Planning The Ultimate New England Road Trip



Fall in New England is something I’ve always wanted 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.  Like I said, this took 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.

A travel dream come true – empty seats next to yours! We had this row to ourselves.


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 over night.  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.

What a beautiful fall day in Connecticut.


Day 3

Depart New Haven for Providence, making a quick stop in Mystic to check out the infamous seaport.  We also diverted to Newport to see the famous mansions. Upon arrival in Providence, drop off the rental car, explore downtown and Federal Hill, before boarding a train bound for Portland, Maine for an overnight stay. This will also allow for a brief stop in Boston as well.

Newport Bridge.


Downtown Providence offers gondola rides.


Day 4

Pick up another rental car to explore Portland and head out to the Portland Head Light. After late lunch, we decided to branch out, so we headed 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.

The iconic Portland Head Light was commissioned by George Washington in the 1700’s.


Normally a summer hot-spot, not a soul was on Old Orchard Beach besides us.


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!

Vibrant foliage goes as far as the eye can see in the White Mountains.

Relaxing by the fire at our hotel.


Check out the spread at the von Trapp Family Lodge outside of Stowe!



Day 6

Before leaving Stowe in the morning, branch out and prepare for some hiking and excellent waterfall viewing.  Then, stop in Waterbury for a tour at either Green Mountain Coffee or a Ben and Jerry’s, depending on your preference. Once you head south 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. From there, head south toward Albany.

There are so many beautiful waterfalls in New England


Autoferry across Lake Champlain.


Day 7

Drop off the rental car and enjoy the morning exploring downtown Albany.  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!

Such a beautiful state capitol.


The Egg – Albany’s Performing Arts Center


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 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!

Niagara Falls in October is beautiful and less crowded.


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 where 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!!

Quaint New England charm.


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.  Please consider booking your stay through our link.  It’s at no additional cost to you, but may help us offset the cost of running this blog.

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