10 Oldest Boston Neighborhoods and Their Historic Sites

As one of the country's oldest cities, Boston is a treasure trove of American history. First established in 1630, the city played a pivotal role in shaping our nation. What’s more, Boston’s heritage is preserved in its diverse, culture-rich neighborhoods. Each area offers a unique glimpse into historic Boston, from the cobblestone streets and Boston Common in Beacon Hill, to the vibrant markets in North End and the maritime memories in Charlestown. Dive into 10 of the oldest Boston neighborhoods to discover the historic landmarks and what living in each area is like today. [caption id="attachment_334589" align="aligncenter" width="1160"]

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Median Sale Price: $815,000 | Founded: 1628 | Niche Ranking: ANorth of the Charles River, Charlestown is one of the most significant historic neighborhoods in Boston. It was the site of the infamous Battle of Bunker Hill during the Revolutionary War. The battle destroyed nearly the entire town, which wasn't rebuilt until after the war. From the late 1800s to the 1980s, the neighborhood had the city's most significant Irish Catholic community. Today, Charlestown is primarily residential. It’s comprised of blue-collar and upper-middle-class workers, many still holding marine industrial jobs. The neighborhood overflows with historical monuments, and its maritime memories are weaved into its culture today. "Every morning at 8 a.m., the cannons fire from the deck of the USS Constitution, and we can hear it throughout the neighborhood," says Karen Colombosian, Realtor for Coldwell Banker Realty and longtime resident. "It's just one of the things that makes this neighborhood special." A 1920s shipbuilding facility converted into luxury condos called The Basilica is a popular place to live. Meanwhile, most of the other housing is upscale condos and lofts overlooking the waterfront. Its character includes longtime institutions like Monument Tavern and Warren Tavern. As the state's oldest tavern, Warren Tavern opened in 1780 and continues to serve up New England clam chowder and fish and chips. Pier 6 is the top spot for waterfront seafood dining. Additionally, the Charlestown Marina is a popular hangout to explore and sail the Boston Harbor.

• Charlestown Navy Yard: Established in 1800, it was one of the original naval shipyards in the country. It played a pivotal role in the Revolutionary War, Civil War and both World Wars, building and repairing U.S. Navy vessels. A hub for innovation until closing in 1974, it's since become a haven for old salts and history buffs. Charlestown Navy Yard is home to the Boston National Historical Park, working warships and exhibits unraveling the events that led to the American Revolution. 
• USS Constitution: The naval yard's most famous creation, the warship known as "Old Ironsides," earned its reputation in the War of 1812 and is the oldest ship still afloat. 
• Bunker Hill Monument: Commemorates the first significant battle of the American Revolution and marks the end of the historic Freedom Trail. Assembled in 1843, it's one of the country's oldest monuments. 
• Paul Revere Park: Honors the starting point of the patriot's famous midnight ride. 
• St. Mary-St. Catherine of Siena Church: A Romanesque-style church that opened in 1828. It was the second Catholic parish in the state and remains a central hub of worship. 

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Al Straggas/CoStar[/caption]

Median Sale Price: $1.2 million | Founded: 1630 | Niche Ranking: ABeacon Hill is one of its oldest neighborhoods in the middle of Boston. Earning its name from the hill that was topped by a beacon that once alerted residents to foreign invasion, its history is tied to abolitionist and Underground Railroad activity. In 1955, it was established as a historic district, the first of Boston's nine districts. Today, it's known for its iconic narrow cobblestone streets, federal-style 19th-century row houses, and thousands of copper gas lamps giving off a romantic glow; this highly walkable enclave is brimming with history. Of course, its most iconic feature is Boston Common, the oldest park in the nation and used as a military drill field and pastureland before its conversion to a formal park in the 1830s. Residents can stroll along Charles Street to peruse antique shops, upscale boutiques and fancy restaurants. 

