Neighborhoods
Winter Hill, Located roughly north of Highland Avenue and west of the McGrath Highway, Winter Hill is home to a mix of restored homes and aluminium-sided fixer-uppers, replete with china gnomes and bathtub Virgin Marys. Once known as the home base of Irish gangsters Whitey Bulger currently on the FBI's 10 Most Wanted list, James "Buddy" McLean, Howie Winter and the notorious Winter Hill Gang, Winter Hill is now, like much of the rest of Somerville, experiencing gentrification and a resulting rise in property values and rents. Despite these changes, the area continues to hang onto its neighborhood flavor and is home to a large community of Irish, Italians, Brazilians, Portuguese, Cape Verdeans, and other ethnic groups.
Davis Square, This is a great late-night summer hangout, especially given that J.P. Licks is here. J.P. Licks is a trendy local ice cream shop, also seen on Newbury Street in Boston and elsewhere. It's right on the Red Line, and also a major bus transfer point. Tons of Tufts folk linger in the brick plaza. The Somerville Theatre doubles as a second-run movie house and music venue. Davis Square has several bars and coffeehouses, most notably the locally owned Diesel Cafe on Elm Street, that draw people day and night. A number of restaurants serve everything from burgers to crepes to falafel to Indian to East Asian cuisine to fast food.
Teele Square, Just up the street from Davis Square heading west it has a lot to offer in way of local restaurants. It's less crowded than Davis Square and less trendy. Head up this way if you're looking for good subs and pizza Angelina's, Mexican food Rudy's, or multi-ethnic Mediterranean fare from the Balkans and beyond Sabur.
Union Square, It is not on the Red Line, so it's a bit off the beaten path. It is only a 15 minute walk from the Sullivan Square Orange Line station, and there are MBTA (http://www.mbta.com) buses arriving from Central, Harvard, Porter, Davis, Lechmere, and Sullivan Square T stops. It's a nice walk in good weather from the West, but the neighborhoods to the East are less nice. There are a number of Brazilian restaurants and stores around, including a Brazilian butcher-slash-convenience store. The Brazilian community extends to Inman Square Cambridge and there's another pocket in Allston. There's also Indian, Mexican, and Peruvian fare here. The Sherman Cafe and Bloc 11 cafe are two excellent locally-owned coffee houses. Sherman Market sells local produce. Union Square is a nice, brick-based New England intersection of many roads. Ongoing improvements to the square include benches created by local artists. As of mid-2010, major reconstruction of Somerville Avenue as it travels from Porter Square to Union Square is nearing completion, bringing with it an improved streetscape with better lighting, more traffic lights, and raised pedestrian crosswalks. The Brickbottom Artists Studios are just outside of Union Square, under the McGrath Highway.
Understand
Somerville has managed to hold onto its blue-collar roots while at the same time gentrifying. It's fairly ethnically diverse, with populations including Irish, Italians, Portuguese, Brazilians probably the largest ethnic minority, Haitians, Tibetans, Indians, Chinese, and others. It is still the most densely populated city in New England about 80,000 people in four square miles, so visitors will find lots of purely residential territory between the "fun" areas: Davis Square, Porter Square, Union Square, and Powderhouse Square the location of Tufts University. Other notable neighborhoods include Union Square and Winter Hill, erstwhile home of the "Winter Hill Gang", the organized crime group headed by Whitey Bulger in the 1960's and 1970's, as well as East Somerville, probably the last non-gentrified area, which has a substantial immigrant population.
Somerville has a number of "squares", which are areas where several of the larger roads come together and which have various stores and parking. Navigating Somerville is easier if you consider the major squares as "hubs" connected by main streets as "spokes." The major squares include Davis Square, Teele Square, Powderhouse Square, Union Square, Magoun Square, and Ball Square. Many intersections have small plaques dedicating them as squares named after notable Somerville residents, frequently war veterans, but these areas are never actually referred to by those names.