This trip will take you through major cities, national landmarks, and natural landscapes that will astound you. A Northeast road trip will have you falling in love with New England. From the quaint towns to the gorgeous landscapes to the bustling cities there’s something for everyone. So, get ready to hit the road!
After graduating college, my brother Nick and I decided we wanted to go on a celebratory trip. Even though we were from the East Coast, we hadn’t been up to the Northeast. So, we went out on the road and it was one of my favorite trips! I’ve now been back in the Fall as well and I would go back 100 times.
This itinerary is perfect anytime from late-spring through early fall. So, I hope you add it to your bucket list. Below you will find our itinerary and a guide for a great week long road trip!
You Might Also Like These Posts:
- Your Guide to Visiting Acadia in October
- 5 Best Fall Destinations On the East Coast
- The Best New England Fall Road Trip Itinerary
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Table of Contents
Planning Your Northeast Road Trip
Where to Start Your Northeast Road Trip
If you’re going on a Northeast road trip, you have a few options of where to start and where to fly in. If you’re coming from further away than the East Coast, then I recommend flying into New York or Boston.
These airports have a ton of flight options to choose from. New York is just a couple hours south of New Haven. If you fly into Boston, you may want to skip over Connecticut and focus on the spots further North.
For those driving in, you can follow i-95 up North and start your journey!
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Best Time to Go on a Northeast Road Trip
Although the Northeast is an amazing area of the country, the best time to do this road trip is from late spring through early fall. In the winter, everything will be snow covered and you may have to watch out for snowstorms!
In late spring, flowers are blooming 🌸 and everything will begin to get really lush. It’s also a little less crowded than summer and fall.
Summer and fall are the busiest times to go on a Northeast road trip. In summer, locals and people from farther away are enjoying their time off. While in the fall, all of the leaf peepers are coming to see the trees turn miraculous shades of red and orange.
That being said, summer and fall are spectacularly beautiful, so it’s a great time to see any of these destinations!
Places to Add with More Time
If you have longer than a week or are moving fast, you may have time to add additional destinations to your road trip! Below I’ve created a list of spots that are fantastic areas to explore when you’re in the Northeast.
- Woodstock, Vermont – Woodstock is an adorable town in Vermont. Known for having amazing fall colors and a famous covered bridge.
- Stowe, Vermont- Another quaint New England town, it’s known for Mount Mansfield, the Ben & Jerrys Factory, and great fall colors.
- White Mountains, New Hampshire- Explore the enchanting White Mountains in New Hampshire. Visit one of the state parks or drive the Kancamagus Highway.
- Adirondacks, New York– The Adirondacks are a bit further away, but they’re also worth it. These rugged mountains have tons of great towns and hikes to explore!
New England Road Trip Itinerary
Quick Itinerary Breakdown
Day 1- Mystic, Connecticut (stop in New Haven)
Day 2- Newport, Rhode Island
Day 3- Providence, Rhode Island
Day 4 & 5- Boston & Cambridge, Massachusetts
Day 6- Portland, Maine
Day 7 – Bar Harbor, Maine & Acadia National Park
Northeast Road Trip Day One: New Haven & Mystic Connecticut
Coming from the Washington, DC area, getting to the Northeast part of the United States is a bit of a drive. The first day was our largest driving day with a 7 hour drive up on I-95. In order to break up our trip, we decided to make a stop in New Haven, Connecticut.
New Haven
New Haven is the home of Yale University and it definitely has a college town feel. As the first planned city in the US, it’s easy to explore. The New Haven Green is the central part of town with the main streets situated around it. Of course, you have to explore Yale’s campus and you can even take part in a free campus tour.
Once you’re done exploring, it’s time to eat! No stop to New Haven is complete without trying their world famous pizza. Frank Pepe’s is an institution in the city, well-known for their clam pizza 🍕 and inventing New Haven pizza in 1925. This pizza type is called apizza, a wood-fired pizza with a thin crust.
My brother and I are not fans of clams, so instead we ordered a pepperoni pizza and WOW! This was the best pizza I have ever had and I constantly think about driving up to New Haven just to have another slice.
