This time there are options for food and drink along the way—plus we included other communities in the region as well.
BLUE HILL METEOROLOGICAL OBSERVATORY: A LANDMARK HIGH ABOVE BOSTON (AND ON THE CITY’S DOORSTEP)
Here you’ll find jaw-dropping views, rugged trails, steep cliffs, bubbling brooks, deep woods, an observation tower with picnic tables at the base, and a weather observatory that’s easily one of the true hidden jewels of the Greater Boston area.
HITTING THE CIRCUIT: HOW TO HIKE THE HARDCORE MIDDLESEX FELLS ROCK TRAIL
The Rock Circuit’s a loop (hence the “circuit” part of its name) that runs a scant four miles in length as opposed to the seven miles that the Skyline runs. Unlike the Skyline, however, you won’t find many long stretches of relatively level ground here, and as you might also gather from its name, the path is extremely rocky, testing knees and ankles alike.
WORLD’S END IN HINGHAM: WHERE DOWNEAST MAINE MEETS THE EMERALD NECKLACE—15 MILES FROM BOSTON
Rocky Neck is the “thumb” of the baseball glove, and it’s mostly separate from the rest of World’s End, not only geographically, but as just mentioned, in overall feel as well. Doing a little clockwise loop along the water here, you’ll feel like you’ve entered the aforementioned Acadia National Park, with dark and pointy coniferous trees giving a distinct Northwoods vibe to the area.
HOW TO WALK THE BOSTON COASTLINE
A long seaside walk that you can do without leaving the city, and one that’s really more known to locals and longtime Bostonians than newcomers.
END TO END: ON THE BLUE HILLS’ SKYLINE TRAIL
By now, you’re probably pretty tired, but you’ll need a second wind because the hike from Route 28 up to Buck Hill is a bear of a climb, though it is so worth it once you emerge from the woods and realize that you have a nearly 360 degree view
HOW TO WALK ACROSS BOSTON HARBOR WITHOUT GETTING IN TROUBLE
The original Thompson Island hike, which included Thompson Island itself, was something I’ll never forget for several reasons, but this perfectly legal walk includes mostly similar sights and may also give you a bit of cachet, since saying that you walked across Boston Harbor sounds like the stuff of legend.
ONE FOR THE TEAM: A LOCAL’S JOURNEY INTO BOSTON’S SEAPORT DISTRICT
Walking down to the dock brought us to extraordinary views of the harbor and the islands, and since it was around 7:30 pm, a sunset over the water that made our knees weak.
POWDER WALKING (A WINTER HIKING SPECIAL)
Five snowshoe hikes and walks inside Route 128
SPECIAL LOW TIDE FEATURE : THOMPSON ISLAND
Boston Harbor Islands meet the mainland (sometimes)
