13 Best Hiking & Walking Trails Near Boston

Boston is a historic city known for its culture, attractions, and harbor. Despite being densely populated, there are many opportunities to enjoy nature outside the city. In fact, this great city has adopted the title “The Walking City” because it also offers numerous walking trails, parks, and activities perfect for tourists. But with so much variety available, it can be hard to know where to start. So here is a list of the 13 Best Hiking & Walking Trails near Boston. Many of them are perfect for day hikes and offer beautiful forest views. So lace up your shoes and get ready to explore!

Best Hiking & Walking Trails Near Boston

1. Emerald Necklace

If you’re looking to take a leisurely stroll through Boston, the Emerald Necklace is one of the best options for doing so. The necklace is an almost seven-mile trail that loops around and connects six parks. They include Back Bay Fens, Olmsted Park, Jamaica Pond, Arnold Arboretum, Riverway, and Franklin Park. These parks are not only popular recreational destinations, but have also proven valuable in reducing air pollution and contributing to environmental conservation efforts.

The Emerald Necklace was designed by Frederick Law Olmsted, one of the top landscape architects in America. He is known for designing Central Park in New York, although this necklace design came before.

The route loops around so you can walk in whichever order you want. But if it’s your first time through, you might want to start at the Boston Common and continue to Commonwealth Avenue. You’ll see some of Boston’s top attractions along the way, including the Swan Boats, Two Major Art Museums, Three Ponds, A Rose Garden, Wildflower Meadow, and the historic Fenway Victory Gardens.

The good thing is that if you get tired along the way, you can always find a public transportation stop nearby to pick you up. I also have to emphasize that a good pair of walking shoes or sneakers will definitely come in handy if you decide to follow the entire route.

During my visit, some places were just too beautiful that I had to catch my breath. Especially when I took a walk by the Charles River, I was in awe. Every turn offered me something new, surprising, and fantastic to see. It really was a pure pleasure to be there. And because it is open for everyone, I strongly recommend you visit it in the near future. It is one of the best walking trails near Boston that you should do at least once in your life.

2. Blue Hills Reservation

The Blue Hills Reservation is a 7000-acre park that’s located near Boston. It was originally set aside as an area where people could come and learn about the natural world. Today, this area has evolved into one of the best hiking trails near Boston because of its variety of habitats and trails that are specifically designed to accommodate all skill levels.

The most popular trail here is the Skyline Loopapproximately 6 miles long and takes roughly 5 hours to complete. Along the way, you’ll see some of the best views in Massachusetts while passing through dense forests filled with wildlife like wild turkeys, deer, foxes, coyotes, and more. The hills are also home to beavers, minks, and raccoons.

You might also want to visit Blue Hill Observatory and Science Center, an active meteorological observatory that also has exhibits. Also worth checking out is the Blue Hills Trailside Museum, which is a small but interesting natural history museum.

The Blue Hills Reservation is definitely one of the best places to hike near Boston for people of all experience levels. If you’re visiting on the weekend, I recommend starting early in the morning so that you can watch the sunrise from one of its many scenic overlooks. But if you’d rather get more of a workout in, I recommend going during the week so that you can come when it’s not as crowded.

3. The Freedom Trail

The Freedom Trail is one of the best walking trails in Boston. It was originally called the Colonial Heritage Trail, and it passes through sixteen historical points. All the historical points are designated by a red line drawn on sidewalks and other outdoor surfaces. At each location, there are informative plaques that tell you about the significance of each landmark.  

This historic trail is 3 miles long and is a great way to experience the history of Boston and Massachusetts, including stories about the American Revolution.

The trail begins at Boston Common, where you can see the monument that commemorates one of the Revolutionary War’s first important battles. It was such an inspiring visit because it’s where you can appreciate those brave men and women who fought for America.

You can actually download a free audio tour that you can play on your phone as you walk along the trail. But if you don’t want to do this, there are also many historical signs along the way where you can stop and read about the history of the landmarks.

There are many attractions lined up along the way, so you can choose what interests you most and spend more time in those places. It is expensive to go inside all the museums though. So if it’s your first time, I recommend just enjoying being outdoors in nature, looking at beautiful architecture, or even learning about American history.

4. Middlesex Fells Reservation

The Middlesex Fells Reservation is another great place for hiking near Boston. This park has about 2,575 acres of land to explore and features approximately 100 miles of trails open year-round.

The most popular trail here is the seven-mile Skyline Trail, which is great for beginners and experienced hikers. It meanders around ponds, through forests, hills, and the occasional cliffs. The trail is not very crowded here, so it is pretty easy to find your piece of nature.

Most of the trails here are very well organized, so it is pretty easy to find your way around. You can pick up an official park map at the visitors center before you go hiking. You’ll also find several connecting trails that lead to different parts of the reservation. So you can choose to do short day hikes or even spend the whole day walking along many miles of paths.

