12 best hiking spots near Boston

What is it? Boston is no Denver, but there are still a couple of mountains (glorified hills, really) to climb. Just a few minutes outside of the city proper is a 7,000-acre reservation with 125 miles of pristine hiking trails.

Why we love it: Climb to the top of Great Blue Hill and enjoy the unmatched view of the Boston skyline from the Eliot Observation Tower—just prepare to share the scenery with crowds during warmer months and peak autumn.

Time Out tip: For a view of the skyline with fewer crowds, check out the Chickatawbut Overlook. The Skyline Trail is challenging, while the Ponkapoag Pond Loop offers a leisurely stroll along the woodlands marked by majestic pine and hemlock trees. 

Address: 695 Hillside St, Milton, MA 02186

Opening hours: Daily 6:30am–7pm

Expect to pay: The park is free to enter and enjoy, and parking is complimentary at a variety of lots within the grounds, including the Houghton's Pond parking lot.

What is it? Great for both hiking and mountain biking, the 600-acre Breakheart Reservation state park features two lakes, rocky hills, and numerous trails—ranging from easy to challenging—through dense and enchanting hardwood forests.

Why we love it: Seven hills within the park, which spans Saugus and Wakefield, offer views of Boston, as well as New Hampshire and central Massachusetts. The Saugus River cuts through the park, and trails follow along the riverbanks of two freshwater lakes, Pearce and Silver.

Time Out tip: Cool off after a day of hiking with a refreshing dip in Pearce Lake, which offers supervised swimming (and crowds) throughout summer.

Address: 177 Forest St, Saugus, MA 01906

Opening hours: Sunrise to sunset

Expect to pay: Nada. The park is free to enter and hike, and you can find free parking at 177 Forest Street in Saugus and at 100 Hemlock Road in Wakefield. That latter entrance gets you closer to Pearce Lake Beach.

What is it? Just north of Boston, this 2,200-acre state park in Stoneham features more than 100 miles of trails. It's ideal for hiking and walking of all levels, as well as mountain biking and even horseback riding on designated paths. You can explore woodlands, rocky outcrops, and picturesque ponds like Spot Pond, where you can rent canoes or kayaks. The reservation also features historical elements, including remnants of old mill works, and scenic viewpoints like Wright's Tower, offering views of the Boston skyline.

Why we love it: While the reservation has hikes for all levels, the Skyline Trail is both the most challenging and the most popular. It includes seven miles of rough terrain, passing over hills, through wooded forests, and around stunning lakes. Plan about five hours to complete it.

Time Out tip: A climb to the top of Wright’s Tower (when it’s unlocked for most afternoon exploration) affords gorgeous Boston views. Even if the observation tower is closed to visitors, you can still grab those vistas from atop the rocky ledges surrounding the structure. For dog owners, the Sheepfold Meadow provides an off-leash area.

Address: 4 Woodland Rd, Stoneham, MA 02180

Opening hours: Daily 9am–sunset

Expect to pay: The park is totally free to enjoy. You can also find free parking in around seven lots located throughout the park and pull-off availability on Fellsway East.

What is it? Located about an hour north of Boston, Harold Parker State Forest encompasses over 3,300 acres of hardwood, hemlock and white pine forest, which itself features a diverse landscape of ponds (11 of them, to be exact), swamps, rolling hills, and cool rock formations jutting from the ground.

Why we love it: Hikers can enjoy 35 miles of trails of varying difficulties in Harold Parker State Forest, including the popular Yellow Diamond Trail and its characteristic rock gardens that pop up along the path. For a quicker trek, the Yellow Diamond Trail South meanders around lovely Salem Pond.

Time Out tip: Want to linger? Consider an overnight stay at the 89-site campground for tents, trailers, and RVs. There, you'll find a pavilion, picnic areas, a playground, restrooms, and showers.

Address: 305 Middleton Road, North Andover, MA 01845

Opening hours: Sunrise to sunset

Expect to pay: $5 for Massachusetts residents, $20 for non-residents, determined by your vehicle license plate.

What it is: We all know that Wachusett Mountain is a popular winter destination for skiers, thanks to those catchy commercials—but the tallest mountain near Boston also offers hiking across a whopping 3,000 acres throughout the rest of the year.

Why we love it: The surrounding reservation includes the largest area of old-growth forest in Massachusetts, as well as ponds, streams, a raised bog, and 17 miles of trails.

Time Out tip: The 2.6-mile-long Harrington Trail is a popular hike that leads to the mountain's highest peak, a 2,006-foot summit where you can see the Boston skyline and New Hampshire's Mt. Monadnock on a clear day.

Address: 345 Mountain Rd, Princeton, MA 01541

Opening hours: 9am to sunset from Memorial Day to the last weekend in October

Expect to pay: There is a parking fee of $5 for Massachusetts residents and $20 for non-residents, though you can find free parking along roads near the park.

What is it? Locals mostly know the quiet little town of Hopkinton, located 30 miles west of the city, as the starting point of the Boston Marathon. However, Hopkinton State Park is a hotbed of outdoor activities, with 10 miles of marked trails running through its lush, 1,500-acre forest.

Why we love it: Hopkinton State Park gives hikers a chance to explore woodlands, traverse uneven terrain with small hills, or tackle more challenging steep sections with rocks and roots.

Time Out tip: Go swimming! The park also features the Hopkinton Reservoir, which contains two lifeguard-manned public beaches: the Main, or Lower, Beach located near Parking Lot L, and Upper Beach, which is accessible via a marked trail behind the Split Rock Pavilion. The latter tends to be quieter and offers more shade.

Address: 164 Cedar St, Hopkinton, MA 01748

Opening hours: Sunrise to sunset to visit the park; the swimming areas are open daily from 10am to 6pm from late May through Labor Day.

