The largest gay pride event in New England, and one of the most popular on the Eastern Seaboard, Boston Gay Pride takes place each year in mid-June - in 2014, the main parade, festival, and neighborhood block parties take place the weekend of June 14 and June 15, but there are a number of related community events held throughout the prior week (including a Pride Day Celebration at Faneuil Hall), held Saturday, June 6, 2014 - here's a full calendar of Boston Pride Week events.
Saturday, June 14, is the most prominent day of Boston Pride Week. At noon, the 44th annual Boston Gay Pride Parade commences at noon, starting at Boylston and Clarendon streets, jogging down into the city's most gay-identified neighborhood, the historic South End. The parade winds northeast, then north on Berkeley Street into the Back Bay, where it turns east onto Boylston Street and passes by the famed Boston Public Garden and the posh (and very gay-friendly) Four Seasons Boston. It then turns left onto Charles Street, heading north alongside the scenic Boston Common, before turning east on Beacon Street and passing before the Massachusetts State House, then winding around Tremont Street and Cambridge Street to end at Boston City Hall. This is one of the more popular and scenic gay pride marches in the country, drawing enormous crowds and passing before some of the city's most prominent sites. Here's a map of the Boston Gay Pride Parade route.
Also kicking off at noon on Saturday and lasting until 6 pm, the Boston Gay Pride Festival takes place at City Hall Plaza, right where the parade ends. At the festival, you can watch a number of top entertainers (this year's stage is headlined by Karmin and featuring plenty of other talented acts - here's a full list), visit with more than 130 business vendors and community groups, and mingle with hundreds of fellow participants. This is followed by several parties around town that night.
On Sunday the fun continues with a pair of GLBT Block Parties, held in two of the city's most gay-popular neighborhoods, the Back Bay and Jamaica Plain. In the Back Bay (right by the South End), the St. James Avenue Block Party takes place from noon until 8 pm.
Over in Jamaica Plain, affectionately known as "JP", the Jamaica Plain Block Party takes place from noon until 7 pm on Perkins Street, between Centre Street and South Huntington Avenue.
Additionally, numerous gay bars as well as gay-popular restaurants, hotels, and shops have special events and parties throughout Pride Weekend. Check the website of the Rainbow Times, partner of Pride Boston and producer of the official Boston Pride Guide, for more on what to see and do in the area, and also check out other Boston gay papers, such as Bay Windows, Boston Spirit Magazine, and Edge Boston. Also check out my Guide on Gay Boston, and for general travel information, look no further than Greater Boston Convention and Visitors Bureau.