• Boston Common: The 50-acre park has ties to the Revolutionary War, anti-Vietnam War protests and civil rights rallies. Now a hub for neighborhood events, the park also boasts monuments, trails and the Frog Pond for summer swimming and ice skating in the winter. 
• Freedom Trail: A 2.5-mile journey to 16 historic sites winding through several neighborhoods that tells the story of Boston's role in the American Revolution. Starting in Beacon Hill, it hits King's Chapel, Faneuil Hall and the Bunker Hill Monument. 
• Black Heritage Trail: Stops at homes and other historic sites associated with the African American community before and during the Civil War. 
• Boston Public Garden: Built in 1837, it's America's first public botanical garden. Home to the Make Way for Ducklings and George Washington statues, the garden is known for its Swan Boat rides in its lagoon. 
• Boston Athenaeum: A 600,000-volume library founded in 1807 offering collections of New England history, state history and American literature. 
• Massachusetts State House: Sitting atop Beacon Hill, the 1798 Federal-style structure was built on a cow pasture John Hancock once owned. With a 23-karat gold dome adorning its top, the building is home to the governor's office and the state legislature. 
• Cheers: Founded in 1969, this bar inspired the infamous '80s hit comedy TV show. Favorites include the "Giant Norm Burger" or "Carla's Meatball Sub." 
• 21st Amendment: This 1899 historic pub was first a luxury hotel with a passenger lift catering to presidents and other high society elites. While still attracting lobbyists and well-known political figures, the establishment has become a laid-back pub serving comfort food and cold pints. 

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Al Straggas/CoStar[/caption]

Median Sale Price: $665,000 | Founded: 1630 | Niche Ranking: BBoston's largest neighborhood at six square miles and a fifth of the city's population, Dorchester is comprised of Polish, Vietnamese, Cape Verdean and Irish communities. It was home to the country's first town meeting in 1633, the first free public elementary school, the first community health center and the first Vietnamese Community Center. The neighborhood treats residents to the world-famous Franklin Park Zoo, Boston's largest city park, eclectic restaurants and museums. 

• Walter Baker Chocolate Factory: Established in 1765, it's the nation's first chocolate factory.
• First Parish Dorchester. Built in 1630, it's the oldest religious organization in present-day Boston. 
• James Blake House: Built in 1661, it's the oldest home in Boston and managed by the Dorchester Historical Society, which offers public tours.
• Strand Theatre: A 1918 vaudeville theater turned cultural and educational institution that hosts big-name acts.
• Dorchester Park: Created in 1891 as part of the Emerald Necklace and listed on the National Register of Historic Places. This hidden gem is home to a popular annual classic car show and a mini forest.

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Al Straggas/CoStar[/caption]

Median Sale Price: $862,000 | Founded: 1630 | Niche Ranking: AKnown as "Southie," this urban neighborhood was once where George Washington's army set up to force the British out of Boston. Irish and Polish communities fueled its early growth and shaped its culture, from churches, charitable organizations, pubs and the neighborhood's iconic St. Patrick's Day celebration, a tradition since 1901. The festival is the oldest and most prominent in the country. South Boston is loved for its locally owned restaurants, sandy beaches and historic landmarks. Italianate-inspired homes, high-end condos and mid-rise multi-family buildings with Old Harbor views fill the neighborhood. 

• Castle Island: Home to historic Fort Independence, which provided defenses from European powers since the 1630s and a refuge for British soldiers. 
• Medal of Honor Park: Designated as a public space in 1897, the park holds the country's first memorial to Vietnam veterans and honors fallen marines from the area who died during all the country's wars. 
• Dorchester Heights Monument: A 115-foot marble tower honoring the evacuation of Boston during the Revolutionary War. 
• Fort Point Channel Landmark District: Boston's most extensive collection of 19th and early 20th-century industrial loft buildings. 

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Anhella Sanchez/CoStar[/caption]

Median Sale Price: $740,000 | Founded: 1630 | Niche Ranking: AOne of the city's most diverse neighborhoods, Jamaica Plain came to life post-Civil War from large farms and evolved into one of the country's first streetcar suburbs. This walkable neighborhood 6 miles from downtown Boston is now beloved for its green space. Jamaica Plain is home to the historic Olmsted Park, the 70-acre Jamaica Pond and the 281-acre preserve in The Arnold Arboretum. It also houses a portion of Boston's famed Emerald Necklace Conservancy, a 7-mile stretch of contiguous parks. 

