Best Walks and Hikes in Boston and Nearby Area

Jan 2021

Winter hikes in Boston? Oh yes, the residents of this New England destination are a hearty and resilient crowd. Where else can you find bikes pedaling through the snow in winter and sailboats on the water as soon as the ice is out. This plow friendly city and surrounding neighborhoods have trails aplenty for lovers of the outdoors in every season!

Within the city limits, visitors will find abundant green space to satisfy their desire for a Boston hike or good walk. Rich with over 1,200 acres of green space, a series of interconnected parks and trails form the famous Green Necklace. Close by, many nature venues add an additional level of hiking experiences.

The newly developed waterfront gives visitors access to the beautiful Boston Harbor and of course, everyone must take in a few blocks of the historic Freedom Trail . Sprinkled throughout the many places to walk and hike in Boston are pieces of history with which no other city can compete. Don’t let anyone tell you to avoid the cold months in Beantown. This year-round destination is a dream for both indoor and outdoor enthusiasts. In each case, you’ll find a trail suitable for families or serious hikers. Boston’s open space is truly an extraordinary abundance of green treasures with a trail for everyone.

Table of Contents

Winter Hiking Tips

Make sure to download an app such as Alltrails. Trail maps are no longer available at many of these locaions following COVID 19 protocols.

Choose your route wisely. Winter weather can affect all hikers in different ways and it is not the best season to test yourself.

Use a backpack and dress in layers. Overheating and hiking wet is not fun.

Check the weather. New England is notorious for having very changeable temperatures and weather patterns.

Make sure to share your plan with someone in case of emergency.

Bring water and make sure to stay hydrated.

Follow the sun to enjoy the best and warmest part of the day

Best Hikes and Walks in Boston Proper

Harborwalk

One of the first things I like to do when visiting a new destination–especially a new city– is take a good walk. Winding through the city’s waterfront neighborhoods, the design of the HarborWalk allows the public to connect with the beautifully restored Boston Harbor.

View of Boston on Harborwalk

In a city known for its different localities, this trail highlights sections of South Boston and Fort Point Channel. In addition, you’ll see some of the city’s best views of sparkling high rises. Plenty of good restaurants dot the path to take some time to warm up with top notch coffee or hot chocolate.

The Harborwalk’s online interactive map is a great place to start. Along the route, various entry points are marked to connect with the trail.

The 411 on the Harborwalk

43 Miles of the Boston Harborwalk. Stretching from East Boston to Dorchester, the Harborwalk affords public access to a complex estuary with a rich history and wide-ranging present-day uses.
8 Boston Harborwalk neighborhoods include : East Boston, Charlestown, North End, Wharf District, Seaport District, Fort Point Channel, South Boston, and Dorchester
9 Public beaches along the Harborwalk

One of the great characteristics of the planning of green space in Boston is the interconnected nature of trails and parks. The Harborwalk connects to a number of additional inland trails and greenways, including the Emerald Necklace, Charles River Esplanade, Rose Kennedy Greenway, Freedom Trail and East Boston Greenway. Take note that with the exception of wheelchairs, the Harborwalk is for pedestrian traffic only. Bicycles are welcome on the portion of the Harborwalk from the Neponset River Greenway to Castle Island State Park. North of Castle Island, however, pedestrian traffic becomes heavier and bicyclists should move to bike lanes.

Make sure not to miss the many artworks along the trail. One of my favorite finds are the whimsical fish sculptured benches by Judy Kensley McKie in Eastport Park. In East Boston, the trail will take you into the Shipyard and Marina. Observe the murals and outdoor sculpture park HarborArts.

Others can be found on the University of Massachusetts Boston campus, Between the Institute of Contemporary Art and John Joseph Moakley Courthouse and by Harbor Towers. Last, but not least, the musical interactive Charlestown Bells by Paul Matisse (grandson of Henri) is located along the walkway of the Charles River Dam.

Address:

Official site: https://www.bostonharborwalk.org/

The Freedom Trail

Already on the radar of many history buffs, visitors can not visit Boston without walking at least part of the 2.5-mile Freedom Trail. As one of the country’s most iconic walks, this inner- city trail highlights the events leading up to the American Revolution.

Any of the 16 historically significant sites the trail passes through will give you a taste of Boston’s deeply signifigant history, and there are great stops along the way to recharge. Although the red brick markings on the route might be harder to spot after a recent snowfall, download the map from the official site, or use maps.me for the route.

