The Coolest Neighborhoods in Boston

Discover Charlestowns beautiful architecture
Discover Charlestown's beautiful architecture | © Ingfbruno

While there are many smaller overlapping communities within the city, there are officially 23 diverse neighborhoods, according to the City of Boston. Every area is unique based on its community, culture, and architecture. Many have changed rapidly in the past several years as the city continues to develop and expand, and they will likely continue to evolve in the coming years. Here are a handful of the coolest neighborhoods in Boston, with some of the best bars, restaurants, shops, and pieces of the city’s rich history.

1. Beacon Hill

Historical Landmark

A typical street in the Beacon Hill neighborhood of Boston, Massachusetts.
© Felix Lipov / Alamy Stock Photo
Receiving its name from the beacon that once stood high on the hill to warn the city of any invaders, Beacon Hill is one of the oldest neighborhoods in Boston. This trendy, upscale area has unique shops and restaurants on Charles Street, cobblestone streets, and architecture that reflects an earlier colonial time. There is a mix of wealthy families, professionals, and students who reside in this area, known for its brick row houses, lamps, and intricate ironwork. Beacon Hill was once home to many famous Americans, including Robert Frost, Louisa May Alcott, and Sylvia Plath.

2. North End

Historical Landmark

Narrow street in the North End of Boston, Massachusetts.
© Enrico Della Pietra / Alamy Stock Photo
The North End is the city’s oldest residential community. This 234-acre neighborhood has a large Italian-American population and dozens of the finest Italian restaurants in the city – making it a delicious, and costly, place to live. Wander the cobblestone streets, shop at small general stores, and take part in many of the Italian feasts and processions that occur during the summer months. The area is lively and aware that their Hanover Street is one of the top tourist attractions in the city. One perk of living in the North End is that you get to eat at some of Boston’s best restaurants without a line during the week. It is also close to North Station and the T, as well as the waterfront.

3. South Boston

Historical Landmark

South Boston is largely a working-class community, and it is expanding rapidly in the Seaport and Fort Port areas. It is primarily residential and coveted for its proximity to downtown and its amenities. There are many beaches along the water and local bars, markets, and restaurants in the neighborhood streets. “Southie” has a strong community and is also home to Dorchester Heights, now a national historical park, and the historic hill where George Washington’s army used cannons to force the British out of Boston in 1776.

4. Charlestown

Historical Landmark

4. Charlestown
© Wikimedia Commons
Charlestown is a neighborhood on the north side of Boston, situated on the banks of the Mystic River and the Boston Harbor. The area is full of the city’s rich history, with landmarks such as the USS Constitution, the Bunker Hill Monument, and the Charlestown Navy Yard. The Freedom Trail also runs through Charlestown. Young professionals, immigrants, and families all reside here, along with the area’s traditionally Irish population. The Main Street and Square have several restaurants and bars, including the Warren Tavern – the oldest tavern in Massachusetts, rumored to have served George Washington and Paul Revere.

5. Fenway-Kenmore

Historical Landmark

The Fenway-Kenmore neighborhood may be one of the liveliest in Boston – at the very least, it is during the MLB season. Home to the historic Fenway Park and the Red Sox, this area is brimming with sports bars, clubs, and restaurants on or near Landsdowne Street. However, that’s not all that it offers. It also extends to the beautiful, cultural Museum of Fine Arts and the world-renowned Boston Symphony Hall. Close to multiple T stops on the Green Line, Fenway-Kenmore is home to many professionals and students of the surrounding colleges. As for green spaces, Frederick Law Olmsted designed the Back Bay Fens, the neighborhood’s main park.

Allston and Brighton

Allston and Brighton are two neighborhoods often talked about as one as they are next to each other. These two communities are where the majority of college students reside for more affordable rent and nightlife. In recent years, the two areas have grown more diverse, and many young professionals also live here. There are a variety of delicious cuisines and ethnic restaurants located on the popular streets of Harvard Avenue, Commonwealth Avenue, and Brighton Avenue.

Allston and Brighton, Boston, MA, USA

6. Back Bay

Historical Landmark

Back Bay is filled with trendy shops, boutiques, restaurants, and vintage brownstone homes on Commonwealth Avenue. With many of the city’s main shopping areas nearby – Newbury Street, Prudential Center, and Boylston Street – this neighborhood is in the middle of the hub. There’s no need for residents to venture far to have a good time. The 200 Clarendon (John Hancock) tower, the Boston Public Library, and the Trinity Church are also in the vicinity.

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