7 Day New England Road Trip Itinerary [CT, RI, ME, VT, NH]

During the summer of 2021, Teddy and I took a road trip through New England. We each had a few things we were looking forward to on the trip. For Teddy, it was light houses, waterfalls and to watch a game in Fenway park. For me, I was excited to go to a new National Park, and explore the White Mountains.

We were lucky enough to be able to do all the main sights we wanted to visit along our trip. While we would have loved to have extra time in some areas, we only had so many days, so plan to visit again (hopefully in the fall!)! You can check out what we did on the 7 Day Itinerary Below.

Day 1 – New Haven

  • Travel Connecticut by Plane or Car
  • Visit the park with the 5 Mile Point Lighthouse in New Haven, CT
  • Eat dinner downtown in New Haven and explore the area
  • Check into your hotel for the evening

Day 2 Mystic, Newport, & Providence

  • Drive into downtown Mystic, CT.
  • Visit Sift Bakeshop, Bank Square Books, and walk by the water where you may get to see the drawbridge go up
  • Continue on to to Newport, CT. Drive along Bellevue Avenue and check out the historic mansions
  • Continue on ocean drive for beautiful sea views and find a spot to walk along the Cliff Walk for even more incredible views
  • Stop by Fort Adams State Park before heading back into town for lunch. Wharf Southern Kitchen and Whiskey Bar is a great stop right near the water.
  • Drive through Providence and check out the downtown. Grab some ice cream, coffee, or walk around the shops downtown.
  • Continue your drive to Boston for the night.

If you have an extra day or two, add Cape Cod to your list!

Day 3Boston

  • Start off your morning at Boston Public Gardens. Walk the gardens or take a ride on one of he well known swan boats
  • Walk through the historic street of the Beacon Hill neighborhood
  • Walk the Freedom Trail beginning at Boston Common and ending about 2.5 Miles Later at the Bunker Hill Monument.
  • Stop for lunch at Quincy Market along the trail
  • Head back to your hotel to freshen up (or nap!) before dinner
  • Check out Little Italy for dinner and then head to a show or go to a Red Sox Game
  • Stay overnight in Boston

Day 4 – New Castle, Portsmith, Cape Elizabeth, Kennebunkport, Freeport

  • Drive toward New Castle, New Hampshire
  • Go to the Great Island Common park to get a view of the Portsmith Harbor Lighthouse
  • Drive into Downtown Portsmouth to grab lunch and walk around town. We had a great lunch at the Portsmith Brewery and then coffee at Kaffee Vonsoln
  • Drive to the Nubble Lighthouse in Cape Neddick, Maine and get great views of this lighthouse on an island off the coast.
  • Then drive through the little town of Ogunquit, Maine and then onto Kennebunkport.
  • You have to go to the Clam Shack and get at least 1 lobster roll. They are divine. Explore the downtown shops and take in the beauty of this small sea town.
  • Continue your drive up Maine’s coast to Fort Williams State Park so you can see the Portland Head Light, a historic lighthouse in Cape Elizabeth.
  • Keep driving north and stop in the L.L. Bean store in Freeport, Maine.
  • Continue north toward Bar Harbor. Stay overnight in the area.

Day 5Bar Harbor, Acadia National Park, Mount Washington

  • Catch the early sunrise over the water in Bar Harbor, Maine from The Shore Path. We caught one of the most beautiful sunrises here and there was really nobody around.
  • Head into Acadia National Park. Depending if Acadia is requiring timed entries to Cadillac Mountain, visit the top. of the mountain for the most beautiful views.
  • Grab coffee and breakfast in downtown Bar Harbor at the Coffee Hound before going back into the park.
  • Drive the Park Loop Road and stop at the various pull outs and hiking trails. Pick a few stops you want to make along the way.
  • Drive over toward the Bass Harbor Lighthouse and hike down to the rocks to see it from the shore.
  • Go to Charlotte’s Legendary Lobster Pound for lunch and make sure to get a lobster roll. Enjoy some yard games while you wait for your order to be ready.
  • Drive into New Hampshire and stay overnight at the Glen House in Gorham, NH which sits at the base of Mount Washington. Enjoy dinner in the hotel and views from the porch.

Day 6 Mount Washington, Kancamagus Scenic Byway, The Flume George

  • Wake up early to drive the auto road on Mount Washington. If you get there when it opens, you can go up without must issue of having to pass cars coming down the mountain.
  • Enjoy your time at the top – grab a snack, take in the views, and watch the riders come up on the Cog Railway trains coming up the other side of the mountain
  • Drive a bit to Glen Ellis falls and take the short hike to the base of the waterfalls
  • Drive along the Kankamangus highway. Make sure to stop at the one of a kind waterfall – Sabbaday Falls
  • Visit the Flume Gorge and check out waterfalls, a beautiful forge, and historic covered bridges
  • Drive to Killington, VT and check into the Mountain Meadows Lodge

Day 7 – Killington

  • Go for a hike along the Appalacian Trail that goes through the backyard of the Mountain Meadow Lodge
  • Enjoy breakfast and coffee on the porch before packing up and heading home


  • We started driving after work on the first day rather than taking another day off. If you take a full day, you will have more opportunity to do things during the first day than we did. Teddy and I travel pretty quickly through areas on a road trip. So while we may be content with only a few hours in an area, you may want more. When making your own itinerary, budget in some extra time or eliminate some of the stops we made.
  • We enjoyed New Hampshire and Vermont the most along our trip. While we appreciate the beautiful beaches and shore, mountains are always going to be our preferred scenery
  • When we visited Acadia, it was quite busy and on a one way road, there wasn’t much opportunity to stop or turn around and go back to something so we didn’t get to stop everywhere we wanted. I’d recommend planning your stops in Advance.
  • Teddys favorite stops on the trip were Newport, Bar Harbor, Mystic, the Portland Headlight, and Kennebunkport. I loved Mount Washington and the Glen House hotel at the base of the mountain, the views from Cadillac Mountain, the Flume Gorge, and the Mountain Meadows Lodge and overall experience in Killington.
  • We visited during the summer, so some of these things may not be open during Winter or early Spring because of snowfall and ice.

Related Blogs

Leave a Reply