Best Boston Day Trip Things to Do for Teenagers

Top photo:  USS Constitution at the Charlestown Navy Yard, (c) Boston Discovery Guide

Boston Discovery Guide is a reader-supported publication.  When you buy through our links, we may earn a commission at no additional cost for you.  Learn more

---

What a great day in Boston you'll have with your group of teens! The city is very compact and perfect for walking, so you can see lots of different things in a short time.

Since you ask about unique attractions, want to have fun, and not spend too much money, let's start with activities for teens).

Since I don't know where you live, I'm going to make the assumptions that 1) you don't live in Massachusetts or New England, and therefore 2) most of the kids in your group haven't been to Boston before, or at least not recently.  Since I also don't know if 1) you have a small budget that might cover food plus 1-2 activities, or if 2) you'd rather not spend any money except for food, I'm also going to focus on free or very inexpensive things, but add in a couple of things that do cost more money if your budget has the wiggle-room to consider them.  If not, no worries - you can have a great day here without spending any money.

A wonderful and unique framework for planning the day in Boston with teens is the Freedom Trail, a group of 16 significant historical sites related to America's quest for liberty.  The trail itself, marked by a red stripe on the sidewalk (paint or red bricks), is 2.5 miles long so you can either walk the whole length, or pick a section.

A cool thing about the Freedom Trail is that it takes you through the heart of the city, through various neighborhoods, through the most historic areas, and past many other interesting sites where you can make small detours - so it's a great way to see Boston as well as for your kids to soak up (without necessarily thinking of the trip as "educational") some interesting bits of information related to historic places and events in America's history.

So here's how I might plan a day with teens in Boston (and I'm speaking as the mom of daughters in their early 20s who I used to do these things with when they were teens), mixing fun with a little exposure to some meaningful things, using the Freedom Trail as a framework, and not spending a ton of money.

I'd start at Boston Common, which is the natural starting point for the Freedom Trail, and also the oldest park in the country, dating to 1634.  If you're arriving by bus, have it let you out at the Visitor Information Center on Tremont Street.  Go inside and pick up a free Freedom Trail map at the counter (you have to ask; also, you'll see lots for sale but the free one is just as good, and in fact, is my favorite Boston city map.)

If you want, you can join a free 90 minute Freedom Trail tour given by a Ranger from the National Park Service.  You can find contact information for arranging a tour on the National Park Service website here.  The Ranger-led tours don't cover all of the sites, but will definitely hit many interesting ones. 

You can easily do a self-guided Freedom Trail tour with the help of the map, which has the advantage of letting you set your own pace.  Another option, which costs money but not too much, is to join one of the tours led by professional guides.  They excel at weaving entertaining stories and facts about colonial Boston history and culture together in a way that holds everyone's attention.  These tours last about 2.5 hours.

If you're going to tour the Freedom Trail without a guide, you may want to first head over to the Public Garden, another park just across Charles Street, about a 5 minute walk.

In addition to being a gorgeous Victorian-era park, the Public Garden is the site where, if you're familiar with the book, Make Way for Ducklings by Robert McCloskey, the fictional Mr. and Mrs. Mallard finally decided to raise their brood of 8. You can take a 15-minute Swan Boat ($4.50 for 15 and under; $4 for 16 and up, although check before you go as this may change) ride around a lagoon containing the island where they built their nest in the story (in real life, the park's resident mallards do that too).  Then walk over to statues of the ducklings near the corner of Charles St and Beacon St.  You'd think that teens would feel too old for this, but they actually love it - partly because it's an ideal spot for taking selfies.

Now, to get back to the Freedom Trail, cross back over Charles St and continue walking up Beacon St. Across from the Massachusetts State House (you can't miss the gold dome), you'll see near the fence a big monument to Robert Gould Shaw and the Fifty-fourth Regiment.  It honors the bravery of the first Black regiment to serve in the Civil War, and their leader, Robert Gould Shaw, who lived in Beacon Hill - they were the subjects of the film, Glory, starring Denzel Washington.

From that point, you can follow the Freedom Trail past several historic sites in the oldest part of Boston. Granary Burial Ground is interesting because a) it's very old, and b) a number of prominent heroes from the American Revolution such as Samuel Adams, Paul Revere, John Hancock, and five Boston Massacre victims are buried here. 

Very soon, you'll pass another graveyard - King's Chapel Burying Ground.  The first generation of Puritan settlers are buried here.  Particularly interesting are the images on the gravestones - lots of skulls and crossbones on the oldest stones, and then a generation or two later when life became a little easier, angels.

