New England Road Trip By a Local (Fall 2025)

New England is home to the some the most beautiful mountain villages, beach towns, and unique cities in the USA. I am a proud New Englander and have been to so many adorable areas all around the northeast. This New England Road Trip is the perfect thing to do for first time visitors looking to see the highlights of New England along with some hidden gems. Read on to discover your New England Road Trip.

Best Time To Visit New England

Mid October is the best time to visit the northeast as the fall foliage is at its peak. Also halloween is such a fun holiday in New England so all though the month of October all things halloween will be in full swing.

Another great time to do this road trip is over the holidays. Christmas in New England is magical and gorgeous.

You could also do this road trip in the summer. If you don't like the cold the summer is a perfect time to visit New England. Even in the summer it never gets too hot in the northeast, but definitely more comfortable than other seasons.

What To Expect In New England

Language: English 

Currency: US dollar

Plugs: type A & B

Safety: New England is super safe, but always take normal precautions. (Avoid walking alone at night, keep belongings on your person, etc.)

The Best New England Road Trip

First Stop On Your New England Road Trip: Boston

Fly into Boston, Massachusetts and rent a car and stay the night (or a few days).

Where To Stay In Boston

I would recommend staying in the Seaport, Beacon Hill, or Downtown to start  your New England road trip off right. You would be on the water and in close proximity to the cities best restaurants and coffee. A great hotel in the Seaport is the Seaport Hotel. If you want to see the historical side of Boston I would recommend staying closer to the Boston Common, or the downtown area. The Newbury is a beautiful hotel in the heart of Boston.

For a more in-depth guide to Boston's neighborhoods and hotels checkout our guide to where to stay in Boston!

Coffee In Boston

First things first - coffee. Go to Tatte. This bakery has the best pastries and coffee in the city.

What To Do In Boston

There is so much to do and see in Boston. You could Visit the historical Fenway Park, walk the freedom trail, or walkdown Newbury street to see the beautiful Boston architecture. For of my local recs for Boston - here is our locals guide to Boston.

Where To Dine In Boston

For dinner you have to go to the North End. Seriously the best Italian food outside of Italy. My favorite restaurant in the North End is The Daily Catch, but you can go wrong, everything is insanely good. For drinks go to Hecate.

☘️Read Next - A Locals Guide To Boston

Drive North Of Boston

Hop in the car and head north. 30 minutes from Boston is a gorgeous hiking spot, Holt Hill. It's only a 40 minute hike and you will find two spectacular view points on it!

Another perk to Holt Hill is that it is a complete hidden gem in New England. I am always walking my dogs in the woods and this is the most beautiful hike I have come across.

If you are hungry in North Andover, get something from Pita Thyme.

Spend The Night In Portsmouth, New Hampshire

My favorite weekend day trip is 1000% Portsmouth.

Where To Stay In Portsmouth

Stay the night in Portsmouth. I would recommend staying in the Residence Inn. I stayed there a few years ago and it was wonderful, in a great location and reasonably priced. 

If you are looking for something a bit more upscale Hotel Thaxter.

Coffee In Portsmouth, New Hampshire

When you get there go to Popovers on the Square. Get yourself a fresh popover with maple butter and coffee. These are the best popovers I’ve ever had.

Holidays In Portsmouth

Portsmouth during the holidays is so fun. They have Christmas wreaths on every lamp pole and and huge Christmas tree they light every night. And during the autumn - pumpkins, scarecrows, and halloween decor. If you are staying the night here go for an evening stroll and get some hot chocolate.

What To Do In Portsmouth

Anyway, while in Portsmouth explore Market Street, Visit Strawbery Banke Museum, or Moffatt-Ladd House & Garden. Honestly - my favorite thing to do in Portsmouth is look in the unique shops and sip coffee on the sidewalk cafes. It's just a vibey town. For more on what to do in Portsmouth checkout our guide to Portsmouth, New Hampshire.

