5 Day New England Fall Road Trip

Join me on a five day New England fall road trip that’ll sweep you off your feet! On this whirlwind New England escapade, you’ll witness colorful Vermont foliage, stroll through Massachusetts’ charming streets, embrace Maine’s stunning shoreline, and discover New Hampshire’s scenic marvels.

As part of this exhilarating 1,000-mile road trip, I’ll reveal the route I took to bask in the region’s picturesque fall splendor over just a few days.

In search of the perfect travel plan, I delved into Pinterest travel boards and scoured countless New England road trip itineraries.

Searching for more hidden gems, I joined a Travel New England Facebook group to cherry-pick destinations, creating a flawless route.

Months of meticulous planning culminated in the unforgettable New England road trip itinerary I’m delighted to share with you. Along the way, I’ll offer insights on my favorite stops, lessons learned, and the places worth revisiting or skipping altogether.

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For as long as I can remember, I have wanted to see New England in the fall. The idea of the trees changing colors is foreign to this South Texas girl. We’ve got cedar trees and more cedar trees, which means green or brown, but not much in between.

Eager to become a “leaf peeper,” I set out on an ambitious road trip with my sisters.

For those unfamiliar with the term “leaf peeper,” it describes the multitude of travelers drawn to the Northeastern United States during autumn, anxiously seeking out the colorful fall foliage.

A Five Day New England Fall Road Trip Itinerary

When you plan your New England fall road trip, you have many options for where it should begin. With so many airports in this region, find the one with the best flights from your home city.

For us, Boston’s Logan International Airport was the best choice. With many daily direct flights, it is easy to start here. The website Skyscanner.com is a great place to begin your search for affordable flights to New England.

Skyscanner scours the web for the best airfares from your city. You are given the results sorted by the best deal, cheapest flights, and time traveled.

You will need a rental car for your New England road trip. Book your car as far in advance as possible, especially during autumn, when many tourists flock to this area.

Day One: Getting to New England

I recommend flying in the day before your road trip begins. Book a Boston hotel near the airport so getting your rental car the next morning is easy.

Once you pick up your rental car, the first leg of your road trip will be from Boston to Stowe.

Travel from Massachusetts to Vermont on day one. You will make stops along the way in quintessential New England towns, like Woodstock, to see the iconic Sleepy Hollow Farm, covered bridges, and scenic landscape.

Plan to spend the first night of your road trip in Stowe, Vermont.

Day Two: Vermont

On day two, you will want to explore Stowe, Vermont, and the surrounding area. I would recommend spending at least a full day in Stowe.

Start out by visiting the Cold Hollow Cider Mill for the best apple cider donuts in the area.

Spend the day exploring Smuggler’s Notch State Park or the many outdoor activities at the Trapp Family Lodge.

Plan to spend another night in Stowe so you don’t miss out on the other attractions in this area. Burlington is a short drive to the west, and the Ben & Jerry’s Ice Cream Factory is nearby too.

Day Three: New Hampshire

On day three, continue your New England trip with a scenic drive from Vermont to Maine.

You will absolutely love seeing the massive properties along the way.

The red and white barns, picket fences, and colonial homes offer picturesque landscapes worth the trip.

Drive the Kancamagus Highway

A New England foliage road trip should include a drive on the Kancamagus Highway in New Hampshire.

You will drive through White Mountain National Forest.

Prepare to enjoy some of the best leaf peeping in the state, fantastic overlooks, and mountain views across a lake.

Stops along the Kancamagus Highway also include some of the best hiking trails in New England, including hikes to beautiful waterfalls.

These historic railways offer a unique opportunity to witness the stunning scenery from the comfort of a vintage train car.

While I did not personally ride on these, I did enjoy a similar journey on the Essex Steam Train trip in Connecticut.

Go Apple Picking

Picking apples at an orchard is a quintessential New England thing to do in the fall. You’ll find a great apple-picking farm in New Hampshire.

