New England Road Trip

Last month, we went on an “always on my bucket list” New England Road Trip. We hit six states in seven days with an 8-month-old. Yes, we kinda came home feeling like we needed a vacation from our vacation, but I blame that on lugging the extra baby items around for a week. He did awesome and we saw so many amazing New England sights. So many people were curious about our itinerary and where we hit, so I thought I’d share our New England Road Trip Itinerary – or Six New England States in Seven Days Road Trip.

Later, I’ll share a post in detail about each day and all the things we saw, but for now, here’s a fly over! We were there for New England fall foliage, but this could make for a great New England winter drive or just day trips in New England exploring each day as its own excursion.

Day 1:

Fly into Boston, MA – rent a car
Afternoon – take a Freedom Trail Tour
- Side note, we did go to the JFK Presidential Library first and then went to do the Freedom Trail. We were mildly impressed with the Library especially since we lost a beautiful outside day with the time in there. We can say we checked it off our list, but I would suggest just going on to the Freedom Trail and taking in as much of Boston as you have time.
- Dinner – Faneuil Hall or Quincy Market
- Stay Boston

Day 2:

Drive to Salem, MA
- Check out the visitor center for a map and any ideas about places to visit for the day
- Walk around and see the sites: The Salem Witch Museum, The House of Seven Gables/Nathaniel Hawthorne Birthplace, Custom House/Derby House, Witch House, Witch Trial Memorial and Burial Ground, Pirate Museum
- Eat: Ugly Mug Cafe or somewhere you can find on Trip Advisor. It was super busy, but all the food looked so good and this place was great for our family.
Drive on to Portland, ME
- Visit lighthouses around Portland and Cape Elizabeth, including Portland’s Head Light. Most of them will show up on Google maps – there are 6 lighthouses around the coast.
If time, go to Freeport, ME for dinner and a stroll
- Home to L.L. Bean Co and a cute downtown
- Dinner at Jamestown Tavern
Drive back to Portland and stay for the night

Day 3:

Get up for sunrise over the Portland Lighthouse – a picturesque and beautiful moment
Drive to North Conway/Conway, NH
- Grab lunch before you take off on the Kancamagus Highway and make sure to get gas
Kancamagus Scenic Byway
- Check in at the SACO Ranger Visitor center – here you can find out what the weather outlook is for the day, see a camera from the top of the mountain and buy your $5 parking permit
- Stop along the way. Many of the main spots will be marked, but there are great spots that others will be pulled over for and they don’t have a sign or when you see something, safely pull off. The 2 most breathtaking views we did catch were not at marked spots on the map.
Take it North
- We drove next to/through Franconia State Park. It was a rainy day, but I plan was to take a gondola ride up to the top of the mountain. And, we considered walking the Flume Gorge, but with the rain, we held off and kept on driving back around to make our loop
- Follow Route 3 to 302 and drive across past Mount Washington, through Crawford Notch, into Bartlett, NH.
Stay in Conway for the evening and find a fun place to eat

Day 4:

Depending on where you are headed, you have the choice to drive 302 and on to Stowe or go back across the Kanc. We took the high road because it was shorter and we were ready to get on with our “food” day.
Drive to Montpelier, VT
- Stop at Cabot Creamery and Farmer’s Store – taste cheese and tour
- Stop at Bragg Farm Sugar House
- Lunch in town if you still have room – we ate at Skinny Pancake and walked around Downtown for a bit
- Drive by the Vermont State House
Drive on to Waterbury
- Visit and tour Ben and Jerry’s
- If time, stop at the Waterbury Center for chocolates, more cheese, coffee, and shopping
Drive on to Stowe
- Check in and get your surroundings
- We took a detour on up to the Trapp Family Lodge and drove around at sunset before heading to dinner. If you get there early enough you can take a tour.
Dinner and stay in Stowe, VT

Day 5:

Start your day kinda early and drive up to Derby Line, VT to the Haskell Free Library and Opera House. It is built on top of the US/ Canada border. Or, if you have your passports, drive across the line and come back. There are cross points closer than Derby Line.
Travel back to Stowe and follow Historic Route 100 south.
- Meander the small towns and pull off as you see something interesting
- We downloaded and used the Gypsy Guide app and it talked to us as we drove
- Also, of note, every town has a small white church, random General Store, and beautiful cemetery. Just know that going into it but you will see some beautiful farmland and scenery that no other state really can provide.
- We got as far as Ludlow before we took the road to get on the Interstate. But, It does keep going further south.
Stay in Hartford, CT

Day 6:

Tour Hartford
- Mark Twain House
- Harriet Beecher Stowe house at the Stowe Center
Drive to Mystic, CT
- Old Mystic Village
- Mystic Seaport
- Mystic Aquarium
Drive to Providence, RI
- Depending on when you arrive, make your way to Pawtucket and see the park and Mill or drive around the old Exchange buildings
Stay in Pawtucket or Providence
- While we never made it there, Federal Hill and Benefit Street make for great tourist spots and dinner destinations

Day 7:

Drive to Newport, RI
- Tour the Newport Mansions – 3 was enough for us, but they have several tour options including one that had a meal. That was the option we choose, not sure that it saved us much.
- The Breakers and Marble House are a must. Rosecliff was the other one we saw.
- Drive out to the Newport Lighthouse and visit Castle Hill Inn
- Drive along Ocean Ave and take in the water. These waves and this time proved to be one of our best experiences.
- Bowen’s Wharf – this is where we spent our final evening. Sunset dinner at the Lobster Company, but there are several restaurants out on the docks.
Stay at the same hotel in Providence/ Pawtucket

Day 8:

Travel back to the airport and fly home. If you take a later in the day flight, make time to toodle around Providence or get back to Boston and catch things you missed.

Our trip was full as you can see from our New England Road Trip Planner, but we loved it and we loved all the places we saw. This was the first time exploring New England for both of us and we already have some trip ideas swarming for future excursions.

Have you traveled to New England? What’s your favorite spot and where do we need to make sure we come back and travel to?

Other posts to come:

Traveling with a baby – what we learned on his first big trip
Boston, MA
Salem, MA
Portland, ME
Driving the Scenic Kancamagus Highway (aka “the Kanc”) and beyond (Franconia National Park and Crawford Notch State Park)
Vermont – Waterbury and Stowe
A side trip to Canada
Historic Vermont Route 100
Highlights in Connecticut and Rhode Island
Newport, Rhode Island
The Ideal New England Road Trip