Boston skyline as seen from the bay; Boston, Massachusetts, United States of America


As a city built on the back of the Revolutionary War, Boston’s the perfect place to instill in kids an appreciation for American history. Luckily, the famously great walking city makes it easy on parents by making its most interesting monuments easy-to-find and accessible for all ages. Great hotels, classic food, and waterside geography only strengthen the argument.


  • The Liberty Hotel

    The Liberty Hotel

    215 Charles St., West End | 617.224.4000

    Originally built as a jail in 1851, the Liberty Hotel is one of Boston’s architectural landmarks, thanks to the fact that the dramatic space was reimagined by a team of designers and architects who collaborated closely with both historians and conservationists. So, despite its transformation in the 2000s, much of the building remains unchanged, which sounds off-putting, but in person, the total effect actually feels strangely magnificent. The center of the hotel is a soaring, 90-foot atrium; light spills in from all the interiors, and the hotel affords stunning city and Charles River views. The wrought-iron work windows are still there; the catwalks are now elegant black iron-railing balconies, and the exercise yard a garden courtyard. In sum: pretty cool, full of luxe amenities, and thrilling to kids.

  • Seaport Hotel

    Seaport Hotel

    One Seaport Ln., Seaport District | 877.732.7678

    An excellent harbor hotel, the Seaport checks a lot of the amenity boxes (including great views), and they also have a cool sustainability mission. They offer complimentary bikes for getting around town, and are pet-friendly, should you be traveling with your fur babies in tow.


  • Carmen


    33 N. Sq., North End | 617.742.6421

    North End is a fun destination for dinner, specifically for Italian food, where your best bet is Carmen Trattoria, which has a lovely, low-key, exposed brick dining room. It’s a good idea to call ahead for a reservation. If you can, save room, and walk to legendary Mike’s Pastry after dinner. The cannolis get all the attention, but the lobster tails are really where it’s at. (Side note: Another popular spot for old-school Italian in Boston is Giacomo’s, which has a location in the North End, as well as one in South End, and a third outside of the city.)

  • Union Oyster House

    Union Oyster House

    41 Union St., Downtown | 617.227.2750

    Housed in a pre-Revolutionary building and open since 1826, Union Oyster House is a little touristy but it makes sense why: It’s iconic Boston and the clam chowder is out of this world. Go at least once—it’s located on the Freedom Trail (see below) so you can stop in along your walk. Bonus: It’s also steps from the famous New England Aquarium (which is right on the water), where littles can check out a multistory tank, a gorgeous penguin sanctuary, and up-close-and-personal seals.

  • Flour Bakery

    Flour Bakery

    1595 Washington St., South End | 617.267.4300

    Best known for their pastries and desserts (owner Joanne Chang famously beat Bobby Flay when he tried to take on her sticky buns in Throwdown), which are more than enough to justify a visit. Less famous but equally good are her lunchtime sandwiches and salads, which can be ordered at the counter and taken to-go. Needless to say, the bread on the sandwiches is game-changing (we’re partial to the focaccia). The original location is in the South End, but you’ll also find outposts in Fort Point, Back Bay, and Cambridge.

  • Toro


    1704 Washington St., South End | 617.536.4300

    While Boston isn’t known for its tapas scene (though there is more than one option in the South End), Toro serves truly good Barcelona-style dishes using locally sourced ingredients. A collaboration between noteworthy Boston Chefs Ken Oringer and Jamie Bissonnette, Toro is open for dinner every night (no reservations), weekday lunches, and Sunday brunch. (They also have a terrific bar, though perhaps that’s for another trip.) Big on sustainability, Toro composts all biodegradable waste, makes their take-out products from renewable/biodegradable materials, and serves organic, biodynamic wines and spirits.


  • Walk the Freedom Trail

    Walk the Freedom Trail

    Boston Common | 617.357.8300

    In 1951, the citizens of Boston preserved and dedicated the historic Freedom Trail, a 2.5-mile walk through the city that passes 16 historically significant sites, starting with Boston Common and ending with the USS Constitution. While the Freedom Trail Foundation offers tours—led by guides in colonial outfits, no less—it’s actually more fun to grab a map and do a self-guided version, as the red line marking the trail’s path throughout the city makes it all but impossible to get lost. Just make sure you don’t miss the Old State House (where the Declaration of Independence was first read to the people of Boston in 1776), Paul Revere’s House, and Old North Church (where Robert Newman famously hung two lanterns in the belfry, alerting Revere that the British were coming over the Charles River).

