Best Hikes in Massachusetts by Region; 20 Must-Do Trails

ByKristen Valenti Updated on

If you're looking for the best hikes in Massachusetts then you've come to the right place! Find hikes with amazing views, scenic waterfalls, and unique trails across each region of the state.

  • bash bish falls waterfall in fall surrounded by orange leaves.
    The tallest waterfall in MA
  • view from the top of mount greylock with woman and two big black dogs in the photo on a sunny day
    Tallest mountain in MA
  • ward reservation in andover massachusetts hike in october with blue skies and red leaves on the trees
    Preserve near Boston, hike 14 on the list

I lived in the Berkshires in western Massachusetts for years and though I live nextdoor in Connecticut now, I continue to take day trips across the CT border to hike the best of Massachusetts' trails. There's so much to choose from...

From the 90 miles of hiking on the Appalachian Trail running through western MA, to the 15 miles of the Holyoke Range in Pioneer Valley, and incredible preserves and reservations in eastern MA (close to Boston!) - there's a ton to hike in Massachusetts and so many reasons for me to keep visiting!

This post includes 20 hikes which made the list because of their incredible views, flowing must-see waterfalls, off-leash dog priveleges, or other unique features. They vary in miles and difficulty and they're all special!

red and orange colored trees in autumn surrounding a lake with a white poodle standing on the shore next to a bench at lake cochichewick
Hike 11 on our list, just north of Boston in Andover, MA 🍁❤️

There is truly something for everyone on this list and I'm excited to put all my Massachusetts favorites in one spot! I've written detailed guides about several of the hikes here so if you're looking for more information and direction you'll be able to find it in those guides.

The list is organized by region. So let's get to it! Grab a pen and paper and make your Massachusetts trail bucket list!

🥾The Best Hikes & Views in Massachusetts; By Region🗺️

Hikes in Western Massachusetts (The Berkshires & Pioneer Valley)

1. Mount Greylock (Adams)

  • woman and two dogs at top of mount greylock in the fall
  • top of veterans memorial at greylock
  • woman and two dogs at top of mount greylock in the fall

Standing 3,491 feet tall, we must start this list off with the tallest mountain in Massachusetts- Mount Greylock. 😍 You'll find sweeping views at the top but also from the top of Veterans War Memorial Tower. Bring cash in case Bascom Lodge is open and you need a snack!

I've hiked Greylock in every season and have taken many different routes to the top. You can find a full trail guide for the best route up Greylock if you're hiking in late spring through fall the Mount Greylock via Sperry Road and Hopper Trail is ideal and the most moderate.

hike up to mount greylock in fall

If you're want a longer route or hiking in winter take the Bellow's Pipe Trail which is longer but it's one of the few whose parking lot will be open. 🙂 You can also check out my full post ➡️ 4 Distinct Routes Up Mount Greylock if you'd like to explore more!

2. Mount Race via Race Brook Falls Trail (Sheffield)

  • woman with pony tail and light pink tank top and blue shorts walking up mount race with brown dog and green hills in background.
  • race brook falls waterfall tumbling down in summer surrounded by green trees.
  • race brook falls waterfall tumbling down in summer surrounded by green trees.

Mount Race is a must-do hike in Massachusetts for it's wide open views and waterfall combined in one epic hike. Located in the very western corner of the state, you'll find it worth the drive!

The Race Brook Trail to Mount Race hits the major highlights including the wide open views atop Race and Race Brook Falls on the way up. You'll get a classic New England hiking experience as you'll be on the white-blazed Appalachian Trail for a good chunk of it. If you'd like a shorter or even longer hike to the top of Race check out the post I wrote ➡️ Best Routes Up Mount Race.

  • woman with pony tail and light pink tank top and blue shorts walking up mount race with brown dog and green hills in background.
  • woman smiling in black jacket and black hiking pants with black dog atop snow covered Mount Race in Massachusetts with a golden sunrise in the distance.

