As one of America’s oldest cities, Boston is easily recognizable by its 19th-century brick row houses, narrow cobbled streets, and traditional gas streetlamps. But the city’s ubiquitous charm and character is just as apparent when viewed from afar. Stepping above it all brings a whole new perspective to the stacks of steely towers and maze of charming streets clustered in to this coastal locus on Massachusetts Bay. Lofty roosts allow you to glimpse the glowing city lights reflected in the rolling Boston Harbor waves, and see glossy skyscrapers—the Prudential Center, Hancock Building—in stark contrast with neighboring centuries-old facades. Deeply rooted history stands firm in the company of a modern face-lift, and with renovations and new developments constantly in the works and a promising future ahead, Boston’s skyline isn’t settling anytime soon. Not surprisingly, some of the most iconic buildings in Boston’s skyline offer equally memorable views.
Standing beyond Boston’s borders, the panoramic view of the distant city and surrounding landscape from this hilltop tower is breathtaking. Find this lookout in Watertown at Mount Auburn Cemetery, a memorial garden founded in 1831 and a serene reprieve from the city bustle. In autumn, the granite tribute to General George Washington provides photo-worthy treetop views of the vibrant New England foliage.
From the 50th floor of Prudential Tower, you’re at the height of it all. See the Charles River dotted with sailboats, the golden glint of the Massachusetts State House, the far-off string of Harbor Islands, and even inside Fenway Park. On nights when there’s a Red Sox game, you can use a coin-operated optical to get a peek at the players running the bases. Scale two more flights for dinner at Top of the Hub, a romantic restaurant with unparalleled sunset views.
Bunker Hill Monument
What was once a wooden pillar just shy of 20 feet is now a 221-foot granite obelisk and a prime observation point. From the top of this historic site commemorating the Battle of Bunker Hill, you can see as far north as Charlestown, the Zakim Bridge, Boston Harbor, and other Freedom Trail landmarks, such as the Old North Church and U.S.S. Constitution. In 1842, the monument had a steam-powered elevator, but now the only way to the top is via 294 winding steps.
Located on the East Boston waterfront, this park juts out over the water to mingle with sailboats and cruise liners. It’s beautifully landscaped, with gazebos, shaded benches, and dramatic views of the skyline across Boston Harbor. Whether it’s gray and drizzling, blisteringly hot, or snowing like it’s the end of the world, locals love how the beauty of this neighborhood jewel withstands the many faces of Boston weather.
If you have to pick a place to get stuck in traffic, the Longfellow Bridge is it. Affectionately nicknamed the “Salt and Pepper” bridge for its shaker-shaped ornamental towers, the road and railway extends over the Charles River to connect Boston with Cambridge. Take a walk across the eastern side to see a beautiful view of the layered city skyline, from the Esplanade tracing the curve of the Charles to the brownstones etched into the slopes of Beacon Hill.