A walk up Broadway takes one past some of Manhattan’s most celebrated buildings—the Custom House, the Woolworth Building, City Hall, the Flatiron. Along the way there are also countless other fascinating, if less well-known, structures that are worth more than just a casual glance. Here are some favorites:

Bowling Green Offices (5-11 Broadway)

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The Bowling Green Offices is a large building, but it is easy to overlook. The fun here is in the architect’s mixture of ancient building styles. The overall massing of the building is bold and sculptural, almost Egyptian in feel. The crisp and elegant detailing, however, is a veritable encyclopedia of ancient Greek motifs.

8 Thomas Street

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Just a few steps west of Broadway is one of the few surviving buildings in New York that embrace the design principle of the great English Victorian critic John Ruskin. Each floor of this vigorously designed brick and stone structure has its own distinct personality.

463 Broadway

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A contemporary building that addresses multiple design challenges with grace and style. The five-story main block houses retail tenants and tactfully maintains the historic roof line along Broadway. A setback apartment tower rises above. It has a separate entrance around the corner on Mercer Street. Notice how the architect has left the northern quarter of the lot open to provide light for the apartments and a private green space for tenants.

670 Broadway (Brooks Brothers)

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Since its founding in 1818 Brooks Brothers has had five homes in New York, this is the fourth and architecturally the most arresting. The building is muscular and assertive: dark red brick, contrasting stone, distinctive cast iron. There is crisply incised ornament, patterned brickwork, ornamental iron, and some of the most personality-filled capitals in the city.

1407 Broadway

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Despite a misguided recent renovation that stripped the building of its original pink and green trim, 1407 is still an exciting building in the way it manages to address both the Manhattan street grid and Broadway’s diagonal path. The three lower stories are placed parallel to the avenue while the tower above pivots to align with the grid. At 39th Street the base and tower merge.

240 Central Park South

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An apartment house with an inventive and complex plan at the dramatic spot where Broadway meets Central Park. Multiple towers of differing heights are arranged to ensure maximum light and air to the apartments. At street level shops zig-zag diagonally down Broadway. Their roof is a private garden.

Broadway Fashion Building (2315 Broadway)

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A stylish surprise in this staid neighborhood of brick and stone. Steel, glass, and glazed terra cotta rise to a parapet with stylized mountain peaks. The materials may be industrial, but the effect is glamorous – perfect for what was intended as an uptown shopping destination.

NW Corner Building, Columbia University

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A smart and eye-catching anchor for the NW corner of Columbia’s main campus. The building is visually compelling and provides an effective transition from town to gown. The upper section is a complex abstract composition of diagonal trusses and louvers. The lower floors in textured pink marble establish a link to the University’s older buildings.

Church of Intercession

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One of the most beautiful and least visited churches in Manhattan. Set within the Trinity Church Cemetery, this classic Gothic revival composition includes not just the church itself, but an intimate cloister, parish house, vicarage, and tall asymmetrical tower.

United Palace

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Built in 1930 as one of five “Loew’s Wonder Theaters,” the building’s exterior is a little shopworn today, but the interior in all its wacky and eclectic Hollywood glory survives as a home to film, live performance, and church services. 3400 seats and acres of gilt decoration.

Campbell Sport Center

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Columbia University‘s uptown sports complex does not waste time trying to be ingratiating. This edgy industrial composition of solids and voids is criss-crossed by diagonal stairways and seems to be involved in a lively conversation with the neighboring subway viaduct.

William J. Hennessey is the author of the new book Walking Broadway: Thirteen Miles of Architecture and History from Monacelli Press.