3. Bash Bish Falls (Mount Washington)

  • bash bish falls waterfall in fall surrounded by orange leaves.
  • woman sitting on rock along bash bish falls in fall surrounded by orange leaves.

Of course, the tallest waterfall in MA has to be on our list - the 200 foot tall Bash Bish Falls. The final cascade of Bash Bish Falls plunges nearly 60 feet into a sparkling pool, surrounded by dramatic cliffs. It’s a must-see for waterfall lovers and one of the most photographed natural spots in the state.

I've got a post that covers 2 different trails to Bash Bish, both are short and easy to follow but one is from NY and one is from MA. You can read more and choose here! ➡️ Trail Guide to Bash Bish Falls 💦 The info below for the trail starting from the MA parking lot!

4. Monument Mountain (Great Barrington)

sunrise hike at monument mountain in great barrington
Monument Mtn at sunrise
sunrise view from a snowy mountain with yellow and orange colors in the sky
Monument Mountain sunrise

Known for its literary history—Herman Melville and Nathaniel Hawthorne once hiked here—Monument Mountain is beloved for its rocky cliffs and panoramic views. The trail is moderate yet rewarding, making it a favorite stop in the southern Berkshires.

Located minutes outside of Great Barrington, you can combine a hike up Monument Mountain with exploring the town of GB and making a day of it! Day Trip Great Barrington 🥾

The info below is for a 2.5 mile loop hitting all the views and cliffs at the top - the Hickey and Peeskawso Peak Loop. There are several lookout spots here and the ridge faces east in case you'd like to try it for sunrise!

  • 🌟What makes it special: Wide open ledge views close to downtown Great Barrington, numerous lookouts
  • 🥾Miles & Difficulty: 2.5 mile loop, moderate
  • 📈Elevation Gain: 669 ft
  • 🚙Parking: Click to navigate to 42.24342, -73.33539

5. Mount Tom via New England Trail (Holyoke/Hadley)

Located right outside Hadley, Mount Tom's traprock ridges rise steeply from the Connecticut River Valley, offering a series of several ledges and lookouts.

I couldn't believe how many views there were here and it felt like every 100 feet we would pop out on the ridge for more views of farmland and the rolling hills of western MA. The view at the very end of the hike (the top of Mount Tom) is not the best compared to all the ones leading up to it so if you want some good photos be sure to stop along the way!

  • 🌟What makes it special: wide open ridge trail with western facing lookouts (so many lookouts!)
  • 🥾Miles & Difficulty: 3.9 miles out & back, moderate
  • 📈Elevation Gain: 990 ft
  • 🚙Parking: Click to navigate to 42.2648, -72.63876

6. Mount Norwottuck (Holyoke/Hadley)

  • horse caves on the way to mount norwottuck in massachusetts
  • woman smiling on top of mount norwottuck with black dog and green mountains in the background
  • view from the top of mount norwottuck with greenery and red leaves in the front at the start of fall

Part of the Mount Holyoke Range, Mount Norwottuck offers some of the best views in the Pioneer Valley. From its rocky summit ledges, you'll can see farmland, small towns, and even the distant Berkshires.

Along the way, the trail passes through unique traprock cliffs and caves, including the historic Horse Caves—a fascinating spot with Revolutionary War legends. Norwottuck combines geology, history, and sweeping views, making it a must-hike in western Massachusetts!

woman smiling on top of mount norwottuck with black dog and green mountains in the background

And for trail details and turn-by-turn directions to see all the views and the not-to-miss Horse Caves check out my guide ➡️ Mount Norwottuck Trail Guide 🥾

  • 🌟What makes it special: breathtaking views (2 different lookouts), plus the Horse Caves
  • 🥾Miles & Difficulty: 3.6-mile loop, moderate
  • 📈Elevation Gain: 748 ft
  • 🚙Parking: Click to navigate to 42.30495, -72.52802

7. Sanderson Brook Falls Loop (Holyoke / Hadley)

  • sanderson brook falls waterfall
  • woman smiling at the view at sanderson brook falls hike
  • dog looking out from the view at top of sanderson brook falls loop

Tucked inside Chester-Blandford State Forest, the Sanderson Brook Falls Loop leads to one of the prettiest waterfalls in the Berkshires. The falls drop gracefully over rocky ledges, especially impressive in spring when the water is high.

