15 Stunning Hikes in Massachusetts for All Levels - Urban Outdoors
Some of our posts include affiliate links. When you make a purchase from one of these links, The Urban Outdoors may receive a commission at no additional cost to you. As always, we only recommend products and services we actually use - no BS necessary.

While Massachusetts may be best known for its historical landmarks, delicious seafood, and plethora of top-tier universities, it’s also quite a diverse and beautiful state for outdoor activities. Hiking in Massachusetts is one of the most fun and exciting ways to explore everything this beautiful New England state has to offer. From rocky mountain scrambles to serene seaside strolls, there’s something for everyone here! Don’t take our word for it – here’s a list of some of the best hikes in Massachusetts for all experience levels so you can plan your next outdoor adventure!

Looking for the perfect gift for your favorite hiker? Here’s a comprehensive list of our
35 favorite (practical) gifts for hikers, updated for 2020!

Things to Know Before Hiking in Massachusetts

  • Fall is the best time to go hiking in Massachusetts. While hiking is a year-round activity in Massachusetts, there’s no time of year more magical than the fall. The vast forests in the state turn yellow, orange, and red, creating a spellbinding landscape for just a few short weeks each year. Plus, the air is cool and dry, and you can enjoy delicious fall treats like apple cider and pumpkin pie once you’re finished with the trails.
  • Most of the hikes in Massachusetts are easy or moderate. While there are hiking trails spanning all levels in Massachusetts, the vast majority are easy or moderate. The majority of the state has fairly flat land, so if you’re looking for some more challenging hiking, head to New Hampshire or Maine.
  • For harder hikes, check out the western part of the state. If you’re looking for a fun challenge or to level up your hiking skills, head to the central or western part of the state for a day or a weekend trip to make the most of your outdoor time!

Easy Hiking in Massachusetts

Bash Bish Falls

  • Location: Bash Bish Falls State Park (South Egremont, MA)
  • Trail Length: 2.1 miles
  • Elevation Gain: 521 feet

Located on the border with New York, Bash Bish Falls is a wonderful (and dearly beloved!) place for hiking in Massachusetts. This 2.1-mile trail leads through a forested path to a scenic set of two waterfalls, which is a very popular spot for photography in the state. You’ll cross the MA/NY border and enjoy some pretty creek views along the way, and the falls at the end drop nearly 60 feet, which is a spectacular sight.

Because of the short length and variety of sights on the trail, it’s an especially popular choice for families with young children. Because this trail is so easy and accessible to all experience levels, it can get extremely crowded during summer and fall weekends. Head there early or on weekdays for the best experience!

Photo Credit: Michael O’Brien (Flickr CC)

Halibut Point Trail

  • Location: Halibut Point State Park (Rockport, MA)
  • Trail Length: 1.6 miles
  • Elevation Gain: 121 feet

As one of the most beautiful and scenic hikes in Massachusetts, the Halibut Point Trail is a short, easy hike along the rocky shorelines. This exceptionally beautiful seaside area boasts a 1.6-mile hiking trail that passes a lighthouse, several tide pools, and a rocky coastline with breathtaking views of the sea. 100 years ago, the area served as a granite quarry, and visitors can still see some of the remnants of it in the large granite rock piles. Locals really love this trail, saying it’s easily one of the most beautiful in the state.

During the fall, the vegetation area turns bright colors, painting an even more spectacular landscape. While this trail is easy, some parts can be jagged with the coastal rocks, so we’d recommend wearing closed-toed shoes or hiking boots to keep your feet safe! We’d recommend coming here on sunny days, as wet conditions can make the rock areas slippery.

Keystone Arch Bridges Trail

  • Location: Walnut Hill Wildlife Management Area (Chester, MA)
  • Trail Length: 5 miles
  • Elevation Gain: 501 feet

Some think easy hikes are always short hikes, but that’s definitely not always the case. The Keystone Arch Bridges Trail is a great example of one of the easy hikes in Massachusetts that’s also a bit longer than most. Combining historic stone bridges with beautiful, peaceful forest settings, this trail is a wonderful way to spend a few hours enjoying nature and seeing some of the most beautiful scenery in Massachusetts.

You’ll traverse several of the stone bridges throughout the 5-mile hike, but if you want to see them from the waterside, you’ll need to embark on some pretty difficult and steep terrain to get down. There are also several swimming areas along the way, so during the warmer months, be sure to bring a swimsuit!

Photo Credit: cmh2315fl (Flickr CC)

World’s End Trail

  • Location: Boston Harbor Islands National Recreation Area
  • Trail Length: 3.8 miles
  • Elevation Gain: 282 feet

For some of the most spectacular views of the Boston skyline, the World’s End Trail is a local favorite. Located in the Boston Harbor Islands National Recreation Area, this easy, accessible trail offers beautiful rocky shoreline paths, bird watching, and views over the harbor of the city. For easy hiking near Boston for the whole family, you can’t go wrong with World’s End! We’d recommend heading here on clear days for the best views and hiking conditions.

