Cue the Practical Magic music or the Gilmore Girls theme song. Get ready for the best East Coast road trip in the fall, y’all!
Our kids are on a modified year round schedule, so we get this fantastic fall break each year and it is true travel perfection. We’ve done a few different road trips, but this trip from NC to Maine takes the cake.
I’ve shared pieces about it before, but if you want to follow our map or jump on at a certain destination, here are all the details you need!
Enjoy the Mountains or Coast of VA
Heading north from NC, you have many choices, but with our end goal in mind we were choosing between I-95 through Richmond, and the coastal route through Norfolk and Cape Charles. We opted for the coastal route and were not disappointed.
Our kids loved the Chesapeake Bay bridge. It seems to stretch forever with a couple of cool tunnels, which they loved.
The bridge lands you in Cape Charles, which is the cutest little town. We loved taking some time to explore the town, the coast, & avoiding the highway traffic on 95.
Choose your own city adventure – DC or Philly
As your headed north, the clear option is to take a day or more to visit either Washington, DC or Philadelphia, PA. We skipped DC on our bigger road trip, as I knew we wanted more time to really explore that area on it’s own and it’s an easy weekend trip from NC. If you have time to stop for longer, find our 3 day DC with kids guide here.
If, like us, you’re trying to make the most of a full East Coast road trip, I’d definitely recommend spending a full day in Philly. We’d love to go back for more Philadelphia fun (or some games!), but we really had an epic day trip and saw so much in our quick stop.
We stayed in Wilmington, Delaware, which is also a wonderful town we’d love to explore more. BrewHaHa had delightful coffee and it was such an easy commute in & out of Philadelphia for the day.
Make an easy stop to see the Statue of Liberty
Continue north to my actual favorite road side stop. Liberty State Park is less than a mile off of I-95 and is so worth the stop. Get alllll the details in this post, but I can’t say enough how much fun this is on a road trip.
Getting to take the ferry and look out over Manhattan, maybe even especially when you’re not planning to explore the city, is really cool. No lines, great weather, easy parking – it’s a major win for one of the US’s best attractions.
Wander around Mystic, CT
Good gracious. Talk about adorable fall North Eastern towns. Mystic, CT is a dream.
We started the day in Olde Mistick Village, which honestly I’d skip, although the Deviant Craft Coffee & Donuts were a delight. From there we explored the waterfront and stopped at Mystic Knotwork for some of our favorite souvies of the whole trip.
A lifelong Julia Roberts fan, of course I debated making Mystic Pizza the center of this trip, but honestly didn’t even plan to stop. Turns out we needed lunch and it was nearby, so we did!
Explore Boston, MA
Add it to the “we should come back for more time” list, but even just a couple of days in Boston is worth the stop. Clearly this one deserves a whole post, but our kids loved the duck boat tour and the USS Constituion. Beacon Hill Books is also the cutest bookstore I’ve ever been in. Don’t miss the kids section!
We drove through Salem, MA and would’ve loved to stop, but do so at your own risk in October! I head heard that parking would be crazy, but I had no idea. Any other time of year I think it would be an amazing stop, but it wasn’t worth the crazy to us.
Fall in love with Maine
Honestly, that’s all there is to it. Maine is magic. I’ve heard that’s true at other times of year, but it takes no time to see that in the fall.
More details on our entire Maine road trip here. We went through Portland and other towns on the coast, but stayed in Damariscotta for the first part of this trip.
Eventually we made it all the way up to Acadia National Park, which is another absolutely incredible stop. Read that post for a full list of favorites in and around the park, but trust me when I say other parts of Maine also has plenty to offer!
Tips for planning your fall break travel
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Planning transportation is always the first step. If you’re flying instead of road tripping, we love to use Kayak to scout out the best flight deals. It’s easy to check for the cheapest and best timing across airlines this way.
If your journey requires a vehicle, you can also use Kayak to compare rental cars for your group size.
For accommodation, we always prefer looking for a great VRBO when we travel with kids. It makes it so easy to relax in the evenings and, we think, provides a deeper connection to the place you’re calling home for the week.
Need more help planning? Check out these posts sharing more travel planning tips.
