18 Best Hiking Trails In Massachusetts: The Top-Rated Hiking Trails To Visit In 2024

From the ocean to the mountains, from Cape Ann to Cape Cod, and all the cities and towns in between, the Bay State offers so much resplendent beauty. And with that beauty comes a variety of state parks and hiking trails to explore it all and immerse ourselves in nature. We’ve put together an epic list of trails for some of the best hikes in Massachusetts and you may want to do them all!

Best Hikes In Massachusetts

Visit the summit of the state’s highest peak, take in views of Boston, and enjoy seeing some of the most beautiful areas of the state along the best hiking trails in Massachusetts.

Blue Hills Reservation, 695 Hillside St, Milton, MA 02186, USA

Kate O'Hare/AllTrails

• Location: Milton
• Mileage 3-mile loop trail
• Difficulty: Moderate
• FYI: This trail goes through the forest of Blue Hills Reservation and is marked by blue blazes. There's a parking lot across from the park's headquarters on Hillside Street in Milton. Dogs are allowed on leash.

Make your way to Great Blue Hill via the Skyline Trail at Blue Hills Reservation where you'll have epic views of the Boston City skyline once you get to the top. You'll find the Eliot Observation Tower sits at the summit of Great Blue Hill and you can climb the tower for a better vantage point.

Watatic Mountain State Wildlife Area, Ashburnham, MA 01430, USA

Kate Rodrigues/AllTrails

• Location: Ashburnham
• Mileage 2.8-mile loop trail
• Difficulty: Moderate
• FYI: This is an excellent hiking trail for year-round use and leads to scenic views. There's an elevation gain of 711 feet. Dogs are allowed on this trail as long as they are on leash.

Trek to Mount Watatic and Nutting Hill via Wapack Trail at Watatic Mountain State Wildlife Area, a scenic hiking destination in Central Massachusetts. At the summit of Mount Watatic, you can take in panoramic views including views of the Boston city skyline.

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Mount Greylock, Adams, MA 01220, USA

Stephen Kosche/AllTrails

• Location: Adams
• Mileage 5.9-mile out-and-back trail
• Difficulty: Hard
• FYI: This challenging hike takes over 4 hours to complete. The trailhead is located at the Gould Road/Bellows South parking area. The best times to visit this trail are between April and November. Dogs are allowed on leash.

Visit the summit of Mount Greylock via Bellows Pipe Trail. Mount Greylock is the highest peak in Massachusetts at 3,491 feet and, from the top, you'll have views up to 90 miles away on a clear day.

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Best Short & Easy Hikes In Massachusetts

If you’re looking for a short and easy hike, perhaps one that’s a bit more family-friendly, check out the following best places to hike in Massachusetts.

Walden Pond State Reservation, 915 Walden St, Concord, MA 01742, USA

Sean Murphy/AllTrails

• Location: Concord
• Mileage 1.9-mile loop trail
• Difficulty: Easy
• FYI: Best to explore between April and October, this trail will take nearly 40 minutes to complete. This trail is kid-friendly but leave your fur babies at home as dogs are not allowed.

Head to Walden Pond State Reservation and take the Walden Pond Path that circumnavigates the pond made famous by writer Henry David Thoreau in his book Walden. You'll see several nods to Thoreau along the way. If you're here during the summer, feel free to take a dip in Walden Pond's cool waters.

Middlesex Fells Reservation, 4 Woodland Rd, Stoneham, MA 02180, USA

David Finkenaur/AllTrails

• Location: Medford
• Mileage 0.9-mile out-and-back trail
• Difficulty: Easy
• FYI: This easy trail is great for birdwatching, hiking, and running. Dogs are allowed but must be on leash. The trail begins at Bellevue Pond on South Border Road.

This trail is located within Middlesex Fells State Reservation, which spans the towns of Medford, Stoneham, Malden, Winchester, and Melrose. The Pine Hill trail will take less than a half-hour to complete and leads to Wright's Tower, a historic stone tower constructed in 1937.

4 Woodland Rd, Stoneham, MA 02180, USA

Chris O'Brien/AllTrails

• Location: Melrose
• Mileage 2.9-mile loop trail
• Difficulty: Easy
• FYI: This trail is best used between April and October. Dogs are allowed as long as they are on leash.

