Search a hike or location

search
Best difficult hikes in Massachusetts
Share:

Best difficult hikes in Massachusetts

Got your game face on? These difficult hikes are designed for hikers who are looking for a serious adventure.

Here are some great hikes to explore in Massachusetts.

Most popular hikes

1

Difficult

Vermont Long Trail

Berkshire County, Massachusetts · star 4.8 (9) · 400.0 km · Est. 27 days

2

Difficult

Metacomet-monadnock Trail

Hampden County, Massachusetts · star 4.9 (8) · 196.3 km · Est. 12 days

3

Difficult

Robert Frost Trail

Hampshire County, Massachusetts · star 4.7 (17) · 61.7 km · Est. 4 days

4

Difficult

Mount Holyoke via NET-MandM Trail

Hampshire County, Massachusetts · star 4.6 (15) · 4.3 km · Est. 1 hrs 15 min

5

Difficult

Jug End to Bear Mountain via Appalachian Trail

Berkshire County, Massachusetts · star 4.8 (12) · 18.8 km · Est. 1 day 0 hrs

6

Difficult

Allandale Woods Iii Loop

Suffolk County, Massachusetts · star 4.6 (19) · 3.3 km · Est. 47 min

7

Difficult

Mount Williams via Appalachian Trail

Berkshire County, Massachusetts · star 4.4 (8) · 9.8 km · Est. 3 hrs 9 min

8

Difficult

The Cobbles Trail

Berkshire County, Massachusetts · star 4.4 (14) · 2.8 km · Est. 57 min

9

Difficult

Cheshire to Mount Greylock Trail

Berkshire County, Massachusetts · star 4.5 (19) · 23.4 km · Est. 2 days

10

Difficult

Trail of the Ledges and Overbrook Trail Loop via Pike's Pond

Berkshire County, Massachusetts · star 4.5 (11) · 4.1 km · Est. 1 hrs 19 min

SHOW MORE HIKES

Reviews for difficult hikes in Massachusetts

avatar

Vermont Long Trail

PathForester32 路 reviewed over 1 year ago

star star star star star

Jonathan Maidment avatar

Metacomet-monadnock Trail

Money Maker 路 reviewed over 1 year ago

star star star star star

avatar

Robert Frost Trail

t davies 路 reviewed over 4 years ago

star star star star star

fantastic, far better than expected. i'm a local and i found so many new wonderful places along the route. did it north to south in 2 days as far as Lawrence Swamp area. it was a bit longer per day than would be ideal.

Antoine Mitchell avatar

Mount Holyoke via NET-MandM Trail

ExplorerTrailmaster56 路 reviewed about 1 year ago

star star star star star

Miss Giuseppe Lehner avatar

Jug End to Bear Mountain via Appalachian Trail

WildwoodTrekker83 路 reviewed about 1 year ago

star star star star star

Frequently asked questions for hikes in Massachusetts

What is the climate like for hiking in Massachusetts?

Massachusetts showcases a varied climate that shapes the hiking experience across seasons. Spring (March-May) offers cooler temperatures and budding vegetation, though trails can be muddy from snowmelt. Summer (June-August) presents warm, sunny days perfect for hiking, but hydration is crucial due to the heat.
Fall (September-November) is ideal for hiking with moderate temperatures and stunning fall colors. Winter (December-February) provides serene snowy landscapes for well-equipped hikers. Autumn is often recommended for the most comfortable hiking experience. Always check the weather before setting out. The Massachusetts Department of Conservation and Recreation (https://www.mass.gov/orgs/department-of-conservation-recreation) and the National Weather Service (https://www.weather.gov/) are excellent resources.

Do I need a permit to hike in Massachusetts?

In Massachusetts, most hiking trails are open to the public without requiring permits. However, for certain activities such as camping or fishing, you may need a permit. To obtain permits and get further information, contact the Massachusetts Department of Conservation and Recreation (https://www.mass.gov/orgs/department-of-conservation-recreation).

Is wild camping allowed in Massachusetts?

Wild camping in Massachusetts is generally restricted to designated campgrounds within state parks and forests. Some areas may require a camping permit. To protect the natural environment, always follow Leave No Trace principles. For camping regulations and permit information, visit the Department of Conservation and Recreation's website (https://www.mass.gov/orgs/department-of-conservation-recreation).

Are there mountain rescue services in Massachusetts?

In case of emergencies during hiking in Massachusetts, dial 911 to reach local authorities who will coordinate with the appropriate agencies for mountain rescue. The Massachusetts Department of Conservation and Recreation's Park Watch Program is also involved in rescue efforts. Visit their website for more information (https://www.mass.gov/orgs/department-of-conservation-recreation).

Are there dangerous plants in Massachusetts?

Hiking in Massachusetts, you'll find a variety of flora including oak, maple, and pine trees, along with a diverse array of wildflowers. Be aware of poison ivy, especially in wooded areas. For more on Massachusetts' flora, the Native Plant Trust's Go Botany website (https://gobotany.nativeplanttrust.org/) is a helpful resource.

What wildlife should I be aware of when hiking in Massachusetts?

Hikers in Massachusetts might encounter white-tailed deer, squirrels, and a variety of bird species. Be mindful of ticks and mosquitoes during the warmer months. Black bears are present, though encounters are rare. The Massachusetts Division of Fisheries & Wildlife (https://www.mass.gov/orgs/division-of-fisheries-and-wildlife) provides useful wildlife information.

More hikes in Massachusetts

by difficulty

by type

by activity