Boston Neighborhood Guide

I have a friend from another city who is considering a Ruby job in Boston. He asked me for advice on places to live.

Cost of living

Expect to pay between $750-$1,250/month for a clean apartment close to Boston. You should be able to knock it down to $500/month if you share a bedroom with someone or live in Jamaica Plain.


I’ve mostly lived in Cambridge over the last 5 years so let’s start here. The Wikipedia entry hits the high points of Cambridge culture: Harvard University, MIT, the Charles River, and The Red Line.

The Blue Line encompasses the sections of Cambridge I’d recommend: most of Cambridge except areas that are more industrial or North Cambridge, which is just a little too far from downtown Boston for my tastes.

I put three pushpins in Boston for reference: Fenway Park, the Prudential Center, and Park Street at Boston Common (where the thoughtbot office is located).

If, like my friend, you’re not working downtown, but instead in Watertown, Waltham, Somerville, Medford, or Charlestown, I’d strongly recommend Cambridge.


Again, the Wikipedia entry will give you a good overview of the town and its culture: John F. Kennedy, The Country Club, and The Green Line.

This is an area I’d recommend for people with kids. Quiet, safe, and great schools. It’s close to Waltham, Watertown, and the Mass Pike if you’re working out along Route 128. It’s also extremely convenient if you’re working in the Longwood area, perhaps at one of the many hospitals and universities.

Within Brookline, Coolidge Corner, Washington Square are the two areas I would focus on. They’re both right on the Green Line along Beacon Street and have plenty of things worth walking to.

Jamaica Plain

Wikipedia calls Jamaica Plain The Eden of America. I can see that.

This is where you want to be if you'e a park lover or a real artist. The population is diverse. The Milky Way Lounge (Latin dance nights), JP Licks (ice cream), and Doyle’s Cafe (oldest Irish pub in Boston, longtime evening hangout for the city’s Irish politicians) are iconic institutions.

The area I’d recommend is bounded by the Orange Line on the right, the ponds on the left, and is split by Centre Street, which is filled with attractive cafes, galleries, restaurants and shops.

South End

Scan through the Wikipedia entry then take a walk through the area. If you’re not touched by the signature brick architecture of Boston that is prevalent in the South End, you have no heart. You’re probably a vampire. Might want to get that checked out.

The South End is known as a gay and artistic neighborhood. Tremont Street may have the greatest concentration of “Saturday night date restaurants” in the city. Unbelievable food. Lots of theaters, lots of music, lots of visual arts.

I’ve bounded the South End by some major streets.

It’s a tricking balancing act of trying to live in the South End, however. The closer you are to Copley, the closer you are to some of the highest rent areas of Boston. The closer to Washington Street, the further you are from all subway lines and the closer you are to some higher crime areas.

Back Bay, Beacon Hill, North End

It wouldn’t be tour through Boston’s neighborhoods if I didn’t point out the Back Bay, Beacon Hill, and the North End

These are all awesome neighborhoods but pricey.