Beginning at the visitor center in Boston Common, the walk includes the site of the infamous Boston Massacre and the Old Granary Burying Ground where Paul Revere, Samuel Adams and John Hancock were laid to rest.

Another option is to begin at the Old North Church where the notable lanterns hung prior to Paul Revere’s ride. The benefit of this leg of the trail is a stop in Boston’s equally historic Italian North End. After carbo loading on the best pasta or cannoli the city has on offer, continue on to the USS Constitution. If the wind is not blowing (doubtful in winter), a fun return trip can be via the water shuttle taxi back to Central Wharf. Enjoy outstanding views of Boston from the inner harbor along the way.

Walking Tours are also available with a professional guide.

Official site: www.thefreedomtrail.org

Emerald Necklace Hike in Boston

More than 100 years ago, the preeminent landscape architect Frederick Law Olmsted envisioned a long green space connecting downtown Boston to the suburbs. This jewel – known as the Emerald Necklace – has survived mostly intact, and today connects more than 1,000 acres in six different parks from the Boston Common to Franklin Park.

You can walk the entire seven miles or any part of it, each offering its own Instagram worthy photo opportunities. Make your return either on foot or by public transportation. On the way to Dorchester, the route passes my favorite art museum, the Isabella Stewart Gardner. In addition, look for Boston’s famous Swan Boats, a stunning rose garden, the historic Fenway Victory Gardens, three ponds and the Arnold Arboretum. The largest parcel, Franklin Park has over 15 miles of trails for hikers and joggers, several athletic fields and the well-known Franklin Park Zoo.

Boston Public Garden

The Arboretum has events throughout the year relating to whatever is in bloom. Established in 1872 and owned by Harvard University, it represents one of Olmstead’s landscapes remaining most true to his original design. The 261 acres of native, curated trees, plants and shrubs is a scenic beauty in any season of the year.

As the trail continues from the Public Garden, the tree-covered park in the center of Commonwealth Avenue is stunning in winter after a dusting of snow. Lined on either side by rows of distinguished brownstone and brick town houses that were homes to the “Boston Brahmins, this is some of the most desirable and expensive real estate in the city. You can walk the portion from Charles Street, through the Public Garden and the length of Commonwealth Avenue for a 2.5-mile round-trip, or add another 1.6 miles by strolling through the Fenway community gardens and the rose garden.

A popular side trail on the Emerald Necklace circles Jamaica Pond; the main trail runs along its south side, where there is a scenic overlook.

Address: Shattuck Visitor Center, 125 The Fenway, Boston, Massachusetts

Official site: http://www.emeraldnecklace.org

The Rose Kennedy Greenway

The Rose Kennedy Greenway is another wonderful wander. The 1.5-mile greenway connects parks, public art, and several neighborhoods. Pull up the Interactive Map to find things to see and places to stop along the way.

I moved to Boston when a unsightly elevated highway ran down the strip that has been beautified into the Greenway. It’s hard to believe this scenic ribbon of parkland running through downtown Boston was once an ugly ribbon of rusted metal that made me shiver every time I braved the expressway separating the city’s residents from the waterfront.

Now this pleasant mile and a half park land is a great way to get from Chinatown to the North End. Along the way you’ll find seven decorative and interactive fountains; a carousel where lobsters, codfish, harbor seals, and other local animals take the place of horses; and a variety of food trucks for when you need to recharge with a taco, a grilled-cheese sandwich, or a cupcake. The Greenway’s visitor center for the Boston Harbor Islands National Recreation Area has information and ferry tickets.

Address: Atlantic Ave, Boston, Massachusetts

Official Site: https://www.rosekennedygreenway.org

Charles River Reservation

The sixteen mile Charles River Link provides some of the best views of Boston, not least of which is the impressive Skyline. Running between Boston and Cambridge, the river has walking and hiking trails on either side. Stroll by the Boston Pops famous Esplanade on the Boston route and the campuses of Harvard and MIT on the other. This span makes a great loop of differing lengths thanks to the well-spaced bridges along the way.

The trail picks up parts of the reservation and connects back to other parks and green spaces around the city, including the scenic Longfellow Pond. There are additional scenic stretches connecting green spaces in the suburbs of Newton, Wellesley, Needham, Natick, Dover and Medfield.

