By Land and SeaFall in New England is something many travelers wish to experience. From the vibrant foliage to covered bridges and quaint villages, this has always been a travel goal of mine. How convenient it was when some friends of ours informed us they would be getting married in Connecticut in October – peak season! We were thrilled to accept their invitation to join them on their special day. We also wanted to seize this opportunity to spend time in this area in prime leaf-peeping season. From that moment, we were absolutely determined to cover New England utilizing our October vacation time.
After a few years of battling October hurricanes in the Caribbean, we were thrilled to be experiencing something entirely different. So, with some creativity and careful planning, we were able to visit seven states in eight days. We set out and visited nearly one state a day. While that sounds daunting to some, it is important to remember that, for the most part, these states are very small. The scenery on a trip like this is beautiful!
Here is a list of the places we visited:
Connecticut – Hartford, New Haven, Wallingford, Guilford, and Mystic Seaport
Rhode Island – Newport and Providence
Massachusetts – Boston
Maine – Portland and Old Orchard Beach
New Hampshire – Conway, White Mountains, and Franconia
Vermont – Montpelier, Waterbury and Stowe
New York – Saratoga Springs, Albany, and Niagara Falls
Ontario – Niagara Falls
That’s right, we covered this many places in just over one week. Again, this takes some creativity and planning. Not only did we have to determine where all we wanted to go, but how and when we would manage this. This involved looking at a lot of maps (one of my favorite things) and determining a route to best utilize the time we had.
We actually tasked a travel agent with planning this trip for us. She failed, and we ended up planning it on our own!
Here’s exactly how we did it!
Day 1
Fly into Hartford, CT. Pick a budget hotel with a free shuttle near the airport. We arrived late at night and went straight to our hotel.
Day 2
Take the free shuttle back to the airport, pick up rental car. Doing it this way saves the cost of paying for a rental to sit in the hotel parking lot overnight. Drive to New Haven and spend the day exploring the city. This includes a visit to Yale’s campus and the famous Frank Pepe’s Pizza. We stayed overnight in Wallingford as this was also the day of our friends’ wedding in nearby Guilford.
Day 3
Depart New Haven for Providence by car. Along the way, make a quick stop in Mystic to check out the infamous seaport. We also diverted to Newport to see the famous mansions. It was pouring rain however and we elected to only view them from our car instead of getting out to explore.
Upon arrival in Providence, drop off the rental car at a downtown lot. This allows you to explore downtown and Federal Hill by foot. In the evening head to the Amtrak station to board a train bound for Portland, Maine. Here, plan for an overnight stay. This will also allow for a brief stop in Boston as well. We had been to Boston a few years prior, so we were both ok going without much time in this awesome city! If you haven’t been to Boston, you will definitely want to plan more time there.
Day 4
In the morning, pick up another rental car to explore Portland and head out to the Portland Head Light. Downtown Portland and the port area are great places to spend the day strolling the streets, taking in all this charming city has to offer.
After late lunch, we decided to branch out, so we headed south to Old Orchard Beach for a few hours. We had the freezing northern Atlantic to ourselves, as well as the local arcade, which was one of the only open businesses as everything was closed for the off-season. After spending some time here, we headed to New Hampshire on scenic back country roads for lodging at the base of the spectacular White Mountains.
Day 5
Spend the day exploring the White Mountains of New Hampshire. Take the scenic route – the Kancamagus Highway. This route is gorgeous! And, our best advice on this road is to be prepared to stop often – drive with caution! Be sure to catch the amazing waterfalls and my favorite, Franconia Notch State Park where you will see the fantastic Flume Gorge.
Make your way towards your hotel in Stowe, Vermont that evening. You’ll pass through Montpelier, which is a great spot to visit local maple farms and stroll through the downtown streets. Stowe is a typical ski town, but make sure to check out the von Trapp resort…. Yes, the von Trapps from Sound of Music ended up in Vermont! This is the idyllic spot to enjoy the brewery and soak up the moment!
