I found ten days to be a great amount of time to get a nice overview of New England. You won’t be able to do everything, but you’ll see a lot of highlights and learn which parts of this area interest you. This knowledge will allow you to know which areas you need to dive deeper on and which areas are more of a “been there, done that”. But not everyone has ten days to dedicate to one trip. So, I took my ten day New England itinerary and broke it down in five different ways. On each 7 day New England itinerary, you’ll find a mix of nature and small towns.
It’s important to note that none of these itineraries focus on Boston. Yes, Boston is in New England, but it’s relatively easy to reach (compared to many of the other cities I’ll mention in these itineraries), so I think it’s best saved for another trip (such as a long weekend). Let this trip focus on smaller towns and cities.
What to See in New England
Before we get into the actual New England itineraries, I want to focus on what are the major things you’ll see and do on these itineraries.
Providence, Rhode Island
I’ll admit that I didn’t spend a lot of time in Providence on my visit, simply because I ran out of time. I wandered around downtown, near the Rhode Island School of Design and Brown University, but my favorite part of the day was strolling through Roger Williams Park.
Other options for Providence include the Roger Williams Zoo, RISD Art Museum, touring one of the many historic homes, or doing some shopping. There’s plenty of things to do, so you should have no problem spending a day here.
Newport, Rhode Island
The highlight of Newport is touring its incredible, over the top mansions. The Breakers is a highlight as its the biggest and most over-the-top mansion here. But The Breakers isn’t the only mansion here. Also, look at touring The Elms, Marble House, and Chateau-sur-Mer. To get the most out of your day, I recommend purchasing a “Duo Entry Ticket”, which allows you entry into two mansions.
You can learn more in my Guide to the Newport Mansions.
Beyond the mansions, spend some time downtown. Enjoy lunch and some shopping. Plus, if you have the time, take a drive along Ocean Avenue for some great views of the Atlantic Ocean.
Mystic, Connecticut
Mystic Seaport is an open air museum and a must see when you visit Mystic, Connecticut. It provides a great insight into the history of the town and fishing in New England. I was skeptical about going here, because I thought I wouldn’t enjoy it, but I loved it. Because it’s an open air museum, you will walk from building to building, stepping inside for a look at the past. In some of the buildings, workers are there giving demonstrations and answering questions. This really adds to the experience.
Beyond Mystic Seaport, you can visit Olde Mystic Village to do some shopping or the Mystic Aquarium for an insight into marine life.
Learn more in my Guide to Mystic, Connecticut.
State Parks in Connecticut
I spent one of my days in New England working my way from West Greenwich, RI to Pittsfield, MA. Along the way, I stopped at three different state parks (plus I had visited a state forest the day before). If you have the time, this can be a great way to spend a day in Connecticut.
I visited Pachaug State Forest, Gillette Castle State Park, Kent Falls State Park, and Campbell Falls State Park on my visit and covered all four in a post about Connecticut State Parks.
Pittsfield, Massachusetts and the Berkshires
One of the best sites to explore while in the Berkshires is the Hancock Shaker Museum. This is another open air museum where you can wander through the original buildings built by the Shakers. If you’re not familiar with the Shakers, don’t worry, neither was I. Even if you know nothing, you still enjoy the museum and you will learn a lot.
Like at Mystic Seaport, there were volunteers doing demonstrations and leading talks. When you get to the museum, there will be information about what times these will be offered on the day of your visit.
But that’s not all you should do in the Berkshires. Visit one of the many art museums in this area, wander the botanical gardens, tour Edith Wharton’s home, or doing more shopping. For nature lovers, consider visiting Mount Greylock, which is the highest point in Massachusetts.
Admittedly, I didn’t explore as much of The Berkshires as I had initially planned. The weather did not cooperate and a nasty storm rolled through on my one full day here. While I do plan to go back at some point, I will admit that my experience was limited to just the Hancock Shaker Museum.