The trail itself is peaceful and shady, winding through hemlock groves and along the brook. With its quiet forest setting and rewarding waterfall view, it’s a hidden gem that feels like a step back into old New England.

For trail details and turn-by-turn directions for the 4.4-mile loop to the view and waterfall at the end, check out my guide ➡️ Mount Norwottuck Trail Guide 🥾

  • 🌟What makes it special: Gorgeous views, peaceful state forest, plus Sanderson Brook Falls waterfall
  • 🥾Miles & Difficulty: 4.4-mile loop, moderate
  • 📈Elevation Gain: 1,079 ft
  • 🚙Parking: Click to navigate to 42.25619, -72.94681

Hikes in Central Massachusetts

8. Wachusett Mountain (Princeton)

  • woman smiling at the top of mount wachusett with green mountains behind her and two black dogs with her.
  • dog at top of Mount Wachusett with green mountains in the background.
  • view of ski lift in spring along a loop trail at mount wachusett with bright green mountains and blue sky in the distance.

The highest point in central Massachusetts, Wachusett is known for its wide-open summit views that stretch all the way to Boston. This feels like a true mountain hike with over 1,000 feet of elevation and summit views at the top.

Though there is a tower at the top, it is not one you climb. Still the surrounding views make this hike worth it. There are a couple scramble sections on the way up and down but it's nothing too difficult. We saw people of all ages on this hike. If you'd like more details check out my post all about my experience hiking here ➡️ Mount Wachusett Trail Guide 🥾 for details and turn-by-turn trail directions!

9. Mount Watatic (Ashburnham)

Once home to a ski area, Mount Watatic is now a peaceful hiking destination with a broad, open summit. Its grassy ledges make it a perfect spot for a picnic, and the views toward Mount Monadnock in New Hampshire are outstanding!

The Mount Watatic and Nutting Hill via Wapack Trail gets you to the the top in just 1.5 miles! It comes at a steep price though with an elevation of 725 feet. That means it's going to be steep and challenging from start to finish so choose this one if you're in pretty good hiking shape or want to push it for a workout!

10. Tully Lake Loop (Royalston)

Tully Mountain is a small summit with big rewards—360-degree views that rival higher peaks. Just a short drive away, Royalston Falls adds to the adventure with a dramatic 80-foot cascade tucked in the forest, making the area a great double-hike destination.

  • 🌟What makes it special: Peaceful lake loop plus Doane's Falls waterfall
  • 🥾Miles & Difficulty: 4.4-mile loop, moderate
  • 📈Elevation Gain: 282 ft
  • 🚙Parking: Click to navigate to 42.64978, -72.20085

Hike in Eastern Massachusetts (Boston Area & North Shore)

11. Weir Hill Reservation - Cochichewick Loop (Andover)

  • red and orange colored trees in autumn surrounding lake cochichewick
  • view atop a big hill of a meadow overlooking lake cochichewick
  • red and orange colored trees in autumn surrounding a lake with a white poodle standing on the shore at lake cochichewick

Weir Hill is a hidden gem in the Merrimack Valley, offering a mix of open meadows, wooded trails, and lakeside views. A Trustees of Reservations property, the short climb to the top rewards you with a sweeping overlook of Lake Cochichewick, making it a peaceful spot that feels far from the busy suburbs.

