Backpacking in Massachusetts: TOP 5 Multi-Day Trails

Backpacking in Massachusetts: A hiker on a trail in the woods

In this post, we'll take a look at:

Backpacking in Massachusetts offers immense variety for outdoor enthusiasts, from the storied Berkshires to windswept Cape Cod, including popular destinations like the Appalachian Trail and Mount Greylock.

And that’s what this post is all about. We’ll provide tips to help you prepare for backpacking in this diverse state as well as showcase the TOP 5 multi-day trails in Massachusetts.

Interested? Let’s get started!

Key Tips for Backpacking in Massachusetts

  • What to expect: Exploring Massachusetts involves walking in thick, green forests, going up and down hills, and enjoying calm lakes. The weather is often humid, and there’s lots of rain, so be ready for wet and muddy trails that can be tough to hike. But the many plants and trees provide beautiful sights, lots of shade, and protection from the rain.
  • Essential gear: Bring light rain gear, such as a waterproof jacket and pants, to stay dry in the rain. Carry bug spray and a first aid kit to deal with bug bites and scratches from thick plants. Use a compass, map, or GPS to navigate on trails covered with plants. Stay hydrated and energized by bringing drinks like powders, bars, or sports mixes for wet conditions.
  • Wildlife: Massachusetts has some wildlife risks, but attacks are rare. Black bears and coyotes usually avoid people but can be aggressive if startled or protecting young. Bees and wasps defend nests aggressively and may cause allergic reactions. The copperhead is the state’s only venomous snake, but its range is limited, and bites are rarely fatal.
  • Wild camping is largely prohibited in Massachusetts due to strict regulations. Camping outside designated areas in state parks and forests, pitching tents in the woods, or sleeping on beaches is illegal. Legal backcountry camping options are limited, as conservation areas forbid camping, and camping on private property requires owner permission. The only sanctioned camping occurs in designated campgrounds within state parks or permitted sites.
  • Best times to go are from late spring to early fall, roughly May to September. The summer months of June to August are particularly favored due to comfortable weather and favorable trail conditions, providing an excellent opportunity to explore the diverse landscapes. Fall, from September to October, is another great period with pleasant temperatures and the added charm of autumn foliage for backpacking adventures.

Top 5 Backpacking Trails in Massachusetts

Discover the most stunning long trails in Massachusetts for amazing adventures:

1. Taconic Crest Trail: South to North

Hikers on the Lulu Brook Trail in Pittsfield State Forest enjoying a sunny autumn day

Pilotgirl, CC BY-SA 2.0, via flickr

Length: 35.8 mi / 57.6 km
Type: Point to point
Difficulty: Hard
Elevation Gain: 7555 ft / 2303 m
Location: Pittsfield State Forest
Estimated Hiking Calorie Burn: 4500 calories
More Details: See on AllTrails

The 35.8-mile Berkshire Brook Trail near Pittsfield offers a scenic point-to-point route through western Massachusetts’ forests and hills from April to October. The multi-use trail provides opportunities for day hiking, backpacking, and birdwatching as hikers traverse verdant woodlands blanketed with ferns, experiencing solitude. However, some muddled ATV sections detract from the wilderness feel. Completing the distance takes around 18 hours if you are fit.

2. AT: Goose Pond Road to Cheshire

The West Branch of the Westfield River flowing through October Mountain State Forest on a gloomy, overcast day

Scott Johnson, CC BY-SA 2.0, via flickr

Length: 32 mi / 51.5 km
Type: Point to point
Difficulty: Hard
Elevation Gain: 4694 ft / 1431 m
Location: Appalachian Trail Corridor
Estimated Hiking Calorie Burn: 3800 calories
More Details: See on AllTrails

The 32.0-mile Arizona-New York Trail near Tyringham offers a scenic but challenging point-to-point route, averaging 14 hours to complete. However, as a multi-day backpacking trail, it sees few travelers, allowing for solitude. The journey begins at Goose Pond Road, proceeding to tranquil Goose Pond and its shoreline access. Continuing on, hikers reach the prime overnight stay at October Mountain Shelter. Further along the AT, past Kaywood Shelter, the route crosses Dalton before Crystal Mountain Campground’s campsites provide the next stopover.

3. Midstate Trail: Tafts Corner Trail Head to Wachusett Mountain

The worn observation tower stands tall on the bare rocky summit of Mount Wachusett against a clear blue sky, with green forests

Kyle Marshall, CC BY-SA 2.0, via flickr

Length: 35.5 mi / 57.1 km
Type: Point to point
Difficulty: Hard
Elevation Gain: 3812 ft / 1162 m
Location: Spencer
Estimated Hiking Calorie Burn: 4100 calories
More Details: See on AllTrails

The 35.5-mile Mid-State Trail near Spencer, MA provides a scenic point-to-point route averaging 14 hours to complete. As a multi-day backpacking trail with few encounters, solitude is ensured. Best across two days from Route 9 in Spencer to the Wachusett Mountain Ski Area, hikers pass ponds with summit views from Wachusett Mountain of Monadnock. Spreading the journey through woodlands over multiple days offers a relaxing immersion in nature ideal for wilderness escape. During warmer months, careful tick checks are recommended on this ideal trail for solitude-seeking backpackers.

