The Ultimate New England Road Trip Itinerary With Kids

If you’ve never seen a New England fall, then add this ultimate two-week road trip to your bucket list! Don’t have two weeks? Check out my guide for Fun Family Vacations You Can Drive to (From Boston) or, if you want a bit more room to explore, Family Road Trips in the Northeast United States.

As a travel expert, I’m always learning, whether I’m attending training from suppliers and destinations or planning a mother-daughter trip to Paris, London, or our very own backyard. I grew up just North of Boston and spent all of my summers at lakes in New Hampshire and beaches in Maine, but it wasn’t until I attended a webinar about New England Road Trips that I realized that New England is such a bucket list destination! With so many of my travelers and viewers from all over the country, I knew I had to put together the Ultimate Itinerary to highlight my home.

Since my 2.5-year-old regularly makes the two-hour trip between our home and my parents’ lake house in North Conway, I designed this itinerary with family travel in mind. I kept most of the drives between overnight stops to two hours or less, making it easier on little travelers (and their parents).

That said, no New England itinerary would be complete without Acadia National Park. While it stretches beyond the two-hour mark, it’s a must-visit stop. To make the journey more enjoyable, I’ve included recommended stops at the halfway point so you can break up the drive and still enjoy the adventure.

Day 1-3: Boston: A Playground of Past and Present

Your journey will both begin and end in Boston, a city that serves as an easy gateway to adventure with flights arriving from countless airports. And if you haven’t been before, it’s worth slowing down here for a couple of nights. Imagine tracing history along the cobblestoned Freedom Trail, sparking your kids’ curiosity in one of the many interactive museums, and wrapping up the day under the lights of Fenway Park, cheering on the Red Sox.

Ultimate Boston City Guide for Families 

Day 4

The drive between Boston and Portland is just about two hours, but there are so many fun places to stop along the way! Wind your way to the witchy city of Salem, Massachusetts, wander through Rockport, Massachusetts, a picture-perfect New England port town with shops, views, and that classic coastal charm; or spend time in Portsmouth, New Hampshire, where a living history museum and a nearby state park dedicated to tidal pools let little imaginations make big memories.

Stay at the Portland at the Press Hotel, Autograph Collection

Day 5

Portland’s tourism scene is thriving, thanks in large part to its incredible farm-to-table restaurants and standout breweries. Honestly, I could plan a whole trip just around eating! But there’s so much more to experience, especially for families. STEM-loving kids will enjoy the Portland Science Center, which features rotating, hands-on exhibits for all ages and sits right on the wharf, making it easy to jump on a whale watch or walk the plank to a pirate cruise after your visit.

Of course, no trip to Maine is complete without a lighthouse stop, and Portland Head Light never disappoints; they even have a dedicated children’s garden! The Portland Museum of Art is another family favorite, inviting everyone under 21 to explore for free, complete with exhibits and activities designed just for kids. If you have extra time, take a short drive to Old Orchard Beach, Kennebunk, or York, classic coastal towns filled with charming shops, saltwater taffy, sandy beaches, and lighthouses galore. And whatever you do, don’t leave Portland without stopping at Holy Donuts for their famous potato-based, artisan donuts—they’re a must-try.

Stay at the Portland at the Press Hotel, Autograph Collection

Day 6: Portland to Acadia

From Portland, continue north to Acadia National Park—the longest drive of the trip at about four hours, but you can easily break it up with a stop in Rockport, Maine. One of my favorite seaside towns, Rockport is known for its fantastic food and thriving art scene. Nearby Camden Hills State Park is perfect for a short hike or a picnic, and the Project Puffin Center or Acadia’s beloved Andre the Seal statue are excellent stops for animal-lovers.

Stay at the Harborside Hotel 

Day 7: Acadia

Acadia National Park is the highlight of any Maine vacation, and it’s well worth the drive! The park is super family-friendly, and it’s even one of the top 10 most visited National Parks in the USA! Not only is Acadia gorgeous, but there’s also plenty to see and do, from family hikes to fresh local cuisine.

Stay at the  Harborside Hotel

Day 8: Acadia to North Conway

With a 4-5 hour drive from Bar Harbor to North Conway, this is the toughest part of the trip. If you’re feeling restless, stop by the world’s largest telephone in Woodstock, Maine or seek the summit of the state’s highest peak in the White Mountains before spending the night at the Omni Mt. Washington Resort.

Stay at the Omni Mt. Washington Resort

Day 9: North Conway To Stowe, Vermont

In the morning, head to North Conway and enjoy the railroad or a bit of outlet shopping before cruising down the scenic Kangamangus Highway (fun fact: both my parents and my brother and sister-in-law got engaged here!) on your way to Stowe, Vermont.

Day 10: Stowe, VT

There are so many great hotel options in Stowe. My musical-theater-loving heart will always prefer the Von Trapp Family Lodge, but Smuggler’s Notch is a destination in itself that’s perfect for families. With activities like horseback riding, kayaking, and hiking, you could spend an entire vacation (or two!) without ever leaving the resort. If you want a little time to check out the spa, Smuggler’s Notch offers plenty of kids’ programs, from age-based kids clubs to camps specializing in things like tennis, mountain biking, survival, and high adventure. Go enjoy the spa or local brewery and get a little break from all that family time!

Day 11: Stowe, VT TO Manchester, VT

One of my favorite things to do is stop in Waterbury, Vermont on the way to Manchester. There, you’ll find the Cold Hollow Cider Mill, where you can see cider being made, tour the Ben and Jerry’s Factory, or sample some cheese at the Cabot Creamery store.

Stay at the Kimpton Taconic Hotel

Day 12: Manchester, VT

I love the town of Manchester, Vermont—is is so quintessentially New England, with a charming book store in the center of town and a ton of history. You can visit Hildene, the home of Robert Todd Lincoln, son of Abraham, and Ye Olde Tavern, a restaurant in a converted inn built circa 1790. They have a fly fishing museum and school, but if you or your kiddos are a little more adventurous, there’s an adventure park in nearby Bromley with an alpine slide, aerial ropes course, rock wall, mini-golf—what a fun way to end a trip!

Stay at the Kimpton—it’s one of my favorite hotels to just sit and relax with a book at (it’s just so cozy)!

Day 13: Manchester To Boston 

Your last full day is a drive from Manchester to Boston, but there are still plenty of places to stop! Check out Deerfield’s annual fair and the town’s breathtaking butterfly conservatory, the Dr. Seuss Museum in Springfield, the Six Flags New England in Agawam, Old Sturbridge Village, a living history museum in Sturbridge, or Honey Pot Hill Orchards for apple-picking and cider donuts.

Spend one more night in Boston before flying home.

Of course, New England is huge, and there are plenty of other places that easily could’ve made this list. Whether you’re hoping to take a break from the busy in Boston or another vacation destination, book a FREE vacation consultation with me so we can work to make it happen!

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, Annabelle. Her favorite destinations include Walt Disney World, Wyoming, and Prague.