MILTON – Blue Hills Red Dot Loop

Climbing Blue Hills is a rite of passage for those who live in the Boston area. It was our first hiking experience growing up, and one that we requested time and time again. We never got bored of Blue Hills, and, here we are, 30 years later, taking our kids up and down the same trail and eating on the same picnic rock. While we love discovering new trails, we also say “If it ain’t broke, don’t fix it!” (Or something like that!)

Our kids were 2.5/3 years old when they hiked this trail for the first time. If you’re nervous about your kids finishing, recruit some older kids to go with you. That always seems to help us! But if you stop frequently and take water breaks, we believe even a small child will enjoy the experience.

Blue Hills rewards its climbers with incredible views of the surrounding area, including a gorgeous view of the Boston skyline and Boston Harbor.

If you pick one hike to do with your kids, make it this one. #riteofpassage


1904 Canton Ave

Milton, MA 02186

There is a huge parking lot, although it often fills up. There is another lot just past the Trailside Museum heading north on route 138.


We park at the Trailside Museum and follow the red dot trail up to the top of the hill. It’s a straight shot, and the trails are easy to follow. About half-way up the trail, we cross the paved road that leads up to the Weather Observatory, Once we’re at the top, we climb the observation tower for a view of the Boston skyline. We head around the back of the tower and over a little stone bridge. We follow that trail for just a short way until we find the Weather Observatory. Just past the Observatory, there is a small trail. We follow it to the top of the ski hill–from here we can see the chairlift and more great views of the surrounding terrain. When finished, we backtrack to the Observation Tower. Directly in front of the tower is the entrance to the other half of the red loop trail. The way down is more meandering than the way up, and there are fewer places where you have to scramble over boulders. The trail ends back where you started, and from here you can check out the animals at the Trailside Museum.

Trail Map

P.I.N.T. Score

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

P – Parking & Access – 5 (There is huge lot, although it often fills up. Still, there is another lot along 138 just past the Trailside Museum heading north if you need it.)

I – Interest Level – 5 (This is a pretty challenging hike that requires just enough climbing up boulders to keep the kids entertained. Our children love the views from the top, they enjoy looking at the ski hill, and we always have a snack on our picnic rock. As a bonus, there is the promise of animals at the end of the trail!)

N – Navigation – 4 (The trail is very well marked and easy to navigate, but you do have to pay attention to the trail blazes.)

T – Terrain – 1 (Although the hike up is fast and short, there are some surprisingly challenging parts for little kids. We definitely do not think it’s possible with a stroller, and you’d also want to be careful carrying a baby on your back.)

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 Observation Tower

2. The Weather Observatory and Ski Slope/Chairlift

3. Trailside Museum. Honestly, we never go inside…we simply look at the free animal exhibits outside. The otters have always been a family favorite, but they were not there when we visited. (As of June 2021, they are renovating some of the exhibits.)



For great local craft beer, try Trillium Brewing Company. Their brand-new facility is literally at the base of Blue Hills now. Widowmaker Brewing is just down the highway near the South Shore Plaza. For a quick, but delicious sandwich, The Plate in Milton at the Fruit Center is delicious, as is Revive and Co. in the old Bent’s Cracker Company building on Route 28.

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