After graduating college, my brother Nick and I decided we wanted to go on a celebratory Northeast road trip. Even though we were from the East Coast, we hadn’t been up to that part of the country. Let me tell you it was one of my favorite road trips ever!
This trip took us through major cities, national landmarks, and natural landscapes that astounded us. I loved how this trip truly showed us how much this country has to offer. You can start this trip by flying into one of the cities on the route or drive from another spot on the East Coast
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!
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Table of Contents
Northeast 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
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 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.
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.
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.
Day 3: Providence, Rhode Island
We decided to stay in Newport a little longer, because we loved it so much. So we spent the morning shopping, walking around town, and driving by the mansions along the shore before hitting the road.
Providence, the capital of Rhode Island, is only a 40 minute drive from 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.
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.
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.
From there, we tried to see the oldest lighthouse in Maine, the Portland Head Light. It’s the most photographed lighthouse in the country, but due to the fog we could barely see it. I really loved Portland and I wish we had time to see more of it, but instead we kept moving.
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.
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. I definitely want to go back in the fall someday so that I can see the leaves change colors over the mountaintops.
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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