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Our Family’s Day Trip to Boston

Boston, Massachusetts, is a New England city rich in history, charm, and beauty, making it a perfect destination for a family day trip. Known for its deep ties to the American Revolution, iconic landmarks, and vibrant culture, Boston offers a unique blend of education and fun for visitors of all ages. Since I was little, I have wanted to visit Boston, Massachusetts, and was thrilled to finally adventure on a family day trip to Boston with my family!

During our October New England road trip, we traveled from Portland, Maine, to Boston for an unforgettable adventure filled with sightseeing, history, and exploration. The drive was beautiful, and our family enjoyed “leaf peeping” from Maine to Massachusetts.

With four children (ages 2, 4, 9, and 11) in tow, we were pleasantly surprised at how family-friendly Boston was. It is definitely a busy city but clean and well-organized! From sprawling green spaces and historical monuments to interactive museums and architectural marvels, exploring this famous part of America was such a fun day trip!

Boston is a city where the past and the present merge seamlessly. Walking its historic streets, you can witness echoes of the historic moments that have passed there, like the American Revolution, while modern amenities and family-friendly attractions make it a welcoming destination for travelers. Whether you’re interested in following the Freedom Trail, sampling fresh seafood at Quincy Market, or stepping into history at Faneuil Hall, the city offers countless opportunities for discovery.

I hope sharing our Boston adventure with you will encourage you to visit! This blog will detail our experiences, highlight must-see attractions, and provide tips for visiting Boston with children. Whether you’re planning a quick visit or looking for ideas for day trips from Boston, we hope our story inspires you to explore this incredible city.

Getting to Boston

Family Day trip to Boston — Walking down the brick sidewalks next tot Boston Commons with our Dragons.

We journeyed from Portland, Maine, and found the drive to Boston’s downtown area to be quick, scenic, and stress-free—perfect for a day trip. The drive through New England took approximately two hours, making it manageable even with younger children in tow.

We were visiting Maine in preparation for moving there, so seeing how quickly we could travel to areas like Boston, Salem, New York, and other New England cities was really exciting for us. Especially since we were moving from Oklahoma, which is far from everything.

Boston offers several convenient public transportation options for those who prefer not to drive and would like to take a day trip to Boston. The Amtrak Downeaster provides a train ride from Portland to Boston’s North Station, with comfortable seating and scenic views along the way. This can be a fun experience for kids and eliminates the need to worry about parking.

Once in Boston, the city’s public transportation system, known as the “T,” makes it incredibly easy to get around. We recommend purchasing a CharlieCard or CharlieTicket for unlimited subway and bus rides, especially if you plan to visit multiple sites. The subway is efficient and exciting for children who enjoy trains.

Parking in Boston can be challenging, especially downtown, so we recommend using public transportation whenever possible. If you choose to drive your car, consider parking at a garage near Boston Common or the Back Bay area for easy access to major attractions. Parking is PRICEY in Boston! We spent over $50 on a parking garage near the library.

We also recommend arriving early to maximize your sightseeing time. Boston is a walkable city, so wearing comfortable shoes and packing a baby carrier or stroller for younger children can make exploring much easier. Whether you’re arriving by car, train, or bus, getting to Boston is simple, making it an excellent choice for families looking for day trips in New England.

The Boston Public Library: A Highlight for Art & Book Lovers

Our first stop on our day trip to Boston was one of my favorites! We started in the Boston Public Library in Copley Square. Established in 1848, it is one of the oldest public libraries in the United States and one of the most beautiful. The library’s architecture is breathtaking, featuring grand marble staircases, detailed murals, and expansive reading rooms that feel like stepping into a different era.

Prior to visiting Boston, I had watched so many videos and TikToks about how beautiful this library was! It made me tear up to finally stand underneath the breathtaking artwork and statuesI I had dreamed of visiting this amazing place for so long!

Boston Library Family Day trip to Boston 4 — "The Maidens Welcome Sir Galahad" Abbey Room Murals The Quest and Achievement of the Holy Grail Works by Edwin Austin Abbey, installed 1895-1902

The Abbey Room Murals at the Boston Public Library

The Abbey Room in the Boston Public Library’s McKim Building, originally the Book Delivery Room, now houses a series of murals by American artist Edwin Austin Abbey (1852–1911). Commissioned by architect Charles Follen McKim and sculptor Augustus Saint-Gaudens, Abbey’s murals depict Sir Galahad’s quest for the Holy Grail, inspired by Alfred, Lord Tennyson’s Idylls of the King. Completed between 1895 and 1902, the fifteen-panel sequence follows Galahad’s journey, from receiving his divine mission to achieving spiritual fulfillment as King of Sarras. Galahad’s red robe symbolizes purity, and the murals highlight key moments such as his survival of the Siege Perilous, freeing the Castle of Maidens, and finding the Grail, depicted in raised relief—a technique influenced by Abbey’s contemporary, John Singer Sargent.

