And just like that it’s already time for our 3rd annual mother daughter Fall foliage trip to New England. There truly is nothing like it especially being a Texas girl at heart who has never had true seasons. The changing leaves at their peak colors take my breath away every year.

This year instead of trying several new towns like last year we decided we wanted to do a quick trip and go back to our all time favorite spots from the past two years.

The best form of transportation for the trip once you are up there is to rent a car. Thankfully everything is fairly close to each other so you can pack a lot in in a short amount of time. It’s typically more cost effective to pick up the car and drop it off at the same location so we fly in and out of Boston Logan International Airport. My only piece of advise for driving is to do it while it’s light out

Day 1- Stowe, VT
Day 2- Woodstock, VT
Day 3- Woodstock, NH
Day 4- Kennebunkport, ME
Day 5- Boston, MA


Day 1: Stowe, VT– Stowe, VT is the furthest drive that we will do so that’s why we are flying in early and heading straight there. Out of all of the places I’ve been in New England, there’s just something about Stowe (even as touristy as it is) that I just love. Mama didn’t get to do this one two years ago so I insisted we go back! It’s pretty expensive to stay right in town but if you’re only there for one night, WORTH IT.

  • Stay- Airbnb right in town (The Lodge at Spruce Peak is another fantastic option)
  • Must do: Drive through Smuggler’s Notch, take a gondola ride up Spruce Peak and hike the trails (beginner level), walk around town and grab coffee at Black Cap, grab apple cider and donuts at Cold Hollow Cider Mill on way out of town

Day 2: Woodstock, VT– Not to be confused with Woodstock, NH (although we head there next), Woodstock, VT is another more popular destination that is 100% worth the hype. The town looks like it’s out of a hallmark movie! Woodstock, VT is about an hour and a half away from both from Stowe, VT and Woodstock, NH.

  • Stay- The Shire Hotel (Woodstock Inn is another fantastic option)
  • Must do: walk around town and grab a picture in front of Middle Covered Bridge, drinks at Au Comptior, dinner at Prince and the Pauper or The Red Rooster, visit Sugarbush Farms for cheese and maple syrup

Day 3: Woodstock, NH– This is our only new destination this year and it is purely because I wanted to stay at Lumen and also do the train dinner. We’ve tried for two years to do this but it books up SO far in advance. We somehow grabbed an early dinner reservation this year so I’m super excited. We plan on using Woodstock really just as a place to stay and then head onto the pretty leaves further north.

  • Stay- Lumen Nature Retreat
  • Must do: grab a reservation for The Cafe Lafayette Dinner Train (books months in advance)
  • Near by: Artist Bluff hiking trail (most stunning view on top), Flume Gorge, Kancamagus Highway (56 mile stretch of THE most beautiful foliage you will see), Bear Notch Rd., Rocky Gorge Scenic Area

Day 4: Kennebunkport, ME– While Stowe and Woodstock are places that I’m sure are beautiful year round, they are special to me for their Fall charm. On the other hand, Kennebunkport is a place I’d love to go year round for a different kind of charm. It’s less about the Fall foliage and more about a cute town on the coast of Maine. I joke that it’s the 30A/Rosemary Beach of the north 🙂

  • Stay- Airbnb (we typically stay in Kennebunk or a surrounding town since it’s cheaper and close by)
  • Must do: walk around town, grab a drink at Batson River Brewing & Distilling (always decorated so cute for fall), get a lobster roll and clam chowder at The Clam Shack
  • Near by: Nubble Lighthouse, Stonewall Kitchen York Company Store (they serve breakfast)