The perfect Fall New England Road Trip 🍂

This is your sign to take a New England road trip this fall! 🍁

I’ve done this twice now and loved every minute of it. 🚘 🍂 ⁠
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In fact, because everything is so close by, in one day we were able to do breakfast in Massachusetts, lunch in New Hampshire, a snack in Maine and dinner in Vermont! But I would suggest giving yourselves about a week to enjoy it all.⁠
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Check out my suggested itinerary below!
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📍 Boston, MA – Start here. Spend 1–2 days exploring the Freedom Trail, Fenway, North End, Little Italy, and more.⁠
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📍Salem, MA – Just a 40-minute drive north. Great for spooky history and witchy charm. Hocus Pocus lovers must stop.⁠
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📍Portsmouth, NH – About 45 minutes from Salem. Walkable downtown, great restaurants, ocean views.⁠
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📍Kittery, ME – Only 10 minutes away! Outlet shopping + coastal beauty. Visit Fort McClary for lighthouse views.⁠
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📍Woodstock, VT – Head inland, about 2.5–3 hours. Gorgeous drives, covered bridges, small-town magic. Next time I’m staying here longer!⁠
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📍Newport, RI – From Woodstock, drive about 3.5 hours south. Mansions, cliff walks, seaside vibes. Fancy and fabulous!⁠
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📍Plymouth, MA – On your way back to Boston, stop here (about 1.5 hrs from Newport). Visit Plymouth Rock & the Mayflower II.⁠
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📍Back to Boston – About an hour’s drive to complete the loop.

The good news? I can help you find the perfect hotels along the way!