Fall 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!
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.
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.
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.
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.
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 fantasticFlume 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!
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.
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!
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!
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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Welcome Back! Disclaimer: Posts on By Land and Sea contain ads and affiliate links. If you make a purchase, we might make a little extra travel money, at no extra cost to you. As always, all opinions are our own. Be sure to check on the latest updates at your destination.