6 Best Weekend Trips For Boston Families
Sometimes a full week away just isn’t in the cards—between school schedules, work commitments, and, let’s be honest, the family calendar that somehow fills itself. But a quick weekend escape from Boston? That can be exactly the reset you need.
I’ve noticed so many families around here fall into the same weekend loop: if you live south of the city, you head “down the Cape,” and if you’re up north, it’s straight to the Maine coast or the New Hampshire lakes. Those are beautiful options, of course—but they’re not the only ones. There are so many kid-friendly, memory-making destinations just a short drive away that deserve a spot on your weekend lineup.
Plymouth, MA
48 Minutes from Boston
Plymouth is one of my personal go-to weekend getaways. Since it’s only a 50-minute drive from Boston, most kids around here make at least one pilgrimage (pun intended!) to Plimoth Patuxet (formerly Plimouth Plantation), but this coastal town offers so much more than its Mayflower roots!
This seaside town has perennial New England favorites like whale watching, salt water taffy shops, and all the lobster you can eat! If your family loves the outdoors, Miles Standish State Forest is packed with hiking trails, kayaking spots, biking paths, and peaceful places to fish.
And on weekends, downtown comes alive with live music spilling out of the pubs, making it easy to wander, explore, and stumble into something fun.
And let’s not discount the history—it is the birthplace of America, after all! If you’re looking at a pilgrimage to Plymouth, check out Hotel 1620 Plymouth Harbor—it’s one of my favorites!
Salem, MA
38 Minutes from Boston
Most people hear “Salem” and immediately think of the Witch Trials. While that history is definitely part of the city, there’s so much more for families to experience. I wouldn’t necessarily bring little ones during October (the “witchy season” is magical, but it can get a little intense!), but for the rest of the year, Salem is surprisingly kid-friendly.
If you’re hoping to weave in a little colonial history, the Salem Heritage Trail is a great place to start. It’s Salem’s answer to Boston’s Freedom Trail, a red line guiding you through the city with easy-to-follow maps that explain the significance of each stop and statue along the way.
For creative kids, the Peabody Essex Museum is a must. Their hands-on exhibits invite little artists to make their own one-of-a-kind masterpieces, and the Art & Nature Center is always a hit with its playful, nature-inspired displays. Add in maritime museums, harbor views, and boat tours, and you’ve got a well-rounded day of learning disguised as fun.
If you need a little break from history and culture, head to Salem Willows. The old-fashioned arcade and breezy shoreline are perfect for letting little ones burn off some steam.
If you’re making a weekend of it, the Salem Waterfront Hotel is my top pick for families. It’s right on Pickering Wharf, so you’re steps from the water and surrounded by scenic harbor views that make mornings feel extra magical. It’s the perfect home base for a Salem trip that’s more charming than spooky, making it ideal for little ones!
Portsmouth, NH
1 Hour and 5 Minutes from Boston
Just over the Massachusetts border, Portsmouth, New Hampshire is one of those charming seaside towns that feels tailor-made for family trips. The downtown is walkable and full of shops, restaurants, and museums, but if you really want to delight the kids, hop aboard the old-fashioned trolley for some family-friendly sightseeing!
History comes to life at the Strawbery Banke Museum, a living history village where costumed interpreters, hands-on demonstrations, and historic homes make the past feel wonderfully tangible for little learners. And if you have an aspiring scientist in the family, the tide pools and coastal habitats at Odiorne State Park are an absolute must. Plus, they have the most darling little children’s museum that packs a whole lot of history into a small space, making it far less overwhelming than its counterpart in Boston. Kids can explore, play, and learn without the sensory overload.
And if you’re visiting in the summer and need a place for your kids to burn off even more energy? Water Country is just around the corner. With slides and splash areas for every age, it’s the perfect way to cool down after an exciting day of exploration!
Where to stay: Sheraton Portsmouth Harborside Hotel
Providence, RI
56 Minutes from Boston
Rhode Island’s capital is often overshadowed by its larger neighbor to the north, but its small size is exactly what makes Providence such a hidden gem for families. The Coming to Rhode Island exhibit at the Providence Children’s Museum is well worth the trip on its own. Kids can step into the stories of real people who immigrated to Rhode Island, milking cows, loading ships, and experiencing daily life the way families did generations ago. It’s hands-on learning at its best—engaging, meaningful, and honestly, pretty adorable!
Animal-lovers can spend hours exploring the Roger Williams Park Zoo or the Biomes Marine Biology Center in nearby North Kingstown. Biomes calls itself the most hands-on aquarium in the region, and it absolutely delivers—kids can touch, explore, and get up close to marine life in a way that feels both fun and educational.
And when you’re ready to shift gears, Providence has no shortage of other activities: take a spin on the historic Crescent Park Carousel, glide along the Woonasquatucket River in a Venetian-style gondola, or catch a PawSox game.
