Hiking in Blue Hills

Blue Hills Reservation has hiking trails for every experience level.


Blue Hills Reservation has a lot to offer both lifelong hikers and those who want to stroll through stunning scenery. There are 125 miles of trails that will take you over hills, through marshes, across meadows, and more.

Make sure you bring a trail map. You can buy one at Reservation Headquarters or at the Blue Hills Trailside Museum. You can use the map along with the small white markers posted at some trail intersections to figure out exactly where you are on the trail: the markers have 4-digit numbers that correspond to locations on the map.

Also, check the weather before you hike so that you know what clothes to wear, and always bring plenty of water.

Additional Resources   for Overview

What to know

There are lots of ways to explore Blue Hills Reservation, but here are a few hikes we recommend:

Easy hikes

These are great for families with young children.

Wolcott & Border Path
  • Distance: 2.5 miles

  • Time: 1–1.75 hours

  • Starting point: Reservation Headquarters, 695 Hillside St., Milton. Parking available across the street.

A relatively level hike through majestic stands of pines and hemlocks. Follow the woodland lane that starts at Reservation Headquarters (Wolcott Path, intersection #1186 on your map) about ½ miles to the Five Corners intersection (5 trails converge at intersection #1141). Angle right on the green dot trail. Upon reaching Border Path (intersection #1135), turn right and continue to intersection #1175. Turn right and follow the path past intersection #1178, and then turn left back onto Wolcott Path.

Houghton’s Pond Loop
  • Distance: .75 miles

  • Time: 30 minutes

  • Starting point: Houghton’s Pond Recreation Area, 840 Hillside St., Milton

This short hike around Houghton’s Pond is a wonderful way to take in the beauty of fall foliage in Massachusetts. Follow the yellow dot trail marks around the pond to walk the full loop.

Dark Hollow Loop
  • Distance: 2 miles
  • Time: 1.5 hours
  • Starting point: Houghton’s Pond Recreation Area, 840 Hillside St., Milton

This mostly-level woodland loop trail is marked with green dots and takes you around the base of Tucker Hill. To upgrade this hike to a moderate climb, follow the green dots to the Skyline Trail, which is blazed in blue.

Wolcott Path Loop
  • Distance: 2 miles 
  • Time: 1–2 hours
  • Starting point: Trailside Museum, 1904 Canton Ave., Milton

Follow the green dots at the bulletin board in the Trailside Museum's north parking lot to enjoy a level trail through some of Blue Hills Reservation’s hardwood forests. 

Braintree Pass Path
  • Distance: 3 miles 
  • Time: 2–2.5 hours
  • Starting point: Intersection of Route 28 and Chickatawbut Road, Quincy

This hike is one of the gems of the reservation. The trail passes by stands of majestic hemlocks, mountain laurel-covered slopes, and an Atlantic cedar swamp. An old cellar hole marks the Glover Homestead, where farmers settled hundreds of years ago.

Park in the small pull-off (intersection #3024) and walk past the bulletin board down Braintree Pass Path. Pass intersection #3072, and then bear left at intersection #3090. Continue downhill to intersection #3121. Go left again and follow the path skirting the Great Cedar Swamp to your right. To return, take a left onto Bouncing Brook path (intersection #3130) and follow the red path back to Braintree pass. 

Moderate hikes

If you're looking for a more moderate hike, we recommend these trails. 

Hancock Hill
  • Distance: .5 miles
  • Time: 30 minutes 
  • Starting point: Reservation Headquarters, 695 Hillside St., Milton. Parking available across the street.

Hancock Hill is perfect for a quick but rigorous hike that rewards you with a great view from the summit. Follow the North Skyline Trail to intersection #1162. Turn left here, and then left again at intersection #1160, or Wolcott Path, which will bring you back. 

Great Blue Hill
  • Distance: 1 mile
  • Time:1–1.5 hours
  • Starting point: Trailside Museum, 1904 Canton Ave., Milton

Great Blue Hill may be the largest hill in the Blue Hills chain, but the trail itself is just a moderate climb. Follow the red dot trail to head straight up from the South lot parking area, or walk the paved access road from the North lot parking area.

Ponkapoag Pond
  • Distance: 3.75 miles 
  • Time: 2.5–3 hours 
  • Starting point: Interstate 93 exit 3 pull-off on Blue Hill River Road 

For a relaxed and more isolated hike, follow the green dot trail around the largest and most remote body of water in Blue Hills Reservation. Our rangers highly recommend the Ponkapoag boardwalk across the bog, which will take you  through some of the Reservation’s marshlands. The bog is across from the YMCA camp site at intersection #5176.

Challenging hikes

There are many steep and scenic trails to choose from at Blue Hills Reservation. 

Skyline Loop
  • Distance: 3 miles
  • Time: 1.5–2.5 hours
  • Starting point: Reservation Headquarters, 695 Hillside St., Milton. Parking available across the street.

On this popular trail, you can climb several summits within the Blue Hills range, including Great Blue Hill—the tallest peak in Blue Hills Reservation, which offers a commanding view of the Boston Skyline. The blue-blazed Skyline Loop Trail begins behind the park headquarters. Take the stone steps up Hancock Hill and follow the winding footpath over the ridge line to Eliot Observation Tower, which sits atop Great Blue Hill. Climb the tower for a panoramic view. To return, cross over the stone bridge to intersection #1066, and turn left to return via Skyline south.

Buck Hill Loop
  • Distance: 3.5 miles
  • Time: 2–3 hours
  • Starting point: Houghton's Pond Recreation Area, 840 Hillside St., Milton

For an intense climb, make your way up to the rocky summit of Buck Hill. Your reward will be a beautiful panoramic view of the reservation.

From the Houghton’s Pond bulletin board, follow the red dots toward the beach and pass the bathhouse. At intersection #2053, follow the red dots over Breeze Hill to intersection #2072, where the red, green, and blue-blazed trails converge. Turn right to take the red dot/blue rectangle trail. Here you begin a rigorous climb over Tucker Hill and Buck Hill via the Skyline trail. Catch your breath atop Buck Hill and enjoy the view.  At intersection #2210, turn right and follow the red trail back to the paved park road at intersection #2071. Then follow the red dot footpath over Breeze Hill to the parking lot.

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