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Known for its famous historic sites, beautiful green spaces, and tons of universities, Boston is one of the USA’s most beloved cities to visit and live in. Bostonians like to spend time outdoors, especially in the warmer months, and the parks and waterfront areas are often full of people. If you’re looking for outdoor activities in Boston off the main tourist trails, you’ve got a ton of options. One of the best things to do outside to explore the area is by hiking near Boston. We created this guide with some of the best hikes near Boston so that you can plan your next weekend outdoors!

Photo Credit: Wally Gobetz (Flickr CC)

Easy Hikes In & Near Boston

Emerald Necklace

  • Trail Distance: Varies – 70 miles total
  • Location: Begins at the Boston Public Garden/Boston Common

While most cities have several urban trails, Boston’s Emerald Necklace is unique because it runs through a chain of several of the city’s parks and green spaces. In this way, it’s not quite its own separate trail, but rather a connected web of paved trails that span nearly 70 miles (and are projected to expand in the future). Whether you’re looking for a family-friendly hiking trail, a scenic place to run or bike, or a place to stroll on your own, the Emerald Necklace surely has something for you.

Photo Credit: cmh2315fl (Flickr CC)

World’s End Trail

  • Trail Distance: 3.8 miles
  • Location: Boston Harbor Islands National Recreation Area

For some of the most spectacular views of the Boston skyline, the World’s End Trail is a local favorite. Located in the Boston Harbor Islands National Recreation Area, this easy, accessible trail offers beautiful rocky shoreline paths, bird watching, and views over the harbor of the city. For easy hiking near Boston for the whole family, you can’t go wrong with World’s End! We’d recommend heading here on clear days for the best views and hiking conditions.

Note that the park has an $8 entry fee per person, and children enter for free.

Photo Credit: Michael O’Brien (Flickr CC)

Halibut Point Trail

  • Trail Distance: 1.6 miles
  • Location: Halibut Point State Park

As one of the most beautiful and scenic hikes near Boston, the Halibut Point Trail is a short, easy hike along the rocky shorelines. 100 years ago, the area served as a granite quarry, and visitors can still see some of the remnants of it in the large granite rock piles. Lined with wildflowers and beautiful trees, the trail wanders by several stunning lake and oceanfront vistas, offering a peaceful and photogenic adventure for those looking for an easy hike. Locals really love this trail, saying it’s easily one of the most beautiful in the state. We’d recommend coming here on sunny days, as wet conditions can make the rock areas slippery.

Photo Credit: Chris Foster (Flickr CC)

Battle Road Trail

  • Trail Distance: 9.1 miles
  • Location: Minute Man National Historic Park

History lovers will fall head over heels for Battle Road Trail, an easy, leisurely pathway through some very interesting historic sites. It’s one of the best hikes near Boston for learning more about the deep history of the area. While the distance may seem long, you certainly don’t have to do the whole thing, and it’s a pretty easy and flat trail accessible to all levels of hikers, including families with children. The park is full of knowledgeable guides who can provide more information on any of the historic sites on the grounds.

Walden Pond

  • Trail Distance: 1.7 miles
  • Location: Walden Pond State Reservation

For an easy trail in a forested setting, Walden Pond is a fantastic (and historic!) option for hiking near Boston. Known for being the setting of Henry David Thoreau’s book of the same name, this peaceful, scenic wooded trail is not only beautiful, but also a treat for literature lovers as well. Spending some time on this trail will show you why Thoreau was so at peace and inspired by this place – there’s a peaceful pond, thick, wooded paths, and a replica of his one-room cabin where the book was written.

Photo Credit: Ishamari Drennan-Colon (Flickr CC)

Breakheart Reservation Loop

  • Trail Distance: 2 miles
  • Location: Breakheart Reservation

For one of the easiest family-friendly hikes near Boston, look no further than the Breakheart Reservation Loop. This trail offers beautiful forested walkways, views of the nearby lakes and rock formations, and some stunning views from higher elevations. While the trail does tend to get quite crowded, there are many smaller trails that branch off the main one, making for a “choose your own adventure” type of experience. Locals recommend coming in the early evening on clear days for a spectacular sunset atop Breakheart Hill.

