This is the view from Mount Willard in New Hampshire. This view makes you feel like you're on top of the world in New Hampshire's White Mountain National Forest. You can see one of the main roads that cuts through the separate peaks and incredible fall foliage below.

As a Bostonian and New Englander, I may be a bit biased, but I believe one of the best road trips in the USA is a New England road trip, especially in the fall. There really isn’t a bad time to visit New England, as it’s also a wonderful destination in the summer and a great place to spend the holidays-especially if you love to ski or snowboard! This area of America is known for its picturesque small towns, iconic lighthouses, and beaches. I’ve explored most of the coast, including Massachusetts’ island of Nantucket and the very northern Acadia National Park in Maine. As a gal from Boston I’ll share all of its hidden gems to explore during the fall or summer seasons. Keep reading if you’re looking for the perfect New England road trip itinerary!

New England Road Trip from Boston: The best fall and summer itineraries!

When planning a New England road trip, start in Boston. As a Bostonian, I love the city of Boston and think it’s not only a wonderful city to visit but its international airport is perfect for round-trip flights. There are other airports in New England but none that offer as many flights as Boston. You can also rent a car from the Boston airport, which is essential when planning your road trip. Although Boston has a wonderful subway and bus system, you won’t be able to visit all the locations suggested below without a car.

I’ll give you two 10 day New England itineraries, one for fall then one for summer. There’s so much to do and see so keep scrolling!

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The aesthetic in the fall in Boston is lovely especially this area in Beacon Hill with foliage adorning the cobblestone walkways and historic brownstones. You may even see an old oil lamp in this area as well!

How to plan a Fall Road Trip in New England

During the autumn months, you’ll find some of the best fall foliage in the USA in New England. That being said, it’s no secret and can get very, very busy. If you’re planning a New England road trip in the fall, you’ll need to plan at least six months in advance, maybe even earlier. If you aren’t the best planner, there may not be as many rental cars or accommodation choices available to you.

With that in mind, it can be difficult to predict when exactly fall foliage will be at its peak so far in advance. The foliage in New England typically peaks from mid-October to the beginning of November but can vary from year to year based on weather conditions. The foliage will start changing in the northern part of New England and continue south throughout the season.

I’ve created a post about all the best places to stay in Boston, check it out!

When is the best time to take a Fall Road Trip in New England

Even though the forecast can change every year based on weather conditions, early to mid-October is usually a good time to visit for leaf peeping.

What are the best places to see fall foliage in New England?

The best places to see fall foliage in New England are in Vermont’s small towns, along the famous Kancamagus Highway in New Hampshire, and in the city of Boston.

Both New England road trip itineraries in the fall and summer will suggest visiting Boston for a few days. Here are all the best things to do in Boston and the only Boston itinerary you need!

One of the best places to visit on a New England road trip is Woodstock, Vermont. Make sure to visit the Woodstock Inn and Spa which appears like a large, white mansion with a large porch with pumpkins, mums, and fall foliage adorning the large front lawn.

New England Road Trip 10 Day Fall Itinerary

Day 1-2: Explore Boston

Day 3: Drive north to Salem, Massachusetts

Day 4-6: Continue to New Hampshire

Day 7-9: Explore Vermont, including Woodstock and Stowe

Day 10: Back to Boston, or extend your trip

You can extend to the Berkshires, drive the Mohawk Highway, or continue to Connecticut and Rhode Island.

New England Road Trip Itinerary

Below is a New England road trip map that gives a visual picture of both summer and fall itineraries suggested for your New England road trip.

If you're planning a New England road trip, take a look at all the icons for both a fall and summer road trip itinerary in relation to their location in New England.

Need help planning your New England road trip?!

As a Bostonian, this really is my specialty! Contact me as I am a travel advisor and work with some of the best and most luxurious properties and networks around the world!

This is quintessential Vermont in the fall with small town farms and fall foliage adorning them.

Start in the beautiful city of Boston

Similar to the summer itinerary above, start your New England road trip in fall in Boston. You can spend a day or easily three or four days in Boston, depending on how much of the city you want to see. I have included a 2 day Boston itinerary above, or here’s a more comprehensive Boston itinerary to help plan your trip!

Planning a trip to New England in the fall? Here are the best things to do in New England in the fall.

Spend a day in the USA’s Halloweentown

If you’re visiting New England in the fall, especially in October, you have to visit Salem. Who doesn’t want to spend the spooky season in USA’s Halloweentown?! The famous festive movie Hocus Pocus was filmed in this small town, and you can visit most of the sites where the movie was filmed. During the entire month of October, you’ll find crowds in costumes, and the town and local stores are decorated. Salem is also famous for the Salem Witch Trials, but the museum is underwhelming and expensive. Make sure to check out their website, since you don’t necessarily have to visit, especially if you don’t have enough time.

