In late October 2021, I was still traveling domestically because of the pandemic. So, in lieu of international travel, I put together a 10 day New England road trip. If I was going to travel in the United States, why not make it a bucket list trip?
I started in Providence, Rhode Island, worked my way across Connecticut, up through Massachusetts and Vermont, and then across New Hampshire to finish in Portland, Maine. Like most of my trips, this 10 day New England road trip is fast paced. However, I’ve learned that this type of trip works well for me. I get to explore a lot of different areas of the region and learn which places that I want to return to and which places just aren’t my cup of tea. And I learned a lot on this trip.
10 Day New England Road Trip
If you’re looking to do a similar road trip through New England, I’ve laid out my exact route. With most of my itineraries, there are typically small tweaks I would make to improve it for others. This trip is different and I can’t come up with any impactful changes that I would make.
So here’s how I recommend spending 10 days in New England.
Day 1 – Arrival in New England
This 10 day New England road trip starts in Providence, Rhode Island. My flight landed shortly after 12:00pm, which left me with a free afternoon to explore Providence. I picked up my rental car from the Providence Airport. Since it’s a small regional airport, there was no line and it took no time before I was on the road.
For your trip, I recommend trying to find a similar route. Try to land earlier in the day to give yourself a little time to explore in the afternoon.
From the Providence Airport, it’s a twenty minute drive to downtown Providence.
While there’s a lot you can do in downtown Providence, I limited myself to two specific areas. The first was near the campuses of Brown University and the Rhode Island School of Design. In this area, you will find some incredible architecture and great views of the city. After, I went to Roger Williams Park, which is a ten minute drive away. This park has some great walking paths, some beautiful scenery, and it feels a world away from the hustle and bustle of downtown Providence.
I kept driving and ended up in West Greenwich, RI where I spend the night. Of course, you could stay in Providence, or in one of the other cities you’ll visit in the next two days (Newport, RI or Mystic, CT).
However, West Greenwich had the benefit of being a half hour drive from Providence, Newport, and Mystic. You don’t have to stay in West Greenwich, but somewhere in that general area is a good idea. I only picked West Greenwich because that’s where I could get a hotel of my preferred brand.
Sleep: West Greenwich, Rhode Island
Day 2 – Newport, Rhode Island
Today is all about Newport, Rhode Island. The highlight of this city is touring it’s incredible, over the top mansions.
Try to get an early start so you can start your morning with a drive along Ocean Avenue. You absolutely could do this later in the day, but the advantage of being here before the mansions opened was that there were hardly any other cars. Scenic drives are just always more pleasant when traffic is light.
As a note, the most direct route from West Greenwich to Ocean Avenue, requires you to cross the Newport Bridge, which will come with a $4 toll. Thankfully, this was the only toll I had to pay on this trip.
There’s no right order to visit the mansions of Newport, but I recommend starting at The Breakers which is the former summer cottage of the Vanderbilts. As you walk through the mansion, you’ll feel like you were transported to a palace in Europe.
The Breakers is the most popular mansion and therefore is the busiest. By getting here right when it opens (or even a little earlier), you can be one of the first people in and experience it before it gets really busy.
Before your visit, download the Newport Mansions App. The App is free and provides a guided audio tour so you can have context to what you’re looking at.
After touring The Breakers, you have a choice. I recommend purchasing the Newport Mansions Duo Entry Ticket, which gives you entry into two mansions. The first mansion was The Breakers, but you get a choice in your next mansion: The Elms, Marble House, Chateau-sur-Mer, and others are all valid options.
It can be tough to pick which one you tour and I only have experience touring Marble House.
Why did I pick Marble House? Easy. The description mentioned that it was decorated with 500,000 cubic feet of marble and that was enough to convince me that Marble House should be my choice.
After your second mansion, you’ll likely have worked up an appetite so drive downtown to explore and find a place for lunch. There are a lot of options so you won’t go hungry. After lunch, wander through the shops and have a relaxing afternoon.
On your drive back to West Greenwich, you have two options. You could drive back the way you came, which will come with another $4 toll. The other option is to go the long way home.
This drive was a bit more scenic, particularly with the fall colors (it was the first time I actually saw some decent fall colors on this trip), but it loops you up near Providence, so it adds on some more driving. The choice is yours.
Sleep: West Greenwich, Rhode Island.
Day 3 – Mystic, Connecticut
On Day 3 of this 10 Day New England road trip, you’ll leave Rhode Island to visit Connecticut and explore the historic fishing town of Mystic.
