Boston, Massachusetts, is one of the greatest cities in the world for history lovers. The so-called Hub of the Universe is nearly 400 years old and the birthplace of the American Revolution. With its quaint architecture, brick and cobblestone paths, and beautiful old parks, it blankets visitors in an earlier time. It also boasts world-class museums, and it’s the best sports city in America. While there’s always something for a curious traveller to do, the best time to visit Boston is in the fall, thanks to the spectacular foliage, which usually peaks in mid-October.
There is no one right place to stay, but rather many excellent options, depending on your own tastes and interests. Boston has several unique neighborhoods. Here I’ve highlighted the six that I think are the most intriguing. It’s easy to go from one to another. Like most historic cities, Boston is compact, and best explored on foot. Just be sure to wear comfortable shoes, and skip the rental car. Boston is a nightmare for uninitiated drivers, and not much better for locals.
I write from experience. I was born in Salem, the Bay State’s other most historic city, and more recently lived in Weston, a small town 12 miles from Boston. I spent many of my childhood Independence Days picnicking with my family on the Charles River Esplanade, listening to the Boston Pops concert at the Hatch Shell. As an adult, I worked at the Hancock Tower in Back Bay, near where a statue of my great-great-great-great-great-great-great-grandfather Gen. John Glover stands on Commonwealth Ave. Of course, I’ve cheered on the Red Sox at Fenway Park. And I’ve dined, partied, and stayed in some of the city’s best hotels.
I hope this guidance from a native New Englander helps you find the right home base for your visit to Boston.
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Historic elegance and modern bustle meet at Boston’s Back Bay. The neighborhood’s centerpiece is Copley Square, a quaint urban space named for the 18th- and 19th-century Anglo-American painter John Singleton Copley. Here the modern John Hancock Tower, the tallest building in New England, provides an unexpected backdrop to the Romanesque Revival Trinity Church, a National Historic Landmark named one of the 10 most important buildings in America by the American Institute of Architects. You can take a tour of the Church and marvel up close at its ornate architecture, extensive murals, and sparkling stained-glass windows.
The Italian Renaissance Boston Public Library is another architectural gem. You can take a free tour and see its art collection, attend its frequent author talks and book readings, or simply find a great book to read.
The Charles River Esplanade is a waterfront park where you can stroll by day and often hear concerts at night.
And if you like luxury shopping, Back Bay is the place for you. Boston’s iconic shopping avenue, Newbury Street, hosts mostly high-end chain shops these days, but some local boutiques remain. If you prefer a luxury mall, Copley Place boasts brands from Burberry to Versace.
Where to Stay in Back Bay
My favorite hotel in Back Bay, and indeed in Boston, is the Fairmont Copley Plaza. It opened in 1912, and its ornate marble lobby evokes the grandeur of the gilded age. It has a fabulous central location, a clientele including Presidents, and the Oak Long Bar and Kitchen, one of the best hotel bars in America.
With its red-brick row houses and mansions, gas lanterns, and steep, cobblestone streets, Beacon Hill gives a 19th-century vibe, though the old neighborhood was actually first settled in the 1600s. Its name comes from the beacon that warned the people of Boston of any impending invasions.
Today its focal point is the gold-domed Federal-style capitol building, the Massachusetts State House. The oldest building on Beacon Hill houses portraits, statues, and the “Sacred Cod”, a 4’11 carved wooden Atlantic codfish that hangs from the ceiling above the House chamber. Public tours are available.
Founded in 1634, Boston Common is the oldest city park in the U.S. A common was a practical public space used for everything from grazing livestock to hanging criminals. Boston’s colonial minutemen mustered for the Revolutionary War on the Common. Then in the 19th century, Bostonians banned grazing, planted trees, built fountains, and put up statues, and the Common became an urban park.
