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I recently visited this loop trail with friends, it's a wonderful walk around picturesque Gates Pond/Reservoir. The trail is as wide as a road and is easy to follow. Plenty of parking at the end of Taylor Road which is the only access road. Take care the road can be rough. Since this is Hudson's drinking water no swimming but fishing is allowed via a town permit. Very popular with folks walking their dogs or riding horses, watch out for the poop. Highly recommended, especially during the week, weekends are busy but still enjoyable.
Carlstrom Forest is a nice spot to walk in the town of Shrewsbury. There is about 5 trails that go through the woods here and you can make a loop like I did when I visited. The parking area on Gulf Street is small but there is overflow parking allowed along nearby Wheelock Street. Along the trails folks have placed colored and painted rocks here and there, I believe it is encouraged. I recommend this forest if you want a nice peaceful jaunt in the woods, only the distant traffic sounds from Rt. 290 can be heard. There's a brook that flows through the forest and there is also a small pond or pool to explore.
Oak Hill is a great conservation area with a bunch of hiking trails to choose from. I have been here twice now and have only parked at the trailhead on Oak Hill Rd. I believe there is another parking area on Harvard Rd. The highlights of this area to me are Lookout Rock and Tophet Chasm. When I hiked here I did a loop hike that brought me to Lookout Rock first then went on to check out Tophet Chasm. Nice vista from Lookout Rock, on clear days you can see the skyscrapers in Boston in the distance. Tophet Chasm is a cool natural feature where you can walk around the chasm or along its floor. Great local hike and the trails are marked well.
I have hiked here a number of times and have sampled most of the trails. This is a nice reservation with summit views and a westerly vista from a lower point on the mountain. Along the way to the top there is a small pond (Fire Pond) that has many critters to look for such as frogs, salamanders and a large group of goldfish. The trails aren't very difficult and they are marked well, especially at intersections. I have seen many families hiking here along with their dogs as well. Highly recommended especially if you are looking for an easy to moderate hike for the day.