9 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? 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? 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? 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? 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? 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.

Locals mostly know the quiet little town of Hopkinton as the starting point of the Boston Marathon. However, Hopkinton State Park is a hotbed of outdoor activities, with several trails running through its 1,500 acres of forest. There are paths for hikers of all levels, some of which are also used for horseback riding. In the summer, you can cool off and wash the sweat away with a swim in the reservoir.

This beautiful, five-mile path connects historic sites from Meriam’s Corner in Concord to the eastern boundary of Minute Man National Historical Park in Lexington. 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. There are informative markers along the walk and an educational presentation at the visitor center, so your hike can double as a history lesson.