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 NH 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. It’s the kind of beginning—or ending—that turns a trip into a story.

Ultimate Boston City Guide for Families 

Day 4

The drive between Boston and Portland is only 2 hours, but there are so many fun places to stop along the way – Salem, MA the famous witch city – Rockport MA the ultimate little New England Port Town – Portsmouth NH which is home to a living history museum and a state park dedicated to tidal pools.

Stay at the Portland at the Press Hotel, Autograph Collection

Day 5

Portland is currently booming with tourism due to its thriving culinary scene rich with farm-to-table dining and incredible breweries. While I would be happy to just go and eat there is so much to do with boat trips, shopping, and museums. For families interested in STEM check out the Portland Science Center which boasts traveling science exhibits for all ages. It is located right on the wharf so after you can jump on a whale watch or pirate cruise. You can’t take a trip to Maine without a visit to a lighthouse and Portland Head doesn’t disappoint, they even have a dedicated children’s garden. The Portland Museum of Art encourages families to experience art together by allowing everyone under 21 to enter for free and engaging children with exhibits and activities just for them. Also drive down to Old Orchard, Kennebunk, or York which are little beach towns with shops, salt water taffy, and lighthouses galore. Don’t leave Portland without trying Holy Donuts – artisanal donuts made from potato instead of flour.

Stay at the Portland at the Press Hotel, Autograph Collection

Day 6: Portland to Acadia

Head up to Acadia from Portland. This is the longest drive of the trip at 4 hours but you can break it up with a stop in Rockport, ME which is one of my favorite seaside towns, they have incredible food and a thriving art scene, you can hike or picnic in Camden State Park, visit the project puffin visitor center or the Andre the seal statue.

Stay at the Harborside Hotel 

Day 7: Acadia

Acadia National Park is the highlight of any Maine vacation and worth the drive. The park is super family-friendly and is one of the top 10 most visited National Parks in the USA. If you are visiting Acadia National Park with kids there is so much to see, great family hikes and some incredible places to try the amazing local food.

Stay at the  Harborside Hotel

Day 8: Acadia to North Conway

This is the toughest part of the trip a 4 to 5 hour drive from Bar Harbor to North Conway and there really aren’t great places to stop along the way except for maybe the worlds largest telephone.  Before spending the night at the Omni Mt Washington Resort you can drive up to the summit of the states highest peak in the White Mountains.

Stay at the Omni Mt Washington Resort

Day 9: North Conway To Stowe, Vermont

In the morning head to North Conway and enjoy the scenic railroad or outlet shopping before enjoying the scenic Kangamangus Highway (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-theatre-loving heart will always prefer the Von Trapp Family Lodge but Smuggler’s Notch is a destination in itself for families. With activities like horseback riding, kayaking, and hiking you never have to leave the resort. If you want a little time to check out the spa Smuggler’s Notch offers series of camps which range from age related traditional kids club to camps specializing in things like tennis, mountain biking, survival and high adventure. So 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, VT it so 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, and 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!

I love the Kimpton here it is one of my favorite hotels to just sit and relax with a book at, it is just so cozy.

Day 13: Manchester To Boston 

Your last full day is going to be a drive between Manchester back to Boston but there are so many places to stop Deerfield which hosts an annual fair and is home to the butterfly conservatory, the Dr. Seuss Museum in Springfield, the Six Flags New England in Agawam or Old Sturbridge Village a living history museum in Sturbridge or Honey Pot Hill Orchards for a favorite New England fall pastime of apple picking and cider donuts.

Spend one more night in Boston before flying home.

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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, 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.

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