Expect to pay: Daily parking fees, of $8 for Massachusetts residents and $30 for non-residents, are charged from 8am to 5:30pm from May 24 to October 13.

What is it? Despite its daunting name, Mount Misery, at a modest 254 feet, is more of a manageable hill than an intimidating mountain. The 227-acre conservation area—the largest in leafy Lincoln—boasts over 5 miles of well-maintained trails that wind through a diverse landscape of agricultural fields, shady woods and around ponds.

Why we love it: Wander these trails, and you’re bound to see quaint wildlife—from chipmunks and squirrels to birds and deer. The top of Mount Misery offers views of the Sudbury River and Fairhaven Bay. The trails also connect to other conservation lands like Adams Woods, offering the chance for longer hikes.

Time Out tip: Concord’s wildly popular Walden Pond (Henry David Thoreau's inspiration for Walden) is located nearby, so make a day of it and hit up both natural attractions while you're out there.

Address: 60 S Great Rd, Lincoln, MA 01773

Opening hours: 24 hrs.

Expect to pay: Entry is free, and there is ample free parking along Route 117, with an overflow parking lot available at the Canoe Landing.

What is it? Not to be confused with World's End State Park in Pennsylvania, this lush and relatively small (251 acres) nature preserve is a mere 11 miles outside of the city. Its location on a peninsula offers Boston hikers a unique coastal experience with waterside and forested trails and carriage paths designed by Frederick Law Olmsted. Its claim to fame is the four coastal drumlins—spoon-shaped hills formed by glaciers—that jut into Hingham Harbor.

Why we love it: Overlooking Hingham Harbor, there are 4.5 miles of easy-to-moderate trails available for exploring. Hike through rolling hills, past saltwater marshes, and along the shoreline while still catching glimpses of the Boston skyline.

Time Out tip: Keep your eyes peeled for the countless species of birds who call this preserve their home—from red-winged blackbirds and bobolinks to egrets, herons, and the occasional bald eagle.

Address: Martins Ln, Hingham, MA 02043

Opening hours: Daily 8am–sunset

Expect to pay: $8 entry fee per person on weekends and holidays, or $6 on weekdays. Parking passes range from $10 (weekdays) to $15 (weekends).

What is it? Hiking history buffs will love this beautiful, five-mile path that largely traces the original remnants of the historic Battle Road, the site of a significant and bloody clash between thousands of Colonial Militia and British Regulars on April 19, 1775. However, in certain sections, the trail diverges breaks off to follow routes taken by the Minute Men as they moved through farming fields, wetlands, and forests.

Why we love it: The easy, level trail follows the route that Minutemen once took to the battle at Concord Bridge, where they prevented the British from seizing the Colonists’ weapons. Besides history, hikers can take in gorgeous views of woodlands, fields and wetlands. 

Time Out tip: For the avid learners among you, there are informative markers along the walk and an educational presentation at the visitor center, so your hike can double as a history lesson.

Address: 210 North Great Road, Lincoln, MA 01773

Opening hours: Daily from sunrise to sunset

Expect to pay: $0

What is it? Encompassing 475 acres, this urban forest offers 12 miles of trails, both paved and unpaved, catering to hikers, runners, and bikers of all skill levels, though it generally appeals more to those seeking low- to moderate-level hikes. 

Why we love it: Stony Brook Reservation is technically located within Boston city limits, but it feels miles away with lush trees, babbling brooks, forested trails, and beautiful Turtle Pond, which draws people in warmer months for fishing (allowed), swimming (not allowed), and general, revelrous summertime hangs.

Time Out tip: Orient yourself along the inner, 3-mile, paved Stony Brook Path loop with an access point near the intersection of Enneking Parkway and Blue Ledge Drive. From there, you can veer off onto different paths, some of which lead to the center of the woodlands, and some to Turtle Pond. Keep your eyes peeled for the abundance of rock cairns along the path maintained by a local artist.

Address: 95 Turtle Pond Pkwy, Hyde Park, MA 02136

Opening hours: Daily, sunrise to sunset

Expect to pay: Stony Brook is free for all to enjoy. 

What is it? For a natural escape within city limits, the 281-acre Arnold Arboretum, a National Historic Landmark and one of Boston's most verdant spaces, was founded in 1872 through a collaboration between Harvard University and the City of Boston. This prominent center for botanical research, home to 15,000 plants, was planned and designed in partnership with Frederick Law Olmsted.

Why we love it: As part of Boston’s Emerald Necklace, the Arboretum features numerous quiet and hidden pathways, ponds, and natural beauty. There are moderate hills for the intrepid, including Peter's Hill, which offers a stunning view of downtown Boston. 

Time Out tip: For a Zen-inducing experience, wander through the Conifer Path, a serene area sheltered by towering conifer trees of various kinds. The walking path is naturally carpeted with fallen pine needles.

Address: 125 Arborway, Boston, MA 02130

Opening hours: Daily, sunrise to sunset

Expect to pay: Admission is free

What is it? The Deer Island Loop, located in Winthrop, boasts a 2.7-mile paved, water-adjacent path perfect for an easygoing hike with impressive scenery just a hop and a skip from the city.

Why we love it: The Deer Island Loop is perfect for those days when you want to move but don't need to go 100. The relatively flat trail offers continuous and expansive views of Quincy Bay, the Boston Harbor Islands and, just across the water, the Boston skyline, which of course looks prettiest at dusk.

Time Out tip: The loop is paved, so it's a welcome terrain for wheelchairs and strollers. Leashed dogs are also welcome. Also, be aware that a water treatment plant is located in the center of the island, which could detract from the natural beauty.

Address: 190 Tafts Avenue, Winthrop, MA 02152

Opening hours: Daily 24 hrs.

Expect to pay: Not a thing.