Just make sure you are aware of your surroundings before you head out into this well-forested area. If it’s your first time hiking in this park, then I suggest that you join a guided tour to familiarize yourself with the place and learn how to properly navigate through it.

5. Harold Parker Loop Trail

If you’re someone who enjoys spending time outside and would like to do so closer to Boston, then the Harold Parker Loop Trail might be for you. The trail is about 16 miles long and offers a number of scenic spots along the way. It can be done in 5-6 hours by walking at a standard pace without stopping too much for leisure purposes. However, it is also popular for being a challenging workout trail. 

While you’re walking, you can expect to pass by a variety of habitats, including swamps, ponds, meadows, grasslands, and forests. You’ll also find plenty of large rocks, which are great places to sit down along the way to take in the scenery. The path is well marked with green signs, so you know which way to go if you’ve never done it before. 

The hike does have some steep hills that will test your endurance, but it’s still a great choice if you’re looking for a lovely walk near Boston. There are a lot of trees that offer a good amount of shade. So you don’t have to worry about the sun beating down on you as you walk. If you want to make your trip even better, I suggest bringing along some snacks and drinks.

I loved the challenge! It’s a special place where you can get back in touch with nature and be one with the trees, birds, and wildflowers. And for this reason, it has been rated as one of the best walking trails near Boston because of its ease of access and scenic views. 

6. World’s End

World’s End is a great place to visit for those who want to escape the hustle and bustle of city life. It’s about an hour outside Boston in Hingham, Massachusetts. The trails lead you up along the rocky shorelines and beautiful landscapes that let you forget that civilization exists beyond these grounds. 

This park is a state-protected and preserved harbor once used as a site for quarrying and shipbuilding. Today, it’s an area where people come to relax and picnic because of its trails and serene environment. The landscape is nothing short of spectacular and is a fine example of glacial history, the rocky terrain, and the cliffs that set it apart from similar areas in Boston.  

The park itself is roughly 251 acres and features several different activities. Some things you can do there include hiking, kayaking, rock climbing, boating (boat rentals available), birdwatching, canoeing, and horseback riding. Several trails in this park take you through vast landscapes, offering several different views of the area. And from its hills, you’ll get a view of the Boston skyline on a clear day.

World’s End Reservation is definitely a great hiking area near Boston that caters to everyone’s needs. I strongly recommend you go there and explore this place. It can be one of your greatest adventure goals for this year if you follow all the suggestions given above.

7. Charles River Reservation

You can’t talk about walking trails near Boston without talking about the Charles River Reservation. It’s one of the oldest parks in America and still remains as popular as it first opened back. And for a good reason, it provides people with a way to escape into nature while being just minutes away from downtown.

One of the most popular trails is the 16-mile Charles River Link trail. It follows along the Charles River and connects green spaces in Newton, Needham, Wellesley, Dover, Natick, and Medfield. This trail is great for walking, jogging, or just taking in the beauty of nature. There are benches along the trail where you can sit down if needed. Also, frequent visitors often come here with their dogs, so you might want to watch out for them.

What I especially love about this place is that it offers free activities and open space for everyone to enjoy. This park includes a wide spectrum of amenities, including picnic areas, sledding hills, boat launches, and playgrounds. You can also take a relaxing ride on the Charles River to enjoy the surrounding natural beauty from a different perspective.

8. Breakheart Reservation Loop

Located in the heart of Massachusetts, Breakheart Reservation Loop is one of the most beautiful hiking trails near Boston. The trail has some really beautiful landscapes that you will not find anywhere else. As you walk along this trail, you will find marshes, a lake, and plenty of streams. And yes, there are also great views throughout the way.

The reservation covers 640 acres and has a great variety of wildlife. This makes it a perfect place to see a number of different types of creatures in their natural habitat. These include deer, beavers, and various types of birds.

The Breakheart Reservation Loop is an easy 2 miles stretch, which makes for a better and more enjoyable experience. It is also perfect for all the family since it’s easy to get to and offers a calm walk along a natural setting. 

If you love nature, you should definitely visit this place because it has some really beautiful landscape worth seeing. It is truly one of the best places to hike near Boston if you are looking for a new experience. Go check it out.

9. Battle Road Trail

The Battle Road Trail is a beautiful historic trail. It runs through Lexington and Concord, following one of the most important footpaths during the Revolutionary War called Battle Road. During that time, it was used by militiamen to march quickly towards Boston to intercept British troops that were moving toward Concord.

It’s also known as the Lexington/Concord Battle Road, and it’s one of the oldest roads in America. It begins at Munroe Tavern inWest Lexington, which is now a museum that displays artifacts from the Revolutionary War.

The trail is 5 miles long between its beginning point in West Lexington to Concord. A good place to start if you’re not sure where to begin is at the museum. From there, you can follow the trail either way, although the route that goes through Bedford may be slightly less crowded.