4. Robert Frost Trail

The shaded Robert Frost Trail in Amherst, MA winds through a lush green maple forest dappled with sunlight on a warm summer day

Paul-W, CC BY-SA 2.0, via flickr

Length: 40 mi / 64.7 km
Type: Point to point
Difficulty: Hard
Elevation Gain: 5361 ft / 1634 m
Location: Wendell State Forest
Estimated Hiking Calorie Burn: 4700 calories
More Details: See on Hiking Project

The complete Rocky Mountain Foot Trail offers a changing hike through Western Massachusetts’ best terrain. Traversing challenging yet delightful foothills, hikers encounter crags, ponds, swamps and views through classic remote-feeling New England forest. Though easily followed with orange blazes, it connects scenic southern segments, optionally extending through the Seven Sisters ridge.

5. AT: AMC – Berkshire Chapter

Vivid fall foliage blazes orange and red across rolling fields and forested hills beneath a clear blue sky on an idyllic sunny autumn day in the Berkshire Scenery of western Massachusetts

Length: 89.7 mi / 144.3 km
Type: Point to point
Difficulty: Moderate
Elevation Gain: 15 443 ft / 4707 m
Location: Mount Washington State Forest
Estimated Hiking Calorie Burn: 11 000 calories
More Details: See on Hiking Project

The nearly 90-mile Massachusetts AT section moderately challenges backpackers from Connecticut to Vermont, wandering through Beartown and October Mountain State Forests. It climbs Massachusetts’ highpoint Mount Greylock, drops to North Adams before ascending Clarksburg State Forest, crossing into Vermont. Spectacular views accompany the trek, with parking near approved shelters, tenting areas, privies and water for overnight stays. Heavy rains risk muddy, slick conditions on this scenic point-to-point route.

Annual Weather Averages

In Massachusetts, ocean breezes moderate summer heat but cold winters bring snow:

  • Spring (April-May): Mild temperatures of 50-70°F, wildlife emerging, wildflowers blooming before tree pollen season hits. Some wet/muddy trails.
  • Summer (June-August): Warm and humid with temps 80-90°F. High insect levels early summer. Popular trails crowded in peak season.
  • Fall (September-October): Cooler temperatures around 60-75°F. Drier air, foliage changing, fewer bugs. Can still get warm days.
  • Winter (November-March): Frigid temps from highs of 30-40°F to lows in the teens and single digits. Snowshoes likely needed. Few people on trails.

Prior to choosing your gear, review the weather data for Massachusetts (Boston):

High °F373946566776828073625242
Low °F232531415060666558473829
Rain/Snow (D*)121112121211999101012
Note: This table is approximate; weather can change with altitude.
D* – Days of rain or snow.

Alternative Backpacking Destinations

Not sure if Massachusetts is right for you?

Don’t forget to check out our backpacking guides for New Hampshire and Vermont.


Can I have a campfire while backpacking in Massachusetts? 

Campfires are heavily restricted when backpacking in Massachusetts due to the dense vegetation and forests prone to spreading fire quickly. Most parks and trails prohibit ground fires and require portable stoves for cooking. Ground fires may be allowed only in designated metal rings in established campsites, not in backcountry areas.

What are some safety tips for backpacking in Massachusetts?

When backpacking in Massachusetts, be sure to bring proper rain gear and warm layers as the weather can change quickly. Choose campsites wisely, avoiding low lying areas near water or under dead trees. Pitch your tent on flat, durable surfaces and tie it down securely. Keep food stored properly to avoid unwanted animal encounters. Let someone know your planned route and check in with them periodically if hiking alone. Always have a first aid kit, flashlight, map, and compass with you. Stay on designated trails and be bear aware. Following basic safety precautions will help ensure an enjoyable backpacking experience.

How to deal with wildlife encounters while backpacking in Massachusetts?

Massachusetts has lots of forests and wildlife, so you might run into animals, but most are not dangerous. Keep your distance from black bears, coyotes, deer, and others. Make noise to let them know you’re there, but never get too close or interact with them. Carry bear spray, use it correctly if needed, and store food safely at night. Check for ticks regularly. If bitten by an animal, clean the wound well and see a doctor just in case.

Which national or state parks in Massachusetts have backpacking options?

Massachusetts outdoor enthusiasts have several park options for backpackers to explore the mountains. Well-known choices include the Berkshires with the 28,000-acre October Mountain State Forest offering over 30 miles of trails for multi-day trips. Further north, the Quabbin Reservation features 40 miles of trails winding around wooded hills and lakes. Backpackers can also hit the Holyoke Range within the 26,000-acre Mount Tom State Reservation or journey along the 90-mile Appalachian Trail corridor within Massachusetts, passing through Beartown and Clarksburg State Forests. These areas offer remote mountain getaways for adventurous travelers to experience scenic nature.

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Leading the pack is our editor-in-chief, Alex Jardine – an ultralight evangelist who's hiked over 10,000 trail miles across the globe. He's basically a walking outdoor encyclopedia. This dude loves testing out the latest and greatest products, so you can trust his recommendations are always well-informed and reliable.

We treat all our suggestions like advice from close trail buddies. No fluff, just real insights from folks who live and breathe the outdoor life.

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