planning a road trip

The Perfect New England Fall Road Trip

As we head into August, it’s on the back of my mind that the best season is soon approaching. Obviously, I’m taking about Fall.

I love everything about the fall weather, but mostly that I can wear a sweatshirt Last year I took my mom and sister on a New England road trip that I planned myself. While I like to do some research before I go on a trip, I really couldn’t find anything that suited what I wanted to do and where I wanted to go. A lot of the itineraries I found included driving up to Maine, which I would have loved, but I didn’t want to spend most of my time in a car.

So, after mapping out my own travel itinerary, here is what I call the “perfect new England fall road trip.” This will fill you in on everything you need to know about traveling to the East Coast during autumn.


Boston → (3 hours) → New Hampshire → (3 hours) → Vermont (4 hours) → Connecticut (2 hours) → Rhode Island (2 hours) → Boston

getting started

You can map out your route differently depending on where you want to start/end, if you have to fly, etc.

Flying from Nebraska, I found the cheapest flight going to the East Coast would take me to Boston, so I knew I wanted to explore states around there. I booked a roundtrip to/from Boston for around $200, and I bought it about 5 months in advance.

The next thing I did was rent a car. This is going to be more expensive depending on your age. For example, I think if I was going alone, it would have cost me $500 extra because I was under the age of 25. But luckily my mom was coming with so she could sign her name under it and save us some money.

I really am not too picky on car rentals, whatever is cheapest is fine with me.

sleeping arrangements

One part that got me really excited when planning this trip, was thinking about all the cute places we could stay. I personally love Airbnb and found the cutest A-frame cabin, situated in a secluded wooded area that screamed “New England during the fall” to me.

This may have inspired my trip to begin with…

Airbnb in New Hampshire

However, I know that my mom is not the biggest fan of Airbnb all the time. She likes to have certain amenities, like a TV that she can use as white noise while she sleeps. To compromise and make everyone happy we stayed in a mix of Airbnb’s and hotels. We had an Airbnb in New Hampshire and Vermont and hotels during the other three cities.

I actually really liked our hotels in Rhode Island and Boston as they were closer to the city centers than I thought and we could easily walk around if we weren’t driving that day.


Next, I’ve put together a short breakdown of what the trip should somewhat look like, obviously you can choose other activates to do or even add on to your road trip.

DAY 1 

    • Fly into Boston
    • Get rental car
    • Drive 3 hours north to New Hampshire


    • Drive through Kancamagus Highway
    • Explore White Mountain National Forest
    • Go alpine sledding


    • Drive Route 100 into Vermont
    • Stop at an apple orchard along the way


    • Hike Green Mountains
    • Photoshoots at one of the many covered bridges in Vermont


    • Drive through Massachusetts into Connecticut
    • Check out a “haunted” cemetery


    • Drive 2 hours to Rhode Island
    • Try the seafood
    • Spend the night relaxing by a lighthouse


    • Drive 2 hours to Boston
    • Walk around Freedom Trail
    • Return rental car
    • Fly home

what to eat

If you’re going during the fall time, I highly recommend getting apple cider and apple cider donuts at least at some point during your trip. We also consumed a lot of seafood dishes because we were so close to the water (I particularly loved Shell & Bones: Oyster Bar and Grill). I even tried poutine one day. Poutine is traditionally a Canadian dish, but being so far up north we found a few restaurants that served it.

I would also say don’t be afraid to stop anytime something looks good to you! One day, the three of us pulled over on the side of the road because we saw a cute farm selling pies. Yes, we ate a pie for lunch. When you’re on vacation that happens sometimes ;).


When the trip was finally over, I tallied up all my costs and I realized it was a pretty affordable holiday. However in full disclosure my mom did buy most of the meals.

Still, with my plane ticket, the Airbnb’s that I booked, some souvenirs, the occasional Starbucks and renting a car + gas I think my total came out to around $500. (It would have been around $1000, had my mom not came.)

This is an approximation of what you can expect to pay during your road trip.

    • flight $200 (I was coming from the midwest)
    • car rental $300 (split between 3 people)
    • gas →  $150
    • airbnb $200
    • food $200
    • souvenirs $50 (I usually just buy one t-shirt and a keychain)

Obviously some things will vary depending on how many people are coming with you, to split up the cost between car rentals and gas, and also by how expensive the places you choose to eat at are.

Also for some reason car rentals are ridiculously pricing right now? Thankfully when we went that was not the case.

final thoughts

During our time in New England I felt like we managed to get in quite a few “fall” activities, like apple picking and looking for ghosts in a cemetery. However, the most fall thing about New England is the beautiful scenery.

During this road trip you will be in awe of all the colors you didn’t know trees could be, or that you’ve only seen in pictures. Deep reds, purples, hints of green, bright orange and yellow. It was beautiful and everything I imagined it would be.

I hope this post answered some of your questions about planning a road trip and how to make the most of your time in New England! Let me know if you have any questions or are planning a trip yourself!

Like this post? Pin it!


  1. Fall is absolutely the best time of year! I agree with you – sweaters! Haha. It has been a dream of ours to road trip through the New England States during the fall. Thanks for the recommendations.

  2. This is the perfect New England fall road trip! I lived in Vermont for five years. Miss fall foliage season!

  3. That’s a pretty good price to pay for a getaway. Isn’t it wonderful that there are so many fun places within a reasonable drive in New England?

  4. I adore Boston, and love this New England jaunt. I’d definitely suggest spending a little longer in Boston next time – and pop out to Salem for a day trip!

Leave a Reply

%d bloggers like this: