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A bronze sculpture of a seated man on a pedestrian mall. Boston Globe via Getty Images

10 perfect Boston strolls for warmer weather

Shake off winter with ambles through the likes of the Rose Fitzgerald Kennedy Greenway, Beacon Hill’s Acorn Street, and the Commonwealth Avenue Mall

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The onset of warmer weather in Boston will draw both locals and tourists outside more (maybe with kids in tow, maybe not).

Here are 10 perfect strolls for soaking up the city’s sights, sounds, and surroundings. Some routes are more leisurely than others, and some will require a serious time commitment.

All are worth it at least once.

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1. Fenway-Riverway-Jamaicaway-Arborway

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1111 Boylston St
Boston, MA 02215

This is the multi-mile warmer-weather stroll for when you’re done messing around—why, it’s practically a hike!

These four “ways” edge some of Boston’s most beautiful parks, including the Back Bay Fens and the Arnold Arboretum, and some of its most beautiful institutions, including the Museum of Fine Art and the Isabella Stewart Gardner Museum.

Start at Boylston Street and Fenway and end at Arborway and Blue Hill Avenue. Or vice versa.

A lush shot of foliage in an arboretum. Shutterstock

2. Charles River Esplanade

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Charles River Esplanade
Boston, MA

The leafier, lusher run of the Charles River Esplanade—from about Berkeley Street in Back Bay to Charles River Dam Road in the West End—is the best part of it for strolling.

As the name implies, the esplanade hugs the Charles River and provides nonstop downtown views and a wee briskness this time of year.

People ride bicycles along a river esplanade. The bike path has grass on both sides. There are trees on one side of the path. Shutterstock

3. Commonwealth Avenue Mall

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484 Commonwealth Avenue
Boston, MA 02116
(617) 635-4500
Visit Website

If the 32-acre expanse shooting through Back Bay feels like a grand Parisian boulevard, that’s intentional—it was designed as such in the 19th century.

Memorials and statues dot the 1.3-mile run, which ends on its eastern terminus at the Public Garden.

A bronze statue along a pedestrian mall. It’s of a man sitting on a big rock. Boston Globe/Contributor/Getty Images

4. Public Garden

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4 Charles St
Boston, MA 02116
(617) 635-4505
Visit Website

The more bucolic neighbor of Boston Common dates from the early 19th century and includes 24 acres of statuary, flowers, foliage, and assorted other plantings as well as plenty of bench seating.

It can be particularly gorgeous in the spring as most of the plants and flowers bloom. Though, while taking in that kaleidoscope, don’t forget to keep an eye out for the garden’s less obvious gems, too.

Do the whole perimeter if you have the time, or at least down Charles Street.

A large statue of a man on horseback is in the background and in the foreground are colorful flowers. Shutterstock

5. Louisburg Square

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Louisburg Square
Boston, MA 02108

Accessing the wrought-iron-fenced private area of Louisburg Square is probably not in the cards—unless you or someone you know owns one of the uber-expensive spreads surrounding it.

But it is free to stroll the perimeter and to take in the facades of the Greek revival townhouses lining the square.

From Louisburg Square, too, one can jump into the other delights that surrounding Beacon Hill has to offer (Acorn Street, anyone?)

A row of three-story, very fancy townhouses on the other side of a wrought-iron fence. Shutterstock

6. Acorn Street

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Acorn St
Boston, MA 02108

The narrow, short street (it’s barely 250 feet long) in Beacon Hill is often called one of the most beautiful in America—and rightfully so.

Its cobblestone goodness recalls the 18th- and 19th-century buildup of Boston and looks achingly quaint pretty much year-round. Though, be warned: It can be crowded.

After strolling it, there’s plenty to check out in surrounding Beacon Hill.

A narrow cobblestone street going uphill and there are townhouses on either side. Shutterstock

7. Boston Common

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139 Tremont St
Boston, MA 02111
(617) 635-4505
Visit Website

America’s oldest public park dates from way, way back in 1634.

Its 50 acres are particularly inviting and scenic in the cooler months, with a number of statues, markers, and monuments for perusal—some less obvious than others—well as plenty of places to sit should the stroll prove taxing.

We suggest starting across Beacon Street from the Massachusetts State House and ambling your way diagonally down toward Boylston Street.

A lush, busy city park with buildings in the background. Shutterstock

8. Monument Square

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Monument Sq
Charlestown, MA 02129
(617) 242-5641
Visit Website

This area of Charlestown around the Bunker Hill Monument teems with historic homes, many in the federal style so endemic to Boston, on gently sloping streets that lead to and from the monument itself.

That alone is a rewarding walk. Feeling especially brisk, though? Try climbing the 221-foot obelisk.

And then check out the rest of what Charlestown has to offer.

An aerial view of a large monument surrounded by park space. The park space is surrounded by various city buildings in Boston. Shutterstock

9. Rose Fitzgerald Kennedy Greenway

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High Street &, Atlantic Ave
Boston, MA 02110
(617) 292-0020
Visit Website

Pick any point along the 1.5-mile, 15-acre ribbon of parkland born of the Big Dig and you’ve got a prime spot for leisurely taking in the bulk of downtown Boston.

There is also a lot to see within the Greenway itself, including memorials, monuments, and fountains.

10. HarborWalk

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HarborWalk
Boston, MA

The HarborWalk isn’t so much a park as one big string of parkland and boardwalk—about 43 miles total, making it one of the longest linear parks in urban America (and one of the best waterfront parks in Boston).