Walden Pond

  • Location: Walden Pond State Reservation
  • Trail Length: 1.7 miles
  • Elevation Gain: Minimal

For an easy trail in a forested setting, Walden Pond is a fantastic (and historic!) option for hiking near Boston. Known for being the setting of Henry David Thoreau’s book of the same name, this peaceful, scenic wooded trail is not only beautiful, but also a treat for literature lovers as well.

Spending some time on this trail will show you why Thoreau was so at peace and inspired by this place – there’s a peaceful pond, thick, wooded paths, and a replica of his one-room cabin where the book was written. For those who are familiar with Thoreau, this trail is a real treat. But even if you aren’t, you’ll still find a lot to love about this easy, relaxed stroll through the woods.

Moderate & Difficult Hikes in Massachusetts

Purgatory Chasm

  • Location: Purgatory Chasm State Reservation (Sutton, MA)
  • Trail Length: 1.7 miles
  • Elevation Gain: 180 feet

One of the most unique natural landmarks in Massachusetts is Purgatory Chasm, a rocky area that’s made of a deep ravine between two granite rock walls. A beloved area for climbing near Boston, this gorgeous trail is perfect for taking a hike and experiencing the chasm for yourself. With well-maintained, forested trails that border awe-inspiring rock formations and tiny waterfalls, there’s something to see around every turn on this short, moderate trail. Purgatory Chasm State Reservation has tons of trails that are interconnected, so you can definitely follow the signs here and choose your own adventure!

Hoosac Range Trail

  • Location: North Adams, MA
  • Trail Length: 6.2 miles
  • Elevation Gain: 938 feet

Some hikers prefer the fun and challenge of longer trails, and the Hoosac Range trail is one of the best moderately difficult hikes in Massachusetts. The Hoosac Range trail is so beloved by locals that you’ll find people out there during all seasons, even in the dead of winter! With 6.2-miles of trails, this gorgeous hike brings you to the top of the Hoosac Range, which offers beautiful views of nearby mountains, especially during foliage season. When you’re not gazing out at the spectacular vistas, you’ll be traversing miles of forested trails, with lush trees and green, mossy terrain.

Photo Credit: Josh Graciano (Flickr CC)

Noanet Peak Trail

  • Location: Noanet Woodlands (Dover, MA)
  • Trail Length: 3.2 miles
  • Elevation Gain: 492 feet

There are few trails more beautiful during the fall foliage season than the Noanet Peak trail. Located in Dover, MA, this beautiful mountain trail brings hikers up a steady incline to gorgeous mountain/forest views, as well as a lakeside trail with some exceptional reflections. The peak itself is quite rocky but several spots offer really stunning bird’s eye views of the Boston skyline and the surrounding landscape that Eastern Massachusetts has to offer. For a moderate summit hike that’s accessible to all levels of hikers, the Noanet Peak trail is a wonderful option that’s not too far from Boston or Providence.

Borderland State Park Loop

  • Location: Borderland State Park (Easton, MA)
  • Trail Length: 8.5 miles
  • Elevation Gain: 439 feet

Located in Southeastern Massachusetts, the Borderland State Park Loop circles a network of trails around Borderland State Park that offers hikers (and bikers) a wonderful spot for enjoying the diverse landscapes and structures of the park. Filled with towering boulders, vast forests, and crumbling stone structures, this state park offers both history and nature combined seamlessly into one long hiking trail. It’s also the longest moderate hike on our list – accessible to all levels, but certainly a challenge in some areas, the Borderland State Park area is a fantastic day hike to add to your list.

Photo Credit: Jones Road Caddie (Flickr CC)

Great Island Trail

  • Location: Cape Cod National Seashore (Wellfleet, MA)
  • Trail Length: 4.7 miles
  • Elevation Gain: 144 feet

For the best views of the Atlantic Ocean, one of the quintessential Massachusetts hikes is the Great Island Trail on Cape Cod. As one of our favorite hikes on this list, the Great Island trail winds through possibly one of the most beautiful areas on the East Coast. Don’t let the tiny elevation gain fool you – the terrain here is largely sand, meaning you’ll definitely get some exercise just maneuvering through the sandy hills and beaches.

Because it’s on the coast, the best time to go is during low tide on a sunny, clear day to avoid any weather-related complications. The farther in you hike, the less crowded the trail gets, and you may even get stretches of coastline all to yourself.

Mount Wachusett

  • Location: Wachusett Mountain State Reservation (Princeton, MA)
  • Trail Length: 4.9 miles
  • Elevation Gain: 1,151 feet

Perhaps the most popular moderate trail on our list, Mount Wachusett is a favorite hike for Massachusetts locals, with stunning views and varied terrain leading up to a tall fire tower at the top of the mountain. There are lots of trails in the park that lead up to the summit, but many folks recommend taking the Old Indian, Stage Coach, and Bicentennial trails to form a ~5 mile loop hike that passes through the peak. Along the way, there are large boulders, gnarled tree roots, and vast forest areas to explore.