Two Freedom Trail Museums are in this area: the Old State House and Old South Meeting House.  They have exhibits related to events like the Boston Tea Party and other events leading up to the Revolutionary War and take about 30-45 minutes to tour.  Both charge modest admission fees.  They're interesting - but if your budget only accommodates one or two expenses, you may want to prioritize the professionally-led Freedom Trail Tour or entrance to Boston's Tea Party Ships and Museum (more about that in a moment).

At this point, you're getting close to another Freedom Trail site, Faneuil Hall.  Admission is free and there are sometimes interesting exhibits - so pop in for a quick look if you feel inclined.  There are also public restrooms here - I think on the 3rd floor?  Next to Faneuil Hall is Faneuil Marketplace - basically a large open-air mall in historic buildings, with one entire building dedicated to food stalls - more about that in a moment.

Only about 1 block away is the Boston Holocaust Memorial, well worth the detour.  All but the youngest teens will probably have studied about the Holocaust in school.  My experience is that teens find this a very moving place - I would highly recommend walking through it (which is free to do).

If you're visiting on a Friday or Saturday, also stop by nearby Haymarket.  It's a continuation of a market that's been in this spot for almost 2 centuries, and kind of cool to walk through.

Now for food, and back to the Food Hall in the Quincy Market building at Faneuil Marketplace.   Probably everyone will want lunch by this point. This is a favorite place to grab a bite in the city.   There must be 30-40 food stalls with every type of food you can imagine, and most choices are reasonably priced (well under $20). It is much, much better that mall food court-type food.  Although there are some tables, but they're always packed.  However, just go outside and you'll find plenty of places to sit either in Faneuil Markeplace itself, or even better, on the Greenway, which is just a few steps to the east of the Marketplace.

I'm not trying to steer you away from Barking Crab - it's a lot of fun, and one of my favorite places in the South Boston Waterfront (about a 10-15 minute walk from Faneuil Hall).  Just be aware that it's going to be pricey - you're paying for the waterfront location, plus seafood is always expensive here because like any other good seafood restaurant in Boston, they buy the fish and shellfish fresh at the docks each morning and throw out any that's left at the end of the night.  That's why what they serve you is always so fresh.  And don't forget, the tax and tip will add another 25%-30% to your check.  Plus, as far as I'm aware, they do not take reservations.  They're relatively small, so the chance of getting seating together for 24 is low.

Another popular food option, about a 10 minute walk from Faneuil Hall down the Greenway, is Chinatown.  Boston has the 3rd largest Chinatown in the country, and it's full of wonderful, affordable restaurants.  Two that would work well for a large group are China Pearl (9 Tyler St) and Gourmet Dumpling House (52 Beach St).  Please do note, however, if you're in Boston on the weekend, both these places will be packed - so Faneuil Marketplace will be a better lunch choice.

For the afternoon, I have two suggestions (you'll probably have time to visit only one):  The Boston Tea Party Ships and Museum (mentioned earlier) or the USS Constitution Freedom Trail site.

The Tea Party Ships and Museum charges an admission fee and offers an immersive 1-hour tour with holographs, live actors, and a chance to relive events (by playing the role of one of the original colonists) leading up to the actual Boston Tea Party, including throwing some tea into the Harbor.  You also get to explore the two authentically restored replica ships dating from the 18th century.  It's a very cool experience - if you can spend money on only one thing, this might be it. 

USS Constitution, unlike other Freedom Trail sites, is not Revolutionary War era - it's the famous "Old Ironsides" ship that fought against the British in the War of 1812.  It's occupied by a Navy crew of about 70, and they give fascinating free tours of the ship and tell you about what life for sailors was like the the frigate was in her fighting prime. Teens love this tour, and adults often say it's their favorite stop on the Freedom Trail.  Everyone in your group who is 18 and older will need to show a federally- or state-issued photo ID or passport before entering.  You can also go on a free tour of a World War II destroyer, the USS Cassin Young.

While you're in Charlestown, you can also visit the Bunker Hill Monument on the Freedom Trail if you're still feeling energetic.  There's also an interesting (free) museum across the street from the monument.

To get to Charlestown, walk over to Long Wharf (walk up the Greenway if you're at the Barking Crab or in Chinatown), and take the MBTA Ferry to the Charlestown Navy Yard - about $3 for one way.  You can either take the ferry or the T (subway) back, or walk back along the Trail.

By this point, you'll probably be ready to relax for the evening. But if you still have energy, follow the Trail through the North End, where you can visit Old North Church, where Paul Revere arranged for lanterns to be hung to signal his famous ride.  The North End is also full of fabulous bakery/coffee shops - great spot for a little more refreshment!

Hope you and your group have a fantastic time in Boston!

Publisher, BostonDiscoveryGuide.com

---

---

Need a Boston Hotel or Apartment?

Use this handy map from Booking.com to find the perfect place to stay.  Just enter your dates to find what's available, see the best rates, and make your reservations.

Booking.com

---