I would highly recommend visiting the Witch House instead, but you will need a booking in advance!

Find Fall Foliage in New Hampshire

One of the best places to find fall foliage in New England is along the Kancamagus Highway. This area is in the picturesque White Mountains and Franconia Notch in New Hampshire. You may find it odd that you can find plenty of fall foliage locations along a highway, but this isn’t just any highway. This highway, or double-lane country road, winds through the White Mountains and runs between the small towns of Lincoln and Conway. There are multiple areas to stop along this highway that provide the most scenic fall foliage opportunities. Bring your hiking boots if you’re up for a colorful stroll.

This classic farm in Woodstock, Vermont has a red farm house and a large cedar shingle barn at the end of a long, curvy road. It even has a small pond that is so idyllic in front of the property.

Continue to Vermont

Vermont is one of the most popular places for a New England road trip in fall. If you visit during the autumn season it’s easy to see why, it literally looks straight out of a Gilmore Girls set. Here are two of the more popular towns to visit in Vermont, one being my absolute favorite!

My favorite town in Vermont, Woodstock!

Here’s a comprehensive guide to visiting Woodstock, Vermont in the fall. In this guide you’ll find the best things to do in Woodstock including visiting Billings Farm and Museum, Quechee Gorge, and Sugarbush Farm. Make a reservation for the beautiful Simon Pierce restaurant or at the Woodstock Inn Spa. The Woodstock Inn is also one of the best places to stay in Vermont, and I highly recommend a stay when visiting!

The popular Stowe, Vermont

Even though it’s not my favorite area to visit in Vermont, it’s definitely a fan favorite! Here’s a comprehensive guide to Stowe, Vermont in the fall. Don’t miss driving Smuggler’s Notch where you’ll find some of the most beautiful fall foliage on your New England road trip. Start your drive on Route 100, then exit onto Route 108. This highway will take you all the way to the ski resort in Smuggler’s Notch and through very windy roads that aren’t suitable for RVs or large trucks. You can even continue this road all the way to Canada if you wish!

Some of the other best things to do in Stowe, Vermont include visiting Cold Hollow Cider Mill, Percy Corn Maze, the Stowe Gondola, and Moss Glenn Falls. Enjoy a beer at the Von Trapp Family Lodge, or book a stay since it’s one of the best hotels in Vermont.

Visit Cold Hollow Cider Mill

Cold Hollow Cider Mill is one of the most iconic places to visit in Vermont in the fall. They are best known for their delicious cider donuts. You can also buy other treats and souvenirs in their store. Even though this place can get busy, their lines move quickly!

Best Places to Stay in Vermont

When looking for hotels to stay in during your New England road trip, here are some of the best places to stay in Vermont.

This classic Cape Cod home with gray cedar shingles is adorned with white window boxes and a large American flag draped out front. It's adorned with potted plants and a white, picket fence. It's located on the famous Commercial Street in the quaint coastal Provincetown on Cape Cod.

New England Road Trip 10 Day Summer Itinerary

Day 1- 2: Explore Boston

Day 3: Drive north to Gloucester and Rockport, Massachusetts and have a beach day at Crane’s Beach

Day 4-5: Drive further north to Maine, visit Kennebunkport, Ogunquit, or Portland

Day 6-7: Continue from Maine to Rhode Island, visit Newport

Day 8-10: Visit Cape Cod, including day trip to Nantucket

If you want to extend your trip can continue north to Bar Harbor and Acadia National Park but it is quite a drive!

Need help planning your New England?!

As a Bostonian, this really is my specialty! Contact me as I am a travel advisor and work with some of the best and most luxurious properties and networks around the world!

The beautiful Acorn Street in Boston is adorned with a cobblestone walkway, historic oil lamp, and brick brownstones with black shutters and floral window boxes.

Boston 2-day Itinerary from a Local!

Start your New England road trip in Boston. As a local Bostonian, here are some of the best things to do in Boston.

Walk the Freedom Trail and enjoy the North End

Even though you might not have time to walk the entire Freedom Trail, you’ll at least have time to see the highlights. Some of the highlights include the Massachusetts State House in Beacon Hill, which is famous for its gold dome. Other highlights are the Old State House in downtown, the Paul Revere House, and the Old North Church in the North End. The North End is known for its Italian influences and culture. Most of the restaurants and shops you’ll find here are Italian, and the food is delicious. Make sure to make a reservation before visiting. I’ve included some of my favorites in this itinerary of all the best things to see and do in Boston.

