I spent ten days on my trip to New England, but I realize that 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. Each itinerary is special in its own way and I think the beauty of it is that you get to choose an itinerary that really highlights your interests.
It’s important to note that none of these itineraries focus on the city of Boston or Acadia National Park. 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). For Acadia National Park, it’s just a bit too far out of the way, but if you’re interested in Acadia, you can check out my guide to a long weekend in Maine which includes a heavy focus on Acadia National Park.
Let this New England 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 to Connecticut 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 return to the area eventually, 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
It was my time in Stowe that caused me to declare Vermont as my favorite state in New England. 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.
Learn more about the all the stops you can make on the highway’s website.
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 car 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
This itinerary focuses on southern New England. Scoot through Rhode Island and Connecticut before finishing in Albany. This itinerary is great for people who want variety in their travels. You’ll have a good mix of city and nature in this itinerary.
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
Focus on northern New England as you work your way east toward the ocean. This itinerary has the largest focus on Vermont, which is excellent because it’s my favorite state in New England. In addition, you’ll get a lot of great scenery in this itinerary between the drives in Vermont, New Hampshire, and Cape Elizabeth in Maine.
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
For those wanting to stay close to the coast, check out this itinerary. You’ll start in Portland, Maine before heading south for more coastline in Newport and Connecticut. Outside of the scenic drives along the coast, you’ll spend most of your time in cities.
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
For those wanting nature, here’s another variation. Start in Vermont and work your way down to Connecticut stopping at state parks along the way. You’ll have some time in cities, but you’ll get a decent mix of nature on this route as well.
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 – Explore 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 Visit New England
If you can, do this New England road trip in the fall. Yes, you’ll likely have the high crowds, but the leaves will be changing and it makes the drives that much prettier. Flexibility is your best bet for seeing the best fall colors. I was locked into my itinerary when I did this trip, so I had to hope for the best.
I traveled in the very last week of October and the leaves were hit and miss. In some places it felt like the leaves had barely started to change while in other places most of the leaves had already dropped. I found out that I missed the leaves on the Kancamagus Highway by about three days! Again, flexibility is key if you want to see the best colors.
I’ve also visited Maine in September on a separate trip. I traveled in mid September and it was just a bit too early for the fall colors. Given that, if fall colors are a priority, I’d try to aim for the middle of November. That’s no guarantee that you’ll get peak fall foliage, but it’s your best chance.
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 Connecticut, make sure to visit the historic fishing village of Mystic or one of its many state parks. Portland, Maine has a lot to offer, including the Mail Boat Cruise and an easy day trip to picturesque Cape Elizabeth. This itinerary features a quick detour through Albany, New York, but it’s a great addition to your trip. In Rhode Island, you can’t miss the over the top mansions of Newport. Don’t skip Stowe, Vermont, one of my favorite stops in all of New England.
Acadia National Park: Located in New England, but notably missing from this 7 day New England itinerary, Acadia is wonderful. In one day you can see the highlights, but two days allows you to go slower and see more. Whether you’re looking for a hike or want to drive the scenic Park Loop Road, there’s lots for everyone at Acadia. Learn even more in my Acadia Travel Guide.
More Itineraries: 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. If you have less time, consider focusing solely on Maine in this five day itinerary. For another itinerary that mixes nature and cities, consider my road trip from Washington DC to Savannah, GA.