• Forest Hills Cemetery: A garden-style cemetery built in 1848 where abolitionists, famous poets and Nobel Prize winners are buried. 
• The Footlight Club: The oldest community theater in the country, producing local dramas, musicals and comedies since 1877. 
• Hyde Square: Established in the 1660s, Hyde Square is known as Boston's Latin Quarter, with authentic restaurants, retailers and traditions defining the area. 
• Loring-Greenough House: Served as a military hospital during the Revolutionary War and now serves as a community hub and museum for Jamaica Plain history. 
• Eliot School House: Dating back to the 17th century, it started as a grammar school for African American and Native American children and continues to offer arts and crafts classes. 

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Anhella Sanchez/CoStar[/caption]

Median Sale Price: $675,000 | Founded: 1630 | Niche Ranking: BIn the center of Boston, Roxbury is yet another vibrant and diverse neighborhood. Irish immigrants escaped the potato famine in the mid-19th century, followed by a sizable Jewish community. Later, the Second Great Migration of African Americans made the neighborhood home in the 1940s. Today, it's still a melting pot, home to African American, Hispanic, Caribbean and Asian families. It's also home to New England's largest mosque, the Islamic Society of Boston Cultural Center, a 70,000-square-foot multipurpose center and several commercial districts. This close-knit neighborhood is proud of its heritage, preserving its cultural roots with things like the Frederick Douglass Historic District, the Boston Art and Music Soul Festival, the National Center of Afro-American Artists and locally owned businesses in Nubian Square. 

• Dillaway-Thomas House: A 1750 parsonage of the First Church in Roxbury and headquarters for General John Thomas and the Continental Army during the Siege of Boston in 1775. 
• Hibernian Hall: Home to the Irish community in 1913 as a famous dance club. Today, it's a cultural hub for the arts, theater and other creative programs. 
• Roxbury High Fort: A historic fort site that once contained fortifications of the Continental Army during the Siege of Boston. The Fort Hill Tower and a park were added in 1869. 
• Eustis Street Firehouse: Constructed in 1859, it's Boston's oldest original firehouse structure. 

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Median Sale Price: $957,500 | Founded: 1630s | Niche Ranking: A+The oldest residential community, North End, is known as Boston's "Little Italy," and it's one of the most iconic immigrant neighborhoods. Irish, Jewish and Italian communities flocked to the area in the early days. By 1930, it was nearly all Italian residents. While it's a quaint village, North End has helped define much of Boston's historic and culinary culture. It embodies a European spirit, home to over 100 cafes, bakeries, street vendors, and Italian eateries. Nearly all locally owned, North End has kept true to its roots with places like Modern Pastry, a staple since the 1930s. There’s also Caffé Vittoria, the oldest Italian café in Boston, which has been in operation since 1929, and no-frill pizza parlors like Regina Pizzeria. The neighborhood also celebrates Roman Catholic traditions like Saint Anthony's Feast, an annual parade with hundreds of Italian street vendors and religious services. 

• Freedom Trail: Also winding through North End, the 16-site trail winding tells the story of Boston's role in the American Revolution. 
• Paul Revere House: Home of the famed Revolutionary War hero, it opened in 1908 as one of the country's first historic house museums. 
• Paul Revere Mall: Brick walkway with an equestrian statue of Revere. 
• Copp's Hill Burying Ground: The city's second-oldest cemetery, established in 1659 and the resting place of prominent historical figures from abolitionists to soldiers. 
• Old North Church: Boston's oldest standing church, built in 1723, its story in history wasn't cemented until 1775 when church sexton Robert Newman climbed the steeple holding a lantern to signal to Paul Revere that British troops were advancing on Concord by sea. The church hosts 500,000 attendees a year. 

