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Just outside of Boston's city center is Dorchester, Boston's largest neighborhood. Dorchester's population is a tapestry of cultures and backgrounds, and its strong immigrant roots make it one of the most interesting areas in all of Boston. In addition to its strong sense of community and its modern energy, Dorchester is known for its rich history. This historic neighborhood was initially founded by the Puritans in 1630, and it's in Dorchester that you can find Boston's oldest home. So if you're looking for history and community in Boston, you should check out Dorchester. For my recent trip to Boston, I used HotelTonight to book my last-minute hotel in Dorchester, where I was able to get a great beat on the heart and soul of this diverse neighborhood.


Since Dorchester is such a large neighborhood (six square miles, to be exact), I knew I wouldn't have time to explore every inch of this sprawling Boston district. So to make the most of my limited time in Dorchester, I asked a few locals where I should visit to get the best feel for the neighborhood. Many of them recommended Ashmont, a charming section of Dorchester that is known for its beautiful Victorian style houses and its small-town feel. Since Ashmont is a residential community and not a tourist hot spot, I simply spent the morning enjoying life like a local--eating at quaint cafes and wandering the quiet, historic streets.

Clam Point

Clam Point, also known as the Harrison Square Historic District, is where you can find some of Boston's most beautiful historic homes. This small area of Dorchester boasts some incredibly coveted homes, some of which are worth millions of dollars. So if you like to ogle grand, historic real estate, you should meander through the streets of Harrison Square, particularly Mill Street. From the stunning old architecture to the manicured lawns and well-maintained streets, you'll discover just why Harrison Square is one of the most exclusive neighborhoods in Boston.

The Bay

Dorchester features miles and miles of waterfront property, so you can find plenty of great outdoor activities and beautiful views along the bay. During my brief stay in Dorchester, I visited the Neponset River and the Dorchester Bay, both of which provide scenic walking trails and a fantastic glimpse into local life in Dorchester. Since Dorchester isn't as compact as the city center, there's much more open space and natural scenery in this neighborhood, so I made sure to explore the more natural side of Dorchester during my recent trip to Boston.

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Dorchester may not be where most visitors choose to stay while in Boston, but I discovered that this residential area of the city is peaceful, diverse and very welcoming. I would definitely stay in Dorchester again, so when I plan my next trip to Boston, you can bet that I'll use HotelTonight to book a great hotel in Dorchester. After all, the heartbeat of Dorchester isn't driven by tourists--it's driven by locals and that's exactly the kind of people I want to be surrounded by when I'm exploring a new city.