Day 6
Before leaving Stowe in the morning, branch out and prepare for some hiking and excellent waterfall viewing. After a walk in the woods, head it will be time to get back on the road. Head south and stop in Waterbury for a tour at either Green Mountain Coffee or a Ben and Jerry’s, depending on your preference. Set your GPS towards Saratoga Springs, New York via Burlington, you’ll get to cross Lake Champlain by auto ferry.
Plan your trip to Saratoga Springs right and you might be able to catch a horse race while you are in town. We stopped for lunch here and strolled around the area for a bit. From there, head south toward Albany.
Day 7
Save money on parking by dropping off the rental car at yet another downtown lot. Enjoy the morning exploring downtown Albany, including the New York State Capitol and The Egg. Later, head to the train station to depart on the six-hour Amtrak journey to Niagara Falls, New York. This is some great downtime to rest and catch up. There are more departure options and more affordable prices if you go to the New York side as opposed to the Canadian side! Then, take an Uber to your hotel!
Day 8
Get up early to get a jump on all the excitement of Niagara Falls. We were able to get soaked on the Maid of the Mist, soar over the water on the MistRider (and we thank them for hosting our visit), and get blasted by the Cave of the Winds. This is a fun place to just spend the day walking around, taking pictures, eating, and adventuring! Just remember to bring at some quarters so you can pay the fee to cross back to the American side when you’re done for the day!
Day 9
Catch a ride to the Buffalo Airport for departing flight. We made it home in time for dinner!
While we know that this trip doesn’t do justice to all New England has to offer, we were pleased with our experience here. We were able to see spectacular foliage, rushing waterfalls, and rugged coastlines. We enjoyed peaceful mountain serenity and the hustle and bustle of big cities. This mix of planes, trains, and automobiles allowed us to cover hundreds and hundreds of miles within these beautiful states. Our days were busy and intense – generally going for 12 hours or more and were filled with sites, food and fun! We are so glad we got to have this experience road tripping through New England!!
Start planning your fall foliage adventure now!
If you’re curious where to stay, you can see the hotels we stayed at in each city by visiting our Hotel Recommendations page. It is important to remember that this is peak-season and prices can be high. We selected budget-friendly options in each city.
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Thanks for visiting By Land and Sea!
This is high up on my wish list. Thank you for all the info 🙂
You’re most welcome! Glad you enjoyed the post!!
You’re killing me with all the fall colors!! All of your spots look so beautiful, but definitely want to check out Maine soon!
Maine is beautiful!! Would love to explore it even. Ore, especially Acadia!
Fall in New England looks wonderful, especially the Kancamagus Highway (I assume the photo of you two and those vibrant autumn colors & mountains was made there)! You´ve really done a lot in one week! #FeetDoTravel
Yes, that’s where we took the pic! It was breathtaking!
I don’t even know where to begin with this post! What an epic road trip, so many amazing things you did! The Falls in October – wow! It looks like they are amazing any time of year really, and the Autumn/Fall colours are stunning. But hello! Von Trapp Resort?? They settled in Vermont – I did not know that! I need to add this to my bucket list and take my Finnish friend who I worked with on Gili Air, we used to sing Sound of Music songs haha. Pinned. What a great trip #feetdotravel
Such a wonderful region to explore. I’ve given you yet one more reason to head to the States, right!?!?
I’ve read so many articles about New England in Autumn, there’s always loads of articles in the newspapers here in the UK advertising trips, however I’d much rather do what you did and create your own road trip, looks like a great adventure too! The colours of the trees in that picture of you guys looks fabulous. Oh and how brilliant getting an empty row of seats! love it. It’s only happened to me once where I scored the middle row of seats on a flight from London to LA 🙂 Thanks for the itinerary, have pinned for ref. Garth.
It was so fun to go road tripping on our own as opposed to a tour (although it was more complicated)! We highly recommend it – let us know if you ever have planning questions.
I would so love to take this exact trip! I’ve been to New England in the fall but not as far north as Maine and New Hampshire. We would for sure want to plan our own trip (not go on a tour), so I’m pinning your post for future travel!
