Beacon Hill / Charles Street, Boston

Most of the commercial activity in Beacon Hill nowadays centers around its primary street, Charles Street. In the not-so-distant past, this area was renowned for its antique shops, but in recent decades, upscale, independently owned boutiques specializing in gifts, jewelry, and women's clothing have established a presence and occupied the valuable commercial real estate in this affluent neighborhood.

Even if you don't visit any of the shops, you'll be captivated by the design and character of the homes and buildings, as well as the evident dedication of their owners to not only preserve but also showcase them in the best possible light. While many of the street's buildings date back to the 19th century, some received new facades during the 1920s due to widening efforts. The Charles Street Meeting House, designed in 1807, was constructed for a Baptist congregation known for practicing immersion in the nearby river.

For the most celebrated architecture in Beacon Hill, head to Upper Mount Vernon and Chestnut streets, where you'll find Federal-style mansions designed by Charles Bulfinch in the early 1800s. (The charming one-story structures between 50 and 60 Mount Vernon originally served as stables for the elegant residences on the adjacent block at 13, 15, and 17 Chestnut Street.)

Don't forget to take your time exploring Louisburg Square, a picturesque cobblestone street surrounding a central private garden that epitomizes Beacon Hill for many. The neighborhood's delightful Christmas Eve tradition of carolers, bell ringers, and candlelit windows originated here in the 1860s. Additionally, don't forget to wander down Cedar Lane Way and the block-long Acorn Street, the latter of which features cobblestone streets and charming small houses. These dwellings were originally constructed for the coachmen whose employers resided in the mansions on either side.