  • Harvard University

    Harvard University

    Cambridge | 617.495.1000

    Harvard’s quintessentially New England campus is a pretty ideal place for strolling, particularly if you have a high schooler in need of a bit of motivation. While there, check out the collection at the Peabody Museum of Archaeology and Ethnology, which is housed in a quaint old building, and the Harvard Museum of Natural History, which is famous for its gorgeous glass flower replicas: Both are open to the public. When you’ve had your fill of the campus, tool around in Harvard Square—restaurants, shopping, street performers galore—and then take a walk along the Charles River, where you’ll find the boathouses for the sailing and rowing teams of all the local universities.

  • Boston Common

    Boston Common

    Boston’s largest park occupies land that was once a community cow pasture right in the middle of town. It’s a great jumping off point for exploring Beacon Hill or Newbury Street (not to mention that it’s the starting point for the Freedom Trail), but the park itself also justifies its own trip. Take littles to check out the Make Way for Ducklings statue based on Robert McCloskey’s famous children’s book, or for a ride on the unabashedly fun swan boats, which occupy the small lake in Boston Public Garden. In the winter, the frog pond on the northern edge of the Common hosts ice skating. A visit to the original Cheers is also a cheesy-but-worthwhile outing for nostalgic grown-ups.

  • USS Constitution Museum

    USS Constitution Museum

    Charlestown Navy Yard, Building 22, Charlestown | 617.426.1812

    The USS Constitution was commissioned and named by George Washington back in 1797; at the time, it was capital ship (a.k.a. one of the navy’s most important warships). The Constitution gained her nickname, Old Ironsides, during the War of 1812, when the ship defeated more than five British warships; after that victory, she became a darling of the public, who fought hard to save her from scrapping and devoted a museum to the ship’s history. Today the ship, which is technically still fully commissioned by the navy, is actually being restored in dry docks, which are open to the public. When it’s not being restored, its permanent home is in Pier 1 at Charlestown Navy Yard, where it can be boarded and explored by visitors to the museum. If you must see ships in the water before Old Ironsides’ makeover is finished, check out the Boston Tea Party Museum’s ingenious replicas at the seaport.

  • Fenway Park

    Fenway Park

    4 Yawkey Way, Fenway | 877.733.7699

    There is nothing more Boston than walking down Yawkey Way on game day—even if you’re not a baseball fanatic, Fenway can make you feel like it for a few hours. The stadium, which was originally built in 1912 and then reconstructed in 1934, is arguably the most historic in the MLB. Bonus points if you see a home run over the Green Monster while you’re there. If nothing is on the schedule while you’re in town, keep in mind that they still offer tours on non game days, where you can go up in the green monster and peek into the locker rooms.

  • Minute Man National Historic Park

    Minute Man National Historic Park

    174 Liberty St., Concord | 978.369.6993

    Every year on Patriots Day (which is a statewide holiday in Massachusetts), the Lexington Minute Men stage a major re-enactment of the Battle of Lexington on the Lexington green—waking up early to fully experience the drama is somewhat of a rite of passage for kids growing up in Boston. Whether or not you’re there for Patriots Day, Minute Man National Historic Park has a lot on offer—visitors can take tours of historic homes lining the fields, kids can try on historic clothing, and the historic Wayside, which was home to authors like Louisa May Alcott, is open for exploring. Be sure to visit Buckman Tavern, where you can see the Tavern’s original door and the musket bullet that’s still lodged in it.

  • Museum of Science

    Museum of Science

    1 Science Park, West End | 617.723.2500

    You’ll find the city’s epic science museum located on the stretch of Boston that connects Cambridge to the West End. Permanent, family-friendly exhibits include a tropical world butterfly garden; a hands-on Discovery Center (complete with an engineering-focused experiment station); a park simulation set-up (that lets kids move while teaching about motion, mechanics, and math); and an Apollo module that you can climb inside—and then watch the first moon landing from the cockpit seats.

  • Essex


    About 30 miles outside of Boston, the riverside town of Essex is a great, definitively New England, mini-trip, especially in the summer. It’s right near Rockport and Gloucester, complete with a beautiful shoreline and beach, and a cool maritime history. If you go to Essex, you have to eat at the famous Woodman’s—clambakes, lobster rolls, clam chowder, corn on the cob, etc.

Read & Watch

Not many places as diverse as Boston have such a unified, citywide identity—the mashup of rich history with colorful characters and some serious hometown loyalty make it a complex, interesting background in literature like Run or movies like Good Will Hunting. We’ve also included some classic reads to refresh your memory on Revolutionary War history and more.