Best Hiking And Trekking Spots In Boston, Massachusetts

hiking in boston
Anupama
Anupama 
Updated
| 4 min read

Are you wondering if there are any trails in Boston where you can enjoy some fresh air and a good hike? You’ll be thrilled to learn that there are a few such spots in the city. Additionally, there are many possible choices in the outskirts as well. So, for residents of Boston or visitors who want to go hiking, check out some of the best spots listed here. These places are frequented by hikers on any given day, but especially when the weather is good. Most of the spots are within a two-hour drive from Boston, so if you are looking for a full day of adventure and spending time in the lap of nature, you’ll need to plan ahead. Pack your backpack and prepare to go hiking on one of these trails - even if you are an amateur simply looking to enjoy the great outdoors, don’t worry as some of the trails are perfect for beginners. Check out these best hiking and trekking spots in Boston, Massachusetts.

1. Charles River Reservation

Charles River Reservation
Source: Photo by user Jaytailor used under CC BY-SA 4.0

Charles River Reservation is situated near Auburndale in Massachusetts. There is a 3.4-km (2.1-mi) trail here that is good for beginners. You can bring your dogs along on the hike, but they need to be leashed. There are a lot of outdoor activities that you can partake here, and you also have the option to indulge in water sports. The best time to visit this place is from April to December.

Charles River Reservation

Address: 1175A Soldiers Field Rd, Boston, MA 02116

Opening hours: 7am - 6:30pm (daily)

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2. Arnold Arboretum of Harvard University

Arnold Arboretum in Autumn
Source: Photo by user TanRo used under CC BY-SA 4.0

There are ample hiking and trekking spots at Harvard University’s Arnold Arboretum. The garden is well-maintained, and you can easily get to Harvard University in Cambridge, just a short drive from Boston. There are a variety of flowers to see, and it is also a great place for a family picnic. Just sitting under the shade of trees is relaxing, and you can enjoy an afternoon siesta here. Be sure to collect a map from the visitor center before you go on your hike.

Arnold Arboretum of Harvard University

Address: 125 Arborway, Boston, MA 02130

Website: Arnold Arboretum of Harvard University

Opening hours: 7am - 7pm (daily)

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3. Boston Harbor Islands National and State Park


Boston Harbor Islands National and State Park is just a short distance from Downtown Boston and is a favorite hiking and trekking spot among locals. Thousands of hikers visit this place each year. The spot is composed of 34 peninsulas and islands. There are five trails that range from 1.4 km to 6.1 km (0.9 mile to 3.8 miles). Some trails are kid-friendly, so you can also take the little ones along to experience the wonders of nature.

Boston Harbor Islands National and State Park

Address: 191w Atlantic Ave, Boston, MA 02109

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4. Schoolmaster Hill Trail

Pathway up Schoolmaster Hill, November 2009
Source: Photo by Wikimedia Commons user Erik Hansen used under CC BY 2.0

This is another favorite spot for hiking enthusiasts in Boston. It is also a place where families and groups of friends come for picnics. It became a public park in 1882 and was designed by Frederick Law Olmsted. It is a perfect choice if one wants to spend time outdoors and soak up some fresh air and sunshine. You can plan a full-day outing to this place and enjoy the relatively easy hike.

Schoolmaster Hill Trail

Address: 1 Franklin Park Rd, Boston, MA 02121

Opening hours: 24 hours (daily)

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Boston Tour Guide

Naim Benmayor

Naim Benmayor

As a Boston tour guide, I have the added experience of being a world traveler. For many years, I frequently visited Europe, Asia, and Latin America on business. During this time, I also organized tours of the USA, Europe and Asia for my business clients. I now bring this passion, excitement and expertise to the Boston area.By exploring the globe, I was exposed to various cultures, and this unique perspective has taught me what appeals to people when visiting a new part of the country or a new part of the world. My fluency in English and Turkish, and my advanced skills in Spanish and intermediate skills in French, also help me to service a wider range of tourists and business people.I moved to Boston, Massachusetts several years ago, and I now reside in Brookline. I have three children, so I develop my tours to accommodate families with kids, couples, and individuals who want to visit and learn about the rich history and culture of Boston. As a parent, I know that Boston is a great place for higher education, and I have knowledge of the colleges and universities in the area.I customize tours to suit the needs and preferences of my customers. Whether you want a walking tour, a riding tour, or a little of both, I can create an itinerary that showcases the best of what Boston has to offer.My one day tours are educational and entertaining, and include the history, culture, personalities, architecture and, even the shopping areas of this renowned city. At the end of the tour you will be happy and satisfied when you realize you've seen so much in just a short time.I am here to share my knowledge of Boston, Cambridge and all of New England with you, and help you to enjoy your visit so you can explore the must-see parts of this great city. I look forward to meeting you and guiding you around the city, so please send me a message if you have any questions.Thank you for reading.