Wander Beacon Hill, Charles Esplanade, and the North End

Don’t leave Boston without wandering through Beacon Hill and the Public Garden. These are some of the most beautiful areas in Boston, and the most historical. You’ll find Boston’s famous brownstones in this neighborhood, and cobblestone streets. A few of my favorite places in this area are Tatte cafe, Beacon Hill Bookshop, and one of the most photographed streets in America- Acorn Street!

The Charles Esplanade isn’t a far walk from Beacon Hill, and it offers beautiful views of Boston’s ‘other skyline’- Cambridge. From the Esplanade you can see the prestigious Massachusetts Institute of Technology, or MIT. After a long day make sure to book in for reservations in the North End, which is Boston’s ‘Little Italy’. Some of my favorite restaurants in the North End include Mamma Maria, Carmelina, and Regina’s Pizzeria. You also can’t miss trying a cannoli for dessert at Mike’s Pastry or Modern Pastry.

Visit Fenway Park or a Boston museum

On your second day, one of the best things to do in Boston is to visit Fenway Park, even better if you can see the Red Sox play! If you’re visiting during the off-season, you can tour this famous ballpark on a guided tour. This is one Boston tour I always recommend to family and friends when they visit. All the guides have such a great sense of humor and really make the tour memorable.

Close to Fenway Park is one of my favorite museums in the world, only second to the Louvre in Paris! The Isabella Stewart Gardner Museum is a true gem, a piece of Europe in Boston that houses an impressive collection of European, American, and Asian art. The real showstopper of this museum is the courtyard and garden in the middle of the museum. The courtyard is multiple stories tall with foliage that changes with the seasons. It really is one of the most beautiful places in Boston, so don’t miss it on your New England road trip!

If you have the time and energy, you won’t regret walking around beautiful Back Bay and down the brownstone- and tree-lined Commonwealth Avenue (my husband’s favorite part of Boston).

Enjoy a Boston Duck Tour

Before ending the day in Boston, consider booking a Boston duck tour. This is such a great way to see the city, as you not only see it by land but by sea. It’s of course a touristy thing to do but surprisingly so worth it! You could even book a tour for the beginning of your stay, which will help you get a better sense of direction while visiting.

Drive north to Gloucester and Rockport

After visiting Boston for a few days, continue your New England road trip north, and stop along the coast in Gloucester and Rockport. Gloucester has quite a few beaches along the coast if you want to have a beach day or visit Bearskin Neck in Rockport and the famous Motif Number 1. This former fishing shack offers an idyllic New England scene among the harbor. It’s famous because it’s known as “the most often-painted building in America.”

Visit Crane’s Beach

Crane’s Beach is one of my favorite beaches in New England, and it’s not far from another European gem in New England, The Crane Estate. Be prepared if you’re visiting in the summer, as some days-especially weekends-require you to make a reservation in advance. Keep in mind, if you’re visiting mid-July to early August the greenhead flies are quite prevalent, and they really bite! You can always check out their website for up-to-date information during the season.

Here’s a comprehensive list of the best beach towns in New England.

This famous Earth at Hidden Pond restaurant feels like you're dining in a private storybook forest as one of the walls is adorned with tree stump decor and there are branches decorated with small lights hanging from the ceiling. There are potted plants throughout to continue the nature theme.

Continue to Maine during your New England Road Trip

Stroll through Kennebunkport and Ogunquit

Heading farther north toward Maine on your New England road trip, make sure to stop at one of the most beautiful lighthouses in New England, Cape Neddick Lighthouse. You can also plan to enjoy a beach day near Kennebunkport at Gooch’s Beach or Goose Rocks Beach, as these are some of the best beaches in New England. Don’t miss having a delicious lobster roll for lunch at Langsford or Nunan’s. Kennebunkport also has the quaintest downtown area with lots of shops and restaurants. If you’re looking for somewhere to dine in the evening, I highly recommend Earth at Hidden Pond at the luxurious Hidden Pond Hotel. This restaurant has such a beautiful, rustic aesthetic, and the most delicious food!

Even though I’m quickly switching from summer to winter, this quaint Maine town is magical during the holiday season. Here’s a comprehensive guide for all the best things to do in Kennebunkport in winter.

This is Cape Neddick Lighthouse which is located on a small island that's appears like a classic New England scene. The white lighthouse also has a white farmhouse connected and a small red barn right in front, surrounded by its rocky island in the ocean.

Stay at Cliff House, Maine

One of the best hotels in Maine is the Cliff House. This four-star property overlooking the Atlantic Ocean spans 70 acres and has four pools, an adults-only spa, and an extensive fitness center. It will be the perfect spot to stay in Maine during your New England road trip.