Albany, New York
Depending on your itinerary, you may not stop in Albany, but I found it to be worth the detour. I spent the morning checking out the Empire State Plaza and the New York State Museum and highly recommend making this detour.
Learn more about a detour through Albany.
Stowe, Vermont
Vermont because my favorite state of this region and it was my time in Stowe that caused me to fall in love with it. There is a lot to do here, but your time is limited so it’s important to have a plan and be prepared.
Stowe is home to the Ben and Jerry’s Factory, which offers tours. There are also some cute shops in Stowe, several places to sample some tasty treats, and some fun, short hikes to get some exercise.
Learn more in my Guide to Stowe, Vermont.
Burlington, Vermont
Admittedly, I have not been to Burlington since I ran out of time during my own trip, but there’s plenty to keep you busy. Check out the pedestrian only area near Church Street for shopping and restaurants. Take a hike or enjoy the waterfront.
Kancamangus Highway, New Hampshire
This is a 34.5 scenic byway that connects Lincoln, NH and Conway, NH through the White Mountains. There are many places to pull off to take photos or do a short hike. Since you’re not going to be spending a lot of time in New Hampshire, take the extra time to do a scenic drive.
Portland, Maine
One of the best things to do in Portland, is to get out on the water. The easiest way to do this is by utilizing the Mail Boat Cruise. This scheduled ferry service connects the small islands in the bay. For a reasonable price, they let tourists ride along to experience the views.
After your cruise, you can explore the Old Port. Admittedly I didn’t spend a lot of time here due to a torrential downpour, but there’s some great restaurants and plenty of shops.
While you’re in the area, don’t forget to head over to Cape Elizabeth and the Portland Head Lighthouse. This lighthouse is the most photographed lighthouse in the United States, and it’s easy to see why. The area around is beautiful, so take your photos, but also remember to take some time to just enjoy the scenery.
7 Day New England Itinerary – 5 Options
All of five of these New England itineraries are point to point trips. You’ll need multi city plane tickets, which should not cost much more than a round trip ticket. You’ll also have a one way rental which will incur a fee.
So given that, it’s a good idea to look at doing these itineraries in reverse. You may be able to save some money, but it will require a little additional effort and research up front.
New England Itinerary 1 – Provide to Albany
Day 1 – Arrive in Providence. Settle into a hotel in a central location. I stayed in West Greenwich, RI.
Day 2 – Newport, RI
Day 3 – Mystic, CT
Day 4 – State Park hop your way across Connecticut to the Berkshires. Sleep in the Berkshires—I stayed in Pittsfield, MA.
Day 5 – Pittsfield, MA and the Berkshires
Day 6 – Mount Greylock and Albany. Sleep in Albany, NY.
Day 7 – Fly home from Albany, NY.
Hotels Needed
Day 1-3: West Greenwich, RI
Day 4-5: Pittsfield, MA
Day 6: Albany, NY
Total Driving
Day 1: 30 minutes
Day 2: 1 hour
Day 3: 1 hour
Day 4: 4.5 hours
Day 5: minimal
Day 6: 2 hours
New England Itinerary 2 – Albany to Portland
Day 1 – Arrive in Albany.
Day 2 – Drive from Albany to Stowe, VT. If you didn’t have any time to explore Albany yesterday, you can do it in the morning before heading to Stowe.
Day 3 – Stowe, VT
Day 4 – Burlington, VT
Day 5 – Drive from Stowe, VT to Portland, ME on the Kancamangus Highway. Sleep in Portland, ME.
Day 6 – Portland, ME
Day 7 – Fly home from Portland, ME.
Hotels Needed
Day 1: Albany, NY
Day 2-4: Stowe, VT
Day 5-6: Portland, ME
Total Driving
Day 1: minimal
Day 2: 3.5 hours
Day 3: minimal – depends on what you see and do
Day 4: 1 hour
Day 5: 4.5 hours
Day 6: minimal
Day 7: minimal
New England Itinerary 3 – Portland to Providence
Day 1 – Arrive in Portland, ME.
