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.

Lowell is a diverse city populated by immigrants from England, Canada, Poland and Ireland in the early 1900's. Lowell was the first American city to be named a National Historic Park. A cluster of buildings in the center of town, connected by the trolley and canal boats comprises Lowell National Historical Park.

Springfield is the third-largest city in Missouri. It is the sports, culture and shopping center for the western Ozarks region of the state. Springfield's location along Interstate 44 makes it a popular stopping point for travelers entering and leaving Missouri.

Sturbridge is a small town southwest of Worcester. Old Sturbridge Village is a living history museum re-creating life in 1830's New England. It contains forty restored structures filled with the antiques and collectibles of its creators, the Wells brothers. Sturbridge has a number of accommodations, as it is in close proximity to the Mellea Winery in West Dudley, the Hyland Orchard & Brewery and the Brimfield Antique Show and Flea Market six miles west of Sturbridge.