Hiking in Massachusetts

What Massachusetts lacks in elevation, it makes up for in variety across the whole state. Close to Boston you can hike the Skyline Trails in the Fells and the Blue Hills in Milton give you a view of Boston from the North or South.

On the Eastern Seaboard and it has hikes that are beach related, like Great Island on the Cape and Plum Island on the North Shore. In the middle there are plenty of State Forests and a lovely overnight hike or long trail run can be had on the Tully Trail on the Trustees of the Reservations property in Athol, Massachusetts.

The Taconic range is host to Bash Bish Falls, the highest waterfall in Massachusetts at Bash Bish State park in the Southwestern portion of the state. And don't forget the Berkshires, where you can drive to the top of Mt Greylock, (as well as hike).
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Guides
Breakheart Reservation Trails
Breakheart Reservation Trails
Oakland Vale, Massachusetts, United States
 
Easy: 4.3 miles, Half day
Use this guide to help you explore the best spots of Breakheart Reservation

Use this guide to explore a large loop encompassing all the major featurs of this 640 acre park. You will climb to the top of 5 different rocky hills and will pass along the shores of two beautiful lakes. There is a beach for you to relax at and from the top of your climbs you will have great views over the lakes and to the skyscrapers of Boston in...
Middlesex Fells Skyline Trail
Middlesex Fells Skyline Trail
Symmes Corner, Massachusetts, United States
 
Moderate: 6.9 miles, 1-3 hours
The most difficult loop hike on the west side of I-93 through woods to many rocky outcrop viewpoints.

This is the most difficult of the trails on the western side of the Middlesex Fells Reservation. The nearly 7-mile path follows the outer perimeter of the Reservation and is mostly through woods but also travels to the top of several rocky viewpoints towards the city and the reservoirs below. This is a hiking only trail. The trail runs roughly parallel...
Mt. Greylock Loop Hike
Mt. Greylock Loop Hike
Sweets Corner, Massachusetts, United States
 
Moderate: 10.5 miles, Half day
Climb the highpoint of Massachusetts in this beautiful Loop Hike

Although there is a road to the top of this state highpoint you wouldn't want to be lazy and actually drive to the top would you? There is a tower at top you can climb up and a summit building to explore. Take your whole family, and a camera.
Bowers Spring
Bowers Spring
Bolton, Massachusetts, United States
 
Easy: 3.1 miles, 1-3 hours
3 mile hike through Bowers Spring, Bolton, MA

This is a pretty level and leisurely hike. The area around the ponds seems a popular location for dogs. There is a lot of beaver activity as well. I am not sure that horses are allowed in the Bolton Parks location, however they are allowed in the State and Harvard properties. Many of the trails in these areas are wide and well suited to horses....
Harold Parker State Forest
Harold Parker State Forest
Lowell Junction, Massachusetts, United States
 
Follow this guide for an extensive loop around this enormous Forest Preserve which is packed with trails to explore

This Forest, 20 miles north of Boston, has some really incredible mountain bike trails within its boundaries. There are a variety of trails from roads to paths to single track covering over 35 miles. Use the included track to guide you on a loop around the circumference of the main trails which passes by sevaral bodies of water where you can also...
Eagle Pond at Callahan State Park
Eagle Pond at Callahan State Park
Framingham, Massachusetts, United States
 
Easy: 3.8 miles, 1-3 hours
3-4 mile hike through Callahan State Park, Framingham, MA

This is just one of many routes that are possible through Callahan State Park. There are trails that criss-cross throughout the park and the adjacent Sudbury Conservation Land. The first trail - Pipeline - is probably the steepest trail along the hike. The trails are well marked, and there are trail maps placed through-out to help. Most of the trails...
Reformatory Branch Trail
Reformatory Branch Trail
Arlington, Massachusetts, United States
Easy: 4.2 miles, 1-3 hours
A great bike path connecting the Minuteman Bikeway in Bedford to Concord the Great Meadows Wildlife Refuge

This guide will take you from the Bedford Station and the end of the Minute Man Bikeway to Concord, MA. This is a 4 mile path but I've included in this hike a very cool side trip around the Great Meadows Wildlife Refuge area so you can hopefully see some birds and other wildlife. The path around the Wildlife Refuge is gravel so you won't be able to...
East Middlesex Fells Rervation Loop Trail
East Middlesex Fells Rervation Loop Trail
Malden Highlands, Massachusetts, United States
Moderate: 3.8 miles, 1-3 hours
Take this mountain biking loop around the East side of the Middlesex Fells Reservation to get away from the city life

Follow this track along the rock circuit route on the east side of I-93 for some great mountain biking trails. You'll follow this trail over a series of rocky outcrops with views towards Boston in the distance.
Cold Harbor Trail
Cold Harbor Trail
Northborough, Massachusetts, United States
2.2 mile trail near Northborough, Massachusetts

This is an hike through woods and along streams and marsh. Part of the trail is also a road. Not much to see this time of year but I imagine a fair number of birds during the warmer seasons. There are recent signs of beaver activity in the area.
Beebe Pond at Callahan State Park
Beebe Pond at Callahan State Park
Framingham, Massachusetts, United States
Moderate: 3.4 miles, 1-3 hours
3.4 mile hike through Callahan State Park, Framingham, MA

This is another hike in the Callahan State Park. This area of the park is more 'wilderness' trails. They tend to be narrower trails with steeper and rockier sections. Overall, still fairly easy hiking. There are several trails criss-crossing the area , all fairly well marked, however trail names are often difficult to find. There are a few maps...
Vaughn Hill
Vaughn Hill
Bolton, Massachusetts, United States
Moderate: 3.1 miles, 1-3 hours
3 mile hike through Vaughn Hills Conservation, Bolton, MA

