The 8 Best Hikes In Boston

Published by: BouncePosted Updated

Boston is a city loaded with American history. Everywhere you go you come across historic sites that have to be seen. But what if you want to explore the nature of New England? You can absolutely combine the two! Yes, you are in luck because you can do that too, and you don't even have to leave the city to do it. Of course, not all the best hiking trails are right in the city; for some, you may have to take a short trip to the surrounding mountains.

But the beauty of the countryside makes it so worth it. So how do you decide what trails are right for you? We have put together a list of some of the best trails for all levels of hikers to help you narrow down your list.

The last thing you want to be doing is hauling your extra gear around on a hiking trip. Instead, store it at one of our convenient luggage storage locations in Boston. Then, enjoy a day on the trails!

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Our Top Hiking Trail Picks in Boston

Skyline Trail

This is a serious hikers trail covering 15 miles (out and back) of steep inclines, a lot of rough terrain, and rocky areas that require some climbing over. Located in the Blue Hills Reservation, this trail is considered one of the best hikes near Boston. The hike will provide not only a great workout but incredible views of the Boston skyline.

Starting at the Willard Street parking lot you will summit 4 hills, including Great Blue Hill, the highest point in the reservation at 635 feet. Besides the natural beauty of the Blue Hills Reservation, you will also come across some historical landmarks and structures. Make sure you have plenty of liquids, a snack or two, and proper footwear for this rugged 6-hour trek.

Great Blue Hill Loop

The 2.3-mile moderately challenging loop will test your stamina a little with a climb to the top of the hill. Once at the top, take time to go up into the Elliot Observation Tower for a stunning panoramic view of the entire region of Boston. The hilltop is also a great spot to do a little bird watching.

Although not the longest hiking trail it will still take about 2 hours to complete. The starting point is easy to find too; from the Blue Hills Reservation Headquarters, you cross the street to the parking lot and look for the Skyline Trail. The route is pretty clearly marked and not too technical but hiking poles would be a good idea.

Breakheart Reservation Loop

This is a moderate family-friendly 2-mile trail with one slightly steeper three-quarter-mile incline (the reason for the moderate rating). The trail is great for jogging, bird watching, and taking your leashed dog for a nice walk. Smoothly paved asphalt means it is accessible no matter what the weather is doing, although the best time to go is between March and October.

There are areas to have a picnic, play volleyball, a playground for the little ones, and a beautiful beach to bask on. The walk itself might only take an hour but with all the other activities, and plenty of other trails to explore, you could easily spend the day here.

Great for both hiking and mountain biking, this state park features numerous trails—ranging from easy to challenging—through dense hardwood forests. Seven hills within the park, which spans from Saugus to Wakefield, offer views of Boston as well as New Hampshire and central Massachusetts.

The Freedom Trail

This is the ideal trek for museum and history lovers. One of the most famous trails in the United States has got to be this one. Imagine 2.5 miles of American history instrumental in the shaping of the country we know today. The easy-to-walk paved route winds its way through downtown Boston, just follow the golden markers along the red brick path.

There are guided tours available, or you can simply grab a map for a self-guided tour. Along the Freedom Trail, you will see such famous places as the Paul Revere House, the USS Constitution (Old Ironsides), and the spot of the Boston Massacre. The trail ends with a climb up the stairs to the top of Bunker Hill. Even though this is a shorter walk, how long it takes will depend on how many stops you make.

World's End

Located in the Boston Harbor Islands National Recreation Area, the 3.8-mile easy trail is a favorite for the locals of Boston. Walking gravel paths, you will enjoy the beautiful scenery along rolling hills and marshland between Hingham Harbor and the Weir River. Within the marshes, you will find a variety of birds such as herons and egrets with a spectacular view of the Boston skyline as a backdrop.

World's End is a great hike for the entire family. Even your furry best friend is welcome, as long as they are on a leash. The trail is accessible all year, although there is a small fee for adults. There are a number of tree-lined carriage paths to stroll, all designed by the famous landscaping artist Frederick Law Olmsted.

Halibut Point Trail 

Only 1.6 miles long, the easy walk through Halibut Point State Park will delight you with a gorgeous Atlantic ocean view. The trail wanders through the woods past the 100-year old historic granite quarry where you can still see piles of the larger granite rocks. Along the way, you will be guided by signage explaining points of interest, or you can grab a visitor's brochure at the start.

While walking the rocky shorelines, the sound of the crashing waves, wildflowers, and the picturesque woods will transport you to a world of tranquility. A short walk that might take less than an hour but with stops to investigate tidal pools and enjoy the sights will make it longer. Be careful on wet days as the rock areas can be very slippery.

