Blue Hills Milton, MA – Hiking The Blue Hills Reservation

The Blue Hills Reservation in Eastern Massachusetts is a sprawling 7,000 acre preservation located just outside of Boston. The Blue Hills Milton area in particular has some great trails for both the walker and the hiker; with an observation tower at the top that gives stunning views of Boston. Exploring Blue Hills is the perfect break from the hustle and bustle of daily life to recharge and refresh the mind and soul.

What to Pack for a Trek Up Blue Hills

Blue Hills is both a great place for an invigorating. nature hike and a great place for a scenic picnic with friends.

If you plan on hiking, bring shoes that grip and wear pants that allow freedom of movement. There are easier walking trails to the top if you don’t want to hike; for those trails you will not need any special attire as they are relatively flat paths.

Tree in the middle of Skyline Trail at Blue Hills Milton
A tree growing in the middle of the path along the Skyline Trail at The Blue Hills Reservation

I brought a backpack to carry everything I brought. My backpack held my Nalgene bottle, apples, bananas, almonds and the bagel sandwiches we bought from The Back Bay Bagel Company (we stopped there before we set out).

We try to keep our diet somewhat healthy and fruit is easily portable and a natural source of sugar.

The two things that we forgot was napkins and hand sanitizer for cleanup. Eating fruit makes everything sticky!

Getting to and Parking at Blue Hills Reservation

While the official headquarters is in Milton, the reservation itself stretches across Milton, Canton, Braintree, Quincy, Randolph and Dedham.

The Blue Hills Reservation Headquarters is just a short drive off of  I-93. Take exit 3 onto Blue Hill River Road and head towards Houghton’s Pond.

There are a ton of parking lots, if you’ve never been here before, it can be confusing. I hadn’t been here in years and the friends we were meeting said to park in the lot near Houghton’s Pond. Sounds simple enough, right?

Well it wasn’t, there are actually 3 lots surrounding Houghton’s Pond, one off of a dead end outcropping of Blue Hill River Road, one off of the main Blue Hill River Road and one off of Hillside Street. It caused quite a bit of confusion.

Pro Tip: Be very clear which parking lot you’re meeting at to avoid delays and confusion. There are many parking lots in the area that are not within walking distance of each other.

This is the official Houghton’s Pond parking lot so you don’t get confused like we did:

View Larger Map

Parking is free and we had no trouble finding a spot, it was relatively empty. During the summer months though, these lots fill up quickly and early as swimming in Houghton’s Pond is a popular, family activity.

Houghton's Pond Parking Lot in Milton
The Houghton’s Pond parking lot is located on Hillside Street and it’s free.

Situated nearby is a walkway around the water and a hut with picnic tables. If you didn’t feel up to hiking, an alternative is to have your lunch in the hut by the water for a relaxing afternoon.

Picnic area around Houghton's Pond in Milton
This is a great spot for a picnic or lunch, it’s located right next to Houghton’s Pond in Milton, MA

Blue Hills is open from dawn until dusk, try not to get there too late in the afternoon if you plan on doing a longer hike.

The Blue Hills Reservation Headquarters in Milton

The headquarters is where the Skyline Trail begins. It’s about a 10 minute walk down Hillside Street from the Houghton’s Pond parking lot.

Blue Hills Reservation Headquarters located in Milton
The Blue Hills Reservation Headquarters is located in Milton, MA. There are bathrooms and a map stand in the back.

There is some parking across from the headquarters but it wasn’t much and it was full. I’m guessing these lots fill up quickly as it’s the closest to the trails. The Houghton’s Pond lot is a safer bet.

The mustard-colored building in the back houses the map and information stand as well as the bathroom. There’s only one bathroom so the wait can be a while, but it’s worth it to take care of everything before setting out.

The Skyline Trail Starting at the Blue Hills Milton Section

The Skyline Trail stretches the entire reservation and is a total of 9 miles long. That’s quite a feat of athleticism and endurance! Fortunately, by starting at the reservation headquarters, this reduces the distance to the observation tower to just 1.5 miles.

Skyline trail at Blue Hills Reservation can be challenging
The Skyline Trail is a total of 9 miles long. If you start at Blue Hills Reservation HQ, however, it’s just a 1.5 mile hike to the observation tower.