Make your way to Applecrest Farm Orchards in Hampton Falls, NH. It is the oldest and largest orchard, making for a great fall experience.

Applecrest Farm Orchards is enormous. It has acres and acres of fruit trees and fields of flowers. It is so big that you even take a tractor out to pick your fruit or flowers.

Honestly, these are the best apples I have ever tasted. Hands down!

TRIP TIP: Try the Lobster Macaroni and Cheese at The Orchard Grille at Applecrest Farm. It is delicious, but beware, it comes at a market price. One we didn’t realize until it was time to pay!

Day Four: Maine

Visit the LL Bean Flagship Store

On day four, travel to the coastal Maine towns of Ogunquit and Kennebunkport, but not before making a stop in Freeport, Maine, at the LL Bean Flagship Store.

Beyond shopping, the store also hosts events and offers a wide range of outdoor activities, making it a must-visit destination in the heart of Maine.

Escape to the Coast of Maine

Although you may not see much foliage along the coast of Maine in the early fall months, Ogunquit and Kennebunkport are two beachfront cities in Maine that you won’t want to miss on your five day New England fall road trip.

These two coastal towns are two of the most charming beach towns I have visited.

Ogunquit and Kennebunkport, Maine, exude those classic New England vibes with their picturesque coastal views, charming seaside cottages, and historic architecture.

You won’t find many people visiting during the fall, so it will seem like you have the coast to yourself.

Plan to spend the night in Ogunquit.

This area has some fantastic hotels, including the Gorges Grant Hotel. This small hotel is perfect for an overnight stay.

If the Gorges Grant is unavailable, the Sparhawk Oceanfront Resort is a highly-rated oceanfront hotel, and the Admiral’s Inn Resort offers spacious rooms in a great location.

Day Five: Massachusetts/Rhode Island

On day five, leave Maine and travel to Cape Cod, Massachusetts.

If you want to see a little bit of everything in New England quickly, this five day New England fall road trip will inspire you to start planning your perfect trip.

What did I learn from this five-day New England fall road trip?

We logged over 1,000 miles in five short days, and it was totally worth the adventure. Now, if I could afford three weeks on the East Coast, I would, without a doubt, explore much more. But, if you only have five days, you will still have a fantastic time.

Reflecting on this magnificent road trip, taking this whirlwind five-day road trip across five enchanting New England states in the fall was nothing short of extraordinary.

We marveled at the kaleidoscope of fall foliage, conquered majestic mountains, and dipped our toes in the frigid waters, all in the span of a thousand miles.

Along the way, we wandered through charming towns, savoring the essence of each unique community.

Our non-stop vacation was a thrilling adventure that left us breathless and utterly content.

The memories we created, the sights we witnessed, and the experiences we had made every mile worth it.

New England’s autumnal magic is a treasure that lingers long after the journey ends, leaving you with a profound appreciation for this remarkable region.

I’m delighted to have had the chance to explore the best of New England. While this adventure is entirely achievable, I wouldn’t describe it as a leisurely getaway. Expect to be constantly on the move.

Advice for you to consider when you plan your trip

If I had to change the itinerary after visiting, here is what I would do differently.

• I would spend more time in Vermont, especially in the Stowe area.

• The L.L. Bean flagship store is neat, but I would skip it and spend more time on the coast of Maine. I regret missing out on going to Bar Harbor and Acadia National Park.

• The Kancamagus Highway is 100% worth the drive.

• Cape Cod is amazing, but I would save it for its own trip. The time it took to drive there is not worth it since many restaurants and shops are closed for the season.

• Instead, I would spend that time in Rhode Island, especially Newport. (Since originally writing this post, I returned to Rhode Island and Connecticut, and wholeheartedly agree Newport is worth a visit. I also found many fall activities in Connecticut worthy of your time.)

In conclusion, no matter which route you take, New England is beautiful in the fall. The crisp, cool mornings and the vibrant fall colors greet you and encourage you to get out and explore nature and its beauty.