Mystic Seaport is an open air museum and a must see when you are here. 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. I was wrong and 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, which really adds to the experience.
For lunch, grab a bite to eat overlooking the ocean. I was here on a gorgeous fall day and my meal was made that much better with the incredible view.
After lunch, you can drive up to Olde Mystick Village to do some shopping. This is a fun little area to wander and see what’s all being sold. It is a bit touristy, but I still enjoyed it. Plus it’s right down the road from Mystic Seaport.
When you’re ready, you can start working your way back towards West Greenwich. If you have a nice day, it’s worth taking a detour to Pachaug State Forest and hiking to Mount Misery for a great view.
As a note, this is not a difficult hike (I did it in a basic pair of sneakers), but it felt great to do something a bit more active.
Another option for the day is the Mystic Aquarium. This is highly promoted when you research things to do in Mystic, but I skipped this for some other activities.
Sleep: West Greenwich, Rhode Island.
Day 4 – Rhode Island to the Berkshires
On Day 4 of this road trip through New England, check out of your hotel in West Greenwich to move west to explore more of Connecticut before arriving in Massachusetts.
There’s two ways you can get here. The first is more direct, but comes with tolls. You can reach the Berkshires in about two and a half hours by taking this route.
The second option takes you across Connecticut. This is the route I took because it allowed me to visit several state parks across Connecticut. As I drove, I stopped at Gillette Castle State Park, Kent Falls State Park, and Campbell Falls State Park.
Between the stops at these three parks, and the actual drive across Connecticut and into Massachusetts, this took the entire day. But it was a one of my favorite days of my New England road trip.
In the Berkshires, you’ll have lots of options for where to stay. I chose Pittsfield because of the convenient location for my exploring the next day.
Sleep: Pittsfield, Massachusetts.
Day 5 – The Berkshires
It’s the halfway point of this 10 day New England road trip and we’re going to spend it by exploring 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. But essentially, this was a religious community, but because of their belief in celibacy, their numbers quickly dwindled.
Even if you know nothing about the Shakers, you’ll still enjoy the museum and you will learn a lot. It’s actually super interesting. 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. Make sure to check these out.
In the afternoon, consider visiting one of the many art museums in this area, the botanical gardens, Edith Wharton’s home, or doing more shopping.
I had plans to do some of these things, but the weather did not cooperate. During my visit, a nor’easter was moving through so we had rain and storms all afternoon. Aside from the Hancock Shaker Village, I unfortunately didn’t do a lot of exploring of the Berkshires.
Sleep: Pittsfield, Massachusetts.
Day 6 – The Berkshires to Stowe, Vermont
It’s another driving day on this New England road trip, this time between the Berkshires and Stowe, Vermont. You have two options if you want to break up the three and a half hour drive.
The first (and my original plan) is to visit Mount Greylock, the highest point in Massachusetts. I skipped this because it had rained so much the day before and I didn’t want to hike through mud. But if the weather is better on your trip and you’re looking for more nature on your New England road trip, consider visiting Mount Greylock.
The second option (and what I eventually did) is to visit Albany, New York. I was here for just under two hours, but it was enough to visit Empire State Plaza and the New York State Museum (which was a fantastic museum).
Regardless of how you choose to spend your day, you’ll eventually spend a decent chunk of time driving through Vermont. The route is scenic and it’s one of my favorite stretches of highway driving on this New England road trip.
Sleep: Stowe, Vermont.
Day 7 – Stowe, Vermont
Today is all about Stowe and falling in love with 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 (although tours were suspended during my visit because of the Coronavirus pandemic).
There are also some cute shops in Stowe, several places to sample some tasty treats, and some fun, short hikes to get a little exercise. I think this was my busiest day during my trip and I enjoyed every minute.
If you have energy at the end of the day, you could even venture beyond Stowe. I climbed Hubbard Tower and did a quick walk around downtown Montpelier.
Sleep: Stowe, Vermont.
Day 8 – The Kancamangus Highway
It’s your last big driving day of this New England road trip and you’ll be driving across New Hampshire to connect Stowe, Vermont with Portland, Maine.
While I don’t have a list of stops for this drive, I do recommend driving the Kancamagus Highway, which involves a slight detour to reach. The Kancamagus Highway a 34.5 scenic byway that connects Lincoln, NH and Conway, NH through the White Mountains. As you drive, you’ll find several places to pull off to take photos or do a short hike. Learn more about the all the stops you can make on the highway’s website.
Since you’re not going to be spending a lot of time in New Hampshire, take the extra time to do a scenic drive. It’s one of the prettiest of this 10 day New England road trip.
