CANTON – The Eleanor Cabot Bradley Estate

We are huge fans of the Trustees of Reservations. They do amazing work making nature available to the masses while simultaneously preserving historic buildings and promoting the history of Massachusetts. The Bradley Estate, with its 90 gorgeous acres, is no exception. It’s immaculately kept, convenient, and beautiful. The estate hosts weddings from May to October, features amazing gardens in the spring and summer, and offers a wooden reindeer hunt and holiday light walk-through in the winter. Located near Route 95 and the Blue Hills, the Bradley Estate is easy to get to. Parking is a breeze (although it costs $6 if you’re not a member of the Trustees), and you really cannot get lost here, which makes this property a much less intimidating option than the Blue Hills across the highway. Speaking of the highway, that is the one downside to this spot–you will hear the constant hum of cars during your whole hike. However, after a while, it becomes white noise, and you’ll be more focused on your burning calves–this property has a fair amount of steep hills!



2468B Washington St.

Canton, MA 02021


We entered the trails near the main parking lot, to the right of the house on the property. The trail hugs a stone wall and is flanked by a farm on the right side. We followed the trail around the very edge of the property, passing a bench before entering the woods–and the hilly part of the property. If you want a relatively easy stroll on wide, smooth trails, stay on the main loop, which is about a mile long. However, we combined the wooded trails (and the hills) with the loop. We used the highway as a guide and followed all the trails up and around the huge hills that were next to the interstate. Honestly, there are no blazes so it’s not always clear which way to go, but there are maps at a lot of trail intersections that show you where you are. You really can’t get lost since the highway provides a boundary, and the loops feel fairly intuitive if you’ve looked at a map. After wandering around in the wooded trails, we made our way back to the loop trail and finished up by exploring the house on the property.

Trail Map

P.I.N.T. Score

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

P – Parking & Access – 4 (There is a large main lot and an overflow lot, so parking is easy. But we’re giving it a 4 because you have to pay $6 for a day pass.)

I – Interest Level – 3 (The kids found plenty to look at here in the woods and around the house. They loved “the Butt Tree,” running down the hills, and the dance floor/patio! But it’s just not the most exciting trail the kids have visited. So a 3.)

N – Navigation – 4 (Easy to follow, but no trail blazes. Instead, there are maps at frequent intervals that show you where you are. Honestly, though, it’d be really hard to get lost here. The highway serves as boundary and as a way of orienting yourself.)

T – Terrain – 4 (The main loop is wide and relatively smooth with pine needle cover and not a lot of exposed rock or roots. However, there are a few steep parts. The wooded part also has smooth trails, but quite a few very steep hills. You could do this with a jogging stroller–but you’d need some strength and energy to get it up and down these hills!)

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.


  1. The bench. This will help you find the path near the start of the loop trail. Head toward the bench once you get past the farm. If you continue straight, you’ll reach a dead end that seems to be the “garbage dump” of the property. See #2!

2. The dumping ground. Here you’ll find piles of gravel, mulch, trees, leaves, etc.

3. The fort. This is along the wooded trails, not the main loop.

4. The weird tree trunk

5. The “Butt Tree”

6. The House, gardens, and patio (a.k.a. the dance floor!)

And here are some pictures from our day! It was a cold and windy 47 degrees–just one day after a 78 degree sunny day! Gotta love New England weather! It was slightly jarring to feel like we needed gloves while seeing the beautiful magnolias, azaleas, daffodils, and forsythia trees in bloom.

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