Boston with a Baby or Toddler

Boston with a baby or Toddler

Filled with pivotal historical sites, beautiful parks and delicious food, Boston is a great city to visit with your baby or toddler.  After recently visiting Boston with our baby (8 months old) and toddler (2 years old), we learned a lot about spending time in Boston with littles.  Further, to make the most of our time in this historical city with our baby and toddler, we compiled insight about visiting Boston with little kids from as many local parents and fellow traveling parents as possible.  We loved exploring Boston with our kids and know our ‘Boston with a Baby or Toddler’ guide below will help you enjoy your time here with your baby and/or toddler too.    

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FYI This post is written based on a trip taken in mid April. We took this trip when our daughter was 2 years old and our son was 8 months old.  For more information on exploring with a baby, please see our Top 10 Baby Travel Tips, How to Hike with a Baby, 5 Top Baby & Toddler Flying Tips and Flying with a Baby posts. 

Boston with a Baby or Toddler: Walk the Freedom Trail

Our first Boston with a baby or toddler recommendation is to walk the Freedom Trail.  This 2.5-mile trail takes you through the city to 16 different historical sites that were vital during the Revolutionary War and other historic events.  Walking this trail is a great way to see a lot of historical landmarks located in Boston relatively quickly.  It’s also a great first day in Boston activity because it will help orient you to the downtown area.  Further, it’s a great Boston with a baby or toddler activity because you will have complete time independence if you tour the trail on your own.  

Be Your Own Guide

Before your visit, download the Freedom Trail Brochure for more information on each spot on this trail.  We printed off this brochure and then took turns reading about each historical site when we got there while walking the trail.  Being your own guide also allows you to spend more or less time at each spot or deviate from the path as desired.  This time flexibility is vital for not getting frustrated when traveling with a baby and/or toddler (see our Top 10 Baby Travel Tips). The Freedom Trail is easy to follow too.  Locate the brick path (sometimes painted on sidewalk) that marks the trail (2 bricks) in the middle of the sidewalk (picture centered above of what bricks look like) and simply follow it.  We had to curb hop maybe once or twice on the trail but otherwise it was extremely stroller friendly.  

We’d recommend budgeting at least 4-8 hours to walk this trail.  We started and ended the trail at the same point (walked the trail back and forth so 5 miles total).  With our littles and all the time we spent at the parks, getting lunch and deviating off the trail, it took us about 7 hours.   The most efficient way to walk the Freedom Trail is to start on one end, walk to the end and then Uber back to the beginning (if need to get back to your car).  We opted to start in the middle of the trail at Faneuil Hall/Quincy Market and walk it both ways as mentioned above.  We first went southwest towards Boston Common and then we retraced our steps back to Faneuil Hall/Quincy Market for lunch.  Then we continued on the trail northeast to the North End/Bunker Hill.

See our 5 Day Boston Itinerary for more information on walking the Freedom Trail including logistics and add on deviations from the trail we took.  

Boston Common and Boston Public Gardens

Visiting these two parks was really one of the main highlights of our time in Boston with a baby and toddler.  We had such a good time at each, we visited both twice. Once while on the Freedom trail and then once again after watching the Boston Marathon.  

Boston Common Park

Boston with a baby or toddler

Boston Common Park is the oldest public park in the US.  It used to be a pasture for sheep and then a training ground during the Revolutionary War.  Now it is a park where many famous people including Martin Luther Jr. and John Paul II have spoken.  It has a lot of open green space and paths.  There’s also a playground at this park and a carousel (not in operation during our visit though) that your littles are sure to enjoy.   

Boston Public Garden

Boston with a baby or toddler

Boston Public Garden (across the street from Boston Common Park) was one our favorite places to explore in Boston. This park is home to statues of the ducks from the Classic Robert McCloskey Make Way for Ducklings book.  Our toddler loved visiting these ducks SO much.  She ‘fed’ and hugged each.  She also had her stuffed cow ‘play’ with them.  The simple statues were such a hit.  If you have not already, be sure to read this book to your toddler prior to visiting Boston.  At Boston Public Garden, there are also the iconic swan boats you can ride in the pond here (although not in operation during our early spring visit).  Both parks are very stroller friendly. 

Marlborough Street and Commonwealth Avenue

Another great place to explore with your baby or toddler in Boston is Marlborough Street and Commonwealth Avenue.  These picturesque streets are located just east of the parks mentioned above (can easily visit on the same day).  They are lined with pretty townhouses and a tree-covered path even runs through the center of Commonwealth Avenue.   The Northeast charm is in full effect on these streets and they are perfect for a leisurely stroll with your baby or toddler.  This street is very stroller friendly. 