Sleep: Portland, Maine.
Day 9 – Portland, Maine
Today is the last full day of this New England road trip and you will be spending it in Portland.
Start your morning with the Mail Boat Cruise, which is a scheduled ferry service connecting the small islands in the bay. You won’t be able to get off at any of the islands, but you can buy a ticket just to take the ride and enjoy the views. Hopefully the weather is a bit nicer for you than it was for me.
In the afternoon, explore the Old Port. I don’t have a lot of recommendations for the Old Port because the weather did not cooperate. When I finished the Mail Boat Cruise, there was a a torrential downpour and exploring this area just became miserable. I was soaked (even with an umbrella) and I decided it was going to be an early day.
If you have an early flight home tomorrow morning, consider limiting your time in the Old Port, to do what I have listed for Day 10. I think this is totally worth it.
Sleep: Portland, Maine.
Day 10 – Goodbye, New England
I had an afternoon flight, so I had some time to explore in the morning before I left. I drove down to Cape Elizabeth to see the Portland Head Lighthouse and I recommend you do the same.
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 take a walk and enjoy a great end to your trip.
When you’re done, return your rental car to Portland Airport. Your 10 day New England road trip is over.
Recap & Hotels Needed
Here’s a final overview this 10 Day New England Road Trip, including all of the hotels you’ll need:
Day 1: Fly into Providence, RI. Sleep: West Greenwich, RI.
Day 2: Explore Newport, RI. Sleep: West Greenwich, RI.
Day 3: Explore Mystic, CT. Sleep: West Greenwich, RI.
Day 4: Drive to The Berkshires. Sleep: Pittsfield, Massachusetts.
Day 5: Explore The Berkshires. Sleep: Pittsfield, Massachusetts.
Day 6: Drive to Stowe, VT. Sleep: Stowe, VT.
Day 7: Explore Stowe, VT. Sleep: Stowe, VT.
Day 8: Drive to Portland, ME. Sleep: Portland, ME.
Day 9: Explore Portland, ME. Sleep: Portland, ME.
Day 10: Fly home from Portland, ME.
With Less Time
If you don’t have 10 days to dedicated to this New England itinerary, I created a series of one week New England itineraries. Each itinerary focuses in on one area of New England, allowing you to still have a great adventure, just in a shorter amount of time.
More Notes on This New England Itinerary
You’ll notice that this 10 day New England road trip skips Boston, even though it’s arguably the most famous city in New England. If you’re on limited time, like I was, skip Boston and focus on the smaller towns. You can always come back to visit Boston for a long weekend.
You can definitely do this New England road trip in reverse (starting in Portland and ending in Providence), but this is just the way I happened to do it. I don’t think there is one direction that is necessarily better than the other so I would recommend doing it in whichever order is cheaper for flights and hotels.
This New England itinerary is a point to point, so you’ll be doing a one way rental. When you rent you car, you’ll likely have an additional fee for this. The fee is annoying, but it can be worth it for the time savings. When I did this, the one way fee was very reasonable (although this hasn’t been the case on every one way rental I’ve done). If the fee is outrageous, you could consider doing a round trip and flying in and out of the same airport (you could even use Boston even if you don’t explore the city). Just make sure to allow yourself enough time to get back to the airport.
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.
Final Thoughts
I’m very happy that I took this New England road trip. My 10 days in New England were awesome and I’m really glad I focused more on the smaller towns and the nature in this region.
That said, I do wonder if New England in the fall is a bit overhyped. Was it pretty? Absolutely! However, there are plenty of other places throughout the United States that have the same beautiful fall colors but less tourists (my home state of Wisconsin says hello!). But, I’m still glad I went and saw everything I could. It was a great road trip through New England and one that I would recommend to most travelers.
Continue Your Adventure
Connecticut: Make sure to visit the historic fishing village of Mystic or one of its many state parks.
Maine: Portland has a lot to offer, but one of the highlights is doing the Mail Boat Cruise to tour around the many islands of the bay. And for an easy day trip from Portland, look at picturesque Cape Elizabeth.
New York: This itinerary features a quick detour through Albany. It’s not a lot of time, but you can still visit a great museum.
Rhode Island: One of the highlights of Rhode Island is touring the over the top mansions in Newport.
Vermont: Many travelers fall in love with the charming town of Stowe. It was definitely one of my favorites.
More New England Itineraries: For those with less time, check out my one week New England itineraries.
Similar Trips: For another trip that combines a little of nature and cities, check out this 10 Day Itinerary from Washington DC to Savannah, GA.