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I've only ridden there once and stuck more to the north side along Westboro Road. At first it was slow going. Trails were kinda soft and rooty in some places. After I crossed Southboro Road I found some pretty packed down singletrack that was nice and fast. Didn't get to the Hopkinton Rd side yet but keep meaning to go back and explore more
Hows the riding at Upton State Forest? I'm particularly interested in the side boardering Hopkinton Rd.
Upton used to be half way decent, but it's really not worth riding more than once a year unless you happen to live right next to the park.
What used to be 2 of the better trails - Mammoth Rock and Grouse haven't seen any TM in so long, they have become blown out, and look like $hit. Water runs straight down both trails, and has eroded them badly.
Rabbit Run, Old Hopkinton Spring, Hawk, and Whistling Cave are ok, but not destination riding by any means.
Nuthatch, Dean pond, Middle, and Park rd. (closest to Hopkinton Rd) are all old carriage paths.
My $.02 - Go to Whitehall or Blackstone Canal instead.
I forgot the map was so well labelled. I noticed a similar thing when I was there. Mammoth and Grouse both looked like they had potential but were in real rough shape. The erosion exposed a lot of roots, could have used a bridge or 2, and just wasn't a ton of fun. I took Mammoth over the street (walked up that hill when you first cross the street) and from there it got better. Old Hop/Spring trail was meh. Rabbit Run and maybe some un-named trails over there were where I had the most fun. Rabbit had some packed-down trails with a few swoopy sections. I live in Hopkinton so it's close by but I've only been able to get myself there once. Like Steve said, Plummer's Landing is close and better. Haven't made it to Whitehall yet but I hear good things. Depending on where you're coming from, I also had a blast on a Blackstone Valley ride at Rayburn in Millbury.