The 10 Best Hiking Trails in Massachusetts

The 10 Best Hiking Trails in Massachusetts

Massachusetts is probably the last state in New England that you would think of when it comes to hiking trails. The Bay State actually has some of the best trails that will accommodate all levels of hikers. Let’s explore the 10 best hiking trails in Massachusetts.

Be Prepared for Your Hike

Before heading out on a hike, it’s important that you are prepared. Make sure you have water, snack bars, and be appropriately dressed for the weather. Wear comfortable hiking socks and boots.

One of the best hiking socks to wear is Flip Socks. This ingenious sock has a skirt attached to the ankle portion that you “flip” over the top of your boot. It stays securely in place preventing dirt and stones from getting into the boot as you hike.

10 Best Hiking Trails in Massachusetts

Here are the 10 best trails in Massachusetts for hiking, mountain biking, climbing, and more according to AllTrails:

1. Great Blue Hill, Milton – This is rated at the top of the list for its skyline trail and Eliot Tower that offer a view of downtown Boston. It’s a short, moderately challenging hike through the forests of the Blue Hills Reservation.

2. Mount Watatic and Nutting Hill, Ashburnham – This nearly 3-mile loop is popular for snowshoeing, running, and hiking. Dog are welcomed but must be on a leash. It’s a moderately challenging trail; the beginning incline is steep.

3. Skyline Outer Reservoir Loop, Medford – An 8-mile, moderately challenging route takes a little over 3-hours to complete. March through November are considered the best period to visit.

4. Mount Greylock, Adams – At 3,491-feet, Mount Greylock is the highest point in the Bay State. Start at the Bellows Pipe Trail from the Gould Road/Bellows South parking area. The trail connects to a portion of the Appalachian Trail and allows you to return to the parking area through the same route. The Bascom Lodge is at the summit where you can see 90 miles on a clear day.

5. Mount Norwottuck, Amherst – This is the highest mountain in the Holyoke Range. Start from the visitors’ center at the combine Robert Front and M&M trails. If you stay left when you reach the split of the Robert Frost Trail, you will reconnect with the M&M Trail that takes you up to the summit through ledges.  

6. Blue Hills Skyline Trail, Quincy/Milton – Begin the 15.2-mile hike in Quincy on Willard Street. It takes more than 8 hours to complete but you will be rewarded with great views and the chance to take in the reservation’s meadows, swamps, ponds, marshes, and endangered species. It is moderately challenging to even hard in places.

7. Blue Hills Skyline Loop, Quincy – This is a 5.4-mile loop that will take a little over 2 hours to complete. In addition to walking, hiking, and running, it is also popular for horseback riding.

8. Rock Circuit: Melrose Rock, Black Rock, and Pinnacle Rock, Medford – Start the 4.2-mile loop at the skating rink where you can park. Be aware there is some climbing to do, and the trail can be difficult to navigate at times.

9. Bash Bish Falls Trail, Mount Washington – The 2.1-mile trail through this verdant gorge features the highest waterfall in Massachusetts. According to Mass.Gov, the twin waterfalls cascades about 80 feet into an emerald pool. Park on Falls Road or you can also park at the nearby Taconic State Park in New York state.

10. World’s End, Hingham – At just under 2-miles, this loop is pretty easy to traverse. It’s popular for birding, cross-country skiing, and hiking. There are views of the Boston skyline from the tree-lined carriage paths designed by famed landscape architect Frederick Law Olmsted.

So, there you have it! The 10 best hiking trails in Massachusetts. Lace-up your boots and enjoy!