Boston, the capital and largest city in Massachusetts, is one of the oldest and wealthiest cities in the nation. Boston is a city steeped in American history. Boston is a haven for university life, with over sixty colleges calling the greater Boston area home. Harvard University, in neighboring Cambridge, is the oldest college in the country. Boston is a popular shopping destination with exclusive Newbury Street offering up designer stores and boutiques, while Copley Place has an opulent variety of stylish European stores. Fenway Park, one of the most notable baseball stadiums in the country, hosts the Boston Red Sox.

Neighboring towns Lexington and Concord are known as being the site of America's first battle with the British at the start of the Revolutuionary War. Lexington is primarily suburban, while Concord remains the quiet country town of its origins. Concord is a town of literary history. Louisa May Alcott and Ralph Waldo Emerson once lived here and Henry David Thoreau's Walden Pond is just south of Concord.

Gloucester is a fishing town and one of the oldest settlements in New England. The movie, A Perfect Storm, was based in Gloucester. Located along the coast of Gloucester on Cape Ann is an artists' colony called Rocky Nest, the Hammond Castle Museum featuring European art, and Beauport Mansion, an artful backdrop for local concerts and events. There are several whale watching boats shuttling tourists out to prime locations for whale spotting. The local area beaches like Wingaersheek in Gloucester, and Pebble and Long Beach in nearby Rockport draw thousands of visitors each year.

Salem is most noted in history for the Salem witch trials that took place in 1692. It is a commuter suburb of Boston, located along the northern shores of the state. An area rich in maritime heritage, Salem has beautiful architecture and a diverse population. The House of the Seven Gables, made famous by Nathaniel Hawthorne's novel, is located in Salem; and is one of the oldest mansions still standing in New England.

Worcester is the second largest city in Massachusetts, and is one of the fastest growing. It serves as a crossroads between several major New England cities including Providence, Hartford and Boston. The Worcester Art Museum is notable as the city's main attraction. Worcester is also home to the American Antiquarian Society which holds more American material published before the early 1800s than the Library of Congress. Shopping and dining options are available in the downtown area, and new developments are cropping up all over downtown including a Broadway theater project.