The 10 Best Hikes in the Boston Area

There’s more to enjoy in this East Coast area than city life. All around the Boston area are state parks and local nature preserves just waiting for you to discover a new side of Massachusetts.

The Best Hikes in Boston

Breakheart Reservation Loop

Explore this 2-mile semi-moderate and beautiful nature-lined trail. Breakheart Reservation Loop is a very popular paved trail, and the area is used by many for walking, running, and birding.

This type of hike is suitable for the whole family as it’s stroller friendly, and there are additions to the park, like a children’s playground, a volleyball court, a beach, and an area for picnics.

There are some steep areas, but for the most part, it’s a pretty easy-going trail, and there are benches and rest areas placed along the loop when a break is needed. Explore the family-friendly hiking area that is Breakheart Reservation Loop.

• Location: 177 Forest St, Saugus, MA 01906

Great Blue Hill Loop

Take a trip to Milton, Massachusetts, for an adventure along this hiking trail.

Great Blue Hill Loop is considered to be a moderate loop route about 3 miles in length, and you’ll likely see others as it’s a popular area for walking, hiking, and running.

Dogs are welcome to join, but they must stay on a list while inside the reservation and on trails.

Not only will you be surrounded by the wilderness throughout this trek, but you’ll also be treated to views of the downtown Boston skyline.

You’ll want to stop at Eliot Tower for the best view of the entire city. There are some steep and rocky areas where you’ll need to pay attention to footing, but it’s not overly technical. Get a great hike at Great Blue Hill Loop.

• Location: 695 Hillside St, Milton, MA 02186

Harold Parker Loop Trail

Twenty miles north of Boston, this massive state forest includes a lengthy and exciting hike.

Harold Parker Loop Trail is found within Harold Parker State Forest and makes the perfect backdrop for a moderately challenging hike that will take most of the day to complete.

While this is a popular trail, and you’ll often see others hiking, mountain biking, and birding, there are also areas where you’ll find yourself in complete solitude.

Your dog can even roam free in some of their off-leash areas. This 16.6-mile hike is one of the longest in the area, but as you pass by water, wildlife, and a serene environment, you won’t want to leave Harold Parker Loop Trail.

• Location: 133 Jenkins Rd, Andover, MA 01810

Ipswich River Wildlife Sanctuary Trail

This is the trail for you when you’re looking for an easy-going hike that will expose you to some wildlife.

Ipswich River Wildlife Sanctuary Trail is run by the state Audubon Society, so the proceeds from the entry fee go to help support them and their conservation efforts.

This is a popular trail and area for people to go hiking, birding, and snowshoeing in the winter. With the emphasis on bird watching, no dogs are allowed to come on this adventure.

This short loop will take you across wooden walkways over bodies of water and beautiful wooded areas.

Be prepared to hand-feed the birds in this area of the Ipswich River Wildlife Sanctuary Trail as they’re waiting for the feed conveniently located along this loop.

• Location: 87 Perkins Row, Topsfield, MA 01983

Lynn Woods Reservation

Explore this natural area with a moderate 5-mile hike through this reservation.

Lynn Woods Reservation is a popular area surrounded by water where people go to enjoy horseback riding, hiking, and mountain biking.

This trail recently sustained some fire damage from a forest fire. However, it did not damage the entire area, and most of the trail can still be enjoyed while the surrounding area works on growing back.

Dogs are welcome to join this hike; they just have to remain on a leash. You also want to keep in mind that with the surrounding lakes, this trail does get buggy.

Lynn Woods Reservation is the perfect short hike to get out into nature.

• Location: 106 Pennybrook Rd, Lynn, MA 01905

Mount Monadnock

While technically located in New Hampshire, this hike is still not far from the city of Boston.

Mount Monadnock is a massive mountain peak surrounded by a state park and lots of hiking trails.

This area is completely protected, so those who use the area for hiking, biking, and more must respect the terrain.

Of the numerous trails to pick from, the White Dot and White Cross Trails are the best options for those wanting a challenging hike.

Dogs aren’t allowed on this popular trail, but you’ll likely see many other hiking humans. Mount Monadnock requires reservations for the park entrance, and the views will be completely worth it.

• Location: 169 Poole Rd, Jaffrey, NH 03452

Noanet Peak Loop Trail

Give this 3.2-mile hike a try; it results in some amazing views without too much effort or time dedication.

Noanet Peak Loop Trail is a popular area for enjoying the outdoors, so you’ll likely see many other people on your route.

It’s considered moderately challenging, but oftentimes you’ll see whole families, kids included, trekking through the trail, so it’s not too complex.

You’ll enjoy views of the beautiful Massachusetts wilderness along with lots of wildlife. Noanet Peak Loop Trail is the perfect weekend hike.

• Location: Powisset St, Dover, MA 02030

Wachusett Summit Loop

Take yourself on a small adventure with this 6-mile hike through the Wachusett Mountain area.

The Wachusett Summit Loop is a popular trail in the reservation for hiking and walking, so you’ll likely see others along the way.

You’re also likely to find some solitude during quieter times of the day, so you can decide what you’d like your hike to be like.

This is considered a moderate trail but kid-friendly, so it’s not too technical.

This route takes you in a loop, but there are other trails that split off throughout the park if you want to change the hike a little.

Wachusett Summit Loop is the perfect way to spend an afternoon in nature.

• Location: 345 Mountain Rd, Princeton, MA 01541

Walden Pond Path

One of the shorter hikes on this list; it’s also one of the easier ones.

Walden Pond Path is part of Walden Pond State Reservation and takes under an hour to complete the loop.

This area is very popular for people walking, running, and hiking, but dogs are not allowed to join on this trail.

At just under 2 miles, this quick loop around Walden Pond gives almost continuous views of the beautiful natural water feature.

Due to conservation purposes, there is an entrance fee which helps keep the park in order.

Take a quick break from the hustle and bustle of the city with a hike along Walden Pond Path.

• Location: 915 Walden St, Concord, MA 01742

Ward Trail Loop

This moderate hike is also moderate in length at 3.6 miles to complete the loop.

Ward Trail Loop is a popular natural location for exploring any time of year.

You’ll likely see people hiking, birding, and snowshoeing in the right season.

Dogs are even welcome to join your trek. Some of this trail is paved, and other parts are kept cleared off and easily visible.

You’ll pay a fee upon entrance, but it’s to help maintain the park and conservation efforts in the area, a good cause.

The perfect way to spend an afternoon, Ward Trail Loop is a great way to experience nature not far from civilization.

• Location: 34 Prospect Rd #42, Andover, MA 01810

Final Thoughts

See waterfalls, rivers, and even swampy marshes. There’s so much more to the Boston area than the city, and it’s just waiting to be explored.