17 Scenic and Historical Hikes near Boston for All Levels

Updated November 30, 2022

Known for its famous historical 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. You’ve got many options if you’re looking for outdoor activities in Boston off the main tourist trails. One of the best things to do outside to explore the area is hiking near Boston. We created this guide with some of the best hikes near Boston so that you can plan your next weekend outdoors!

Easy Hikes In & Near Boston

Emerald Necklace

Trail Distance: Varies – 7 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 entirely its own separate trail but rather a connected web of paved trails that span nearly 7 miles. Whether you’re looking for a family-friendly hiking trail, a scenic place to run or bike, or a place to stroll, the Emerald Necklace indeed has something for you.

World’s End Trail

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

The World’s End Trail is a local favorite for some of the most spectacular views of the Boston skyline. Located in the Boston Harbor Islands National Recreation Area, this easy, accessible trail offers beautiful rocky shoreline paths, bird watching, and views over the city’s harbor. 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: $10 fee per vehicle or $8 per adult ($6 on weekdays). Reservations are encouraged.

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 love this trail, saying it’s easily one of the most beautiful in the state. We recommend coming here on sunny days, as wet conditions can make the rock areas slippery.

Note: DCR Parking Pass needed or pay $5 per vehicle (MA resident) or $20 (non-resident)

Battle Road Trail

Trail Distance: 5 miles
Location: Minute Man National Historic Park

History lovers will fall head over heels for Battle Road Trail, an easy, leisurely pathway through some interesting historical sites. It’s one of the best hikes near Boston for learning more about the area’s deep history. 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 historical!) 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 beautiful and a treat for literature lovers. 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 most accessible, 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 tends to get quite crowded, many smaller trails 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.

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 several rock formations 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 and 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 takes you across several ski runs, where you can see the lifts and 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.

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, the 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 the 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 other trails. Originally designed for horseback riding, this trail is wide and passes by historical stone structures, like the former Harvard College Library.

Note: $6 parking fee for non-members of the Essex County Trail Association.

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 forested areas with a few beautiful lakes and streams. Depending on the route you take, there are also several ascents and descents, so beginners and more experienced hikers can find a challenge here!

Note: May – October, parking fee applies ($5 MA license plates, $10 non-MA license plate). Free parking with a DCR pass.

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, you can see panoramic views of the countryside and 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.

Note: $10 parking fee for non-Mass Audubon members

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 roundtrip
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 New England’s most popular summit trails, the trail tends to get quite crowded, especially in the warmer months.

Requiring some serious scrambling and steep ascents, this short hike is 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 tremendous sense of accomplishment at the summit.

Note: Reservations are recommended, as visitors will be turned away if the park is full. $15 per vehicle plus a $1 transaction fee.

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.

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 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 historical landmarks and structures located within the Blue Hills Reservation. Looking for more? Blue Hills Reservation has over 125 miles of trails to explore.

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

Additional Resources on Hiking near Boston

What to Pack

Breathable hiking clothes – For warmer hikes, you’ll want to wear a sweat-wicking shirt and breathable pants, like these Patagonia hiking shorts for men and women. For cold-weather hikes, we recommend dressing in layers, including merino wool baselayers for men and women, a down puffer jacket for men and women, and a Northface waterproof outer shell for men and women (a must for hiking in Seattle). And don’t forget a pair of the best women’s and men’s hiking socks!

Trekking poles – You won’t need these for every single hike, but we suggest throwing them in your car just in case. We recommend the Black Diamond Trail Ergo cork trekking poles, which are lightweight, easy to transport, and durable.

Water bottle – Having water available at all times is a huge must. To limit disposable plastic, we recommend bringing your own refillable water bottle. We’re obsessed with Hydro Flask water bottles because they keep water cold for hours.

Sunscreen and bug spray – Sweatproof sunscreen and DEET bug spray can help you avoid sunburn and bug bites, two of hiking’s most annoying after-effects. Our favorite kind of sunscreen is Sun Bum, as it is free of harsh chemicals and safe for marine life, including coral reefs.

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 the Osprey Tempest 20 or the Talon 22 day packs because they’re comfortable and breathable for long hikes. For more information, check out our best day packs for any terrain guide.

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.