Mystic
After you’ve stuffed yourself it’s time to keep moving. The drive to Mystic only takes about an hour more and it’s a good stopping point for the evening. Mystic is a cute little seaport town that garnered fame from the movie Mystic Pizza that starred Julia Roberts.
It’s a small, quaint town, where you can wander around or spend time at the Mystic Seaport Museum or Mystic Aquarium. Also, in the middle of town you can see an old-fashioned drawbridge, but if you’re not careful you may get stuck on the wrong side while it goes up.
Where to Stay in Mystic:
Mystic is a small town, but it has wonderful hotels to suit anyone’s needs. You can find places that are incredibly family friendly or small Bed & Breakfasts with a welcoming feel.
Hotels in Mystic:
Day 2: Newport, Rhode Island
Newport is only an hour’s drive from Mystic, so you won’t have far to go this morning. Newport is a seaside town that is well known for the historic mansions that line some of the streets. Touring Newport will make you feel as if you’re the star in a romantic story from the olden days. Looking out from the grand mansion’s gardens as you watch sailboats glide along the glimmering water.
You will surely fall in love with this gorgeous town. You can take in the majestic scenery as you stroll along the Cliff Walk, a 3.5 mile walkway along the shoreline that backs up to various mansion’s yards or learn about the town’s history at a mansion tour.
The most famous mansion is The Breakers, the summer home of the wealthy Vanderbilt family. My brother and I took an audio tour there and we found the house to be quite impressive. History buffs will also want to stop at Rough Point, the Marble House, and Touro Synagogue. When you’re not touring around you can stop on Thames Street for a bite to eat or stores to shop in.
Where to Stay in Newport Rhode Island:
Newport is a very popular vacation destination for New Englanders and people coming from further away. With a gorgeous coastline, great shopping, and exceptional boating excursions, it’s no wonder. So, there are tons of amazing hotels to choose from.
Best Hotels Newport:
Day 3: Providence, Rhode Island
Providence, the capital of Rhode Island, is only a 40 minute drive from Newport. So, you can easily get over to Providence in a day trip after you’ve had your fill of Newport.
We were a bit tired from our previous day, so we did not get to explore as much as we could. We stopped at Brown University to see the beautiful campus before retiring to our hotel. If you have the energy there are plenty of cool things to see in Providence like the RISD Museum or the Roger Williams Park Zoo.
Providence has a large Italian immigrant population, meaning that there are plenty of delicious Italian restaurants to dine at. Head to Federal Hill to explore the various cafes, restaurants, and shops along Atwell Avenue. We had reservations to dine at one of the oldest Italian restaurants in the city: Angelo’s Civita Farnese. We enjoyed three courses of delicious food including meatballs, gnocchi, and brownies that left us full and ready to fall into our food comas.
Day 4 & 5: Boston & Cambridge, Massachusetts
Boston is one of the USA’s largest cities and it’s got a real unique charm. Boston is one of the oldest cities in America, so you cannot escape the history that shaped it.
We spent our first day in Boston walking along the 2.5 mile Freedom Trail that takes you to over 16 historic sites and paints a picture of what made our country what it is today. While walking along it was tiring, we loved seeing all of these noteworthy spots including Paul Revere’s House. This trail starts in Boston Common, the oldest public park in America, which is a fun place to spend a few hours. Ride the swan boats or just spend a couple hours in the grass soaking in the sun.
Once you’ve learned about Boston’s history and spent a few hours walking around the city you may be hungry. We decided to head to the North End, which is one of the oldest residential parts of this city. It’s famous for the Italian immigrants that live here and there are lots of delicious Italian restaurants to choose from. After dinner, you can head to Mike’s Pastry for one of their famous cannolis before heading to sleep.
Cambridge
The next morning, you can wake up and head to Cambridge for the day. Cambridge is part of the larger Boston Metropolitan area and home to both MIT and Harvard. MIT has a very industrious look and contrasts the historical look of Harvard.