Where to stay: Courtyard Providence Downtown
Portland, ME
1 Hour and 47 Minutes from Boston
Thanks to a thriving culinary scene with farm-to-table dining and incredible breweries, Portland is a go-to tourist destination. While I’d be happy to go there just to eat, Portland is packed with family-friendly adventures that make it a perfect quick getaway.
If you have a STEM-loving kiddo, start at the Portland Science Center. It boatsts a series of traveling science exhibits designed for all ages, and the location couldn’t be better—it’s right on the wharf! When you’re done exploring, you can walk straight onto a whale watch, a scenic boat tour, or even a pirate cruise if your little one is in full swashbuckler mode.
And of course, no trip to Maine is complete without a lighthouse stop. Portland Head Light is iconic for a reason. It’s stunning, the views are breathtaking, and they even have a dedicated children’s garden where little explorers can wander, imagine, and play.
For art-loving families, the Portland Museum of Art is wonderfully welcoming. Kids and teens under 21 get in free, and there are interactive exhibits and activities designed specifically with young visitors in mind.
Before you head home, don’t miss The Holy Donut. With artisanal donuts made of potatoes instead of flour, they’re one of those “worth the trip alone” treats—soft, flavorful, and absolutely unforgettable.
Where to Stay: Courtyard by Marriott Portland
Additionally, if you want something a little different than the typical downtown city stay, consider the Sebasco Harbor Resort, a stunning resort set on the rocky midcoast of Maine, about an hour’s drive from Portland. The resort manages to exude that stuck-in-yesteryear feel while offering an array of simple pleasures, from lobster bakes and canoeing to golf and spa treatments. If you’ve ever wanted to stay at Kellerman’s (where are my fellow Dirty Dancing fans?), you’ll love this place.
Mystic, CT
1 Hour and 43 Minutes from Boston
Mystic is just one of those places that feels tailor-made for families. Start at Olde Mistick Village, a sweet little outdoor shopping area with plenty of spots to grab snacks, wander, and soak in that cozy New England atmosphere. But the real standout is Mystic Seaport, a living history museum that brings maritime life to life, letting your little ones explore the everyday lives of sailors and fishermen.
Spread across 17 waterfront acres, Mystic Seaport is designed as a full 19th-century village, complete with 30 period-appropriate buildings from around New England. You can stroll through at your own pace or hop on a horse-drawn carriage, stopping at workshops, stores, and exhibits that show how sailors and fishermen lived and worked.
Kids will be mesmerized by the ships—hundreds of them!—from towering whaling vessels to smaller fishing boats. And if your family loves getting out on the water, you can board a coal-burning steamboat or rent a rowboat for a little adventure of your own.
Just a few minutes away, the Mystic Aquarium is another must-do. Its interactive exhibits are wonderful, but it’s the beluga whales that truly set it apart. You can even set up a private Zoom call to ask their “beluga team” questions while you watch one of their belugas paint a one-of-a-kind painting. They’ll even mail the masterpiece right to your door!
Where to Stay: Howard Johnson by Wyndham Mystic
Honorable Mention: Great Wolf Lodge
1 Hour and 6 Minutes from Boston
When winter feels never-ending and the kids are bouncing off every wall in the house, sometimes you just need an easy escape. It may not be the most original destination, but if you just need to get the kids out of the house, try Great Wolf Lodge.
With the massive indoor water park, themed kids’ activities, MagiQuest adventures, arcades, story times, and cozy family suites, it’s the perfect place to burn off cabin fever and make memories—even when it’s freezing outside.
A weekend away doesn’t have to be complicated—or far. Whether you’re wandering through history in Plymouth, eating your way through Portland, splashing at Great Wolf Lodge, or getting hands-on with maritime life in Mystic, these quick escapes remind us that adventure doesn’t always require a plane ticket. Sometimes, the most meaningful memories come from those simple, close-to-home getaways where you slow down, reconnect, and discover something new.
Whether you’re a Boston local or simply looking to explore, I’d be thrilled to help! I can cater every detail of your trip, giving personalized recommendations based on your kids’ ages, interests, and your family’s travel style. If that sounds like a good fit, schedule a complimentary call and let me “showcase the world” for you and your family so that you can take a break from the busy.
Who is Christina?
Meet Christina Vieira, a Traveler, a Planner, and a Mom. She is also the owner of Showcase the World Travel, a modern travel agency that helps busy Moms take the vacation they deserve without adding “planning it all” to their to-do lists. After all, Mom should get to enjoy their vacation, too!
She specializes in Disney, the Caribbean, and Europe and has helped dozens of families have magical vacations that they will always remember. She loves traveling with her four-year-old daughter, Annabelle. Her favorite destinations include Walt Disney World, Wyoming, and Prague.
