There’s nothing better than walking through adorable towns with a warm apple cider in your hands and orange trees all around. 🍁 It’s time to go on your New England Fall road trip for the ultimate autumn adventure. You will absolutely fall in love with the charm and beauty of these gorgeous destinations.
I’ve now gone on three different trips to New England for leaf peeping. 🚙 So I feel like I’ve figured out the very best destinations and the perfect route for your journey. I could seriously go back to this area of the country every single autumn, because the colors are insane and the vibes are immaculate!
Below you’ll find everything you need to plan the greatest adventure to New England. This road trip is perfect for people who have at least a week to spend in this area, but it can be extended to even longer. Now, get ready for a wonderful trip!
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Table of Contents
New England Fall Road Trip Itinerary
Quick Itinerary Breakdown:
Portland, Maine: 1-2 Days
Acadia National Park & Bar Harbor, Maine: 1-3 Days
White Mountains, New Hampshire: 1-3 Days
Stowe, Vermont: 1-2 Days
Woodstock, Vermont: 1 Day
Portland, ME
Fly into this adorable coastal town to start your Fall New England road trip off on the right foot! What was once a small port town ⚓️, it’s turned into a wonderful destination for travelers near and far.
Stay a couple of days in the area so you can see the famous lighthouses, get out on the water, explore Victorian mansions, and try all the delicious food. There are plenty of wonderful restaurants and shops t the fishing wharves, then you can visit the Western Promenade nearby with stunning views. You’ll come to fall in love with this quaint small city.
⭐️ ROAD TRIP TIP: You can stop at Red’s Eats for the best Lobster Rolls or the LL Bean Headquarters on your way from Portland to Acadia! ⭐️
Things to Do in Portland, Maine
- Visit the Portland Head Light
- Get donuts at Holy Donut
- Take a boat out
- Go on a brewery tour
Where to Stay in Portland
Portland is a coastal city with lots of great options for lodging, it’s grown a lot in the past few years. So, they have plenty of chain hotels in the downtown area as well as more boutique places to stay.
I recommend being close to the Old Port, so that you can walk around and explore. Plus, this area has great options with water views to take in the scenery.
Hotels in Portland Maine:
Acadia National Park, ME
Acadia National Park is like a painting in the Fall. This National Park encompasses the scenic Mount Desert Island. Pine trees mix with rugged mountains all over a rocky coastline. 🌊 It’s truly the ultimate fall destination!
Start your morning by seeing the first sunrise in the continental US at Cadillac Mountain 🌅, then spend the day doing one of the fantastic hikes in the park, and finally make sure to stop by the beautiful Jordan Pond.
Once you’ve had your fill in the park, you can journey to the town of Bar Harbor. Get a delicious lobster roll 🦞 or just stroll through the charming area!
Tip: You must get reservations to see sunrise at Cadillac Mountain!
Things to Do in Acadia
- Watch the first sunrise in the country at Cadillac Mountain
- Visit Jordan Pond
- Hike up the Beehive or Precipice Trails
- Walk around Bar Harbor
Where to Stay in Acadia & Bar Harbor
Acadia is a very popular park, especially in the summer or fall. So, if you are planning on visiting then I would make reservations early! You can stay at one of the campgrounds within the park or stay at the cute hotels in the town of Bar Harbor.
There are two campgrounds in the Mount Desert area of Acadia: Blackwoods and Seawall. They require reservations in advance and are usually open through mid-October.
Best Lodging Near Acadia:
White Mountains, NH
The White Mountains may have some of the best fall foliage in the entire country! 🍂These sprawling mountains cover over a quarter of the state of New Hampshire and getting to see them in the autumn is spectacular.
You could spend a full week in the White Mountains, but I recommend having at least two days if you can. On the first day, you can explore the East side of the White Mountains. Take the stunning Conway Scenic Railway and take the Railway up to Mount Washington, the highest peak in the Northeast.
Then, on your second take you can drive the Kancamagus Highway, which is full of orange and yellow trees in the fall. Before heading to Franconia Notch State Park and seeing the iconic Artist Bluff viewpoint. 📸
Things to Do in the White Mountains
- Take the iconic Conway Scenic Train
- Trek to Artist’s Bluff
- Head up to Mount Washington
- See the view at Table Mountain
- Drive the gorgeous Kancamagus Highway
Where to Stay in the White Mountains
Choosing where to stay in the White Mountains may be one of the hardest decisions you need to make on this New England fall road trip. There are a number of towns you can choose to stay in, so you may want to choose based on where you want to spend the most time.
Some of the best towns to stay in are Littleton, North Conway, Jackson, Sugar Hill, Woodstock or Lincoln.
If you are a camper or van lifer, there are plenty of free camping areas in the White Mountains, so you can move more easily through them.
Hotels in the White Mountains:
- Eastern Slope Inn Resort (North Conway)
- The Inn at Thorne Hill (Jackson)
- Sugar Hill Inn (Sugar Hill)
- Woodwards White Mountain Resort (Lincoln)
Stowe, VT
Stowe is well known as being a fantastic skiing destination, but it’s also a wonderful place to venture to in the months of September and October. Mount Mansfield sits above this charming Northeastern town with colors covering the area and tall church steeples. It’s like something out of a story book.
