Where To Go For Boston Skyline Views

No matter which side of the Charles River or Boston Harbor you're on, these five spots are guaranteed to give you the best views of the Boston skyline.

As one of America's oldest cities, Boston is easily recognizable by its 19th-century brick row houses, narrow cobbled streets, and traditional gas street lamps. But the city's ubiquitous charm and character are 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 into this coastal city on Massachusetts Bay. Lofty roosts allow you to glimpse the glowing city lights reflected in the rolling Boston Harbor waves and see glossy skyscrapers like the Prudential Center and 200 Clarendon Street (formerly John Hancock Tower) 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, the Boston skyline isn't settling anytime soon.

Not surprisingly, some of the most iconic buildings in the Boston skyline offer equally memorable views. Here's a look at some of our favorite viewing spots. Visit all five on your next trip, whether you're in town for a few days on a weekend getaway (in that case, these hotels are definitely worth a gander) or just passing through.

Related: These Are the 30 Best Things to See and Do in Boston

Washington Tower

Standing beyond the city's borders in Watertown, the panoramic view of the distant Boston skyline and surrounding landscape from Washington Tower is breathtaking. You'll find this underrated lookout at Mount Auburn Cemetery, a memorial garden founded in 1831 and a serene reprieve from the hustle and bustle. In autumn, the granite tribute to General George Washington provides photo-worthy treetop views of the vibrant New England foliage as well.

Skywalk Observatory

From the 50th floor of the Boston skyline's prominent Prudential Center, you're at the height of it all. You'll be able to 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 by visiting the Skywalk Observatory. On nights when there's a Red Sox game, you can use a coin-operated optical viewing machine to get a peek at the players running the bases.

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 for viewing the Boston skyline. From the top of this historic Bunker Hill Monument, which commemorates the Battle of Bunker Hill, you can see as far north as Charlestown, the Zakim Bridge, Boston Harbor, and several other landmarks along the city's famous Freedom Trail, such as the Old North Church and U.S.S. Constitution. In 1842, the monument had a steam-powered elevator as well, but now the only way to the top is by climbing its 294 winding steps. Note that for safety reasons, just 20 people are allowed up at a time, so plan your visit accordingly.

Piers Park

Located on the East Boston waterfront, Piers 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 Boston skyline across the harbor. Whether it's gray and drizzling, blisteringly hot, or snowing like it's the end of the world, locals and visitors alike love how the beauty of this neighborhood jewel withstands the many faces of Boston's infamous, ever-changing weather.

Longfellow Bridge

If you have to pick a place to get stuck in traffic, the Longfellow Bridge has to be 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 nearby Cambridge. Take a walk across the eastern side to see a beautiful view of the layered Boston skyline, from the Esplanade tracing the curve of the Charles to the brownstones etched into the slopes of Beacon Hill.

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