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New England Leaf Peeping 7 Night Itinerary

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Last month, we spent 7 nights driving around New England for some leaf peeping. It was an amazing trip and you can read our initial recap here, but we wanted to put together a specific New England leaf peeping 7 night itinerary for anyone that is looking to head north next fall to enjoy colorful leaves and beautiful weather.

New England Leaf Peeping 7 Night Itinerary

New England Leaf Peeping 7 Night Itinerary - Charleston Crafted

Day One: Boston to Newport, RI

  • Fly into Boston in the morning and rent a car.
  • Drive south to Providence, RI, for lunch at East Side Pockets for amazing Greek food. Get some wraps and hummus. You won’t regret it. Then walk around Brown University for a little while.
  • Drive another hour to Newport, RI. Walk to the 40 Steps and walk along the Cliff Walk between the Atlantic Ocean and the mega mansions until you’re too tired to go further.
  • Eat at Midtown Oyster Bar for the best lobster roll you’ll have all week (all downhill from here, lol jk). Don’t forget the mussels frites too…

Our New England Leaf Peeping Recap - Charleston Crafted

Day Two: Newport to Conway, MA

  • Grab breakfast at a bakery and then go check out the Newport Tower and walk around in the park.
  • Drive to the Yankee Candle Village if you’re feeling touristy, or skip it and go straight to Northampton, MA for lunch at Banh Mi Spot and walk on the greenway to stretch your legs.
  • If you’re really into history, drive to Deerfield, MA for a small old town feel and get a tour.
  • We slept in Conway, MA on a farm, which was an amazingly unique place to stay, next to the animals and a river.
  • If you can’t stay there, stay in Shelburne Falls, MA. Walk through the Bridge of flowers at least four times. It’s the most amazing collection of flowers hovering over a river you’ll ever see. Eat dinner at the Blue Rock.

Our New England Leaf Peeping Recap - Charleston Crafted

Day Three: Conway, MA, to Burlington, Vermont

  • Drive from Conway to the Magic Hat Brewery outside of Burlington for a few beers and great grilled cheese. Then drive a mile and check out the World’s Tallest Filing Cabinet. Seriously.
  • Stop by Citizen Cider for a flight of ciders on the way into town.
  • Take a walk along the waterfront to watch the sunset over Lake Champlain.
  • Eat dinner at the Skinny Pancake, a local crepe place that will blow your mind.

Our New England Leaf Peeping Recap - Charleston Crafted

Day Four: Brewery Hopping in Burlington

  • Grab breakfast at August First for fresh baked goods or awesome breakfast sandwiches.
  • Take a walk around the University of Vermont campus if you’re feeling nostalgic for your college days.
  • Check out the local breweries. Most of them you can walk to. Our favorites were Switchback, Zero Gravity, Foam Brewers, Vermont Brewery and Zero Gravity’s second location downtown for dinner.

Our New England Leaf Peeping Recap - Charleston Crafted

Day Five: Burlington to Ogunquit, ME

  • Drive to Ogunquit after breakfast. Start by walking around Perkins Cove, which is a quaint fishing bay and then do the Marginal Way walk toward downtown Ogunquit.
  • Walk out to Ogunquit Beach and dip your toes in the frigid water, then reward yourself with a beer at one of the bars.
  • Walk back along the Marginal Way walk and have dinner at Barnacle Billy’s in Perkins Cove. It’s not fancy, but the lobster roll is on point.

Our New England Leaf Peeping Recap - Charleston Crafted

Day Six: Enjoy Ogunquit

  • Walk down to the one village market to grab some pastries and coffee. Then drive to Mount Agamenticus. They have an amazing trail system there and you can spent anywhere from 1-6 hours hiking depending on how much time you want to spend.
  • Drive 15 minutes to Nubble Lighthouse. Yeah, in Maine you can be on top of a mountain and then standing next to a lighthouse in 15 minutes.
  • Drive to Kennebunkport. If you’re really into touristy things, spend a ton of time here. If not, drive through the main part of town and walk along the cliff walk. When you get back to downtown, grab lobster poutine at Alisson’s Restaurant.
  • Drive back to Ogunquit and have pizza and beers at Cornerstone Brewpub.

Our New England Leaf Peeping Recap - Charleston Crafted

Day Seven: Ogunquit to Boston

  • Drive toward Boston in the morning and stop in Salem. Take a quick walk around the historical part of town and down by the water. Have lunch at Salem Beer Works.
  • Drive to Boston and stay in the Beacon Hill area. We walked down to the water and to Paul Revere’s house and then spent the night eating and drinking at the Bell In Hand Tavern.
  • Say in Boston for one night or as many as you want, but make sure you spend time walking around the public garden and park.

Our New England Leaf Peeping Recap - Charleston Crafted

Here’s a Google Map of all these places for your New England Leaf Peeping 7 Night Itinerary. We did this entire route and can promise you that the driving is worth it for checking out the area. Breaking it up into a week makes the 700 miles not seem bad at all.

Comment below if you complete this itinerary and what you thought of our choices!

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