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Brett Osswald/CoStar[/caption]

Median Sale Price: $685,000 | Founded: 1836 | Niche Ranking: BAcross Boston Harbor and home to New England's largest international airport, East Boston's waterfront location led to a bustling shipbuilding and maritime economy that continues today. "Eastie," as locals call it, is another melting pot In Boston. Since 1940, it's been home to diverse communities that have defined its economy and culture. Iconic eateries like Santarpio's, or "Tarps" to locals, has been a staple since 1903, serving pizza and skewers. Saigon Hut is a must for Southeast Asian cuisine. Rincon Limeño Restaurant serves up authentic Peruvian fare. Residents enjoy a big nightlife scene here, too. Tall Ship (a floating oyster bar) is a popular spot, as is The Quiet Few, a whiskey tavern. The neighborhood is home to ICA Watershed, a favorite seasonal art exhibition space on the marina and Constitution Beach. 

• Eagle Hill Historic District: A residential area developed between 1834 and 1900 decorated with Italianate, Second Empire and Renaissance Revival-style buildings. 
• Baker Congregational Church: Founded in the late 1830s and added to the National Register of Historic Places in 1998, it was the first church for the community and is still active today.
• Clipper Ship Monument: A tribute to Donald McKay, known for his record-setting extreme clipper sailing ships. 

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Matthew Stott/CoStar[/caption]

Median Sale Price: $1.4 million | Founded: 1859 | Niche Ranking: A+Sitting along the Charles River, Back Bay was designed to look like Parisian boulevards. People flock to the neighborhood for its stunning 19th-century architecture, renowned for its preserved Victorian brownstones. Beyond the district's historic architectural allure, it's home to the scenic 17-mile Charles River Esplanade, a famous shopping and dining area and cultural landmarks. 

• Copley Square: Home to Trinity Church, a historic landmark founded in 1733, and its design is the birthplace of the Richardsonian Romanesque style. It caters to 100,000 attendees a year. 
• Commonwealth Avenue Mall: A 32-acre French-boulevard-style walkway built in 1856 with green space linking the Public Garden and park system. 
• Prudential Tower: A 52-story structure built in 1964 and a staple of Boston's skyline filled with shops and restaurants. 
• Newbury Street: One of Boston's earliest roads - coming to life in the 1800s, it's now a renowned shopping destination, with over 120 luxury retailers and 60 upscale restaurants. The eight-block strip has become one of the most expensive streets in the world.
• Boston Public Library: Built in 1895, the first free public library in the country. 

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Anhella Sanchez/CoStar[/caption]

Median Sale Price: $540,000 | Founded: 1874 | Niche Ranking: AAnnexed in 1873, Brighton was New England's Wild West with cattle drives, stockyards, saloons and stampedes through the streets in the mid-19th century. This primarily residential neighborhood is home to Boston University and Boston College. It is filled with a diverse mix of young professionals, students, newcomers and families who have been there for generations. The neighborhood is primarily made up of Chinese, Russian, Irish and Brazilian communities. That melting pot has spilled over into the culture and restaurant scene with places like Brighton Bodega, which offers international street food, Peka, a Venezuelan restaurant and its abundance of ethnic grocery stores. Daniel's Bakery, Johnny D's Fruit and Produce and the steakhouse, Stockyard are also beloved longtime staples. 

• Brighton Center Historic District: Home to restaurants and shops, the Market Street Burying Ground (1764), Washington Building and Imperial Hotel (1900) and other historic buildings with grand architectural styles ranging from Queen Anne to Gothic Revival, Tudor and Victorian. 
• Brighton Allston Congregational Church, UCC: This historic local church serves Brighton's first congregation in 1868, and it hosts a food pantry, thrift store, concerts, and community events. 
• McMullen Museum of Art: Inside Boston College, founded in 1863, the museum displays 16th and 17th-century Italian paintings and 19th-century American paintings. 
• Brighton-Allston Heritage Museum: Chronicles the neighborhood's development back to the 1600s.