Boston with a Baby or Toddler: Greenway Carousel

Another one of our toddler’s favorite Boston spots was the Greenway Carousel.  This carousel is unique in that it is filled with animals native to the area.  It has whales, sea turtles, squirrels, rabbits, foxes and owls.  Our toddler got a real kick out of both the fox and rabbit (and her stuffed cow got to ride too).  Each ride is only a couple dollars.   This Carousel is not far from the Quincy Market on the freedom trail.  

Boston with a baby or toddler

Boston with a Baby or Toddler: Boston Tea Party Museum

Another fun activity in Boston with your baby or toddler is to visit the Boston Tea Party Ships and Museum.  At this museum, you’ll take a 75 minute tour of the Boston Tea Party ships and learn more about the history of the events leading up to and after the Boston Tea Party.  The actors that perform on this tour really make it fun and engaging.  You’ll even get to throw tea overboard into the harbor at one point–certainly a highlight for our toddler! 

In general, we are not big fans of timed tours because they do not allow for much flexibility, and typically we do not recommend taking tours like these with littles.  However, the Boston Tea Party Ships and Museum has tours nearly every 30 minutes and a lot of same day tour availability, allowing you the flexibility to just hop on the next available tour that works for your family.  You’ll have to leave your stroller at the beginning of this tour and they have an attendant that watches over it while you are on the tour. 

Martin’s Park

Boston with a baby or toddler

After the tour, be sure to head over to the free park, Martin’s Park, only about a block away from the Boston Tea Party Museum across the Harbor Walk.  A lot of the equipment here is geared towards kids a bit older. However, the giant pirate ship was a HUGE hit with our toddler.  It is also very cool how this park is right in the hub of the skyscrapers. This park is right next to the Children’s Museum as well (great rainy day activity for your littles). 

Parking Tip: If visiting on a weekend and driving into Boston, park in this uncovered lot for only $5 (you will not find parking cheaper anywhere else in Boston, elsewhere $25-$45, weekends only). 

Boston with a Baby or Toddler: Day Trip to Portsmouth

Portsmouth with a baby

Taking a day trip to Portsmouth is also a great Boston with a baby or toddler activity. Portsmouth is a charming New England port city about an hour north of Boston in New Hamshiphere.  It is actually the 3rd oldest town in the US and is filled with colonial architecture.  Portsmouth’s downtown area has many local boutiques and restaurants.  Market Square, the center of this picturesque downtown, is easy to locate with the tall white steeple North Church as the focal point.  Start your visit to Portsmouth at Market Square as it is a good stepping off point for exploring the rest of the downtown area by foot. We spent the morning walking on brick lined streets and checking out the different local shops.  There is a really cute toy shop, Treehouse Toys, your kids are sure to love. 

Portsmouth Activities

Beyond the downtown area and local shops, this town has many other highlights including parks, museums and waterfront eateries.  We enjoyed lunch at the River House.  Here we were able to dine on the waterfront and have some really delicious seafood (the best of our trip).  They were able to set us up with two high chairs on the seasonally heated patio (a real treat for us traveling from the midwest winter).  

We then headed to waterfront Prescott Park.  This simple park has some walk out piers and some nice green space for your toddler to run around.  Right next to this park is the open air Strawberry Bank Museum.  Although closed during our visit (open May-October), we were able to see some of the preserved historic buildings on the outside of the grounds.  Right across the street from some of the buildings of this museum is a park of swings which was surely the highlight of our visit to Portsmouth for our toddler.  Here everyone including grandpa, grandma and her stuffed animals went for a swing ride.  To round out our visit to Portsmouth, we drove across Memorial Bridge into Maine (we were able to be in 3 states in one day with only an hour of driving).  Portsmouth streets are very stroller friendly. 

Stop at a Local Ice Cream Stand

On your way back to Boston from Portsmouth (right on the way if you set GPS to avoid tolls), be sure to stop at Lagos Ice Cream, a homemade ice cream stand with the BEST ice cream.  If you know us in real life, you know we take our ice cream very seriously and this ice cream was SO good.  There were about 50 homemade flavors to choose from here.  We tried the Funky Panda which was a vanilla based ice cream with caramel, oreos and coconut.  It was delicious and seriously the best ice cream we have had in a long time. And we eat ice cream pretty often so that is saying a lot! Our toddler and baby very much approved of this stop too! Important note–only cash is accepted.