Also located within Middlesex Fells Reservation is another easy trail that most can enjoy. The Rock Circuit Trail Loop goes around Middlesex Fells Reservoir as well as other smaller ponds. There are also several viewpoints along the way, so. not only is this an easy hike but a scenic one!

Hardest Hikes In Massachusetts

Since we covered easy hikes, it’s now time to talk about some of the hardest hikes in the state. These arduous hikes are lengthy and the elevation gain isn’t for the faint of heart. Hiking these trails also takes some extra preparation and precautions. Here are some of the most challenging hikes in Massachusetts:

Mount Greylock, Adams, MA 01220, USA

Sherri Rulison/AllTrails

• Location: North Adams
• Mileage 15-mile loop trail
• Difficulty: Hard
• FYI: With 15 miles and an elevation gain of 4,790 feet, this trail will take over 9 hours to complete. Make sure you set aside enough time to do this trail if it's a day hike or make overnight arrangements at the park's campground if hiking over the course of two days. April through October are the best months to enjoy this trail that's popular for hiking, backpacking, and camping.

This hike through Mount Greylock State Reservation is as challenging as it is rewarding. The trail begins at Pattison Road and the Appalachian Trail and leads to Mount Prospect, Mount Williams, Mount Fitch, and Mount Greylock. And just to reiterate, you must come prepared for a hike like this. However, if you're able to make this trek, it's so worth it!

Mount Greylock, Adams, MA 01220, USA

Tom Oakes/AllTrails

• Location: North Adams
• Mileage 14.9-mile loop trail
• Difficulty: Hard
• FYI: This difficult trek has an elevation gain of 4,750 feet and will take over 9 hours to complete. It's best to to take this trail between March and October. You can take your dog with you as long as you keep it on a leash.

Another challenging trail at Mount Greylock State Reservation, Bellows Pipe Loop Trail leads to Mount Williams in two different spots. It also leads to the summit of Mount Greylock.

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Tom Oakes/AllTrails

• Location: South Egremont
• Mileage 17.5-mile loop trail
• Difficulty: Hard
• FYI: This challenging trek will take over 9 hours to complete and has an elevation gain of 4,104 feet. As with all hard hikes, make sure you take plenty of food, water, and gear with you if you plan on hiking this trail in its entirety. The best time of year for this trail is between April and November. You can bring a dog with you and let it off-leash in certain areas.

If you're up for a challenging hike, this is certainly the one to take as you'll summit several peaks along the way. Located at Mount Everett State Reservation, it's best to do this trek over the course of two or three days. There are campgrounds within the park where you can spend the night.

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Best Waterfront Hikes In Massachusetts

Some of the best places to hike in Massachusetts lead to the water. Between the Atlantic Ocean, the bays, rivers, ponds, and lakes, there are numerous waterfront trails for those who love to be by the water, Here are some of the best waterfront hikes in Massachusetts:

Middlesex Fells Reservation, 4 Woodland Rd, Stoneham, MA 02180, USA

Alison Hines/AllTrails

• Location: Medford
• Mileage 7.7-mile loop trail
• Difficulty: Moderate
• FYI: March through October are the best times for this trail which takes just over 3 hours to complete. The elevation gain is 941 feet. Dogs on a leash are welcome.

As one of the most scenic hikes in Massachusetts, the Skyline Outer Reservoir Loop is located at Middlesex Fells Reservation. The trail leads to and around the reservoir for some awesome water views!

Skyline Trail, Quincy, MA, USA

Benn Sherman/AllTrails

• Location: Quincy
• Mileage 15.2-mile out-and-back trail
• Difficulty: Hard
• FYI: March through October are the best months to take a trek on this trail which will take over 8 hours to complete. Dogs are allowed on a leash. There are some rocky sections of the trail so be sure to wear a sturdy pair of boots. The trailhead can be found on Willard Street.

Blue Hills Skyline Trail is a difficult yet gorgeous trail located at Blue Hills Reservation in Quincy. Along the way, you'll traverse through the forest, past a lake, and to the summits of several hills for some epic views!

Jennie Chaplin/AllTrails

• Location: Melrose
• Mileage 4.2-mile loop trail
• Difficulty: Moderate
• FYI: With 524 feet of overall elevation gain, this trail is considered moderate and will take nearly 2 hours to complete. The best times to take this trail are between April and November. Dogs are welcome as long as they are on a leash.

