72 Hours in Boston

An old city full of new tricks.


Boston is the urban heart of New England. With a city population of 617,519 people, it’s nearly four times larger than the next-largest city in the region, Worcester. History runs deep here: it’s been home to the Boston Massacre, the Boston Tea Party, numerous Revolutionary War battles, and the oldest college in the country, Harvard. It’s also a city that doesn’t stand still, a worldwide leader in healthcare, education, and a hotbed for tech startups. Throw in its role as headquarters for the Celtics, Bruins and Red Sox, and you can understand why New England rallies behind Boston, bad drivers and all.

Settled in 1630 by English Puritans, the city is a really a conglomeration of small cities and towns (Charlestown, Roxbury, Dorchester and Hyde Park amongst others) annexed throughout its history, as well as filled-in areas of wetlands and parts of the original Boston Harbor. The modern turning point for Boston was the much-maligned but very impressive Big Dig project, which over the course of 15 years reshaped the city by moving its above-ground major arteries underground. In the process, the city became more accessible and attractive and added greenways and parks. Most of Boston is well connected by the MBTA (Boston’s public transportation system); $20 on a Charlie Card (subway pass) will have you well suited to get around the city. Here’s what to see while you’re there.


Where to Stay
Taking a cue from the boutique hotel revival, The Boxer Hotel, situated in the historic Flatiron building, makes for a cool and comfortable stay; smack dab between the North End and Beacon Hill, it’s within walking distance of most of historic Boston. For a more slightly more glamorous stay, head over to The Liberty Hotel. Based in the old Charles St. Jail, The Liberty overlooks the Charles River, is a short walk to downtown, and even has a bar named Clink where you can have a drink inside the old cells. For great access to Kenmore Square, the site of some of the city’s best food and Fenway Park, and the Green Line, which provides access to much of Boston, book a room at the Hotel Commonwealth. If luxury is your goal, the XV Beacon, right next to historic Beacon Hill, offers amenities like in-town car service by Lexus, personal trainers at its gym, and dog-walking service should you want to bring a four-legged friend.

Where to Eat
While jokes about boring haddock sandwiches may remain, great eats are plentiful in Boston these days. For some the best food in town, make a reservation at Craigie on Main. Chef Tony Maws experiments with his menu frequently, incorporating local ingredients wherever possible. It’s working: Craigie keeps raking in the awards for the Best Burger in Boston and routinely making the list of best restaurants in town. For lunch, hop the Red Line out to Davis Square in Somerville to drop into Dave’s Fresh Pasta; the line can be long, but the first crunchy bite of their roasted lamb panini is worth it. For a killer and creative brunch, take the Green Line to Brookline and visit Ribelle, where Chef Tim Maslow serves up such wonders as truffle egg toast and brisket hash to beat any hangover. For dessert, make your way to Harvard Square to Lizzy’s Homemade Ice Cream (a true hole in the wall) for generous portions and a fantastic waffle cone. For a great burger wander a little farther into Harvard Square to Mr. Bartley’s, which has been around since 1960. If an active dining experience is your idea of a good time, take the Red Line back to Somerville and go to FlatBread Company, where you can get the best pizza in town while bowling a few frames of New England Candle Pin in a converted bowling alley. The North End is well known for its Italian food and desserts. Most tourists make a beeline for Mike’s Pastry to grab a cannoli — locals skip the line at Mike’s and head to Modern Pastry instead. Seafood is a New England staple, and no one’s been serving it longer than the Union Oyster House. Food has been served here since 1826, making it the oldest restaurant in the US; it was frequented by both Daniel Webster and John F. Kennedy. To get a taste of Boston’s thriving microbrew scene, head to the fast-growing Slum Brew’s Assembly Row tasting room in Somerville. Their Belgian-influenced brews aren’t to be missed. Downtown (walkable from South Station) is arguably Boston’s best brewery, Trillium. They only sell their beer to go in growlers, so be sure to grab one there.

What to Do
If you’ve ever seen a New England sports team’s celebration parade, you know about the Duck Boats: amphibious buses spotted throughout Boston in the warm months, cheesy as can be. But they provide a fun and entertaining tour of the city. When it’s time to work off some of the food and libations, grab a Hubway bike and make your way to the River Charles for a ride that winds through town with great views, parks and a cool breeze. For watery adventure, head to Boston Harbor and rent a kayak from Charles River Canoe & Kayak to get out on the river and harbor for a better view of how entwined the city is with the local waterways. Come night, see who’s playing at The Sinclair in Harvard Square. Boston has a rich musical heritage (The Bosstones, Pixies, Dropkick Murphys and Passion Pit all hail from Boston), and its newest music venue brings in great acts with an intimate atmosphere reminiscent of subway stops of yore. For a touch of culture roam to the up-and-coming Seaport neighborhood and check out the ICA for the latest contemporary art and a great view of Boston harbor. To truly immerse yourself in the history of Boston, look for the painted red line along many of the city’s sidewalks: this is the Freedom Trail, a 2.5-mile trail throughout the city with 16 historical stops. Even if you’re not interested in the whole Freedom Trail, head to Charlestown and visit the Bunker Hill Monument, which memorializes one of the first battles between Continental forces and the British army during the Revolutionary War. Climb to the top of the 221-foot tower for one of the best views of Boston.

Venture Out
One of the beauties of Boston is that it’s big enough to have the great parts of a major city, but small enough to easily escape. For a quick day trip, head south to World’s End in Hingham, MA. Trace the coast on the drive down for great views of the Massachusetts Bay; once there, enjoy hiking around this woodland preserve with views of Boston and the sound of the ocean. On the way back, stop into Columbia Point and visit the JFK Presidential Library, designed by architect I.M. Pei. For a perfect afternoon picnic lunch, take a boat out to Fort Warren, a well preserved Civil War-era fort that’s part of the Boston Harbor Island National Historic and State Park. In the warm months, the Cape Flyer train runs each weekend out to beautiful Cape Cod where you can get in a great day at the beach.
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