Boston with a Baby or Toddler: Visit Salem

Another great place to visit with your Baby or Toddler when in Boston is Salem.  This city is where the infamous Salem Witch Trials took place in 1692. Salem is steeped in history and New England Charm as well. 

Spend at least a ½ day, if not a full day, exploring this spooky city with your baby and/or toddler.  We spent a full afternoon in Salem with our kids.  

Start your visit in Salem by stopping at the Salem Visitors Center first.  Here, the staff will be able to tune you into any local happenings that day and give you a map. We found Salem easy to navigate ourselves and appreciated being able to explore at our own pace, especially with our baby and toddler.  From the visitors center, head to the Salem Witch Trials Memorial, about a block away north of the visitors center.  This simple memorial has stone benches for each victim of the witch trials.  Reading how each person died (most hung, one pressed to death) really drove home what happened here in the 17th century.  

Essex Street and McIntire District

After visiting the Salem Witch Trials Memorial, head north a couple blocks to stroll down Essex street.  This street is filled with many local and spooky themed stores.  Halloween is really a year round season here.  A toddler is sure to love all the costumes and halloween trinkets at the stores here.   On Essex street you will also be able to stroll past the Elizabeth Montgomery Bewitched Statue and the House of Seven Gables.  This house was made famous in Nathaniel Hawthorn’s book.  You can go inside of this house too but the consensus is that it is not worth the admission cost. 

From the House of Seven Gables, continue west on Essex street.  You’ll walk past the medieval appearing First Church in Salem and the historic Ropes Garden and Mason.  From here, head south on Chambridge street to Chestnut street.  Chestnut street is part of the McIntire District in Salem.  This district is filled with some of the finest pre-twentieth century homes.  Many of Salem’s most important citizens lived in homes here including Nathaniel Hawthrone.  Each house says the year it was originally built and any historical figures who lived there.  Walking up and down this street was our favorite part of our visit to Salem.  You can also head north and explore Federal Street to see more of these picturesque homes.  

Local Ice Cream, Coffee & Parks

Salem with a toddler

After walking around Salem, head back downtown to get coffee and/or ice cream at two local shops, Odd Meter Coffee Co. and Melt Homemade Ice Cream, only one door apart from each other.  The homemade carrot cake ice cream at Melt was the perfect afternoon treat and the shop workers were so kind to our toddler.  After this, we headed to Salem Common Park where there was a nice playground for our toddler to play on and a swing for our baby.  If looking for a less bustling option to end your time in Salem, head to the lighthouse at Winter Island Park.  

Boston with a Baby or Toddler: Visit Lexington/Concord

Another fun short day trip with your baby or toddler when in Boston is to visit Lexington which is where the Revolutionary war started on April 19, 1775.  On this day, Paul Revere rode from Boston to Lexington to warn the town that the British were coming.  The Revolutionary War started here when the Redcoats arrived and clashed with the Minutemen.   

Boston with a baby or toddler

The main historic attraction in Lexington to tour is the Lexington Green.  The Lexington Green is in the center of town and where that first clash between Minutemen and Redcoats happened.  Before walking around the Lexington Green, be sure to stop in the Lexington Visitors Center for a map that explains the different Lexington Green sites.  We were able to walk the green at our own pace this way with our baby and toddler. It was perfect for our family to tour it this way.  Also, at the Lexington Visitors Center, they had some fun colonial hats and kid books on the revolutionary war. Including our visit to the Visitors Center, we spent about an hour here.  Walking the Lexington Green, other than walking up to the Belfry, is stroller friendly.  

Concord is only 5 minutes away from Lexington.  Like Lexington, it is another hub of key historical sites.  Here you can walk across North Bridge, the site of the Shot heard around the world, and watch the 30 minute “The Road to Revolution” presentation at the Minute Man Visitor Center.  If only doing these activities, budget an hour here.  Like visiting Lexington, all of this is on your own time which is perfect for visiting with a baby and toddler. 

Boston with a Baby or Toddler: Visit Harvard

Boston with a baby or toddler

Another great Boston with a baby or toddler activity is to head to Harvard for a free guided tour.  Harvard is the first college founded in the US in 1636.  It’s very interesting to learn about this historic and prestigious college.  The college campus is beautiful as well with many historic brick buildings.  Our toddler loved exploring and running around the campus. She told us she is going to school there one day.  We’ll see.   