I loved the diversity of this hike from the trails all along the lake to the wide open meadow and view from the top. For a full guide about this hike check out this post ➡️ Weir Hill Trail Guide 🥾 for details and turn-by-turn trail directions!

multiple big dogs resting atop a big hill of a meadow overlooking lake cochichewick
  • 🌟What makes it special: Trail all along scenic Lake Cochichewick plus wide open meadow with views
  • 🥾Miles & Difficulty: 5.5-mile loop, moderate
  • 📈Elevation Gain: 505 ft
  • 🚙Parking: Click here to navigate to 42.68925, -71.10634

12. Gibbs Mountain Loop

  • black dog in beebe pond at gibbs mountain with blue water and green trees all around.
  • black dog on wide pine needle trail going through green grass and trees at Gibbs Mountain in Massachusetts.
  • open green meadow green grass and blue sky Gibbs Mountain in Massachusetts.

Located within Callahan State Park, the Gibbs Mountain Loop is a quiet woodland trail that offers rolling hills and a lakeside trail. It’s a gentle hike with rolling terrain, perfect for hikers of all ages looking for a scenic walk without a strenuous climb.

If you'd like more details about this hike check out my post ➡️ Gibbs Mountain Trail Guide 🥾 for lots of details including turn-by-turn trail directions!

  • 🌟What makes it special: peaceful paths in pine forests and around the lake
  • 🥾Miles & Difficulty: 3.8-mile loop, moderate
  • 📈Elevation Gain: 452 ft
  • 🚙Parking: Click to navigate to 42.33899, -71.49944 

13. Rocky Woods Reservation- Ridge and Cedar Hill Loop, Medfield

  • big black dog on rocky summit with green trees and hills in the distance on a hike in Massachusetts.
  • big brown dog and big black dog walking side by side on brown pine trail lined with green trees.

This Trustees of Reservations property is known for its network of forest trails and several small ponds. What drew me to this hike to begin with and a big reason why it's on this list is because of its approved off-leash trails for the dogs.

Of course your dog needs to be well-behaved and still under your control so it's definitely not a dog park - just a beautiful network trails through tall pine trees where you and your best friend can frolic! 🐶 If you'd like more details and a full guide to this hike that takes you up on a ridge then by multiple lakes, check out my post ➡️ Rocky Woods Trail Guide 🥾 for turn-by-turn trail directions!

big black dog in front of lake with reflection of green trees and blue skies above in Massachusetts.
  • 🌟What makes it special: off-leash trails for the dogs! plus super peaceful pine paths and multiple scenic lakes plus a view!
  • 🥾Miles & Difficulty: 3.1-mile loop, easy to moderate
  • 📈Elevation Gain: 383 ft
  • 🚙Parking: Click to navigate to 42.20646, -71.27665

14. Ward Reservation, North Andover

  • holt hill view in fall with boston skyline in the distance
  • two dogs at sunrise time at ward reservation in andover massachusetts with orange and yellow leaves framing the photo

Another beautiful Trustees property, Ward Reservation features rolling hills, open fields, and the famous Solstice Stones—a unique stone circle aligned with the sun’s path. The hike to Holt Hill, the highest point in Essex County, offers panoramic views that stretch all the way to Boston!

I loved visiting the area too, in North Andover where there are tons of cafes to choose from and shops to explore minutes from the hike. With its historic boarding schools tucked into the heart of downtown, Andover has the charm of a classic New England town.

For more details on this hike check out my post ➡️ Ward Reservation Trail Guide for a map and turn-by-turn trail directions!

two dogs at sunrise time at ward reservation in andover massachusetts with orange and yellow leaves framing the photo

15. Breakheart Reservation

  • black dog on top of stony outcrop looking out over green trees on a sunny day with blue skies at Breakheart Reservation.
  • man sitting on large rock with big brown dog swimming on summer day in large blue lake lined with green trees at Breakheart Reservation in Massachusetts.
  • black dog walking on rocky outcrop at breakheart reservation.

Breakheart is a surprisingly rugged oasis just north of Boston. Its rocky hills, forested ridges, and quiet lakes make it feel wilder than its urban location suggests. With multiple loops and scenic overlooks, it’s a favorite for local hikers and trail runners needing an escape from the city.

I loved the 3.7-mile loop we did here which gave us a tour of Breakheart's highlights including the two lakes and views from Castle Rock and other little lookouts along the way.