For a map of the entirety of Blue Hills Reservation, see here.

The Skyline Trail (marked blue on the map) can be challenging at times, a lot more challenging than when we went hiking in Dana. It involves steep, rocky inclines and slippery, jagged declines. Like I suggested above, wear comfortable clothing that allows freedom of movement and shoes with a grip.


The Skyline trail at Blue Hills is rocky and steep
The Skyline trail is steep and rocky, wear good shoes and clothes that allow freedom of movement.

The First Vantage Point

A short ways into the hike, I’d say about .25 miles in, you reach the first stunning vantage point.

First amazing viewpoint along the Skyline Trail at Blue Hills
After a short ways into the Skyline Trail, the first cliff viewpoint gives you amazing views of the reservation

Climb up on the rock outcropping, turn around and face the sweeping  view into an eternity of trees and blue sky.

Looking out into the eternity of the Blue Hills Reservation
Me being a little too serious looking out into expanse of Blue Hills

Come here during mid-autumn and get a great view of the leaves in various stages of changing color.

Here’s a video I snapped of the view from atop the first cliff:

The only downside is when you look up the hill and see how far you still need to go.

The Observation Tower really far in the distance at Blue Hills
The Observation Tower is a little speck in the distance of that next hill on the Skyline Trail

Eliot Tower (The Observation Tower)

Finally after much struggling, climbing and walking, you’ll reach the observation tower at the top.

Observation tower at the top of the Skyline Trail
The Eliot Observation Tower at the summit of Blue Hills along the Skyline Trail

Don’t get too comfortable, there’s more climbing ahead.

Climbing stairs to the top of the observation tower at Blue Hills
More climbing! Stairs up to the top of the observation tower for the great views of Boston and the reservation.

Head inside and up the stairs to the top. On one side there are views of the pond and the wild yonder. On the other side you get a clear view of Boston with all of its gleaming skyscrapers and beautiful architecture.

Skyline view of Boston from the observation tower
At the top of the observation tower you can see the Skyline of Boston in the distance
A view of Blue Hills Reservation from the top
From the other window at the top of the observation tower you can see this gorgeous view of the Blue Hills Reservation.

It was a Saturday when we went and it must have coincided with a local, school field trip (lucky us). When we got to the top, the place was swarming with kids. I didn’t mind but you can hear their chatter in the video I shot of the view of Boston from the top of the tower.

When you’re done, head back down the stairs. There are a few picnic tables on the side of the tower. Go and enjoy your lunch, you’ll be tired and hungry by this point and everything will taste amazing.

Eating lunch and picnicking at the observation tower at Blue Hills
The picnicking area next to the observation tower at the top of Blue Hills.

Heading Back to the Parking Lot

Now it’s time to choose: you can head back the long, challenging way or you can opt for the easy shortcut. We were exhausted by this point and, while Matt and I are pretty fit, the rest of my party was starting to feel the effects of the hike.

Taking a shortcut down the Skyline Trail to get home
Take a shortcut back you say? Never! ;)

We opted to take the shortcut. (On the map) we headed down trail 1066 then down the Notch Path to the main road.

If you’re looking to bypass a lot of the climbing and go straight to the observation tower, you can take this route in reverse and it’s very simple.

The autumn foliage along the Skyline Trail at Blue Hills
Enjoying the Autumn Foliage back to the parking lot at Blue Hills

Once on the street, we walked east for a ways and ended up back at the Houghton’s Pond parking lot.

Other Activities at Blue Hills Reservation

Blue Hills offers more than hiking and nature walks. You can also mountain bike, go horseback riding, go rock climbing and, in the winter, go downhill and cross country skiing. For more information on those activities, see the official Massachusetts page.

Recharge that Weary Mind!

The Blue Hill Reservation in Milton, Massachusetts offers a great variety of outdoor activities. Located conveniently close to Boston and right off of I-93, trips to Blue Hills can be done in a morning. Blue Hills is a great change from the grind of cubicle life and will leave you feeling refreshed, recharged and ready to take on new challenges.

And here’s a picture I took that I thought was artsy but couldn’t quite find a spot for on this post:

Wolcott Path near the Blue Hills Reservation Headquarters
The Wolcott Path can be entered at the Blue Hills Reservation Headquarters

How was your last experience at Blue Hills?

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