It’s so easy to find things to do in Stowe when you visit. First, venture out to the surrounding areas to try the delicious fall treats of apple cider donuts and hot apple cider 🍎. Then, take a day to either hike up or drive up to the peak of Mount Mansfield. It’s a fantastic year round destination.
Things to Do in Stowe
- Hike to the top of Mount Mansfield
- Get apple cider donuts at Cold Hollow Cider Mill
- Take a tour at Ben & Jerry’s
- Visit Smugglers Notch State Park
Where to Stay in Stowe
Stowe is a popular ski town, so there are plenty of inns and lodges to spend the night. It’s also a fairly compact area, so you won’t find town too far from any of the hotel options! Which means you’ve got a variety of options to choose from for your time in the area!
Hotels in Stowe:
Woodstock, VT
Woodstock is the epitome of small New England towns in the fall. Adorable shops, covered bridges, rolling hills, and historic mansions. It’s one of those places that you will not want to miss on your journey to New England!
I recommend spending a day or two in this adorable town. It’s one of the best places to see the foliage either on the mountainside or by going on a drive through the surrounding mountains. You’ll truly be endeared by this incredible autumn destination.
Note: The road to Sleepy Hollow Farm and other private roads are closed during the fall. 🚫
Things to Do in Woodstock
- Explore the covered bridges
- Try syrups and cheeses at Sugarbush Farms
- Shop in the adorable downtown
- Hike up Mount Tom
Where to Stay in Woodstock
Woodstock is an adorable small town, which means most things are very close together. The Woodstock Inn & Resort is probably the most famous place to stay and it’s right along the main strip, so it’s very walkable. But, there are many cute spots to choose from. 🤗
Hotels in Woodstock:
Planning Your New England Road Trip
Where to Start Your Road Trip
If you are flying in from other parts of the country, then I recommend the Boston or Portland airports. Boston has a larger airport with more flight options, so they may be cheaper, but the drives will be slightly longer. From there, you will definitely want a rental car to get around. 🚗
I recommend flying into Boston or Portland, Maine! ✈️
For those who are from the East Coast, you can make this drive into a one way route. Plus, you may be able to add more destinations along your drive as well. We came up from DC and stopped in New Haven and Oguinquit on our way North, which were both so charming!
When is Peak Fall Foliage?
Fall foliage predictions change every year and depend a lot on various factors. However, that being said it usually peaks in New England from the last week of September until somewhere in mid-October.
This trip is best from late September to mid-October!
All of the trips that we took were in the first couple weeks of October. During our adventures we were a little ahead of the peak in some destinations, while others were perfectly timed! You can look at updates fall foliage predictions here!
Why You Should Visit New England in the Fall
I think that New England is the quintessential place to experience the fall. It has everything you could possibly want from mountain landscapes covered in foliage, hot fresh apple cider, and adorable small towns.
New England really gives off Gilmore Girls vibes and there’s nothing better than that!
There’s something that is so cozy about wandering through these small towns with a warm sweater on and the crisp chill in the air. 💨 You’ll be amazed at all of the beauty and charm that New England has and you’ll want to spend every single fall there!
Places You Could Add With More Time
If you have more time to explore, then there are so many other great destinations you could add to your road trip. Honestly, you could spend every fall visiting a new destination in New England, because there are so many great places to see, but here are a few ideas.
Spend more time in Massachusetts and add the town of Salem or the beautiful area of the Berkshires to your trip. Salem is a very popular spot in the Fall, because it was home to the Salem witch trails, which makes it a spooky spot to visit. 👻 While, the Berkshires have incredible vistas.
Travelers that are flying into Boston or driving up from the South can add the beautiful state of Rhode Island to their trip. Newport is one of my favorite places on the East Coast and it’s definitely worth seeing. While, Providence is a lovely city with great food as well.
New England Fall Packing Guide
Weather can be all over the place in the Fall, so make sure to pack plenty of layers. Now, many days can be gorgeous and sunny, while others can be bitterly cold or rainy. I expect that you’ll visit a bunch of different weather types on your trip.
On all of my trips up to New England, I always pack a warm jacket, a rain coat, and a cute flannel or sweater. It’s a great time to show off your fun Fall fits! If you want to get outdoors or hike, then you will also want to bring good durable hiking layers.
Packing List
- Comfortable Hiking Boots
- Blundstones or Boots
- Hiking Poles (if you plan on hiking)
- Warm Knit Sweater
- Flannel
- Hiking Pants (if hiking)
- Gloves
- Sunscreen
- Sunglasses
- Winter Hat
- Rain jacket
- Light winter jacket
Final Tips for Your New England Fall Road Trip
Honestly, I think the best tip for taking a road trip in the Fall is to be flexible with your itinerary. Even if you can’t change your hotel bookings, at least leaving the days open for different things. Some days may be beautiful where you want to do a bunch of things, while others can be cold and rainy. 🌧 So, just be open to possibilities and you’ll have a fantastic time!
Let me know in the comments if you enjoyed this guide!
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