Framed by architectural details like a rouge antique marble fireplace, green-flecked levanto marble columns, and a ceiling modeled after the Doge’s Palace in Venice, the murals create a dramatic and immersive atmosphere. While the adjoining Johnson Building now houses the library’s circulating collections, the Abbey Room is used for events and film productions, preserving its status as a cultural and artistic landmark.

Family Day trip to Boston 3 — The Bates Hall Reading Room is incredible!

With its Renaissance Revival style, the historic McKim Building left us all in awe. The Bates Hall reading room, with its arched ceiling and rows of green reading lamps, was a favorite spot for our older kids, who did wonderfully quietly walking through it to soak in the atmosphere.

For families with younger children, the library’s children’s section is engaging and interactive, with cozy reading nooks and hands-on activities. We played in the kid’s section and read a few short picture books with the littlest dragons. The kids thought it was the coolest kid’s section they had ever seen and did not want to leave!

Whether you’re a book lover, history buff, or architecture enthusiast, the Boston Public Library is a must-visit destination.

Boston Common: The Oldest Public Park in America

Our next stop on our day trip to Boston was Boston Common, the oldest public park in America and a highlight for families. Spanning 50 acres, the park offers plenty of room for kids to run and explore. Our two-year-old loved running freely through the open spaces, and our four-year-old was captivated by the beautiful water fountains scattered throughout the park. We found it to be the perfect place to let the kids burn off energy before exploring more structured activities.

Boston Common is not just a green space—it’s a piece of living history. Established in 1634, it has served as a grazing pasture, military training ground, and site for public events throughout the centuries. Today, it remains a central gathering place where visitors can enjoy picnics, playgrounds, and peaceful walks under towering trees.

Famous Statues and Historic Sites

We took time to admire the famous statues throughout the park, including the Soldiers and Sailors Monument, which honors those who served in the Civil War, and the Brewer Fountain, an ornate piece of art that draws the eye and invites visitors to sit and reflect. The Frog Pond was a favorite of younger kids in warmer months and transforming into a skating rink in winter.

Jenni standing in the Historic Central Burying Grounds.

Nearby, we explored the Granary Burying Ground and Central Burying Ground, two historic cemeteries home to notable figures from the Revolutionary War era. These sites sparked discussions with our older children about American history, including The Witch Trials, figures like Paul Revere, John Hancock, and Samuel Adams, whose final resting places are marked here.

The Common is also the starting point for the Freedom Trail. This 2.5-mile route passes through 16 historic landmarks, including the Massachusetts State House, Old North Church, and Faneuil Hall. While we didn’t walk the entire freedom trail during this visit, it’s a fantastic way to combine exercise with education.

Boston Common’s proximity to other attractions like Beacon Hill and the Boston Public Garden makes it an ideal base for exploring the city center on your day trip to Boston. Whether you want to relax in the shade, let kids play, or dive into Revolutionary War history, this park can offer something for everyone.

Dining and Family-Friendly Restaurants

Boston is home to great restaurants offering fresh seafood and New England classics like clam chowder. We recommend checking out family-friendly spots near the Faneuil Hall Marketplace for a quick bite before continuing your adventure. Quincy Market, in particular, has various food options, making it easy to satisfy even the pickiest eaters. With everything from lobster rolls and pizza to smoothies and desserts, it’s a perfect stop to recharge before heading back out to explore.

Remember that Boston’s popularity as a tourist destination means many restaurants can get crowded, especially during peak meal times. As we quickly learned, don’t expect to find a place to sit in fast food restaurants. We grabbed a quick meal on the way out of Boston for our kids to snack on during the ride to Philadelphia. We had to carry it to the parking garage rather than sit down to eat because the entire two-story restaurant building was full of people. If you’re planning to grab something to go, it’s a good idea to scope out a nearby park or open space to enjoy your meal.

For a more relaxed sit-down meal, the North End is famous for its Italian cuisine and pastries. Hanover Street is lined with excellent restaurants and bakeries that make it worth the stop. Whether you’re craving a hearty pasta dish or a sweet cannoli, this area offers plenty of delicious options in a charming atmosphere. Be prepared for a wait at popular spots, but the food and ambiance make it well worth it.

If seafood is on your list, don’t miss the chance to try a lobster roll or a plate of fried clams at one of Boston’s many seafood restaurants. Legal Sea Foods is a well-known chain with locations around the city, offering classic New England flavors in a casual yet polished setting.

Boston’s dining scene truly has something for everyone, whether you’re looking for quick bites or leisurely meals. You can enjoy fantastic food that fits your family’s schedule and tastes with a bit of planning.

Tips for a day trip to Boston with kids

Bring a Stroller or Baby Carrier:

For families with younger children, having a lightweight stroller or baby carrier makes exploring the city much easier and more comfortable. I don’t know what we would do without our Tula Toddler and Ergo baby carriers!

Wear Comfortable Shoes:

You will be walking around the city a lot, and it would be miserable to be in uncomfortable shoes! Comfy, weather-appropriate shoes are highly recommended.

Bring Snacks and Water:

Walking around the city can be tiring for little ones, so keep snacks on hand. Snack bars, fruit gummies, fruit, and refillable water bottles are great options.

