8 Best Sights in Boston, Massachusetts

Often called the city's most photographed passageway, Acorn Street offers its visitors an iconic image of "historic Boston." Short, steep, and narrow, the cobblestone street may be Boston's roughest ride, so leave your car behind. Brick row houses—once the homes of 19th-century artisans and tradespeople—line one side, and on the other, doors lead to Mt. Vernon's hidden gardens. Find American flags, creative door knockers, window boxes, and gas lights aplenty.

You won't see any glaring neon signs, in keeping with the historic character of the area, but Charles Street more than makes up for the general lack of commercial development on Beacon Hill with a plethora of clothing, antiques, and gift boutiques, plus cafés. Once the home of Oliver Wendell Holmes and the publisher James T. Fields (of the famed Bostonian firm of Ticknor and Fields), Charles Street sparkles at dusk from gas-fueled lamps, making it a romantic place for an evening stroll.

Some New Englanders believe that wealth is a burden to be borne with a minimum of display. Happily, the early residents of Beacon Street were not among them. They erected many fine architectural statements, from the magnificent State House to grand patrician mansions. Here are some of the most important buildings of Charles Bulfinch, the ultimate designer of the Federal style in America: dozens of bowfront row houses, the Somerset Club, and the glorious Harrison Gray Otis House.

Less posh than Newbury Street, this broad thoroughfare is the southern commercial spine of the Back Bay, lined with interesting restaurants and shops, and where you'll find the Boston Marathon finish line. Also located here is the Boston Marathon Bombing Memorial, composed of light spires and stone pillars, which pays homage to the Boston Marathon bombing victims at the sites where they were killed on April 15, 2013.

This is the North End's main thoroughfare, along with the smaller and narrower Salem Street. It was named for the ruling dynasty of 18th- and 19th-century England; the label was retained after the Revolution, despite a flurry of patriotic renaming (King Street became State Street, for example). Hanover's business center is thick with restaurants, pastry shops, and cafés, all celebrating the cuisine of the Old Country and most offering valet parking to combat the lack of parking. Hanover is one of Boston's oldest public roads, once the site of the residences of the Rev. Cotton Mather and the colonial-era patriot Dr. Joseph Warren, as well as a small dry-goods store run by Eben D. Jordan—who went on to launch the now defunct Jordan Marsh department stores.

Mt. Vernon Street runs from the flat of the Hill, past Louisburg Square, and all the way up to the Massachusetts State House. Along with Chestnut Street, it has some of Beacon Hill's most distinguished addresses, but Mt. Vernon is the grander of the two, with houses set back farther and rising taller. Henry James once wrote that Mt. Vernon Street was "the only respectable street in America," and he must have known, as he lived with his brother William at No. 131 in the 1860s. James was just one of many literary luminaries who resided here, including Julia Ward Howe, who composed "The Battle Hymn of the Republic" and lived at No. 32, and the poet Robert Frost, who lived at No. 88.

Eight-block-long Newbury Street has been compared to New York's 5th Avenue, and certainly this is the city's poshest shopping area, with branches of Chanel, Tiffany & Co., Valentino, Max Mara, Longchamp, and other top names in fashion. But here the pricey boutiques are more intimate than grand, and people live above the trendy restaurants and ubiquitous hair salons, giving the place a neighborhood feel. Toward the Massachusetts Avenue end, cafés proliferate and the stores get funkier, ending with Newbury Comics and Urban Outfitters.

This ancient and constricted thoroughfare, one of the two main North End streets, cuts through the heart of the neighborhood and runs parallel to and one block west of Hanover. Between Cross and Prince Streets, Salem Street contains numerous restaurants and shops. One of the best is Shake the Tree, one of the North End's trendiest boutiques, selling stylish clothing, gifts, and jewelry. The rest of Salem Street is mostly residential, but makes a nice walk to the Copp's Hill Burying Ground.