Day 2 – Portland, ME.
Day 3 – Drive from Portland to Providence. Settle into a hotel in a central location. I stayed in West Greenwich.
Day 4 – Newport, RI
Day 5 – Mystic, CT
Day 6 – Providence, RI
Day 7 – Fly home from Providence, RI.
Hotels Needed
Day 1-2: Portland, ME
Day 3-6: West Greenwich, RI
Total Driving
Day 1: minimal
Day 2: minimal
Day 3: 3 hours
Day 4: 1 hour
Day 5: 1 hour
Day 6: 1 hour
Day 7: minimal
New England Itinerary 4 – Burlington to Connecticut
Day 1 – Arrive in Burlington, VT.
Day 2 – Stowe, VT
Day 3 – Drive from Stowe, VT to Pittsfield, MA with a detour through Albany, NY. Sleep in Pittsfield, MA.
Day 4 – The Berkshires
Day 5 – State Park hop your way across Connecticut before settling in Mystic
Day 6 – Mystic, CT
Day 7 – Fly home from either Hartford, CT or Providence, RI.
Hotels Needed
Day 1-2: Stowe, VT
Day 3-4: Pittsfield, MA
Day 5-6: Mystic, CT
Total Driving
Day 1: minimal
Day 2: minimal
Day 3: 4 hours
Day 4: minimal
Day 5: 4 hours
Day 6: minimal
Day 7: minimal
New England Itinerary 5 – The Whole Shebang
It is possible to shove most everything in my 10 day itinerary into 7 days, but it will be an incredibly busy 7 days New England itinerary. I’d recommend doing any one of the other seven day itineraries, just so you can go at a more relaxed pace. But for people who want to cram everything in, here’s what it would look like:
Day 1 – Arrive in Providence.
Day 2 – Visit Newport, RI in the morning and Mystic, CT in the afternoon. Sleep in Mystic, CT.
Day 3 – Drive to the Berkshires and spend the afternoon in Pittsfield, MA. Sleep in Pittsfield, MA.
Day 4 – Drive to Stowe, VT and spend the afternoon in Stowe, VT. Sleep in Stowe, VT.
Day 5 – Drive from Stowe, VT to Portland, ME on the Kancamangus Highway. Sleep in Portland, ME.
Day 6 – Portland, ME. Sleep in Portland, ME.
Day 7 – Fly home from Portland, ME.
Hotels Needed
Day 1: Providence, RI
Day 2: Mystic, CT
Day 3: Pittsfield, MA
Day 4: Stowe, VT
Day 5-6: Portland, ME
Total Driving
Day 1: minimal
Day 2: 1.5 hours
Day 3: 2 hours
Day 4: 3.5 hours
Day 5: 4.5 hours
Day 6: minimal
Day 7: minimal
When To Do These Itineraries
While each of these 7 day New England itineraries can all be done year round, I recommend traveling in fall. You’ll get beautiful drives, blazing with color and that just adds to the experience. However, many other people agree with this, so you’ll find fall to be a popular time to visit.
Final Thoughts
I really enjoyed my New England road trip. This is a place where it pays to rent a car and visit the small towns and these itineraries will help you do just that.
Continue Your Adventure
New England in 10 Days: If you have the time, I’d strongly consider spending 10 Days in New England. You can cover most of this list, but at a more relaxed pace.
New England: In Portland, Maine don’t miss the Mail Boat Tour and Cape Elizabeth. In Vermont, the small town of Stowe is a must see. Connecticut has beautiful state parks and the fun town of Mystic. In Newport, Rhode Island, you have to tour the mansions. And don’t forget to try to squeeze in a visit to Albany.
Similar Itineraries: For another itinerary that mixes nature and cities, consider my road trip from Washington DC to Savannah, GA.