Photo Credit: C McKane (Flickr CC)

Moderate Hikes Near Boston

Lynn Woods

  • Trail Distance: 4.4 miles
  • Location: Lynn Woods Reservation

As one of the most popular hikes near Boston, Lynn Woods offers a wide variety of terrain across 4.4 scenic miles of trails. The pathways wind through the forest and along a tranquil lake with some moderate inclines (but nothing too crazy). There’s also an abundance of wildlife here (especially in the earlier hours) and there are several rock formations that line the trails. At the top, you’ll find a stone tower that you can climb to see breathtaking views of the Boston skyline – perhaps the most beloved aspect of this trail.

Wachusett Mountain Loop

  • Trail Distance: 3.6 to 9.4 miles (Varies based on which trails you take)
  • Location: Wachusett Mountain State Reservation

Wachusett Mountain Loop is one of the most beloved hikes near Boston, with panoramic views of the Boston skyline, as well as the surrounding mountains and forests. Coined by Thoreau as the “observatory of Massachusetts,” it’s a fantastic trail for photographers and those seeking some of the best vistas in the state.

The trail itself takes you across several ski runs, where you can see the lifts as well as the views. You’ll also pass by the Balance Rock, a hidden gem of a rock formation carved by glaciers, pushing a large boulder on top of a smaller one. The summit here requires a bit of scrambling, but otherwise, the trail is definitely an easy to moderate difficulty.

Photo Credit: NoahBKaplan (Flickr CC)

Middlesex Fells Skyline Loop

  • Trail Distance: 7.6 miles
  • Location: Middlesex Fells Reservation

Overlooking the city from the outskirts, the Middlesex Fells Skyline Trail runs around the circumference of the Middlesex Fells area, offering jaw-dropping views of the Boston skyline and the surrounding hills. This trail is quite close to Boston, so you won’t necessarily get as much tranquility as some of the other places for hiking near Boston…but if you’re looking for a solid, longer trail with a variety of views and terrain, thee Skyline Loop is a convenient and fun option.

Appleton Farms Grass Rides

  • Trail Distance: 2.8 miles
  • Location: South Hamilton, MA

If you’ve got an outdoor-loving dog, the Appleton Farms Grass Rides trail is a perfect spot for a quiet adventure with your furry friend! While the trail isn’t as diverse in its views or terrain, this grassy, forested pathway is one of the more quiet hikes near Boston to enjoy the outdoors without the crowds of some of the other trails. Originally designed for horseback riding, this trail is wide and passes by historic stone structures, like the former Harvard College Library.

Photo Credit: Massachusetts Office of Tourism (Flickr CC)

Harold Parker Loop Trail

  • Trail Distance: 16.6 miles
  • Location: Harold Parker State Forest

The Harold Parker Loop Trail is a scenic trail that locals love for a longer hiking experience. While the trail is quite urban, it extends a full 16.6 miles for those wanting a longer excursion. Throughout the trail, you’ll pass through largely forested areas with a few beautiful lakes and streams. There are also several ascents and descents, depending on the route you take, so beginners and more experienced hikers can find a challenge here somewhere!

Mount Watatic

  • Trail Distance: 2.8 miles
  • Location: Watatic Mountain State Wildlife Area

For hiking near Boston, the Mount Watatic Trail has it all – amazing views, beautiful forests, wildlife, and rocky outcroppings. This short trail definitely poses a challenge, with a few steep ascents and a bit of scrambling necessary to get up to the final overlook point. Once you’re up there, though, you can see panoramic views of the countryside as well as the Boston skyline! Locals recommend going counter-clockwise on the trail if you’re a beginner, as it’s a bit easier to navigate that way.

Photo Credit: Kristin “Shoe” Shoemaker (Flickr CC)

Ipswich River Wildlife Sanctuary Loop

  • Trail Distance: 3.5 miles
  • Location: Ipswich River Wildlife Sanctuary

For birdwatching and wildlife spotting, there are few hikes near Boston that are better than the Ipswich River Wildlife Sanctuary. Bostonians love coming here for the abundant bird watching opportunities and the sheer beauty of the trail. The trail boasts gravel pathways, marshy boardwalks, and forested areas for a nice, cool, shady hike. There are also no bikes or dogs allowed on the trail, making for a much more peaceful and serene hike than some of the others on our list.

