marathon with another town for the next day. they have 2-centuries, one is 14,000+ and the other is 6,000 elevation I think. I did the 6,000 elevation one and that was plenty for me. For the 14,000+ they have one hill that they have a bagpipe player and officers at the top of the hill to direct traffic (along with a towtruck-adds amusement). The scenery is beautiful, the rest stops are like every 15 miles. I plan on doing it again this year, if you're interested, my house is always available for company.