Spend an afternoon in Portland

Even though itineraries-and even Google and the internet-will suggest spending time in Portland, an unpopular opinion I have is that it’s just ok. I wouldn’t recommend spending the night here, or even a full day as there really isn’t that much to see and do. Portland Head Light is probably the best thing to do in Portland, but when my husband and I visited many summers ago we loved getting out on the water with Nautilus Sailing.

Visit America’s smallest state

One of my favorite places in New England in the summer is Newport, Rhode Island. It will take a few hours to drive from Maine to Rhode Island, but it’s well worth it to visit America’s smallest state. Even though this next comprehensive guide is aimed more towards the winter season, here are some of the best things to do in Newport, Rhode Island any time of the year!

This classic Cape Cod house adorned with hydrangeas and an American flag out front is a classic scene in New England in the summer and one you'll find along your New England road trip.

New England’s idyllic Cape Cod and islands

If you’re planning a New England road trip in the summer, you could spend an entire week on Cape Cod. For the purpose of including it in this itinerary and making time for other New England gems, this itinerary spends at least two days in this idyllic summer destination. I have to be honest; it’s going to be impossible to see the best of Cape Cod in just a day or two. If you are going to spend a night or two, here’s a comprehensive guide to Cape Cod. If you can swing it and plan a day trip to Nantucket from Cape Cod, it’s one of my favorite places in the world! Keep reading to find out how.

These roses adorned cottages can be found in the storybook village of Sconset on Massachusetts's island of Nantucket. This storybook village is adorned with beautiful red, pink, and white roses and pink, purple, and blue hydrangeas. It really is simply magical!

How to Day Trip to Nantucket

Even though I’ve traveled around the world, Nantucket is one of my favorite places. It’s simply unlike anywhere I’ve ever been, and in the summer season it’s even more magical. If you time your New England road trip in the summer during June and July, Nantucket will reward you with the most beautiful roses and hydrangeas in bloom. You’ll think you’ve stepped into a Disney fairytale! Here’s all the information you need to know for how to plan the perfect day trip to Nantucket.

What if I have more than 10 Days in New England in the summer?

If you’re looking to book a New England road trip for more than 10 days during the summer, there are so many options for this! When spending time in Maine, you can continue north to Acadia National Park and spend some time there and in Bar Harbor. If you love the beach, you can spend more time on Cape Cod and its islands, Nantucket and Martha’s Vineyard.

Here’s some information you have to read if you’re deciding which island is best for your New England road trip, which island is better? Nantucket vs Martha’s Vineyard.

One of the best things to do on a New England road trip is to get on the water and to take a sunset sail!

What to pack for a fall road trip in New England

Whether you’re taking a summer or fall road trip, you must pack a pair of comfortable sneakers. These Chloe Nama sneakers are some of my favorites because they are so comfortable and also fashionable. I have a pair in spring colors and also just black for the fall and winter. I also love these Adidas options too.

You’ll also want to pack bug spray for summer and fall, specifically when you travel in more of the northeastern area of New England.

New England, similar to England’s weather, can be a bit unpredictable. Make sure you pack a durable rain jacket and umbrella.

You can get inspiration and shop my outfits on my Shop page.

How many days for a New England road trip?

New England road trip 7 days

We all know Americans only get so many days of vacation, unlike living in London I had a few weeks more. If you can only plan for a 7 day New England road trip, the itineraries above are perfect and both offer a variety of the best things to do in New England. If you want to see more of New England or spend more time in Boston, you will most likely need more than 7 days.

New England road trip 14 days

Even though 14 days may feel a bit too long on the road for some people, this will allow you to see a good portion of New England. If you’re visiting in the summer, you can’t miss spending time on Cape Cod, relaxing on the beach, or going whale watching. You can also visit the Cape’s islands, Nantucket and Martha’s Vineyard even as a day trip! Although I’ve lived in London and explored much of Europe and the rest of the world, Nantucket is still one of my favorite places I’ve ever visited.

If you’re visiting in the fall, you can drive farther north to experience more of New England’s fall foliage in Maine, especially in Acadia National Park.

New England road trip with kids

Both of these fall and summer New England road trip itineraries will be perfect for kids. A few of the best places to visit in Boston with kids is the Museum of Science, Boston Tea Party Museum, New England Acquarium, and Fenway Park.

A few other gems in New England that are perfect for kids are The Mount Washington Cog Railway, Mystic Seaport Museum, Canobie Lake Park, and Story Land for littles.

Final Thoughts for your ultimate New England road trip

A New England road trip is one of the best to take in the United States. This area attracts visitors from around the world in the fall, and New England’s own residents in the summer. Whether you’re planning a road trip in either the fall or summer, both seasons offer a variety of things to do and see. After reading these itineraries you can see it’s possible to see the best of New England in 10 days, but you really can spend even more time during either season! If you feel overwhelmed planning your next New England road trip, feel free to send me a message!