Great Blue Hill & Eliot Tower, Milton MA

• 4-star hikes
• 1 to 4 mile options
• Moderate | Gain 360 to 820 feet
• Milton, MA | MetroWest Region
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A tall stone observation tower built with multicolored fieldstones stands under a clear blue sky with wispy white clouds. Short stone steps with dark metal railings lead up to the open entrance at the tower's base and extend toward an adjacent covered stone pavilion. Vibrant autumn foliage in shades of orange and red framed by green vegetation surrounds the stone structure.

Eliot Tower close to Great Blue Hill's summit.

The Blue Hills Reservation is a large state park located south of Boston and managed by the Massachusetts Department of Conservation and Recreation. It covers a range of rocky, forested hills with ponds and wetlands in the valleys, and much of the terrain features exposed granite. The trails are shared by hikers, trail runners, mountain bikers, and horseback riders, so you should expect to meet other trail users along the way.

Great Blue Hill is the highest summit in the reservation, and both featured hikes climb to the top. Once at the summit, you can ascend Eliot Tower for views over the surrounding area and visit the historic Blue Hill Observatory and Science Center. The Skyline Trail follows the ridge of the hills, where open sections of forest at Hancock Hill and the summit of Great Blue Hill offer distant views of the Boston skyline to the north. We've mapped out two looping hiking routes, starting from different sides of the reservation.

Trail Options Expand KMZ · Google Earth ·

⬤ 4★ Red Dot Loop 1.4 mi loop, moderate, gain 360 ft
GPX File · AllTrails · Directions GPX?

⬤ 4★ Skyline Trail 3.3 mi loop, moderate, gain 820 ft
GPX File · AllTrails · Directions

P Free parking

⬤ 4★ Red Dot Loop 1.4 mi, 360 ft
We enjoy a counter-clockwise loop beginning with a hike up the Red Dot Trail - a mildly challenging climb that quickly becomes rocky, with slick granite surfaces polished by the footsteps of many visitors. This trail leads directly to the observation tower. Follow the Eliot Circle trail to reach the observatory which marks the true summit of the Great Blue Hill. Return down Coon Hollow Trail, taking a sharp left turn onto Abigail Adams Trail as you descend.

Folk concerned about possibly challenging terrain may prefer to use the Abigail Adams Trail section of the loop on an out-and-back basis instead, for a total of 1.6 miles and 370 feet of elevation.

Free parking is available in two large lots located on either side of the Blue Hill Trailside Museum on Canton Avenue.
The museum is operated by Mass Audubon, and focuses on the natural history of the Blue Hills with indoor exhibits on local wildlife and landscape, along with outdoor enclosures featuring live native animals and birds of prey. Combining a visit to the museum with the Red Dot Loop makes for a memorable family trip.

A hiker seen from behind wearing a red short-sleeved shirt and a backpack climbs a rocky forest path scattered with fallen autumn leaves. Sunlight filters through a stand of tall trees, illuminating golden autumn foliage in the background. On the right, a small white sign with an arrow is mounted on a large tree trunk to mark the trail.

Beginning a rocky climb on Red Dot Trail.

⬤ 4★ Skyline Trail 3.3 mi, 820 ft
Combining the north and south sections of the Skyline Trail, this loop features rougher terrain than the Red Dot route, including a few rocky scrambles. We couldn't choose between a clockwise or counter-clockwise direction, as the trails feature steep uphill sections both ways.

Despite its name, Skyline Trail remains mostly forested on this side of the park, and distant views are fairly sparse. Outside of the summit of Great Blue Hill, the only notable overlook along this route is at Hancock Hill near Hillside Street.

Because the reservation is crisscrossed by many intersecting trails, carrying a GPS map is highly recommended. You can begin this hike from Hillside Street, where there are two parking lots available. For a longer hike within the Blue Hills Reservation, consider continuing along the Skyline Trail east of Hillside Street toward the reservation's second highest peak - Buck Hill. We have a separate trail review of this route available, and it can be found linked below under the 'Trailspotting Nearby' heading.