Harvard offers free guided tours daily.  Sign up the Friday prior to the tour you want to take online with the link above.  The tours do not book up instantly but be sure to set an alarm to book the tour time you want to take early in the morning on the preceding Friday to ensure you get the time/date you want. 

Boston with a Baby or Toddler: Where to Eat

There are so many great places to get something to eat in Boston.  Below are some of our favorites that we enjoyed with our baby and toddler.  


If looking for a great dinner spot with super tasty food and tons of variety, head to Paramount in Beacon Hill. This restaurant has been open since 1937 and is well liked by locals and visitors.  As a party of 8, we each got something completely different but everyone liked it.  Even Natalie’s Dad who may be the harshest critic. They were very accommodating to our two littles as well.  

Boston Public Market

The Boston Public Market is filled with local vendors and different food options.  Seafood, donuts, bagels, middle eastern food, etc.  This market’s quieter and less bustling atmosphere was a welcome change of pace from Quincy Market (more info below). The causal atmosphere was appreciated with the kids and the market was stroller friendly.  Note there are no high chairs here but we had the kids eat in the stroller/at the table. 

North End for Cannolis

The North End of Boston is the Italian district with all the best Italian restaurants and pastry shops.  Get a Cannoli from both Mike’s Pastry and Modern Pastry.  Many local Bostonians debate which shop makes a better Cannoli.  Natalie votes Modern and Sam votes Mike’s.  Toddler votes both as “really good”.  You’ll have to try Cannolis from both to decide which one you like better! 

Quincy Market

Quincy Market is a good stop for a relatively quick and inexpensive bite to eat. It’s also right off the Freedom Trail.  This market is filled with many different food vendors so everyone can get whatever type of food their heart desires.  We all opted for different specialty pizza slices from Regina Pizza, a Boston original pizzeria.  There was also an electric violinist in the main dining area and many other small specialty shops in the market.   As travelers who like people but not crowds, beware that this market is rather busy though.  Note there are no high chairs here, but we had the kids eat in the stroller/at the table. If you do bring a stroller, enter from the south end if you do not want to carry the stroller up stairs.

If looking for a concrete plan on how to visit all these spots with your baby and/or toddler, see our 5 Day Boston Itinerary

Boston with a Baby or Toddler: Where to Stay

Central Location

If looking to stay centrally to all the places we recommend visiting in Boston with a baby or toddler, we highly recommend staying at the High Rock Home in Lynn, about a 30 minute commute north of Boston.  Lynn is only 20 minutes south of Salem and 1 hour south of Portsmouth.  It is also only about 35 minutes from Lexington and Harvard.  The central location of this Airbnb made it so we were never driving too much on any one day, a big plus when traveling with a baby and toddler where it already feels like it takes 2 hours to just get out the door.  This upper unit of a duplex comfortably housed six adults and two littles for the week.  Also, it had baby gates, in-unit washer/dryer, high chair and a pack n play–all huge selling points when visiting Boston with a baby or toddler.  Read our full review on this place here

Boston Proper

If staying in the city center of Boston, we highly recommend being as close Commonwealth Ave/Marlborough Street, Boston Common and Boston Public Garden as possible.  These areas are so pretty to walk and perfect for easy afternoon strolls with your baby/toddler. 

Boston with a Baby or Toddler: General Tips

  • Most spots are stroller friendly.   Be prepared to curb hop at times but more often not.  Opt for a narrow stroller that easily goes in doorways.  We love the Graco Ready2Grow Double Stroller. Its narrow, allows a carseat to be clicked into it, gives the option for our toddler to ride on the platform in the back and has a huge basket underneath. It’s our go to travel stroller.  And reasonably priced! 
  • We did not baby wear in Boston/the surrounding area but instead used the Tushbaby to carry our baby and/or toddler if they were not having the stroller.  This made carrying both of the kids around the city SO much easier and was the perfect adjunct to our double stroller.  Use ALWAYSHAVEATRIPPLANNED at checkout for a discount.
  • When we needed one of our kids to sleep in the stroller, we would recline them back in the stroller and place the blackout CoziGo over them to give them a dark place to rest.  Use the link provided for a discount.

We hope this guide helps you plan your trip to Boston with a Baby or Toddler.  Anything you’d add to our guide? We’d love to hear your feedback and questions.  Please leave us a comment!

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