For those who don’t want to hike the entire trail, there are multiple access points where you can actually get on and off. And note that this trail is also not limited to hikers or walkers, but bicycles are allowed.

The trail passes by pretty towns and landscapes along the way, including meadows, forests, rivers, ponds, and lakes. And if you’re visiting in autumn as I did, you’ll catch some beautiful autumn leaves that will make your walk even more enjoyable. This is definitely one of the Top Hiking and Walking Trails near Boston that you won’t regret touring.

10. Black Heritage Trail

The Black Heritage Trail in Boston is a great place for tourists and locals alike to learn about the history of African-Americans in the city. This is where free Africans gathered to celebrate their culture and create a community before the Civil War.

Today, there are historical landmarks along the trail that have been restored or preserved. They include places of worship, homes of community leaders, educational institutions, and more. To use this specific trail while in Boston, you can print out a map to help guide you along its path. There are also audio tours available on your phone if you prefer that option instead.

The trail is well organized with distinct markers, so you know where you are along the route. It also has public art installations that help bring history alive for visitors. One example of this is a stone wall that displays names of African American soldiers who fought in the Civil War.

One part of this trail I really liked was the Boston African-American Historic Site. It’s a small museum that features exhibits on African American history in Boston. They also have a gift shop, research library, and theater screening documentaries most days of the week. Also worth mentioning is the Museum of Afro-American History and Abiel Smith School.

The Black Heritage Trail is another example of Boston’s commitment to diversity. This makes it one of the best walking trails in Boston if you want to learn more about African-American history in the city. It will open your eyes, make you think and hopefully motivate you to act right when something wrong happens around.

11. Walden Pond Path

Most famously known for being the home to Henry David Thoreau, Walden Pond is one of the most popular tourist destinations in Massachusetts. This is the place he wrote his book “Walden” while living in a cabin. He did so to get away from society, enjoy nature and learn more about himself. The same pond is today the perfect place to take a walk around.

You can take a 1.8-mile round trip walk on the path where he used to live. It’s mostly flat and easy to follow, with signs that direct you when needed. You can walk around the pond in either direction, and it doesn’t really matter. But if I had to pick, I’d say going counterclockwise is a bit better since you can see the beautiful woods on your right while walking around.

The trail will take you along almost all of the major historical landmarks in the area, including The Site where Thoreau built his cabin. The trip itself will only take about two hours to complete. And if you read his book before coming here, it would be helpful to bring it along. This can help you get a better idea of what Thoreau was trying to say in his book.

The views at Walden Pond are really beautiful, and it’s definitely a place you can spend hours at. And because of this, I think that it is one of the best walking trails near Boston that you should do on your next visit.

12. Mount Wachusett

Are you looking for a way to enjoy the outdoors but stay close to town? If so, this is one of the best hiking trails near Boston that I recommend. The reason being it offers unique scenery no other trail in Massachusetts can.

Mount Wachusett stands on the highest point in Massachusetts at 2,006 feet. This was once home to spiritual activities and gatherings for Native Americans who used the hill as a lookout point. Today it is one of the most popular hiking destinations and offers a challenging yet rewarding hike.

Surrounded by Wachusett Mountain State Reservation, a 17 miles trail will take you on a winding path that goes through some thickly forested areas, allowing you to experience nature in its most natural state. There are also some nice lookout points throughout the trail, so don’t forget your camera. And once you reach the top, you’ll have a fantastic view of the scenery around you.

Overall, Mount Wachusettwill provide you with a challenging yet rewarding hike that lets you see nature from its finest.

13. Ipswich River Wildlife Sanctuary Trail

If you prefer an outdoor walk in the more natural setting of a wildlife sanctuary, then this is the perfect place for you. The Ipswich River Wildlife Sanctuary Trail is unique because it is one of the largest conserved areas near Boston.

The trails offer plenty of scenic views along wooded areas surrounding the Ipswich River. It also includes several steep hills that will definitely give you a good workout, as well as some stony outcroppings where you can sit and enjoy the view. You’ll also see lots of wildlife, including rabbits, squirrels, turtles, birds, deer, foxes, and much more.

There are over 12 miles of interconnected trails that visitors can explore the sanctuary. Many of them are easy and perfect for beginners, while others are more challenging. But hiking to the vernal pool is one of the fun adventures in this sanctuary. This trail follows along the Ipswich River, offering incredible views of the river and surrounding forest. 

Although the entire area is only about four miles north of Boston proper, it’s a good idea to pack a lunch and plenty of water with you. Just remember that this is a wildlife sanctuary, so there are no trash cans available for you to dispose of your garbage.


Out of the many walking and hiking trails near Boston, these are some of the best. They offer a wide variety of habitats and scenery that will amaze you. If you’re not from Massachusetts and want to take a trip here, allocate some time to explore these trails. Lastly, if you’re visiting Massachusetts for the first time, I recommend trying the Emerald Necklace. This is because it’s free and provides a great opportunity to make the most of the natural environment.