

The sun is shining, the weather is beautiful, and outside is calling your name!
Whether you are hiking, biking, or swinging away, there are endless places in the Boston area to enjoy the outdoors! Feel the sun on your face and the breeze in your hair as you check out some of Boston Moms’ favorite spots!
Just a few minutes away from the hustle and bustle of the city lies the beauty of the forest. Here are a few of Boston Moms’ favorite family-friendly hiking trails!
Blue Hills Reservation
695 Hillside St., Milton, MA
Hikes from the Trailside Museum
Wolcott Path Loop
Difficulty: Easy
Length: 2 miles
Beginning in the parking area of the Trailside Museum, this relatively level hiking path takes you through large hardwood forests. Follow the green dots starting at the bulletin board.
Houghton’s Pond Loop
Difficulty: Easy
Length: .75 miles
This short scenic hike takes you around Houghton’s Pond. This walk is beautiful during the fall foliage season! Walk from the bulletin board at the main parking area and follow the yellow marks on trees to guide the way.
Hikes from Reservation Headquarters:
Wolcott & Border Path
Difficulty: Easy
Length: 2.5 miles
This beautiful woodland hike takes you through majestic pines and hemlocks on relatively level ground. Follow the Woodland Lane that starts at Reservation Headquarters on Wolcott Path and follow the green dot trail.
Ponkapoag Pond
Difficulty: Easy
Length: 3.75 miles
Follow this green dot trail around the reservation’s largest and most remote body of water. For an extra treat, explore over the Ponkapoag boardwalk. The bog is located across from the YMCA campsite. To access this trail, park at the Rt. 93 exit pull-off on Blue Hill River Road, but make sure not to block the gate.
Braintree Pass Path
Difficulty: Easy
Length: 3 miles
This hike is a hidden gem! The easy trail passes through majestic hemlocks, slopes covered with mountain laurel, and an Atlantic cedar swamp. An old cellar hole along the way marks the Glover Homestead, where settlers farmed hundreds of years ago. The trail begins at the intersection of Rt. 28 and Chickatawbut Road. Park in the small pull-off and walk by the bulletin board down Braintree Pass Path.
Borderland State Park
259 Massapoag Ave., Easton, MA
Pond Walk
Difficulty: Easy
Length: 3 miles
Follow the carriage road leading around Lower Leach Pond. This beautiful trail is mostly wooded and passes by the stone lodge, old stone cellar remains, dam and bridge, bird blind, open fields, farmhouse, 1911 mansion, and picnic grounds.
Myles Standish State Forest
194 Cranberry Rd., Carver, MA
Reservoir Hike
Difficulty: Easy
Length: 3 miles
The trail begins over the bridge to the left of the headquarters parking lot. Self-guided brochures are available at headquarters to guide you through this beautiful trail! You will venture through pine forests, over a swamp via a boardwalk, and along the shores of East Head Reservoir.
Waquoit Bay National Estuarine Research Reserve
149 Waquoit Highway, Falmouth, MA
Quashnet River Trail
Difficulty: Easy
Length: 3.5 miles
This easy hike brings you through pine and oak woodlands along the Quashnet River, where you will observe many wetland plants and native woodland species such as pitch pine, low bush blueberry, and trailing arbutus. There is also a herring run in season.
Maudslay State Park
Curzon Mill Rd., Newburyport
Intergenerational Walk
Difficulty: Moderate
Length: 1 mile
Begin at the Pasture Trail to experience a walk through the natural and historical areas of the park along gravel paths. There may be poison ivy along the edges of the trail, so please be careful.
Walden Pond State Reservation
915 Walden St., Concord, MA
Pond Path Hike
Difficulty: Easy
Length: 1.7 miles
This beautiful trail is great for families! See numerous glacial formed coves along the trek, and visit the house site of Henry David Thoreau’s cabin.
Great Brook Farm State Park
984 Lowell Rd., Carlisle, MA
Litchfield Loop
Difficulty: Easy
Length: 1 mile
This easy trail has a great view of the farm! You will see corn fields as well as fields of beautiful wildflowers!