There are lots of trails to choose from here so to navigate the 3.7 mile loop that I loved and included pictures from check out my post ➡️ Breakheart Reservation Trail Guide which includes a custom map and turn-by-turn trail directions! 🙂

view atop rocky outcrop at castle rock in breakheart reservation with green trees in distance and blue skies.
  • 🌟What makes it special: Almost 700 acres with multiple ridge views and two lakes to loop around
  • 🥾Miles & Difficulty: 3 - 5 miles, lots of options here!
  • 📈Elevation Gain: depends on the hike you choose
  • 🚙Parking: Click to navigate here: 42.48333, -71.02755

16. Blue Hills Reservation; Great Blue Hill via Skyline Trail (Milton)

view from stone Eliot Tower in Blue Hills Reservation with view of rolling green hills in the distance.
Black dog atop Hancock Hill in Blue Hills Reservation with a wide open view of rolling bright green hills and trees in the distance and a cloudy sky.

Just minutes from Boston, the Blue Hills Reservation feel like a wilderness escape. The Skyline Trail offers rocky climbs and surprising city views from its ridgeline, making it one of the best quick getaways for urban hikers.

I was very surprised when I did this hike how challenging it was. There are a few steep scramble sections where you will want to use your hands and when we hiked here with the dogs we had to drop the leashes a few times in order to navigate safely down. If you'd like more details check out my post! ➡️ Great Blue Hill via Skyline Trail Guide featuring turn-by-turn trail directions! 🥾

  • black dog standing at doorway of the stone eliot tower in massachusetts.
  • Black dog walking up rocky stone staircase through the woods along the Great Blue Hill Skyline Trail in Massachusetts.
  • 🌟What makes it special: Challenging trail with 270-degree views from Eliot Tower
  • 🥾Miles & Difficulty: 3-mile loop, moderate-hard
  • 📈Elevation Gain: 890 ft
  • 🚙Parking: Click to navigate to 42.21424, -71.09356

17. Middlesex Fells – Skyline Loop (Medford)

North of Boston, the Middlesex Fells is a favorite local playground with miles of trails. The Melrose Rock, Black Rock, and Pinnacle Rock via Rock Circuit Loop takes you to the main views, leading over sometimes rocky and rugged terrain with glimpses of the city skyline through the trees.

Hikes in Cape Cod & Islands

I have not yet done the hikes below but wanted to include a few as a resource for you! They are on my list and I can't wait to try them. If you try them first, I'd love to hear what you think! 🙂

18. Great Island Trail (Wellfleet, Cape Cod)

The Great Island Trail is known for its long, sandy trail winding through salt marshes and along the shoreline, offering some of the best coastal scenery in Massachusetts! With ocean breezes and sweeping dune views, this would be an amazing hike to choose in Cape Cod!

19. Cape Cod National Seashore Trails (Eastham, Truro, Provincetown)

From the Atlantic White Cedar Swamp Trail to the windswept dunes near Provincetown, the Seashore offers truly unique hikes. These trails are perfect for highlighting Cape Cod’s beauty, from forests to beaches.

20. Menemsha Hills (Martha’s Vineyard)

If on Martha's Vineyard, Menemsha Hills is THE hike to do! This island hike leads to bluffs high above Vineyard Sound, where the ocean stretches endlessly before you. With a mix of coastal forest and open overlooks, Menemsha Hills shows off the Vineyard’s quieter, wilder side.

Closing

I hope you enjoyed this round up of some of the best and most beautiful hikes in Massachusetts!

From the rural Appalachian Trail in western MA to the traprock ledges and waterfalls of the Pioneer Valley and coastal trails and reservations near Boston - there's a lifetime worth of exploring in this state.

I plan to continue hiking and adding to this list so check back and if you have a favorite hike in MA you think I should try, I'd love to hear it! Feel free to comment or leave questions below. 🙂

Happy Trails! 💗🐶🥾❤️

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