Where To Dine In Portsmouth

For dinner check out Street. If you are feeling a bit more adventurous go to, my all time favorite 5 Thai Bistro.

🐟Read Next - A Complete Guide To Portsmouth, New Hampshire

Drive North To Stowe, Vermont

Next stop is Stowe, VT.

Where To Stay At Stowe

If you want - splurge on the Stowe Mountain Lodge for accommodation. This hotel is right on the mountain and is a beautiful place to stay. Although if you can't get in at Stowe - The Trapp Family Lodge is also a nice place to stay.

What To Do In Stowe

You should hike Mount Mansfield. This gorgeous hike is non negotiable while in Stowe. After your hike pickup some Vermont maple syrup as a souvenir. There are little shops (that look like cabins) you can get some maple syrup from.

Where To Dine In Stowe

While in Stowe you can dine at The Bench. The food is so good and it is not too expensive.

End Your New England Road Trip In Burlington, Vermont

Last stop of your New England Road Trip has to be Burlington, Vermont. On the shore of Lake Champlain, Burlington is a free spirit city.

Where To Stay In Burlington

You could stay at the Courtyard Harbor if you are looking for an affordable stay. A really cool boutique hotel that we love in Burlington is the Blind Tiger.

What To Do In Burlington

Make your way down church street and pop into a few shops, have a coffee, and people watch.

Be sure to visit a farm! Typically selling pumpkins, apple cider donuts and hay rides. Farms in New England are super fun in the fall and the holidays. In the fall we really get into halloween, pumpkins, apple cider and donuts. During the holidays we will chop down our own christmas tree at the farm and drink hot cocoa.

Where To Dine In Burlington

For dinner check out American Flatbread.

🎃Read Next - A Complete Guide To Burlington, VT

Where To Go From Burlington, VT

If you are not quite done with New England and you want to add on to your trip here are some other stops you should add on.

Portland, ME - Just a tiny bit north of Portsmouth, NH is Portland, ME. So if you decide to spot here do it right after Portsmouth. Portland is full of shops and delicious seafood!

Acadia National Park, ME - Acadia is in northern Maine, so a bit of a drive but it is totally worth it. The National Park has amazing hikes and views. Acadia is the only National Park in the north east. Only go to Acadia in the fall or summer because Maine is absolutely freezing in the winter and parts of the spring. The trails will be way too icy to hike.

Bar Harbor, ME - In between Portland and Acadia National Park is Bar Harbor. Bar Harbor is such a cute town on the water. Make sure you get a Maine lobster roll here.

Nantucket, MA - Nantucket is my favorite place on the northeast. Nantucket should only be visited in the summer as in the winter all the shops are closed and there is nothing to do. Nantucket in the summer is absolutely amazing. With the beaches, food, people and shops there os no where else like Nantucket. The only reason it is not on this road trip itinerary is because you can't drive there, it's an island.

🇺🇲Related Post - 15 Places To Visit In Massachusetts

New England Road Trip FAQs:

What is the best month to road trip in New England?

The best month to road trip in New England has to be October or September. In September the weather is perfect, but in October you get that fall vibe and the foliage is at its peak!

How many days do you need in New England?

There are so many hidden gems in New England that it would take a lifetime to explore all of them. But to see some of the more popular places I would give yourself a week or two.

How long does it take to drive through the New England states?

The New England states are all pretty small. So if you want to see all of them in one trip, it's doable. I would give yourself 4 days to stop and explore each one. If you just want to drive through them all, you could do it in 4 hours.

Which New England state is the prettiest?

Many people will say Vermont and Maine, but I am bias to my home state of Massachusetts.

New England Road Trip Wrap Up

New England is easily my favorite region in the United States. We hope that this New England Road Trip for this fall helps you plan the perfect trip! If you liked this post and are still in need of New England Travel inspirations check out our list of the 11 Cutest Towns In New England - From a Local or What To Pack For Autumn New England.

Happy Travels,

Daisy