If you happen to be staying at the Royal Sonesta Boston, their complimentary bikes are a great way to tackle a riverside path running towards the Museum of Science which often has less pedestrian traffic than other areas. Portions of the riverside trail are used by bikers, rollerbladers and skateboarders, so daydreamers beware.

Address: 1175A Soldiers Field Road, Boston, MA 02116 (but can be accessed from many different locations)

Official Site: https://www.mass.gov/locations/charles-river-reservation

Best Hikes South of Boston

World’s End

One of my favorite organizations to support in Massachusetts is the Trustees of the Reservation. They are a non-profit land conservation and historic preservation organization dedicated to preserving natural and historical places in Massachusetts. As the oldest land conservation non-profit of its kind in the world, the organization is a model for many to follow.

Their portfolio is bold and diverse. Luckily for nature lovers, they hold some jewels close to the city. On the south shore about 15 miles from Boston is a peninsula jutting into Hingham harbor and the Weir river. The 250 acre World’s End park is made up of rolling hills, rocky shorelines and a wonderful habitat for many local bird species.

Frederick Law Olmstead, who many regard as the Father of American Landscape Architecture, designed 4.5 miles of carriage paths providing easy to moderate trails. e 4.5 miles of easy to moderate trails close to Boston. From many clearings, visitors will enjoy the sweeping views of the city skyline. The wide paths form a perfect venue for snowshoeing or cross country skiing in addition to hiking.

Birdwatchers will find a plethora of species along with several boardwalks leading into saltwater marshes for viewing. The rocky shoreline borders the areas drumlins, gently sloping hills left by retreating glaciers. Hundreds of blueberry bushes and cedar trees are found covering granite ledges.

Amenities

Public restrooms. Benches. Drinking water fountain.

Under normal operation: Trustees members and children: FREE
Nonmember adults: $8 weekend/holiday and $6 weekday

Due to COVID-19, those driving to World’s End must purchase admission via a pre-purchased timed ticket. Members can reserve a ticket for free. The fee per car is $10 on weekdays and $15 on weekends. This ticket provides admission to the property.

Annual horseback riding permit required. Call for details.

Address: Martins Lane, Hingham, Massachusetts

Official site: http://www.thetrustees.org/places-to-visit/south-shore/worlds-end.htm

Blue Hills Reservation

Just outside the city limits and reachable by public transportation, the areas largest park, Blue Hills Reservation has over 125 miles of trails that offer a wide range of landscapes. Made up of 22 hills, the paths take hikers through marshes, swamps, upland forests and plenty of enormous boulders.

The summit of Great Blue Hill is the tallest peak on the Atlantic coast south of Maine. Scaling the 640 foot peak will afford views across the reservation and into Boston. On a clear day, lucky hikers might even get a view of Mt. Monadnock, a beauty in the White Mountain state of New Hampshire, almost 70 miles off in the distance.

With 7,000 acres that stretch across the towns of Milton, Quincy, Canton, Braintree and Dedham, this metropolitan area gem even has its own ski hill. Sites within the protected acreage have shown evidence of early farms and old quarries where stone for some of the area’s old historic buildings was excavated.

The six mile Skyline Loop trail is another favorite and will guarantee a burn on your quads. The Blue Hill Observatory is an additional popular climbing point to achieve with views to the ocean and south.

Address: 695 Hillside Street, Milton, Massachusetts

Official site: https://friendsofthebluehills.org/visit/guide-and-maps/

Best Hike North of Boston

Middlesex Fells Reservation

Granite rocks and a gorgeous reservoir are the first things that come to mind when I think of Middlesex Fells Reservation. 120 miles of trails on 2,600 acres nestled within five towns just 10 miles outside of Boston.

My daughter and I like to tackle the Skyline Trail, a seven mile challenge that moves across granite boulders, ponds and a final rewarding, if distant, view of Boston from the stone observation tower. (the tower itself is closed). Expect this particular trail to take about 5 hours, but there are options to make it shorter. Make sure you take water and any equipment you might need if the weather changes. The maine trail head leaves from Bellvue Pond and moves up and down along the impressive granite boulders.

In addition, there are many other trails, some along wide, open carriage paths along the reservoir, and some that take you deep into the hemlock forest. . No matter where you decide to hike, there are many scenic spots along the way.

Trail maps are no longer available at the visitors center; download one from the web site or use your favorite hiking app.

