ROCKLAND – Town Forest/Twin Ponds Trail

This is, by far, one of the wackiest places we’ve ever been out in nature. There are painted rocks, toys, trinkets, tchotchke, and random surprises at every turn on this trail. From rusty old chairs, to bedazzled rocks, to dream catchers, to Christmas trees, to a story book trail, Rockland Town Forest has it all. The kids kept repeating–over and over–“We give this trail a 5 for interest level!” They *LOVED* this place. If you’re looking for purity and nature in its rawest form, this trail might not be for you. But for a bit of whimsy and fun that will draw in the kids, this is your spot!



Rockland Town Forest

North Ave

Rockland, MA 02370


We entered the trail by the tiny parking lot. There are a few places to enter, but to keep it simple, we stayed to the left. The trail is essentially a giant loop, and if you just follow the tchotchke, you won’t get lost! However, when we got to the farthest point of the Town Forest (half-way around the loop; you reach a picnic area and a street), we crossed the street and went into the Twin Pond Trails area. This is a separate trail series. There are no painted rocks or doo-dads on this side of the road. However, there is a pretty pond and a really nice lookout point that are worth the extra walking. Once we visited the lookout, we doubled back, re-crossed the road, and rejoined the Town Forest Trail again. When the trail split, we headed left, finishing the loop there and making our way back to the car.

In the Town Forest, these sorts of things are your trail markers!

When you reach the Twin Ponds Trails, the trail blazes look at bit more traditional:

Trail Map Town Forest

Trail Map Twin Ponds Trails

P.I.N.T. Score

Rated on a scale of 1 (difficult/not good) to 5 (easy/awesome!)

P – Parking & Access – 2 (There is a tiny lot that fits about 5-6 cars, depending on how well people park!)

I – Interest Level – 5 (For our kids, the interest level was off the charts–higher than a 5!)

N – Navigation – 4 (The Town Forest Loop is easy to follow–even though there isn’t a map. Just follow the doo dads…the Twin Ponds Trail is also easy to follow to get to the lookout spot and there is a map posted at the entrance by the road)

T – Terrain – 3 (The Town Forest side is a bit rocky with a lot of exposed roots. There are some narrow spots and some bridges. It would be hard, even with a jogging stroller. The Twin Ponds Trail is wider and flatter. However there is a series of temporary bridges over wet spots near the start that would be challenging with a stroller.)

The P.I.N.T. Score represents our opinions of this trail.  It reflects our experience, perception, and physical health.  Therefore, the scores are not intended to be expert advice, nor will they be accurate for everyone: we cannot judge what may or may not be appropriate for each individual’s different abilities.  Consult a physician or medical expert before attempting any new physical activity. Hiking contains inherent hazards, so hike at your own risk.  You should always make your own decisions about what level of physical activity is appropriate for you and your family. Weather and other factors may affect trail conditions. Remember, trail conditions may change suddenly and drastically at any time.


For this trail, it doesn’t make sense to us to name points of interest–there are too many and they are everywhere! Leave yourself plenty of time to wander slowly, taking everything in. We even left our own contribution to the forest: a painted South Shore Family Adventures rock! 😉 Here are some pictures of our day! Enjoy!

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