Everyone in our family looks forward to road trips, the planning, packing snacks, audiobooks in the car, and discovering little moments together along the way. Our weekend getaway to Boston and Salem was filled with history, cozy bookstores, delicious food, and plenty of family memories, without completely breaking the budget.
If you’re planning a family-friendly New England getaway, here are some of our favorite stops!
Starting the Trip with Pie

The perfect beginning to any road trip? Dessert first. Our first stop was the beloved Flour Bakery + Cafe where my husband ordered a slice of his favorite, apple pie, that immediately set the tone for the weekend: cozy, comforting, and very New England. Some of the best travel memories are the uncomplicated ones, like sharing bites of pie while planning the day ahead.
Exploring Historic Boston

One of our favorite things about Boston is how walkable it is. We spent hours wandering through the city and soaking in the history. We explored Faneuil Hall Marketplace, where little shops tempted us around every corner. We also walked the famous Freedom Trail, which turned history into an adventure for the whole family. The kids especially loved visiting the beautiful Boston Public Garden and seeing the famous Make Way for Ducklings statues, inspired by the classic children’s book by Robert McCloskey.
Museums We Loved

Boston is packed with incredible museums, and we tried to balance educational stops with plenty of fun. We visited the stunning Museum of Fine Arts and the unforgettable Isabella Stewart Gardner Museum, which felt almost like stepping into another world. We also stopped by the moving New England Holocaust Memorial, an important and meaningful experience for our family. And of course, no literary-loving family could skip the gorgeous Boston Public Library. The architecture alone was worth the visit.
Literary New England Adventures

One of the highlights of the trip was exploring the literary history surrounding Boston and Concord. We spent time at Walden Pond State Reservation, where Henry David Thoreau famously lived and wrote. We also visited Minute Man National Historical Park and toured Orchard House, the beloved home of Louisa May Alcott. Seeing the home where Little Women was written felt especially magical! Nearby, we also saw the home of Ralph Waldo Emerson and visited Sleepy Hollow Cemetery, where many famous American writers are buried. For our book-loving family, this part of the trip felt like walking through the pages of American literature.
A Day Trip to Salem

Our drive to Salem added a fun and spooky touch to the weekend. We toured The Witch House and visited the famous Salem Witch Museum to learn about the tragic history of the Salem witch trials. We also explored the beautiful Peabody Essex Museum and toured The House of the Seven Gables, which brought classic literature and history together in such a memorable way. Salem had such a unique atmosphere, historic, artistic, and just a little mysterious…
The Food Highlights

No family trip is complete without talking about the food. We warmed up with bowls of classic New England clam chowder and enjoyed an amazing lobster roll at James Hook & Co..

We also tried:

- Boston cream pie (Omni Parker House)
- A delicious cannoli from Modern Pastry
- A white chocolate mouse and cookie from L.A. Burdick Chocolates
- Fancy avocado toast and soup at Tatte Bakery & Cafe
- Pizza, pasta, and charcuterie in the beautiful Back Bay neighborhood

One thing I love about family road trips is that meals become part of the memories too!

Cozy Shops & Hidden Gems

Some of our favorite moments came from wandering into unexpected little places. We found the sweetest independent bookstore at Beacon Hill Books & Cafe and browsed whimsical treasures at The Fairy Shop. These little stops always end up being the places we talk about long after the trip ends.
Tea Time & Revolutionary History

One especially memorable experience was taking part in the tour and tea experience at Boston Tea Party Ships & Museum. It was interactive, educational, and surprisingly fun for both kids and adults. Drinking tea while learning about Revolutionary history made the experience feel immersive and memorable.
Why We Love Economical Family Road Trips
What I love most about trips like this is that they don’t have to be extravagant to feel meaningful.
Many of our favorite memories were completely free:
- Walking historic streets
- Exploring parks
- Visiting bookstores
- Sitting together over pastries
- Browsing museums
- Talking during long drives
Travel doesn’t have to be excessive to be rich in memories. Our time in Boston and Salem gave us the perfect blend of history, literature, delicious food, and family connection, and we came home already dreaming about our next weekend adventure!