Yet another incredible hike in Middlesex Fells Reservation, this system of trails begins at Rock Circuit Trail which starts at the Flynn Skating Rink. It creates a loop with Black Rock Trail and Pinnacle Rock Trail that circumnavigates the areas around a few small ponds.

Best Winter Hikes In Massachusetts

Don’t be afraid to go hiking in the winter. Of course, you’ll have to go prepared with warm layers, a winter coat, boots, gloves, and other ways to keep warm in the cold air. But hiking during the winter brings about a sense of peace and calm you can’t find during other times of the year. Trails are quieter and you may have some all to yourself!

Notchview | The Trustees of Reservations, 83 Old Rte 9, Windsor, MA 01270, USA

Daniel McCarthy/AllTrails

• Location: Windsor
• Mileage 1.9-mile loop trail
• Difficulty: Moderate
• FYI: This is a popular preserve for cross-country skiing and snowshoeing between the months of December and April from 8 a.m. and 4:30 p.m. Dogs are allowed if on a leash.

Notchview Reservation is a 3,108-acre preserve that's overseen by the Trustees of Reservations. While it's great year-round, it's an especially incredible place during the winter for snowshoeing and Nordic skiing.

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Amherst, MA, USA

Shanna DelPrete/AllTrails

• Location: Amherst
• Mileage 2.6-mile point-to-point trail
• Difficulty: Hard
• FYI: This challenging trail can be picked up from Harris Street and will take over an hour to complete.

This trail is found in Amherst close to the Holyoke Mountain Range. While it's a pretty trail to take any time of the year, there's something quite magical about it during the winter. The route will take you through the woods and over hills and to viewpoints where you can see the gorgeous mountains.

1094 Beacon St, Newton, MA 02461, USA

Alan Nogee/AllTrails

• Location: Newton
• Mileage 1.3-mile loop trail
• Difficulty: Moderate
• FYI: Pick up the trail from the Cold Spring Park parking lot. It's both kid-friendly and dog-friendly.

Located within the city of Newton at Cold Spring Park, the Stream and Esker Loop meanders through wetlands and by a ridge. When hiking, especially in the winter, you'll forget the fact that you're in an urban area. It's an oasis any time of year. but especially so during the winter months.

Best Hikes Near Boston

Okay, city dwellers, these hikes are for you! Just because Boston is a bustling city doesn’t mean there aren’t any hikes to do in and around it. There are plenty of trails to enjoy the city in a different way than just walking around the streets.

Freedom Trail, Boston, MA, USA

Mike Andrade/AllTrails

• Location: Boston
• Mileage 3.1-mile point-to-point trail
• Difficulty: Easy
• FYI: This easy route is marked by red brick and is full of historic sites around Boston. It follows city sidewalks and will take around an hour to complete.

Boston's Freedom Trail is an easy walk through the city. It takes you to 16 historic sites in Boston including the Old North Church, the Granary Burying Ground, and The Old State House. Learn some history while getting to know Massachusetts' capital city.

Charles River Reservation, Cambridge, MA 02141, USA

Lizz Cao/AllTrails

• Location: Boston and Cambridge
• Mileage 3-mile loop trail
• Difficulty: Easy
• FYI: This paved walking and bike trail is approximately 4 feet wide and can accommodate wheelchairs, mobility equipment, and strollers. This is a popular trail throughout the year.

At 20 miles long, the Charles River Preserve is a gorgeous preserve in the middle of the city. Take the Charles River Pathway Short Loop that runs along the Charles River between Boston and Cambridge and then you will eventually get to the Boston Harbor.

2010 William J Day Blvd, Boston, MA 02127, USA

Minxue Liao/AllTrails

• Location: Boston
• Mileage 2.2-mile loop trail
• Difficulty: Easy
• FYI: This easy loop takes less than an hour to complete. The best time of the year for this trail is between April and October. Dogs are allowed off-leash in some areas. There's a parking lot off William J. Day Boulevard with 5 designated accessible spots.

Boston Harbor and Castle Island is a scenic hike at Boston's Marine Park complete with a beach, a historic fort, and a WWII memorial. Not only are there water views but you can watch planes taking off or landing at Logan as you hike.

Whether it’s a beach hike or a mountain hike you’re looking for, a short and easy trek or a long and arduous one, the Bay State really does have a hike for nearly anyone. So, get outdoors and take a trek along one of the trails for the best hikes in Massachusetts. And make sure you have the AllTrails+ app downloaded on your phone before you hit the trails. Happy hiking!