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Hancock Hill

Blue Hills Trails

The quickest summit in the Blue Hills: a short, steep half-mile loop from Reservation Headquarters.

Fall color and open ledges along the Skyline Trail in the Blue Hills

Hancock Hill is the quickest real summit in the Blue Hills. In about 30 minutes from Reservation Headquarters, you climb stone steps to a rocky top with a big view, then loop back on a gentle path.

DistanceAbout 0.5 miles
TimeAbout 30 minutes
DifficultyModerate, short and steep
StartReservation HQ, 695 Hillside St, Milton

Trailhead parking

Directions to Reservation Headquarters →

The route

  1. Park across the street from Reservation Headquarters.
  2. Take the North Skyline Trail, marked with blue rectangles, up the stone steps to the summit of Hancock Hill.
  3. Continue to intersection #1162 and turn left.
  4. At #1160, turn left again onto Wolcott Path and follow it back to Headquarters.
Want more? Hancock Hill is the first summit on the Skyline Loop. Keep going west on the blue rectangles to reach Great Blue Hill and the Observatory.

Before you go

  • If you get lost or hurt, call 911. Give the dispatcher the four-digit number on the nearest intersection post. Those numbers match the DCR map and help responders find you. For non-emergency park concerns, DCR’s 24-hour dispatch is (508) 820-1428.
  • Before you go, share your phone’s location with a friend, and tell someone your route and when you plan to be back.
  • Carry the DCR trail map. Many intersections have a white post with a four-digit number that matches the map. If you get turned around, find the nearest number.
  • Bring water, and dress for wind on the summits.
  • The reservation is open dawn to dusk. Dogs must be leashed. Carry out everything you bring in.
  • Timber rattlesnakes and copperheads live in the Blue Hills. They are shy. Stay on the trail and give them space.

FAQ

How long is the Hancock Hill hike?

DCR lists it at about half a mile, taking about 30 minutes.

Where does the Hancock Hill trail start?

At Blue Hills Reservation Headquarters, 695 Hillside Street, Milton. Park in the lot across the street.

Is Hancock Hill steep?

Yes. It is short but steep, with stone steps at the start. DCR rates it moderate.

Can I continue from Hancock Hill to Great Blue Hill?

Yes. Stay on the blue-blazed Skyline Trail west over the ridge to reach Great Blue Hill and the Observatory. That is the Skyline Loop.

Guided hikes

Hike it with an Observatory guide

Our staff lead groups up Great Blue Hill, connecting the trail to the landscape, the climate record, and 141 years of daily observation. Every guided hike ends inside the Observatory.

Staff-led · By appointment, any day, year-round · Observatory tour included · From $250 per group, members save

See guided hikes

Route details are based on the Massachusetts Department of Conservation and Recreation’s recommended Blue Hills hikes. Trails and markers change, so carry the DCR map and confirm conditions with DCR at 617-698-1802.

Keep climbing

Hancock Hill is the warm-up. Great Blue Hill and its Observatory are the main event.

Plan your visit See the summit now