Adjacent to Boston Common is the Public Garden. It was established in 1837 as a more ornamental space than the Common. It is the oldest public botanical garden in America. One of the most iconic things to do in Boston is to ride on the Swan Boats in the Public Garden’s lagoon. The Public Garden is home to a Survivor sapling, which was cultivated from the Callery pear Survivor Tree found at New York City’s Ground Zero and given as a gift to the city of Boston in the wake of the Marathon bombing in 2013.
Where to Stay on Beacon Hill
The most unique hotel on Beacon Hill, and one of the most unique in America, is The Liberty. It used to be the Charles Street Jail. Original brick and bars remain prominent at the Marriott luxury property. The cells are now guest rooms, and the former gymnasium is the lobby. Dining venues have names like Alibi and CLINK.
Downtown Boston is a bustling neighborhood with several historic landmarks.
Built in 1729, the Old South Meeting House was a Congregationalist church and the staging point for the Boston Tea Party. Today it is a museum open for tours.
Completed in 1742, Faneuil Hall is one of the most significant remaining buildings in American history. It was the site of speeches by Samuel Adams, James Otis, and other Patriots supporting independence from Great Britain. Here Daniel Webster eulogized Thomas Jefferson and John Adams, who both died on July 4, 1826, 50 years after the Declaration of Independence. It is maintained by the National Park Service and open to the public.
In 1826, Quincy Market opened in the Faneuil Hall area. It is a shopping and dining mecca, where you can score free samples of clam chowder.
Where to Stay in Downtown Boston
An intriguing place to stay in Downtown Boston is The Godfrey, where two historic buildings merged into a modern hotel with a great central location.
The North End is Boston’s Italian section. The aromas of basil and garlic waft through the streets, along with the sounds of the Italian language. Dozens of Italian restaurants and bakeries line the narrow streets of the city’s oldest neighborhood.
The North End is also home to a few of Boston’s most important historic sights. On the night of April 18, 1775, two lanterns glowed from the steeple of the Old North Church, the signal that the British were coming by sea, rather than by land. It houses an active Episcopal congregation today, but public tours are available.
On that night, Paul Revere rode through the streets, warning the colonists, “The British are coming!” The House where he lived is now a museum open for tours.
Where to Stay in the North End
The nautical-themed Boston Yacht Haven Inn & Marina is a fine place to stay in the North End and offers spectacular views of the city and the water.
The name of this neighborhood is a little confusing, as much of Boston is on the waterfront. But the Waterfront neighborhood is a specific slice along the Harbor and the Fort Point Channel.
One of the most storied moments in Boston’s long history is the Tea Party. The Boston Tea Party Ships & Museum teaches the story of this event. Visitors can board a ship, and young Patriots can even toss “tea chests” into the Harbor.
Nearby the New England Aquarium features fascinating creatures like Piranhas and leafy sea dragons and a simulated Caribbean coral reef.
Where to Stay on the Boston Waterfront
My favorite hotel on the Waterfront is the Boston Harbor Hotel, which offers spectacular views and easy access to the Boston HarborWalk, a beautiful public trail right along the water.
Boston also boasts the oldest baseball stadium in America. A game at Fenway Park is an experience in cultural immersion; be sure sing along with “Sweet Caroline” during the eighth inning. There are also tours of the park year-round. It’s close to Kenmore Square, and the area is often called Fenway-Kenmore.
Nearby is the world-class Museum of Fine Arts, which holds one of the largest collections of the Impressionist works of Claude Monet outside France. The Boston Symphony Orchestra plays in the neighborhood as well.
Where to Stay in Fenway-Kenmore
My favorite lodging spot in Kenmore Square is the Hotel Commonwealth, steps away from Fenway Park, with rooms looking out to the stadium.
Feeling overwhelmed by all there is to do in Boston and not sure where to begin? No worries. The Freedom Trail is a 2.5-mile walking trail that connects 16 historic sites, including many mentioned in this post. It starts at Boston Common, winds through Downtown and the North End, and then crosses a bridge to Charlestown and ends at the Bunker Hill Monument. You may sign up for a tour, or follow the trail yourself, starting and stopping wherever you choose. It’s a fine way to imagine yourself at the beginning of the American Revolution.