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Did you know that it is possible to go for a 16 mile hike over rugged terrain with over 3,000 feet of elevation gain inside Rt. 128? If not you are not alone, the possibilities for serious hiking in the Blue Hills and, to a lesser extent, Middlesex Fells are one of the best kept secrets of the Boston hiking community. These two areas offer spring training opportunities for those whose fitness has suffered over the winter, and can provide moderately challenging hikes for those weekends when a trip up North is not convenient.

The Area

While there are a few other rugged areas around Boston, none offers the length and variety of trails that the Middlesex Fells and Blue Hills offer.

This 7000 acre reservation is located south of Boston in the towns of Milton, Canton, Randolph, Braintree, Dedham and Quincy (map). Few hikers venture into the areas south of Rt 128 (Ponkapoag Pond section) or west of Rt 138 (Little Blue Hill section), so I will say nothing about them.

There are more than 125 miles of carriage roads and trails in the reservation, I will only describe those that I find most suitable for rugged hiking. Get the map and explore the others!

In the Great Blue Hill section, between Rt 138 and Hillside Street, I use two trails. Almost everyone goes from the Rt. 138 trailhead parking to the summit of Great Blue Hill using the right (south) branch of the red dot trail (blazed with red dots). The Skyline Trail has two branches going from the summit of Great Blue to Hillside Street, together they make a loop.

In the Houghton Pond section, between Hillside Street and Rt 28, there are again two main trails that I use. The Skyline Trail goes directly across this section, over the summits of Tucker and Buck Hills. The orange blazed Massachuseuck Trail goes round Houghton Pond, then winds around the sides of Tucker, Boyce and Buck Hills, joining the Skyline Trail shortly before they both reach Rt 28.

In the Chickatawbut section, between Rt 28 and Chickatawbut Road I use segments of several trails. The Skyline Trail goes across that section over the summits of Chickatawbut, Kitchamakin, Nahanton and the Broken Hills. The Bouncing Brook Trail follows a carriage road south of the Skyline Trail. I use a variety of trails that connect them to make loops.

In the section east of Chickatawbut Road I normally stick to the Skyline Trail in both directions, not attempting to make a loop.

The Hikes


The classic here is the Skyline Trail (blue blazes), from Quincy going West via Houghton's Pond to the summit of Great Blue Hill, and back to Houghton's Pond. This is about nine miles long, with an elevation gain (my calculations, people disagree about the numbers) of 2,500 feet. The Local Walks/Hikes Committee of the Boston Chapter of the AMC does that hike several times a year.

A variation is to continue West from the summit of Great Blue Hill, through the Little Blue Hill section of the reservation, to the Fowl Meadow Reservation, and follow Burma Road to the Neponset Valley Parkway. There are no big hills in the Little Blue Hill section, and Burma Road is totally flat. I have done that hike once, and have no desire to repeat it!

Round Trips

Since both of these require a car at each end they are not very suitable for the individual hiker. It is possible to devise a variety of circular hikes of similar length and elevation gain. Since the largest single elevation gain in the Blue Hills is the climb from the Trailside Museum to the top of Great Blue Hill I usually start my hikes from there, though early in the season I often do the loop from Hillside Street to Quincy because it has less elevation gain per mile.

The simplest way is to head east along the Skyline Trail as far as you want to go, then return the same way. In the table below I give the distances and elevation gains of some round trips.

Hikes Entirely on Skyline Trail (Round Trips)
Trails Distance Elevation Gain
Trailside Museum to Hillside Street 4.5 1,300
Trailside Museum to Rt. 28 8.9 2,300
Trailside Museum to summit of Nahanton 11.6 2,900
Trailside Museum to Chickatawbut Road 13.2 3,250
Trailside Museum to Wampatuck Road 15.5 3,750
Hillside Street to Wampatuck Road 11.0 2,450


I find it more interesting to do loop hikes, they are a bit longer, with a bit less elevation gain, than the straight out and back trips along the Skyline Trail.

