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Boston | © Katie Haugland Bowen / Flickr
Boston | © Katie Haugland Bowen / Flickr
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The Perfect Walking Guide to Boston

Picture of Ashley Kane
Freelance Writer
Updated: 13 February 2017
The best way to get to know a city is, undoubtedly, by foot, and Boston is no exception. The city is very walkable and small compared to New York City or other world-class metropolises. Seeing the sights and walking the streets of locals gives visitors an insight into daily life. Isn’t that what all travelers are curious about when visiting a new place – a look inside a new culture and their way of life? Here is the perfect walking guide to Boston (that is not the city’s famous Freedom Trail).

A. Prudential Center

Start your tour of the city at the Prudential Center, the largest upscale shopping mall in downtown Boston. Have a bite to eat at one of the many restaurants, stroll through Eataly, or go to the top of the Skywalk Observatory. From the sky-high vantage point, you will have 360-degree views of the entire city.

B. Newbury Street

Nearby is the infamous Newbury Street. Walk a few blocks of this well-known, trendy shopping street and stop in the many boutiques to take a look. The street is very picturesque with its brick walks and brownstones. Try out Trident Booksellers & Cafe – a unique bookstore and restaurant – for a cappuccino or hot chocolate.

C. Copley Square

The next stop is Copley Square on Boylston Street, just one street over, running parallel to Newbury. This beautiful open square is home to the Boston Public Library and Trinity Church. Take a tour of the historic, architecturally stunning Trinity Church, and then peek inside the BPL’s Bates Reading Hall.

D. Boston Public Garden

The Boston Public Garden is one of the loveliest green spaces in the city. In the spring, there are blooming tulips, and ducks and swans swim in the ponds underneath a charming bridge. In the winter, visitors can ice skate on the pond with their own gear or go to nearby Frog Pond to rent skates. The Boston Public Garden also has one of the most photographed statues — the Make Way for Ducklings sculpture. Take a picture with one of the ducks from Robert McCloskey’s famous book or go for a romantic stroll past the weeping beech trees.

E. Beacon Hill & Charles Street

The Beacon Hill neighborhood is one of Boston’s quaintest. Make your way here from the garden and stroll over cobblestones as you take a walk into the past. Charles Street is a perfect introduction to the Beacon Hill neighborhood with its pubs, general stores, and mom-and-pop stores. Beacon Hill’s unique brick architecture is protected by its community and is kept up to look as it did many years ago.

Acorn Street | © Rachael Elana Photography
Acorn Street | © Rachael Elana Photography

F. Massachusetts State House

The Massachusetts State House, with its golden dome, is one of the top tourist attractions in Boston and an important place for the governing of the state. Take a self-guided or conducted tour of the State House, or simply walk around its perimeter to appreciate its architecture and grounds. The building is located on a corner of the Boston Common, right at the edge of the Beacon Hill neighborhood.

G. Faneuil Hall

Faneuil Hall may be a predominant tourist site now, but it also played an influential role in United States history. Samuel Adams and James Otis gave important speeches here encouraging independence from Great Britain. Wander among the many shops in the area, and venture into Quincy Market for a bite to eat, just as locals did in this marketplace in the 18th century.

Faneuil Hall Boston | © Tony Fischer / Flickr
Faneuil Hall Boston | © Tony Fischer / Flickr

H. Rose Kennedy Greenway

The Rose Kennedy Greenway was a massive improvement to the city of Boston after the Big Dig. Before the massive construction project that lasted decades – from 1982 to 2007 – the greenway was once a highway that ran through the city. Fortunately, now everyone in the city can appreciate the public green space. Check out the sculptures, public art, and greenery across the greenway, or stop at one of the fountains, perfect for cooling off on a hot day. The newly opened Boston Public Market is also nearby with plenty of delicious local vendors.

I. HarborWalk

Boston is a coastal city and has some beautiful views. One of the most wonderful parts of this city is that the harbor is all protected and reserved for public access through the HarborWalk. Stroll through Christopher Columbus Park along the harbor and pass by the New England Aquarium. There are many outdoor bars in this area during the summer months, and occasionally concerts or other events. Sit down on one of the many benches and enjoy views of the harbor.

J. Hanover Street

End your walking tour of Boston in the North End, the best place in the city to eat Italian food. Hanover Street is the most well-known street in the neighborhood, complete with many delicious family-owned Italian eateries. Chow down at one of the upscale restaurants and then enjoy cannolis and Italian cookies or pastries from one of the famous bakeries. Try Mike’s Pastry, Modern Pastry, or Bova’s. The North End is a captivating, lively neighborhood, so step off the main stretch and wander around the picturesque streets that transport you back in time. If you’re interested in seeing historical sites, Paul Revere’s house is located only a few blocks away and is part of the Freedom Trail.