Back To Boston

Over the past several years, I’ve organized our family trips around themes in my daughters’ school curriculums. While that could sound like a reason for my children to instantly complain or simply run the other way, to the contrary, it has led us enthusiastically to great American cities like Philadelphia and Washington, D.C., as well as Rome, England, and the coast of France.

Most recently, we visited Boston, Massachusetts, as well as Lexington and Concord, to tie in with my daughter Sophie’s upcoming study of the American Revolution. It’s no secret that Boston is filled with fantastic sites that can engage children of all ages in American history. Admittedly, I may be biased as my family is from the Boston area!

With Boston in our hearts these days, I thought it was timely to share some ideas for a fun and educational trip to Beantown for the whole family.

The Freedom Trail

To appreciate the role of Boston in the history of this country, it doesn’t get any better than the Freedom Trail. I’m embarrassed to admit that my daughter initially thought I was taking her on a hike through a “trail in the woods.” Despite the lack of natural wonders, our experience didn’t disappoint. The Freedom Trail is America’s first historic walking tour, which includes 16 official sites along a two and a half mile span of Boston. The trail is identified by red brick or painted brick lines. Visitors can take a self-guided exploration of any or all of the sites or register for a tour led by an 18th century costumed guide.

Our favorites along the Freedom Trail were:

Boston Common

America’s oldest public park is nestled in the middle of Boston, near Back Bay. British troops departed from the Common to face the colonial resistance at Lexington and Concord in April 1775. In addition to its historical interest, it’s also the home of Frog Pond for ice skating in the winter months and a new carousel and an outdoor café in the summer. Adjacent to the Common are the Boston Public Gardens, where you can take a 15-minute ride on the Swan Boat, which has been running since 1877! And you won’t want to miss the “Make Way for Ducklings” statue as you depart.

Old North Church

Tucked in the North End, Old North Church the oldest standing church building in Boston with the tallest steeple. Paul Revere was the neighborhood bell ringer, and this is where lanterns signaled the approach of the British in 1775.

USS Constitution

Set in the Charlestown Navy Yard, the USS Constitution is the oldest commissioned warship afloat in the world. Her nickname is “Old Ironsides” because cannonballs were believed to have bounced off her sides as if she were made of iron. You can board the ship and visit the museum.

Bunker Hill Monument

At 221 feet tall, the Bunker Hill Monument is the site of the first major battle of the American Revolution in June 1775. There is also a museum with dioramas, murals, and artifacts from the battle itself. For the adventurous types, there are 294 steps to climb to the top of the monument for an incredible view over the city.

Faneuil Hall

This was the center of commerce back in late 1700s, and the site where “no taxation without representation” all began. Not to be confused with Faneuil Hall Marketplace, which is bustling with shops and restaurants and is the most visited location in Boston. You’ll want to see them both!

If you are game to venture out to Concord and Lexington, they are both a 1/2 hour car ride from downtown Boston.


The Old North Bridge is a must see in Concord. The “shot heard round the world” that began the Revolutionary War was fired from this spot. Many believe this is the site of the most significant event in American history. Daily ranger programs for children are offered between Memorial Day and the end of October that provide overviews of the historic events in 1775. There’s also a great multimedia presentation at the Minute Man National Park Visitor Center.

Closer to the center of Concord is Orchard House where Louisa May Alcott wrote Little Women. A wonderful period house to tour, even if you haven’t read the book!

For a lunch stop, I highly recommend picking up sandwiches and cheeses from The Concord Cheese Shop on Walden Street. I fell in love and so did the rest of our group.


Lexington Battle Green is the site of the Battle of Lexington, right in the center of this quaint town. Across the street, is the famous Buckman Tavern, where dozens of Minute Men waited for the arrival of the British. There are guided tours of Buckman Tavern if you have time.

Edible Boston

Food is an event in and of itself on our family’s trips, so I included a few local spots that are worth a visit.

The Daily Catch

Open for 40 years in the North End, it has only 20 seats and offers Sicilian-style seafood and pasta all quaintly written on a chalkboard menu.

Union Oyster House

Designated as a national historic landmark, it’s the oldest operating restaurant/tavern in the country. Located along the Freedom Trail, it’s one block from Faneuil Hall, features a kids’ menu, and, if you’re lucky, you can sit in JFK’s favorite booth.

Regina Pizzeria

Established in 1926 and located in the North End, this local favorite is known for its delicious brick oven pizza.

Caffe Vittoria

Stop by for pastries, gelato, coffee, and ice creams, as well as great people watching on a weekend evening

Georgetown Cupcake

Treat your children to fantastic cupcakes and a walk down charming Newbury Street.

After spending almost two decades in her marketing and advertising career, Caroleen H. Mackin turned the page a few years ago to spend more time with her family and succumbed to an obsession with traveling, both near and far. She hopes to share some of the places she has discovered along the way, and some tips for planning your own family trips. She lives on the UES with her husband and daughters, ages 10 and 12.