A good base hike (about ten miles and 2,100 feet) can be done from the Trailside Museum on Route 138. Start by taking the red dot trail from the Trailside Museum to the summit of Great Blue Hill. Then continue East along the South Skyline trail to the summit of Houghton's Hill. Leave the Skyline trail, heading South (right) to Houghton's Pond. Follow the shore of the pond (either the North or the South shore, the latter is slightly longer) to the orange blazed Massachuseuck Trail. Follow it, first North and then East, along the sides of Tucker and Buck Hills. On the East slope of Buck Hill (just above Rt 28) you will meet the Skyline Trail, head back West (left) over the summits of Buck and Tucker Hills to Hillside Street. Then go over Hancock, Hemmenway and Wolcott Hills to Great Blue Hill and back to the start.

You can add about a mile and 300 feet elevation gain by continuing eastwards a bit further. When the Massachuseuck Trail intersects the Skyline Trail continue East on the Skyline Trail, crossing Randolph Avenue, and climb to the summit of Chickatawbut Hill. Descend until you reach the red blazed Slide Notch Path and follow it down (South, right) to the Bouncing Brook Path, then turn West (right again) to reach the Skyline Trail.

Instead of taking the Slide Notch Path you can continue on the Skyline Trail eastbound a bit further, going over Kitchamakin Hill to the Sassaman Notch Path (also red blazed) which also leads to the Bouncing Brook Path. You can go even further East on the Skyline, over Nahanton Hill to the Blue Hill Reservoir, and take the Squamaug Notch Path to the Bouncing Brook Path. Should you really wish to exert yourself, you could climb back up Chickatawbut Hill on the return trip, going up either the Slide Notch or the Sassaman Notch paths. The loop from Trailside to the reservoir and back, including climbing Chickatawbut on the way back, is about 14 miles with an elevation gain of 2,800 feet.

Hikes Partly on Skyline Trail (Loops)
Trails Distance Elevation Gain
Trailside Museum to Rt 28 10.0 2,100
Trailside Museum to Chickatawbut Hill 11.0 2,400
Trailside Museum to Reservoir 14.0 2,800

Miscellaneous Notes

Most people use the Red Dot Trail to climb from the Trailside Museum to the summit of Big Blue. A longer route, with a steep and rugged section, is to go past the base lodge and follow a worn path that leads across a ski slope to the Accord Path as it enters the trees. The Accord Path joins the Skyline Trail as it climbs from Rt 138, and offers a very rugged approach to the summit of Big Blue. This adds about half a mile with no change in elevation gain.

Good lunch spots are the summits of Hancock and Buck Hills, Nahanton, the final summit of the Broken Hills just west of Chickatawbut Road, Rattlesnake Hill and Babel Hill.

For More Information


The DCR web site has a schematic map of the Blue Hills. It is more useful for visualizing the locations of trailheads and major features than anything else.

There is a good topographic map, with trails, of the Blue Hills on sale both at the Trailside Museum (on Rt 138) and the Reservation Headquarters (on Hillside Street).


West area-Red Line to Ashmont Station, high speed line to Mattapan, take Canton and Blue Hills bus to Trailside Museum. For Houghton's Pond area, stay on the bus and exit at Hillside Street at Howard Johnson's. Cross at light and walk one mile east on Hillside.
Central area-Red Line to Ashmont, take MBTA bus #240 or Chickatawbut Overlook is one mile east, Houghton's Pond is two miles west on Chickatawbut Road.
East area-Red Line to Quincy Center, take MBTA bus #238, exit at West and Willard Streets across from the skating rink, cross rink parking lot to St. Moritz Nature Trail.

By Car:
Houghton's Pond. Rt. 128 to Exit 3, turn right at stop sign onto Hillside Street. Houghton's Pond is approximately one mile on the right. Or continue to reservation headquarters on the left next to the DCR stables.
Trailside Museum From route 128 take Exit 2 (route 138 N) towards Milton, less than one mile on right.
Shea Rink on Willard Street, Quincy. From route 93 take exit 8, go South on Willard Street to rink, or from route 128 take exit 6 and go North on Willard Street.

Books and Web Sites

The AMC's Massachusetts and Rhode Island Trail Guide, currently in its 7th edition, has full descriptions of all the trails in both reservations. The map of the Blue Hills included with the book does not show contours, and so is much less useful than the DCR map.

The Metropolitan District Commission (DCR) web site has some very basic information on the Blue Hills. The Local Walks/Hikes Committee of the Boston Chapter of the AMC runs frequent trips in the Blue Hills.