Boston Moms Guide to Getting Outside :: Our Favorite Places to Hike, Bike, and Play!

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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.

If you are looking for a place to slide, swing, and wiggle those sillies out, the playground is the perfect place to be! The Boston area has a ton of great playgrounds to visit. Here are some of Boston Moms’ favorites! For a comprehensive list, visit our Playground Discovery Directory.

Mayor Thomas M. Menino Park

98 16th St., Boston
 

What sets this playground apart is that it is uniquely designed to accommodate kids with physical limitations and restrictions. The park includes more than 60 pieces of inclusive play equipment and ADA-accessible paths and gathering spaces. There is also a climbing area, a seesaw, multiple slides, and a swing set.

 

The Lorber Family Playground at Jackson Square

1516 Columbus Ave., Boston
 

If your kiddos love climbing, look no further than the unique climbing structures at Jackson Square Park in JP. The bright orange climbing wall is challenging and fun for little daredevils.  This European-inspired apparatus is 50 feet long, 5 feet wide, 10 feet tall, and called “Wall-holla.” Inside, multiple levels of curving and twisting soft-coated platforms engage the mental and physical dexterity of children of all ages and physical abilities. The exterior walls are powder-coated steel gridwork offering utmost resistance to wear and tear and weather — all the while keeping children safe and in view as they play freely. They can also enter and exit through various entry holes or an attached tube slide. Foot and handgrips are affixed to the outside of the walls to create a safe but challenging rock-climbing wall. 

Albion Playground

Albion St. at Lowell St., Somerville
 

This community park includes play equipment, a splash pad, picnic tables, and a multi-sport court. There is some challenging climbing equipment for older kids and a smaller toddler-appropriate structure. The playground has rubberized flooring and there is a nice grassy spot to run around in.

 

North Point Park

6 Museum Way, Cambridge
 

North Point Park has more than a playground to offer. River and city views and extensive paved paths make this park a lovely place to go for an afternoon. The kiddos love watching the commuter trains and duck boat tours as they pass by. There are two different play structures for different ages. There is a small splash pad, so bring extra clothes. Make sure to pack a picnic!

 

Alexander W. Kemp Playground

Waterhouse St. & Massachusetts Ave., Cambridge
 

Redesigned in 2009, the playground is a landscape of hills, valleys, sand, wooden branches and stumps, living plant material, and loose wooden blocks to build with. It is a place where kids can invent their own forms of play. Many features are made from naturally decay-resistant wood. Slides are embedded into hills. Turning a crank sends water cascading down a series of tables into the sand area. There is a swing set for toddlers, a multidirectional dish-shaped swing that can be used by several children at once, a see-saw with multiple seats at each end for groups of children (or adults), and a “merry-go-round” that is at ground level to provide wheelchair access.

Menotomy Rocks Park

129 Jason Street, Arlington
 

This lovely park not only is home to a shady playground, it has pretty nature trails, grassy fields, and a pond. After play time on the playscape, go for a hike in the woods and climb mother nature’s playground of boulders, fallen logs, and other fun natural challenges.

 

SMILE (Simple Mobility in a Learning Environment) Playground

40 Fairbank Road, Sudbury
 

This beautiful playground also has a beautiful mission — to provide fun and play to kids of all physical abilities! It is an inclusive adventure park complete with slides, swings, and a sandbox. There are paved walking paths along the perimeter of the playground to provide easy travel for wheelchairs and strollers. There are sound-play components as well as activity panels for visually impaired kiddos. There are also transfer stations for those in wheelchairs to lift themselves onto the playground equipment. For active climbers, there is a large rock wall and a spider web structure. There is a soccer field adjacent to provide green space for extra running and picnics.

Beaver Brook Splash Park and Playground

621 Trapelo Rd., Belmont
 

Beaver Brook has lots of features to explore.  There is toddler-appropriate playground equipment along with play structures for older children. The splash pad is really terrific with water features around rock boulders. Make sure to bring your towel and extra change of clothes! The playground is part of the larger Beaver Brook Reservation. There are lots of nature trails and hikes with a waterfall trail! For extra water adventure, visit the pretty stream along side the playground.

Bradley Lessa Memorial Playground

1258 West St., Stoughton
 

Lessa Playground is a little tricky to find off the road, but it’s well worth it once you do! There are toddler-friendly swings, slides, and climbing equipment. There are play structures that will appeal to older kids as well. There are nature trails, including a storywalk trail, to explore right next to the playground!

Endicott Park

57 Forest St., Danvers
 

Endicott Park has a large green space offering a barn with farm animals, walking trails, an orchard, and a playground. The park’s landscape includes pastoral views, historic farm buildings, orchards, woodlands, and marshes, with a network of trails and gravel roads for stress-free exploration of the park. Passive recreation activities for all ages abound, ranging from hiking, fishing, picnicking, and enjoying the playground in the warmer months, to sledding, cross country skiing, and snowshoeing in the winter.

Nelson Memorial Park

235 Water St., Plymouth
 

This is a total destination playground at the beach. There is a huge playground with tons of swings in a sandy pit. There is a huge green space with a few picnic spots in the shade. Adjacent to the green space is a large splash pad full of fun on a hot day. There is beach access, and there are walking trails nearby. There is a field house with bathrooms and showers and a concession/ice cream stand. Parking is available on-site and at a free lot a block away.