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I don't know when you'll be here. D2R2 is August 20. The Green River ride would be right up your alley.
Also consider Kenda Flintridge Pro or Happy Medium
There is great riding in both cities and there are group rides galore. I currently live in the NY metro area and have lived extensively in Boston. NY (more than Boston) is a very large region and you don't specify were…
The descriptions you've seen are accurate. I've done this many, many times and the vibe is the best of any ride I do. The course is challenging, the cyclists and support all have the right spirit and a beer at the end…