If you’ve known us for a while, you know we have a goal of visiting all 50 states as a family (read our story of Waco, TX). This May, we’re trading Alabama’s warm spring for a whirlwind New England road trip—starting with a rental car at LaGuardia Airport and ending in the salty breeze of Maine’s rugged shoreline.
Departure from HSV – Arrival at LGA
We’ll kick things off with a direct flight from Huntsville to New York’s LaGuardia (Yay Delta has a direct flight into NYC now!), landing us in the heart of the action. But instead of staying in the city that never sleeps, we’re heading to the quieter charm of Connecticut’s coast just outside New Haven for a two-night stay.
2.5 Days in Connecticut
Our first day, Wednesday, is all about Ivy League dreams and cheesy indulgences. We’re heading into New Haven to tour Yale and, more importantly (sorry, Yale), to sample New Haven’s legendary pizza. We’ve heard the hype—now it’s time to taste it.
Thursday is our big city day. We’ll hop on a train and head into New York City for the day—no bags, no car, just energy and excitement. The plan? Squeeze in as much as possible before retreating back to the Connecticut calm.
One Night in Rhode Island
Friday, we’ll jump in the car for a scenic road trip up the Connecticut and Rhode Island coast to Newport, Rhode Island. We’re planning to tour the famous Newport Mansions, dreaming of Gilded Age glamour and oceanfront elegance.
Boston and Baseball
From there, we’re shifting gears to Boston for a two-night stay. On Saturday, we’ll stop in Providence, RI, then continue to Boston for a dose of academia and history. MIT, Harvard, and The Freedom Trail are on our must-see list.
Sunday is classic Boston: we’ll cheer on the Red Sox at Fenway, do some shopping, and soak up the city vibe before taking the ferry to the next leg of our journey.
Monday kicks off three nights on Martha’s Vineyard. We’ll ferry over and spend the next few days biking, beaching, and exploring the island’s iconic charm. It’s the perfect place to reset before our northern push.
Next New Hampshire, Then Vermont
Next, it’s time for a change in scenery—Vermont! We’ll spend two nights soaking in New England’s mountain beauty. On the drive up, we’ll stop in Hanover, NH to visit Dartmouth, then settle into Stowe, Vermont, where hiking trails, biking paths, and a trip to Ben & Jerry’s await.
We’re not done climbing yet—Saturday night is all about the peaks of New Hampshire. We’re staying near the Mt. Washington area, and plan to hike a stretch of the Appalachian Trail, specifically the Webster Cliff Trail off US-302.
Maine Magic
Finally, we’ll end our New England road trip with some coastal magic. We’ll spend three nights along the southern Maine coast, staying beachside in Cape Elizabeth, just outside Portland. We’ll explore the city, savor fresh lobster, and cruise through charming towns like Kennebunkport.
To wrap it all up, our last two nights will be near Bar Harbor, Maine. On our way there, we’ll stop by L.L.Bean in Freeport (because how can we not?) and settle into a quiet lakefront stay. We’re planning to unplug with some hiking, kayaking, and fishing—a peaceful finale to an unforgettable road trip.
Sharing Our Stories
From Ivy League halls to forested trails, from NYC skyscrapers to Atlantic coastlines, this East Coast escape promises a little of everything. Follow us on this New England road trip and catch Sam, Andrew and Paige’s favorite Spaces And Places including the best food, sights, places to stay and experiences to enjoy!