Wompatuck State Park Big Loop

  • Trail Distance: 10.3 miles
  • Location: Wompatuck State Park

If you love longer trails, Wompatuck State Park Big Loop is a fun and more challenging place to go hiking near Boston. Located in Wompatuck State Park, this beautiful trail traverses plenty of rocky, boulder-filled areas and scenic lake views, offering plenty of pathways to choose from for a bit more thrill! Along the path, you can view old military bunkers and beautiful forested areas, and you can bring your furry friends along too!

Challenging Hikes Near Boston

Mount Monadnock

  • Trail Distance: 3.7 miles
  • Location: Monadnock State Park

For more experienced hikers, New Hampshire’s Mount Monadnock is one of the most popular and challenging hikes near Boston. As one of the most popular summit trails in New England, the trail does tend to get quite crowded, especially in the warmer months.

Requiring some serious scrambling and steep ascents, this short hike is definitely not for beginners or the faint of heart. However, if you’re up for the challenge, you’ll be rewarded with stunning views and a huge sense of accomplishment at the summit.

Mount Hitchcock & Summit House

  • Trail Distance: 11.5 miles
  • Location: Mount Holyoke Range State Park

As one of the most challenging areas for hiking near Boston, advanced hikers will enjoy the length and challenge of the Mount Hitchcock and Summit House trail in Mount Holyoke Range State Park. This 11.5-mile trail is beloved by hiking enthusiasts in the area for being absolutely stunning and offering enough of a challenge for adrenaline seekers. The trail runs through lots of nature areas, including streams, lakes, forests, and rocky bald ridge lines. Hikers can expect to spend a full day on this hike, so bring lots of food and water for the journey. Also, beware of slippery areas after heavy rainfall.

Photo Credit: Bob P. B. (Flickr CC)

Blue Hills Skyline Trail

  • Trail Distance: 7.5 miles
  • Location: Blue Hills Reservation

The Blue Hills Skyline Trail is one of the most epic hiking trails near Boston, and is a 7.5 mile point to point trail across the Blue Hills Reservation. With tons of rocky areas, this trail is great for experienced hikers who enjoy steep inclines and some scrambling, as it summits several of the hills along the Blue Hills ridge. Those who complete the trail will enjoy stunning views of the Boston skyline, as well as access to some of the historic landmarks and structures located within the Blue Hills Reservation.

Boston, Massachusetts at the Public Garden in the spring time.

Additional Resources on Hiking near Boston

What to Pack

  • Hiking boots – You can’t hike without appropriate footwear, period. For most trails, we recommend an all-purpose waterproof boot with ankle support. We recommend Salomon hiking boots or Keen hiking boots for a comfortable hike.
  • Breathable hiking clothes – For warmer hikes, you’ll want to stay cool in a sweat-wicking shirt/tank top and breathable pants, like these PrAna hiking pants for men and women. For cold-weather hikes, we recommend dressing in layers, including merino wool baselayers, an insulated puffer jacket, and a waterproof outer shell. And don’t forget a pair of the best hiking socks in the world!
  • Trekking poles – You won’t need these for every single hike, but we recommend throwing them in your car anyway just in case. We recommend the Black Diamond foldable trekking poles, which are lightweight and easy to transport.
  • Water bottle – Having water available at all times is a huge must. To spare disposable plastic, we recommend bringing your own refillable water bottle. We’re obsessed with Hydro Flask bottles because they keep water cold for hours, but a good old Nalgene works very well too.
  • Sunscreen and bug spray – This should be self-explanatory, but sweatproof sunscreen and DEET bug spray can help you avoid sunburn and bug bites, two of hiking’s most annoying after-effects.
  • A brimmed hat or cap – The sun can be brutal in open hikes, so always pack a brimmed hat or cap for day hikes in the sunshine.
  • Emergency blanket and first aid kit – We’d strongly recommend bringing a first aid kit and a lightweight emergency blanket on every hike. Why? Because the unfathomable can happen, and it’s always best to play it safe.
  • Durable day pack – A durable day pack is the perfect spot to stash all your hiking gear. While any backpack will do, we recommend Osprey day packs because they’re comfortable and breathable for long hikes.

Wondering what exactly you should pack for your next hike? Visit our Complete Day Hiking Packing List for our full list and our top gear recommendations.

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Kay Rodriguez is the Chicago-based travel writer and photographer behind Jetfarer and Skyline Adventurer. When she's not blogging furiously on her laptop or editing photos, you can find Kay running, hiking, or paddling in a new city.

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