Pick it up pretty much anywhere the city touches the coastline outside of Back Bay, Beacon Hill, and parts of Charlestown and East Boston.

A walkway next to Boston Harbor with the city’s skyscrapers lighting up at dusk. Shutterstock

1. Fenway-Riverway-Jamaicaway-Arborway

1111 Boylston St, Boston, MA 02215
A lush shot of foliage in an arboretum. Shutterstock

This is the multi-mile warmer-weather stroll for when you’re done messing around—why, it’s practically a hike!

These four “ways” edge some of Boston’s most beautiful parks, including the Back Bay Fens and the Arnold Arboretum, and some of its most beautiful institutions, including the Museum of Fine Art and the Isabella Stewart Gardner Museum.

Start at Boylston Street and Fenway and end at Arborway and Blue Hill Avenue. Or vice versa.

1111 Boylston St
Boston, MA 02215

2. Charles River Esplanade

Charles River Esplanade, Boston, MA
People ride bicycles along a river esplanade. The bike path has grass on both sides. There are trees on one side of the path. Shutterstock

The leafier, lusher run of the Charles River Esplanade—from about Berkeley Street in Back Bay to Charles River Dam Road in the West End—is the best part of it for strolling.

As the name implies, the esplanade hugs the Charles River and provides nonstop downtown views and a wee briskness this time of year.

Charles River Esplanade
Boston, MA

3. Commonwealth Avenue Mall

484 Commonwealth Avenue, Boston, MA 02116
A bronze statue along a pedestrian mall. It’s of a man sitting on a big rock. Boston Globe/Contributor/Getty Images

If the 32-acre expanse shooting through Back Bay feels like a grand Parisian boulevard, that’s intentional—it was designed as such in the 19th century.

Memorials and statues dot the 1.3-mile run, which ends on its eastern terminus at the Public Garden.

484 Commonwealth Avenue
Boston, MA 02116

4. Public Garden

4 Charles St, Boston, MA 02116
A large statue of a man on horseback is in the background and in the foreground are colorful flowers. Shutterstock

The more bucolic neighbor of Boston Common dates from the early 19th century and includes 24 acres of statuary, flowers, foliage, and assorted other plantings as well as plenty of bench seating.

It can be particularly gorgeous in the spring as most of the plants and flowers bloom. Though, while taking in that kaleidoscope, don’t forget to keep an eye out for the garden’s less obvious gems, too.

Do the whole perimeter if you have the time, or at least down Charles Street.

4 Charles St
Boston, MA 02116

5. Louisburg Square

Louisburg Square, Boston, MA 02108
A row of three-story, very fancy townhouses on the other side of a wrought-iron fence. Shutterstock

Accessing the wrought-iron-fenced private area of Louisburg Square is probably not in the cards—unless you or someone you know owns one of the uber-expensive spreads surrounding it.

But it is free to stroll the perimeter and to take in the facades of the Greek revival townhouses lining the square.

From Louisburg Square, too, one can jump into the other delights that surrounding Beacon Hill has to offer (Acorn Street, anyone?)

Louisburg Square
Boston, MA 02108

6. Acorn Street

Acorn St, Boston, MA 02108
A narrow cobblestone street going uphill and there are townhouses on either side. Shutterstock

The narrow, short street (it’s barely 250 feet long) in Beacon Hill is often called one of the most beautiful in America—and rightfully so.

Its cobblestone goodness recalls the 18th- and 19th-century buildup of Boston and looks achingly quaint pretty much year-round. Though, be warned: It can be crowded.

After strolling it, there’s plenty to check out in surrounding Beacon Hill.

Acorn St
Boston, MA 02108

7. Boston Common

139 Tremont St, Boston, MA 02111
A lush, busy city park with buildings in the background. Shutterstock

America’s oldest public park dates from way, way back in 1634.

Its 50 acres are particularly inviting and scenic in the cooler months, with a number of statues, markers, and monuments for perusal—some less obvious than others—well as plenty of places to sit should the stroll prove taxing.

We suggest starting across Beacon Street from the Massachusetts State House and ambling your way diagonally down toward Boylston Street.

139 Tremont St
Boston, MA 02111

8. Monument Square

Monument Sq, Charlestown, MA 02129
An aerial view of a large monument surrounded by park space. The park space is surrounded by various city buildings in Boston. Shutterstock

This area of Charlestown around the Bunker Hill Monument teems with historic homes, many in the federal style so endemic to Boston, on gently sloping streets that lead to and from the monument itself.

That alone is a rewarding walk. Feeling especially brisk, though? Try climbing the 221-foot obelisk.

And then check out the rest of what Charlestown has to offer.

Monument Sq
Charlestown, MA 02129

9. Rose Fitzgerald Kennedy Greenway

High Street &, Atlantic Ave, Boston, MA 02110

Pick any point along the 1.5-mile, 15-acre ribbon of parkland born of the Big Dig and you’ve got a prime spot for leisurely taking in the bulk of downtown Boston.

There is also a lot to see within the Greenway itself, including memorials, monuments, and fountains.

High Street &, Atlantic Ave
Boston, MA 02110

10. HarborWalk

HarborWalk, Boston, MA
A walkway next to Boston Harbor with the city’s skyscrapers lighting up at dusk. Shutterstock

The HarborWalk isn’t so much a park as one big string of parkland and boardwalk—about 43 miles total, making it one of the longest linear parks in urban America (and one of the best waterfront parks in Boston).

Pick it up pretty much anywhere the city touches the coastline outside of Back Bay, Beacon Hill, and parts of Charlestown and East Boston.

HarborWalk
Boston, MA