This is another local afternoon hike. The variability in the terrain makes this hike a little more interesting and fun than some other hikes. The route I took was along the end of the beaver pond , around the rock 'face' of the hill and then up and over the top. the trails are pretty well marked and relatively easy going. There is some climbing over...
Skinner State Park
Skinner State Park
Hockanum, Massachusetts, United States
Moderate: 1.9 miles, 1 hour or less
1.9 mile trail near Hockanum, Massachusetts

Skinner State Park is about 1.9 miles long and located near Hockanum, Massachusetts. The trail is great for hiking and normally takes 1 hour or less. Nice short loop trail.
Trips
Skyline Loop 001 Photo
Skyline Loop 002 Photo
Skyline Loop 003 Photo
Skyline Loop 004 Photo
Blue Hills Reservation - Skyline Loop
by ahhhfresh on May 31, 2009
Milton, Massachusetts, United States
Hiking | 2.6 miles
Our first hike of the Spring was a local one. We're trying to try more of the parks around Boston so we can get more hiking in than when we are up in Maine. Neither of us had ever been to Blue Hills, even though it's only 30 minutes from where we live in Cambridge.The trail was fairly steep in parts, but they were balanced with some significant flat sections...
080920_001-Farm along \\\'bridge out\\\' road to Money Brook Trailhead (Steeles Corners, Massachusetts, United States) Photo
080920_002-Farm along \\\'bridge out\\\' road to Money Brook Trailhead (Steeles Corners, Massachusetts, United States) Photo
080920_006-Crossing creek on the Money Brook Trail (Sweets Corner, Massachusetts, United States) Photo
080920_010-Old chimney in the woods (Greylock, Massachusetts, United States) Photo
Mt. Greylock Loop Hike
by Moun10Bike on Sep 20, 2008
Sweets Corner, Massachusetts, United States
Hiking | 10.5 miles
A group of friends and I got together for this hike today and it proved to be a great choice.  We arrived at the Money Creek Trailhead at approximately 8:30 AM and most had returned to the trailhead by 4:00 PM.  This time included an extended lunch at the summit of Mount Greylock, the highest point in Massachusetts, and stops for available geocaches along the way.We chose to ascend via the Money...
DSC01397.JPG (Mount Tom, Massachusetts, United States) Photo
DSC01413.JPG (Mountain Park, Massachusetts, United States) Photo
DSC01431.JPG (Mountain Park, Massachusetts, United States) Photo
DSC01437.JPG (Mountain Park, Massachusetts, United States) Photo
M & M Trail Section 6 (Mount Tom
by in_the_wind on Aug 02, 2008
Holyoke, Massachusetts, United States
Hiking | 8.9 miles
Great hike for a summer day, however watch out for the afternoon thunder storm. Map can be found at http://www.mass.gov/dcr/parks/trails/Mt-Tom.gif
Start (Hockanum, Massachusetts, United States) Photo
Cabin (Hockanum, Massachusetts, United States) Photo
Trail (Hockanum, Massachusetts, United States) Photo
LittleStream (Hockanum, Massachusetts, United States) Photo
Mt. Holyoke via Dry Brook Trail
by ahhhfresh on Nov 01, 2008
Hockanum, Massachusetts, United States
Hiking | 3.6 miles
A very nice and pleasant hike with great views from the summit.  The start of the loop is a not at either of the main entrances, but off of Old Mountain Road which is one way coming from Hockanum Road (47) near an old graveyard.  You'll split off the path from the summit and follow the Dry Brook trail with is well blazed in blue.  It's a mostly level trek through the...
After lunch Photo
Blue Hills Hike 08.05.24
by robca2 on May 24, 2008
Quincy, Massachusetts, United States
Hiking | 4.0 miles
We hiked the eastern Blue Hills reservation, hitting intersections 3013 -> 3030 -> 3044 -> 3073 -> 3121 -> 3111 -> 3090 -> 3042.
DSC01624.JPG (Farley, Massachusetts, United States) Photo
DSC01625.JPG (Farley, Massachusetts, United States) Photo
DSC02082.JPG (Sky Farm, Massachusetts, United States) Photo
DSC02090.JPG (Sky Farm, Massachusetts, United States) Photo
M & M Trail Sec. 16 (Erving State Forest)
by in_the_wind on Nov 29, 2008
Erving "Farley", Massachusetts, United States
Hiking | 13.5 miles
Early start along a group of waterfalls up to some nice scenic vistas.You could stay on the M & M Trail or take a side trip to the Erving Castle the homestead of the hermit, aka John Smith, who lived there from 1867 to 1906
Ponkapoag Pond 001.JPG Photo
Ponkapoag Pond 002.JPG Photo
Ponkapoag Pond 006.JPG Photo
Ponkapoag Pond 008.JPG Photo
Ponkapoag pond trail
by Hiker68 on Mar 22, 2011
Ponkapoag, Massachusetts, United States
Hiking | 4.7 miles
First hike of Spring. It was cold and windy. the first hike I'd done in almost 3 months. It felt good to get back into nature. Mostly flat terrain, very easy. Walking around the dam was pretty cool. Got lots of pics of the geese. I didn't make it to the end of the boardwalk cause the water level was too high and the boards were floating. Every time I made it to a...
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Keystone trail Photo
Mount Tom State Reservation
by mattyp1 on Sep 05, 2010
Holyoke, Massachusetts, United States
Hiking | 6.7 miles