Wow! That is an impressively ambitious road trip. I’d really like to do this trip to see all if the beautiful waterfalls. I remember seeing a few when we did a New England road trip when I was kid. Thanks for sharing your post and laying out a great fall foliage itinerary #WeekendWanderlust
Looks like the prefect road trip which we would easily do in a week as well, and there are few people who could keep up, or succeed in booking such a trip! #FeetDoTravel
What a great road trip! You covered quite a few miles, and it looks like it was all worth it. #FeetDoTravel
Wow, looks epic. This post is giving me serious wanderlust. And it’s on my bucket list, would like to get there within the next couple of years.
Great photo of Niagara Falls. It’s definitely worth the detour when in the area.
Oh you guys have our number with this one! We have fallen head over heels for New England, and have covered many of the same areas over the past few years. Kancamagus Highway the White Mountains are awesome! Stowe and the Trapp Family Lodge are amazing! We have yet to get to western New York or Maine, though. Soon…but not soon enough! Awesome trip guys – sounds like you love the area as much as we do! (And could I use the exclamation mark any more??? 😉
I love road trips and this just makes me want to jump on a plane straight away! The Autumnal colours are just stunning, I’d love to see New England in person, so thank you so much for the inspiration!
Glad to have inspired some wanderlust!
Love a good road trip! And this is a nice itinerary – worth following your footsteps 🙂
We really enjoyed this trip! Hope it has been inspiring for you!
This looks like the perfect New England road trip! And I would absolutely love to stay at the von Trapp Lodge in Stowe. You covered a lot of ground in 7 days, but it looks like you had a wonderful time.
Yes we did cover a lot of ground, but it was totally worth it!
What a lovely road trip!! Sometimes its better doing the itinerary yourself somehow, more reliable :). New England at fall sounds so dreamy and that state capital building looks amazing! Always wanted co see niagara too! Bookmarking this for future trips! How was Frank pepe pizza? 😍😍
So glad to hear this was helpful to you. Frank Pepe’s was absolutely worth the wait!! Yummy!!
Enjoyed reading your post. Brought back memories of our road trip in New England some ten years ago. But the Von Trapp resort and the family lodge are a pleasant surprise! I would love to visit that place with Sound of Music track playing! I think it’s time for me to make another visit of the beautiful New England in USA! 🙂
The Von Trapp resort was such a cool place to hang out, surrounded by natural beauty! Hope you make it one day!
You visited a good cross-section of places to give a broad spectrum of communities and environments. When I first visited the States I delivered cars across the country, and there’s nothing better than a road trip to explore expansive countries. When you fly, you miss so much.
Oh wow, that sounds like such a great opportunity and a great way to see the country!
My main interest is to go to the White Mountains and then Stowe to see the leaves in the fall. You saw a lot more, too! I’m hoping to make this trip to New England in the next few years!
I hope you make it too – you will really enjoy it!
I’ve heard so much about the glorious beauty of fall in New England and you’ve captured that so well in this post. Those vibrant colors along Kancamagus Highway are captivating. I really appreciate how you listed the day by day plan for this road trip – that will certainly come in handy for trip planning. Hopefully we will be able to plan one such memorable road trip through NE soon.
Happy to hear my post was helpful and inspiring! Happy road tripping!
New England sounds like a great destination to visit. Your photos are so beautiful!
Thank you! It is a great area of the United States.
I have heard about so much of Fall in New England that I really want to go for this road trip. Good to know that downtown Providence offers gondola rides which will give us feel like Venice. And all those beautiful waterfalls make me tempt to visit this place.
A fall foliage trip to New England is a great travel experience! Hope you add it to your list!
This looks wonderful! I would love to go on this trip, and wish the US weren’t so restrictive about letting foreign tourists in. I guess I am spoiled by the EU borders and some European and Middle Eastern Destinations that allow you to travel VISA-free with no worries.
So hopeful that one day you can go on a trip like this!
This would be a bucket list trip. I am always looking to visit the east coast in the Fall.
What a fun fall New England road trip! I would love to visit all of those states and enjoy the view!
Great guide! A fall New England road trip is on my bucket list. Definitely saving for later.
This is such a nice trip! I wish I could do all of the US trips I read about! There is many things to explore, beyond the most tourist sites advertised.