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A 200-year-old codfish, a statue memorializing a licentious Civil War General, and a 23-carat gold dome crowned with a pine cone – such are the curious eccentricities that distinguish Beacon Hill’s most prestigious address (see Massachusetts State House).

Based in the African Meeting House (the oldest extant black church in the US) and the adjoining Abiel Smith School (the nation’s first publicly funded grammar school for African-American children) – the MAAH offers a look into the daily life of free, pre-Civil War African-Americans. The meeting house was a political and religious center for Boston’s African-American community and it was here that abolitionists such as Frederick Douglass and William Lloyd Garrison delivered anti-slavery addresses in the mid-19th century. The museum has successfully preserved their legacy and that of countless others through education workshops, exhibitions, and special events.

An 1804 Charles Bulfinch design, 55 Mount Vernon is one of the earliest examples of residential architecture on Beacon Hill. Rose Nichols, the house’s principal occupant for 75 years, bequeathed her home to the city as a museum, which would provide a glimpse of late-19th and early 20th-century life on the Hill. A pioneering force for women in the arts and sciences, Nichols gained fame through her authoritative writings on landscape architecture and far-reaching philanthropic projects.

Cobblestone streets, a genteel little gated park, and a hefty dose of Boston Brahmin cachet make this tight block of townhouses the city’s most exclusive patch of real estate. Modeled after the traditional residential squares of London in 1826, the square was named in remembrance of the 1745 Battle of Louisburg in modern-day Quebec.

One of the principal developers of Beacon Hill, Harrison Gray Otis (see Harrison Gray Otis (1765–1848))served in the Massachusetts legislature and gained a reputation for living la dolce vita in this 1796 Bulfinch-designed manse. Like a post-Revolutionary Gatsby, Otis ensured his parties were the social events of the year. After falling into disrepair, the property was acquired in 1916 by the historical preservation society and meticulously restored to its original grandeur.

The Appalachian Trail, or the A.T. as it is known to hiking cognoscenti, is America’s premier walking path. Snaking through 2,168 miles (3,492 km) of pristine eastern wilderness – including 90 miles (145 km) in Massachusetts – the trail is maintained by members of the club. With a scale model of the trail, informative plaques on the walls, maps, guidebooks, and a knowledgeable staff, this is an essential stop for those planning a hike.

Although it extends well beyond the Fenway, Beacon Street finds its true essence in the section between the Massachusetts State House (see Massachusetts State House) and Charles Street. Here it passes such highlights as the Bull and Finch Pub – of Cheers TV fame – and the Boston Athenaeum, one of the oldest independent libraries in the country.

This synagogue testifies to the area’s former vibrancy as Boston’s first predominantly Jewish quarter. The congregation was founded in 1903 by immigrants from Vilna, Lithuania. While services are no longer held here, there are plans to rededicate the synagogue as a Jewish cultural center.

The oldest remaining private residence on Beacon Hill built by African-Americans is a highlight of the Black Heritage Trail. George Middleton, a white revolutionary war veteran, commissioned the house’s construction shortly after the war. Legend has it that Middleton commanded an all-black company dubbed the “Bucks of America.”

George Parkman – once a prominent physician at Harvard Medical School – lived in this house during the mid-19th-century. In 1849, in one of the most sensationalized murder cases in US history, Parkman was killed by a faculty member over a financial dispute. Both the crime and its aftermath were grisly – in the ensuing trial dental records were entered as evidence for the first time.