Plan Bathroom Breaks:

Many historic sites and museums have restrooms, but it’s good to know where they are in advance. We started in the Boston Public Library and used the restrooms, which we ended up doing again before packing back into the van. Apps like Flush can help you locate nearby restrooms quickly.

Use Public Transportation:

Boston’s subway system (the “T”) is easy to navigate and fun for kids. It also helps avoid traffic and parking challenges. Parking is PRICEY in Boston! We spent over $50 on a parking garage near the library.

Take a Guided Tour:

A guided tour can provide extra insights if you want to learn more about Boston’s history. The Freedom Trail Foundation offers walking tours that are both educational and engaging for kids. People also rave about the Duck Tours! We don’t often hire a tour guide when visiting cities, but many families love using them to learn more about the area they are visiting! Tour Guides are especially entertaining in spooky cities like New Orleans and Salem, where the guides do seasonal haunted tours.

Pack Layers:

The weather can change quickly, especially in the fall, so it’s best to dress in layers. Bring jackets or sweaters even if it’s sunny when you start out.

Exploring More Historic Sites and Neighborhoods

Boston’s rich history in its city center comes alive as you walk through its cobblestone streets. Though we couldn’t fit everything into one day, we noted several must-visit sites for our next trip:

Faneuil Hall and Quincy Market

Perfect for food lovers and shopping enthusiasts, Faneuil Hall and Quincy Market are great for grabbing lunch and people-watching. Street performers and vendors added to the lively atmosphere, making it a fun stop for families. The historical significance of Faneuil Hall, often called the “Cradle of Liberty,” also provides an educational stop to your visit.

Harvard University

Our oldest daughter has been dreaming about attending Harvard University! We would love to visit the campus next time so she can see how amazing it is and support her aspirations. Strolling through Harvard Yard and visiting the Harvard Museum of Natural History would make the trip even more enriching. Cambridge itself also offers charming coffee shops and bookstores worth exploring.

Paul Revere House and Old North Church

Both are essential stops for learning about the American Revolution and the role of British troops in Boston’s history. The Paul Revere House and Old North Church sites allowed us to dive deeper into the stories we had learned during our homeschool lessons. The guided tours available provide fascinating insights and make these sites must-visits for history buffs.

Beacon Hill and Acorn Street

Charming streets that capture Boston’s historic charm and make for great photo opportunities. The cobblestone streets and gas lanterns provided a glimpse into colonial life. Exploring this area felt like stepping back in time, and it’s easy to see why it’s one of the most photographed spots in the city.

Walking the Full Freedom Trail

Our family walked a good portion of the Freedom Trail in Boston Common, but we would love to go back and complete the full walk in the future. The Freedom Trail Foundation has ensured that it is full of Revolutionary War history. The 2.5-mile trail connects 16 historically significant sites, making it a perfect outdoor classroom for homeschooling families.

Salem

Our family initially wanted to visit Boston during the Halloween season. Still, after reading about how massively busy and touristy Salem was during October, we decided to come back to visit when it was not pure chaos. We plan on revisiting Boston during the spring and will make a trip over to explore Salem when it is more peaceful. We’re particularly excited to visit the Salem Witch Museum and take a walking tour to learn more about the infamous 1692 witch trials.

Boston Antique Shops

I would love to visit the antique shops in Boston on an adult-only trip! The city’s vintage shops and hidden gems make it a treasure trove for antique lovers. Exploring areas like Charles Street in Beacon Hill, known for its unique boutiques and antique stores, would be a highlight. If time allows, a stroll down Newbury Street offers a mix of boutique shops, antique stores, and art galleries for parents and older children to enjoy. The blend of modern and historic styles makes it a shopper’s paradise.

Wrapping Up Our Day Trip to Boston

Our family trip to Boston was an unforgettable journey through history. From walking the Freedom Trail and connecting our studies on life during the American Revolution to enjoying the beauty of Boston Common and marveling at the Boston Public Library, we soaked in every moment of our short day trip experience.

As we packed up to head on our next day trip from Boston to New York, Philadelphia, and Washington D.C., we couldn’t help but reflect on all the memories we created—whether it was the artwork in the library, the grand statues in the Boston Common, or simply wandering the cobblestone streets together as a family.

Boston reminded us why we love exploring new places as a family and made us so excited to move to New England!

If you’re considering a trip to this incredible city, we hope our day trip to Boston inspires you to plan your own Boston adventure. Whether you’re a history buff, a nature lover, or a foodie, Boston truly is a perfect blend of big city and historical adventure and has something for everyone. Plan a guided tour or adventure around by yourself in this beautiful New England city!

Until our next adventure, I wish you and your family safe and happy travels!

Jenni Sekine

Mother of Dragons

Hey there! I'm Jenni, a homeschooling, home birthing, and home growing mama of four little dragons, and I run Dragon's Hearth Homestead with my husband, Bryan Sekine. We are all about teaching others about the things we are passionate about. Come learn with us!

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