Pine Point Loop
Difficulty: Moderate
Length: 2 miles
This mostly shaded trail has some open field areas that are perfect for the kids to play in! Majestic white pine trees line the trails, and open fields are lined with colorful wildflowers.
Tannery Falls Trail
Difficulty: Moderate
Length: 3 miles
This mostly shaded trail brings you by magnificent, historic stone walls. Pre-colonial cellars are present along the trail.
Halibut Point State Park
Gott Ave., Rockport, MA
Babson Farm Quarry Interpretive Trail
Difficulty: Easy
Length: 1 mile
This level walk takes place on graded trails. You can get a park brochure at the visitors center to guide you along the interpretive stops.
Ocean Path
Difficulty: Moderate
Length: 1 mile
This beautiful walk down to the rocky shoreline brings you to open tidepools that are often filled with unique sea life! Be cautious — the rocks along the shore may be slippery.
Harold Parker State Forest
Rt. 114, North Andover, MA
Stearns Pond Trail
Difficulty: Easy
Length: 2 miles
Park at headquarters and begin down Beach Road beyond the gate to follow the trail around the fire road around the north side of Stearns Pond. The trail crosses by the spillway that was built by the CCC in the 1930s, creating the pond. Bird life can often be found in the marshy area to the right of the spillway.
Berry Pond Trail
Difficulty: Easy
Length: 1.5 miles
Park at the Jenkins Road parking area to access the starting point of this trail. The trail travels around the pond, a natural kettle pond formed by a glacier thousands of years ago, with wooden bridges crossing in the dense forest.
Hopkinton State Park
Route 85, Hopkinton, MA
Long Trail
Difficulty: Moderate
Length: 1.5 miles
The longest trail in the park, Long Trail goes from end to end, exposing you to both coniferous and deciduous forest!
Boston is full of amazing places to ride bikes with the family! Here are a few of our favorites!
Looking for a comprehensive list? Check out our full guide to Massachusetts Bike Trails, Paths, and Rail Trails for the Whole Family!
Bay Colony Rail Trail
Needham :: 1.7 miles, crushed stone
Parking is available at Red Wing Bay on the south side of Fisher St.
Charles River Bike Path
Runs from Boston to Waltham :: 22.9 miles, asphalt
Parking is available at the Boston trailhead in the Museum of Science parking garage, and at the Cooper St. parking lot in Waltham.
East Boston Greenway
East Boston :: 2.8 miles, asphalt
Most easily accessed by the Blue Line (Maverick, Orient Heights, or Wood Island stations). Parking is available at Constitution Beach, on Barnes Ave.
Fresh Pond Bikeway (Watertown-Cambridge Greenway)
Cambridge :: 1.25 miles, asphalt
Parking is available near Kingsley Park (250 Fresh Pond Pkwy.) and at William G. Maher Park (650 Concord Ave.). The north end of the bikeway is 0.6 miles away from the Alewife T stop and also accessible by bus.
Mattapoisett Rail Trail
Mattapoisett :: 1.1 miles, asphalt
Access the Mattapoisett Rail Trail from Brandt Island Rd. or from the Phoenix Bike Trail.
Mystic River Greenway
Runs from Somerville to Arlington :: 4 miles, asphalt and boardwalk
Parking is available at Draw Seven Park (Noonan Place, Somerville), at Blessing of the Bay Boat House (32 Shore Dr., Somerville), and at the Mystic River Reservation on Mystic Valley Parkway in Medford. The trail is also accessible from the Assembly T stop.
Southwest Corridor Park (Pierre Lallement Bike Path)
Runs from Boston to Jamaica Plain :: 4.1 miles, asphalt
The northern trailhead is at the Back Bay T station on Dartmouth St., and the southern trailhead is at Forest Hills T station on Washington St. Paid parking is available at these locations.
Upper Charles Trail
Runs from the Holliston/Sherborn town line to the Hopkinton/Milford town line :: 13.2 miles, asphalt and crushed stone
Parking is available in Holliston in Blair Square off Front St., in a municipal parking lot off Exchange St., at Fino Field on Sumner St. in Milford, at Louisa Lake Park in Milford, and in the parking lot on Cedar St. in Hopkinton.