Address: 4 Woodland Road, Stoneham, Massachusetts

Official site: http://www.friendsofthefells.org/trails/

Best Hikes West of Boston

Battle Road Trail

For a scenic level path along the river and through forests, look no further than the NPS Battle Road Trail. Although the area now seems far removed from the American Revolution and Paul Revere’s famous ride, if you happen to be in town on Patriot’s Day (April) you will be lucky to be able to watch the annual reenactment of the start of the American Revolution. This is a great spot for a family outing.

The five mile route is marked with story signs along the way. The visitor’s center has displays and a muti-media presentation. In addition, side paths lead to Concord Bridge and Hartwell Tavern, a beautifully restored 18th century home and tavern sitting on an actual section of the Battle Road. Historically, it’s known as a witness house, as it was the setting for the Minuteman battle on April 19,1775. Staffed from Memorial Day weekend through October by Park Rangers in colonial attire who offer programs daily.

The trail is open year-round, although the visitor center is open only April through October. While you’re there, stop in the Historic Center of Concord and make sure not to miss the homes of Louisa May Alcott, Nathaniel Hawthorne and other well-known authors from the area. The Old North Bridge is also nearby.

Address: 250 North Great Road, Lincoln, Massachusetts

Official site: http://www.nps.gov/mima/index.htm

Beaver Brook

Waterfalls just outside the city limits? A secluded and fairly unknown group of trails known as Beaver Brook can be found just outside the Boston in the town of Belmont. This is a real find in a rather densly populated neighborhood.

Here you will find a number of unmarked trails. One of the loops starts out with a short and fairly steep climp over Mackerel Hill. After this first aerobic challenge, the rest of the trail is pretty flat and straightforward. The property boundary cuts across the town lines of Waltham and Lexington along the way.

I found the many paths confusing, so I would highly suggest downloading a trail map or AllTrails app if you plan on an extensive hike there. I could have easily gotten turned around and lost if I wasn’t with someone who knew the area well. The loop is 2.6 miles and in the immediate area is Lone Tree Hill and an Audobon Wildlife Sanctuary to extend your time in the outdoors into an all day adventure.

The park is open dawn to dusk and there is free parking available at the North and South lots. The trails are also open to mountain bikes. Take note of the poison ivy-a nuisance in three of the four seasons.

Address: 66 Mill St. Belmont, Massachusetts

Official Site: https://www.mass.gov/locations/beaver-brook-reservation

Upper Charles River Reservation

Years have been spent on the Upper Charles River Reservation project and the resulting success has created an active area for bikers, joggers, and hikers on the pathways. Canoe, stand up paddleboarders and fisherfolk can be found in different portions of the water as well. The areas rustic appearance is intentional and provides key habitat for birds and wildlife.

Located within the Charles River Watershed, this portion of the Reservation is a hike of just over 6 miles. The greenway created between 1990 and 2007 starts at Galen Street in Watertown Square and travels westward to Commonwealth Avenue in Newton and Weston. This section links the surrounding communities with the Boston and Cambridge system and provides access all the way into the city.

The stretch from Watertown Square to Moody St in Waltham is a narrow, winding path along the river and bordered with lush vegetation. Native plantings were established during the reclamation of the river banks and are filled with birds and other wildlife. A number of new wetlands were developed to further encourage habitat diversity.

An area in this section is often referred to as the Lakes District and runs from Moody St. to Commonwealth Ave. The water here is broad and quite calm, shorelines are forested, and numerous small islands and coves dot the landscape. Visitors are happy to take advantage of the excellent canoeing and SUP waters created by the damming of the river at Moody Street.

Public parking is available at many sites along the waterway. All entryways to the greenway are marked by granite pillars with heron carvings at the top.

Address: 96 Forest Grove Road, Waltham, Massachusetts

Official Site: https://www.mass.gov/locations/upper-charles-river-reservation

Final Thoughts on Hikes in Boston

Getting outside is one of the best things we can do for ourselves. Science has proven the many health benefits and importance of staying active as we age. Walking and hiking is a great form of exercise and relieves stress. Vitamin D is so important for your bones and immune system, especially when we grow older. Sunlight raises your serotonin levels and helps relieve anxiety. When you raise your energy levels, a calm, level focus follows.

Right now with social distancing being such a critical part of our health, a masked walk with a friend is one of the best ways to safely get the social connection we are all craving. Finally, as someone who struggles with sleep, I can agree that some healthy exercise is critical to your circadian rhythms and getting a good night’s sleep.