We went to Harvard Square and purchased tickets to a tour of the oldest university in the USA. We learned everything from the university’s history to current college traditions. It was a fun tour and we were awe-struck by the campus’ beauty. Make a stop at one of the school’s stores to purchase memorabilia and pretend you go there!
After you’ve toured the campuses, you can head back to Boston for the night. There are so many options for your last evening in Boston like going to a delicious restaurant or going to the historic Fenway Park for a baseball game. Unfortunately, we were in town during the Major League Baseball’s all-star break so baseball was not an option. We decided instead to go on a sunset cruise around Boston Harbor. I loved seeing Boston from the water and it was a great way to spend our last night in town.
Where to Stay in Boston:
Boston is a HUGE city, so choosing where to stay can be overwhelming. It makes sense to choose a neighborhood you want to be, before choosing the hotel. While downtown is near most of the attractions, Back Bay and Beacon Hill are cuter neighborhoods. But, if you’d prefer to be by the water you can stay in the Seaport District.
Best Hotels in Boston:
Day 6: Portland, Maine
We drove two hours from Boston to get to Portland, stopping in the adorable beach town of Ogunquit along the way. You can tell how popular this spot is in the summer as the streets were lined with cars and the beaches were covered with people soaking up the sun. If we had more time, I would have loved to spend time here.
As I was writing this post, a song, named after this town, shuffled on, which I had never heard before. Portland has a real hipster feel to it. You can find plenty of microbreweries and coffee shops lining the quaint streets of town. Spend your time walking around the Old Port or take a boat to Casco Bay Islands for the day.
Unfortunately, we got to Portland late in the day so after stopping into the Holy Donut for some of the best donuts we ever had, we decided to take a boat tour on the Islander, which took us around the harbor pointing out historical lighthouses and the surrounding areas.
One of the must see spots is the oldest lighthouse in Maine, the Portland Head Light. It’s the most photographed lighthouse in the country. On this road trip, it was completely fogged in. But, luckily, I’ve been back and it’s absolutely spectacular!
Where to Stay in Portland:
Portland, Maine is an adorable coastal town and it’s one of my favorite stops on any Northeast road trip! That being said, there are a few wonderful places to stay that are walkable to the water and town.
Best Hotels Portland:
Day 7 & 8: Bar Harbor & Acadia National Park, Maine
As the saying goes: we saved the best for last. Acadia National Park is, in my opinion, one of the prettiest places in the entire country. This park is one of the ten most visited in the country as it protects the natural beauty along this rocky Atlantic coastline.
The green pine tree covered mountains are truly majestic. This park sits right outside of the cute seaside town of Bar Harbor. We chose to spend two days here so that we could see both the town and the park.
Acadia Highlights
Exploring these two places during their peak season meant that we spent a lot of time finding parking spots. Make sure to allow yourself extra time if you plan on visiting in the summer, because this parking is a real time suck and a headache. While you’re in Bar Harbor, you can explore the adorable shops and eat fresh, buttery lobster rolls at the various restaurants while staring out at the sea. It’s a very lively town in the summer.
While you won’t be able to cover all of Acadia National park in two days, there is still plenty that you can do. Some of the highlights of our trip included hiking the South Bubble Trail, exploring Jordan Pond, and watching the sunset from Cadillac Mountain. You can read more about the best hikes in Acadia here!
Where to Stay near Acadia:
If you’re visiting Acadia, then the best area to stay is Bar Harbor, Maine. This town is located right on Mount Desert Island. There are plenty of hotels, inns, rentals, and campgrounds to choose from in this town. You’ll also have quick access to the park and great local restaurants- you can’t leave without trying a lobster roll 🦞!
Otherwise, you can stay nearby in the town of Bar Harbor. This adorable coastal town is a fantastic place to make your home base for your visit with tons of great restaurants and shops. There are a wonderful variety of places to stay!
Best Hotels in Bar Harbor:
Final Tips for Your Northeast Road Trip
I took this trip four years ago and I still have visceral memories of the food we ate and the hikes we took. I hope you decide to go and that you enjoy it as much as I did!
Let me know in the comments if you found this guide helpful
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