Mount Auburn Cemetery Trail

Wandering a trail in a cemetery might seem a bit weird but the rolling hills of the Mount Auburn Cemetery have actually been landscaped for just that. 3.3 easy walking miles through beautifully designed gardens and stone monuments. And of course, it is the burial grounds of many historical figures in American history.

Created by Dr. Jacob Bigelow, this is the oldest arboretum and first garden cemetery in the Americas. The chapel with its stained glass windows, bubbling fountains, and sparkling pools are all sights you will discover on the walk. Make sure you stop at the Washington Tower at the top of the hill, it provides a view of the entire cemetery, Halcyon Lake, Boston, and Cambridge.

The view is something you will surely never forget, but remember to be respectful as you tread upon the hallowed grounds.

Lynn Woods Loop

Near Boston in the city of Lynn is where you will find this fantastic 4.4-mile moderate level loop. The hike will take you around Walden Pond, Birch Pond, and Tomlin's Swamp before you ascend to the top of Burrill Hill. There is a stone tower that you can climb for an amazing view of the area.

The trail passes Dungeon Rock, an underground tunnel, where you can do a little extra exploring if the gate is open. While most of the path is wide with firm footing, there are stretches where the old-growth forest will try and trip you up with exposed roots. Definitely bring bug spray in the summer months.

Easy Hikes in Boston

Near Boston, you will find one of the most unique places for some great hiking experiences. Although one has a name that sounds kind of ominous the trails are divine. And if you have kids, or anyone not into serious hiking, these are the places to have some fun.

Purgatory Chasm Trails 

Purgatory Chasm State Reservation has a variety of trails to choose from but for a family-friendly adventure, its easy trails will fit the bill. In most state parks it is about the trees and flowers, while here it is about the incredible rock formations. There are two trails, in particular, to check out.

Purgatory Chasm Loop and Purgatory Brook Trail will take you through giant 70-foot granite walls, large boulders that are easy to climb, and picturesque waterfalls. Nice and easy trails for all levels, dogs are welcome too but must remain on a leash. The kids will love to explore this area.

Ipswich River Wildlife Sanctuary

Ipswich River is more than just 12 miles of easy walking trails to explore, it is also one of the best outdoor adventures that kids especially love. The trails will lead you through forests, wetlands, and open green spaces, you can even take a break from hiking and go for a paddle on the river.

Within the Ipswich River Wildlife Sanctuary, you will find a variety of bird species, painted turtles, and hard-working busy beavers. Before you head back to the visitor center, do a little more exploring and climb the observation tower for a great look around. There is an entrance, but it is not much and spending a day here is well worth the price.

Intermediate Hikes in Boston

There are many moderately challenging hikes near Boston, but for a truly epic adventure of moderate hiking, there is only one choice.

Robert Frost Trail

With over 40 miles of trail to explore, it would take days to complete, but fortunately, the Robert Frost Trail is actually made up of several trails. This sensational trek will take you through the beautiful New England woods (especially in autumn time). It can be strenuous at certain points as it heads up some fairly steep inclines.

This is easily one of the best hikes in Western Massachusetts. It gives you a view from the fire tower at the summit of Mount Toby that the poet himself would find worthy of his words.

Mount Norwottuck

Located in Mount Holyoke State Park, at just over 3 miles long this loop will give you a pretty good workout. You will traverse the Horse Caves on your way to the highest peak in the Holyoke Range and a stunning view of the valley below. If you are doing the Robert Frost Trail, it is just a short side trip.

Difficult Hikes in Boston

Sometimes the best trails for experienced hikers are not right near the city, sometimes you have to travel just a little bit further to find what you are looking for. And that is why New Hampshire's Mount Monadnock made the list. It is reported to be one of the most climbed mountains in the world.

The Monadnock Lollipop Loop

This is a 3.7-mile trek that will test even the most experienced hikers. Starting at the Poole Reservoir you traverse the White Dot Trail all the way to the famous mountain's peak. Climbing over rocky outcroppings, up steep inclines, you find yourself staring at one of the best views in Southern New Hampshire.

Hiking to Historic Stone Structures and Beyond

New England has so many incredible hikes near Boston it is easy to see yourself grabbing a trail map and enjoying a scenic walk within the city or out in the countryside. And it doesn't matter what your fitness level is, there is a trail for you. Whether you go to a nearby state park or stay within the city limits, you will find a trail that will give you great places to explore. So what are you waiting for? Grab your boots and get hiking.

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