Massachusetts trails · Viewpoint hikes

Viewpoint hikes in Massachusetts

495 trails in Massachusetts reach a named viewpoint. Ranked by our data-richness score; every link opens the full stats or the live map.

Trail	Length	Gain	Reaches
Appalachian National Scenic Trail	117.6 mi	—	Mount Race, Saddle Ball Mountain
New England National Scenic Trail	72.5 mi	—	Mayo Hill, Mount Norwottock
Bay Circuit Trail	49.7 mi	—	Pierce Hill, Noon Hill
Skyline Trail	4.5 mi	—	Nahanton Hill, Buck Hill
Appalachian Trail/Long Trail	11.4 mi	—	Mount Williams, Mount Fitch
Province Lands Bike Trail	7.8 mi	—	Clapps Round Pond, Ocean View Hill
Mahican Mohawk Trail	16.2 mi	—	Clark Mountain, Spruce Hill
Midstate Trail	14.2 mi	—	Crow Hills, Muddy Pond
Falmouth Shining Sea Trail	10.5 mi	—	Quissett Beach, Fresh Pond
Rock Circuit Trail	3.6 mi	—	Black Rock, Boojum Rock
Appalachian Trail	6.7 mi	—	North Mountain, The Cobbles
Ward Reservation	9.2 mi	—	Holt Hill, Boston Hill
Shining Sea Bikeway	6.0 mi	—	Fresh Pond, Quahog Pond
Assabet River Rail Trail	12.2 mi	—	Fort Pond Brook Reservoir, Millpond
South Taconic Trail	3.5 mi	—	Bash Bish Mountain, Alander Mountain
Peaked Mountain	2.7 mi	—	Peaked Mountain, View West
Fort Hill Trail	1.1 mi	—	Skiff Hill, Fort Hill
Simon's Rock Interpretive Trail	0.4 mi	—	SRIT Back to Civilization?, Simon's Rock
Fort Hill Walk	0.2 mi	—	Skiff Hill, Fort Hill
Fort Hill Path	0.1 mi	—	Skiff Hill, Fort Hill
Monatiquot River Trail and Boardwalk	0.3 mi	—	Hollingsworth Pond, Ames Pond
Sudbury Aqueduct Path	0.2 mi	—	Hemlock Gorge, Charles River Reservoir
Cape Cod Rail Trail	9.7 mi	—	Depot Pond, Jemima Pond
Mount Frissell Trail	1.8 mi	—	Round Mountain, Mount Frissell
Monument Mountain	1.3 mi	—	Peeskawso Peak, Monument Mountain
Coggshall Park	3.2 mi	—	Pine Hill, Mirror Lake
Cape Cod Canal Bike Paths	6.7 mi	—	Foundry Pond, Bourne Pond
Money Brook Trail	2.9 mi	—	Money Brook Falls, The Hopper
Brookside Trail	0.2 mi	—	Duck Pond, Mill Pond
Taconic Crest Trail	6.3 mi	—	Berry Hill
Ragged Mountain Trail	0.2 mi	—	Ragged Mountain, The Bellows Pipe
Toboggan Run	0.1 mi	—	Duck Pond, Mill Pond
Skiff Hill	0.1 mi	—	Skiff Hill, Skiff Hill
Plympton Path	0.1 mi	—	Duck Pond, Mill Pond
Tully Trail	2.8 mi	—	Spirit Falls, Long Pond Overlook
Metacomet - Monadnock Trail	0.7 mi	—	Goat Peak, Goat Peak
Menemsha Hills	2.2 mi	—	Menemsha Hills Reservation Beach, Great Sand Bank
Bob'S Way	2.0 mi	—	Royal Pond, Dave's Bench
West mountain trail	1.4 mi	—	West Mountain, view east
Winterberry Way	1.5 mi	—	Vose Pond, Puffer Pond
Stony Ledge Ski Trail	1.7 mi	—	Stony Ledge
Border-To-Boston	25.2 mi	—	Parker River Reservoir
Race Brook Trail	1.6 mi	—	Race Brook Falls
Metacomet-Monadnock	0.1 mi	—	Snake Pond, Overlook
Red Trail	1.7 mi	—	King Phillip's Overlook, Rocky Narrows Overlook
Metacomet - Monadnock And Robert Frost Trails	0.0 mi	—	Mount Norwottock, Horse Caves
Mahanna Cobble Trail	0.8 mi	—	Mahanna Cobble, stone bench vista
Boulder Brook Reservation Trail	0.7 mi	—	Rocky Ledge, Rocky Ledges Overlook
Skyline	1.1 mi	—	Perry Peak, Richmond's Overlook
Warner Trail	1.2 mi	—	High Rock, Sunset Ledge
Pamet Cranberry Bog Trail	1.2 mi	—	Bearberry Hill (West Summit), Bearberry Hill (East Summit)
Prouty Woods Community Forest	1.0 mi	—	Wilderness Hill, Long Pond
Danforth Loop	1.1 mi	—	Phillips Hill, Danforth Falls
Overlook Trail	1.2 mi	—	Weetamoo Cliff, Overlook
Pond Loop	2.5 mi	—	Waiting Hill, North Hill Pond
Peeskawso Peak Trail (red)	0.4 mi	—	Peeskawso Peak, Devil’s Pulpit overlook
Oak Hill	3.1 mi	—	Lookout Rock
Bash Bish Falls Trail	0.7 mi	—	Bash Bish Falls, Bash Bish Falls Viewpoint
Pine Hill Trail	0.3 mi	—	Wachusett Mountain, Pine Hill
Father Loop Trail	3.6 mi	—	clear cut view north