Photo Credit: Bob P. B. (Flickr CC)

Blue Hills Skyline Loop

  • Location: Blue Hills Reservation
  • Trail Length: 5.4 miles
  • Elevation Gain: 692 feet

The Blue Hills Skyline Trail is one of the most epic hiking trails near Boston, and is a 5.4 mile loop across the Blue Hills Reservation. With tons of rocky areas, this trail is great for experienced hikers who enjoy steep inclines and some scrambling (one of the few hikes in Massachusetts that offers this!), as it summits several of the hills along the Blue Hills ridge. Those who complete the trail will enjoy stunning views of the Boston skyline, as well as access to some of the historic landmarks and structures located within the Blue Hills Reservation.

Mt. Hitchcock & Summit House

  • Location: Mount Holyoke Range State Park (Amherst, MA)
  • Trail Length: 13.5 miles
  • Elevation Gain: 2,493 feet

As one of the most challenging hikes in Massachusetts, advanced hikers will enjoy the length and challenge of the Mount Hitchcock and Summit House trail in Mount Holyoke Range State Park. This 13.5-mile trail is beloved by hiking enthusiasts in the area for being absolutely stunning and offering enough of a challenge for adrenaline seekers. The trail runs through lots of nature areas, including streams, lakes, forests, and rocky bald ridge lines. Hikers can expect to spend a full day on this hike, so bring lots of food and water for the journey. Also, beware of slippery areas after heavy rainfall.

Mount Greylock via Gould Trail

  • Location: Adams, MA
  • Trail Length: 6.5 miles
  • Elevation Gain: 2,267 feet

Massachusetts’ highest point is at the summit of Mount Greylock, which is located in the northwest corner of the state. There are many ways to reach the summit, but one of the best ways to go is by hiking the Gould Trail. Along the way, you’ll find interesting rock areas, cabins, and forested areas to enjoy, but the real treat from the top is getting to see the Massachusetts Veterans War Memorial and the surrounding views. Plus, you can say you hiked all the way to Massachusetts’ highest point!

Mount Williams, Mount Fitch, Mount Greylock, and Stony Ledge

  • Location: Mount Greylock State Reservation (Williamstown, MA)
  • Trail Length: 12.4 miles
  • Elevation Gain: 3,015 feet

If one western Massachusetts summit isn’t enough for you, there’s a trail that takes you to four. The Mount Williams, Mount Fitch, Mount Greylock, and Stony Ledge trail hits 4 mountain peaks over the course of 12.4 miles, making for a spectacular full-day hike that even experienced hikers will truly enjoy. Many people are able to finish this trail in around 7 hours, including stops for views and rest at each summit. For hikers who are looking for a challenging and highly rewarding hike through some of the state’s tallest mountains, this trail is definitely for you.

Additional Resources for Hiking in Massachusetts

What to Pack

  • Hiking boots – You can’t hike without appropriate footwear, period. For most trails, we recommend an all-purpose waterproof boot with ankle support. We recommend Salomon hiking boots or Keen hiking boots for a comfortable hike.
  • Breathable hiking clothes – For warmer hikes, you’ll want to stay cool in a sweat-wicking shirt/tank top and breathable pants, like these PrAna hiking pants for men and women. For cold-weather hikes, we recommend dressing in layers, including merino wool baselayers, an insulated puffer jacket, and a waterproof outer shell. And don’t forget a pair of the best hiking socks in the world!
  • Trekking poles – You won’t need these for every single hike, but we recommend throwing them in your car anyway just in case. We recommend the Black Diamond foldable trekking poles, which are lightweight and easy to transport.
  • Water bottle – Having water available at all times is a huge must. To spare disposable plastic, we recommend bringing your own refillable water bottle. We’re obsessed with Hydro Flask bottles because they keep water cold for hours, but a good old Nalgene works very well too.
  • Sunscreen and bug spray – This should be self-explanatory, but sweatproof sunscreen and DEET bug spray can help you avoid sunburn and bug bites, two of hiking’s most annoying after-effects.
  • A brimmed hat or cap – The sun can be brutal in open hikes, so always pack a brimmed hat or cap for day hikes in the sunshine.
  • Emergency blanket and first aid kit – We’d strongly recommend bringing a first aid kit and a lightweight emergency blanket on every hike. Why? Because the unfathomable can happen, and it’s always best to play it safe.
  • Durable day pack – A durable day pack is the perfect spot to stash all your hiking gear. While any backpack will do, we recommend Osprey day packs because they’re comfortable and breathable for long hikes.

Wondering what exactly you should pack for your next hike? Visit our Complete Day Hiking Packing List for our full list and our top gear recommendations.

Related Articles

Avatar
Author

Kay Rodriguez is the founder of Urban Outdoors. She's also the writer and photographer behind Jetfarer. When she's not writing furiously on her laptop or editing photos, you can find Kay running, hiking, paddling, or playing in the snow.

Write A Comment