5. Emerald Necklace

Emerald Necklace, Fenway Victory Gardens, Boston (493517)
Source: Photo by user Robert Linsdell used under CC BY 2.0

Emerald Necklace is near Boston and a good option for those who want something close by for a day trek. More than a million people visit this spot each year, and thousands come for hiking alone. Emerald Necklace stretches from Back Bay to Dorchester. There are six areas under the Emerald Necklace Conservancy, so apart from hiking and trekking, visitors come here for various other outdoor activities.

Emerald Necklace

Address: 125 The Fenway, Boston, MA 02115-3700

Opening hours: Mon - Fri: 9am - 5pm; Sat - Sun: 11am - 4pm

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Nearby hiking trails

6. Battle Road Trail


This is a 14.6-km (9.1-mi) trail that is used by thousands of hikers and joggers each year. It stretches from Lexington to Concord. This is a packed gravel trail and has a history of being part of the Revolutionary War. When you visit, you can check out the nearby Old North Bridge. Beginners can also start on this trail, though it is a favorite for experienced hikers. This spot is open all throughout the year, and leashed dogs are allowed.

Battle Road Trail

Address: Minute Man National Historical Park, 174 Liberty St, Concord, MA 01742, United States

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7. Halibut Point Trail

Rockport2007 008
Source: Photo by user Jrpvaldi used under PUBLIC DOMAIN

Halibut Point Trail is a short trail of 2.57 km (1.6 miles), and it is situated in Rockport near Boston, an hour away by car. It has enchanting natural surroundings where hikers will surely have an awesome experience. There are many wildflowers in the area, and it is an amazing sight when they are in full bloom. One of the best things about this place is that it offers visitors a breathtaking view of the Atlantic Ocean and is readily accessible for all skill levels.

Halibut Point Trail

Address: Gott Ave, Rockport, MA 01966

Opening hours: 8am - 9pm (daily)

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8. Blue Hills Reservation

PonkapoagPondWithGBH
Source: Photo by user Magicpiano used under CC BY-SA 4.0

Another hiking and trekking spot near Boston is Blue Hills Reservation, which has 49 trails of varying distances and difficulty levels. You can choose from one of the many possible trails not only for hiking but for other outdoor activities like mountain biking. Mt. Monadnock in New Hampshire is very clearly visible from here on a cloudless day. Families also like to visit this place for a picnic.

Blue Hills Reservation

Address: 695 Hillside St, Milton, MA 02186

Opening hours: 6:30am - 7pm (daily)

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9. Pitcher Mountain


Pitcher Mountain has a short trail of just 0.96 km (0.6 mi). It is comfortable and very convenient for children, as the walk is not risky and is pretty easy. It is located near Boston, at Stoddard, New Hampshire, a little over an hour away. Beginners, as well as experienced hikers, visit this trail all throughout the year. Dogs are allowed but, as with all trail paths, they need to be kept on a leash. The view from the top is majestic, and this is a favorite spot among locals to watch the sunset.

Pitcher Mountain

Address: Stoddard, New Hampshire

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10. Breakheart Reservation

04-1358-breakheart reservation-lake
Source: Photo by user Joseph Reagle used under CC BY-SA 4.0

Breakheart Reservation is just a 35-minute drive from Boston, Massachusetts and has nine hiking trails of varying difficulty levels. Apart from hikers, runners also visit this place. One can choose a trail depending on their physical fitness, the time they have to spare, and the difficulty levels. Other outdoor activities include horse riding, fishing, and swimming. It is a good choice for school trips, as there are education tours on offer as well.

Breakheart Reservation

Address: 177 Forest St, Saugus, MA 01906

Opening hours: 6:30am - 4pm (daily)

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Explore the scenic hiking and trekking spots in and near Boston

The urban life and the charms of shopping, dining out, and experiencing nightlife attracts many tourists to Boston each year. However, the city also has many hiking and trekking spots that you can enjoy on your visit, so be sure to check them out.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Anupama Passary has contributed to various online publications, showcasing a particular fondness for all things tech and travel-related. She is also a chocoholic, stargazer, and dreamer....Read more

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