One of the simple joys in life is to check a long overdue bucket-list moment, and boy did I do that this summer, and quite a number of them, at that. After so much planning and wishing I finally did the new England trip! Why the name? one might ask. Well, a little obvious history moment – much of the northeastern area was heavily colonized by English pilgrims and puritans, and naming places. after somewhere back home was apparently quite the tradition. I have not been to England (yet), but I can already see why most of the area truly looks like it. My tour started and ended in Boston, with stops in Rhode Island, Connecticut, New Hampshire, and Maine along the way. A little bit of everything, which is how I like to explore.

First stop: Newport, Rhode Island

I landed at Boston Logan under gloomy skies, picked up my rental car, and headed straight to Newport, Rhode Island. It was raining in Newport, but the beautiful view of Easton Bay still gave me plenty to be excited about. My long-awaited New England trip was officially underway!

For a waterfront meal, I stopped at The Mooring Seafood Kitchen & Bar, near Bowen’s Wharf, where I ordered branzino and dined overlooking the water. A seafood meal with a waterfront view felt like a fitting way to kick off my time in Newport.

Then came one of my favorite parts of Newport: driving along Ocean Avenue and out to Brenton Point. The views were absolutely beautiful. This is a stretch of the trip worth leaving time for, because the scenery deserves more than a passing glance through the car window.

For a future Newport visit: I’d add the Cliff Walk, which pairs ocean views with glimpses of Newport’s historic mansions. After seeing the coastline by car, exploring more of it on foot sounds like a good scenery stroll.

New Haven, CT: A little art, a little Yale, and THAT pizza

Next, I drove to New Haven, where I spent time strolling around downtown and exploring Yale. My stops included the Yale University Art Gallery and Yale’s Old Campus. Together, they gave this part of the trip a different rhythm: time to walk around, take in some art, and appreciate the university setting. The rain had reduced to tiny drizzles so I toured much of New Haven by driving.

For dinner, I went for the famous New Haven–style pizza, because, whats a visit to a new place without the culinary exploration of its delicacies? Judging by the long line outside Modern Apizza, I wasn’t the only one who had come for good pizza. That queue was a testament to what awaited inside—and after my first bite, I understood. Easily the best pizza I have ever had, and absolutely worth the wait!

With a very happy stomach, I drove to Providence, Rhode Island, where I spent the night, bringing the first day of my New England adventure to a close. The gallery and Yale were worthwhile stops. The pizza is something I would happily return for.

Providence, Rhode Island

After spending the night in Providence, I started day two with coffee at Bitty & Beau’s. Exploring local coffee shops is one of my favorite little rituals when I travel, so of course a coffee stop had to make it onto the itinerary! Bitty and Beau’s mission of dedicating to help people with intellectual and development disabilities really touched my heart. I was not only supporting a small business but I was also being a small part in supporting an inclusive work place where people with disabilities were given a chance to contribute to meaningful work.

Central Falls, Rhode Island

Next, I drove to Central Falls to see Viola Davis’s high school. From Providence, I drove to Central Falls to see Viola Davis’s high school. I’ve watched her bring so many powerful characters to life on screen, so getting to see a place connected to her younger years felt special. Before the roles, the awards, and the recognition, there was a girl going to school here with a future she had yet to discover. Standing outside her high school, I found myself thinking about how much can unfold between where we begin and where we eventually find ourselves. We usually meet public figures through their accomplishments. Visiting a place from an earlier chapter of her life gave me something else to appreciate.

It was a simple stop, but one I was happy to have made. My New England itinerary absolutely had room for a little Viola Davis appreciation!

Portsmouth, New Hampshire

After my Viola Davis detour, I said goodbye to Rhode Island and hit the road again, this time heading to Portsmouth, New Hampshire – small port city on the Piscataqua River, near the Maine border.

Known for its historic downtown, waterfront, and maritime heritage, it brought another slice of New England into the trip before I continued north to Portland. One of the things I had looked forward to most about this trip was getting to explore several states along the way.

Portland, Maine

After a brief but awesome time in Portsmouth, I made my way to Portland, Maine. Portland reminds me one of my O-level best friends. Our moms went to high school together and were very good friends. Over fifteen years later, we became friends, unbeknownst to us of our mothers’ friendship. How beautiful is that? At sixteen, she left home to attend high school in Portland, Maine. I had never heard of the city before, but from then on, I dreamt of visiting her there someday. Although she no longer lives there, finally making it to Portland felt special. It brought back memories of our friendship and a wish I’d carried since I was a teenager.

Another Portland highlight was spotting Fort Gorges, a 19th-century military fort sitting out on Hog Island Ledge in Casco Bay. Its stone walls and greenery-covered roof caught my attention immediately. I admired it from the mainland, curious about how this fortress had ended up out on the water. Construction began in 1858, and the fort was intended to help defend Portland Harbor. But military technology moved faster than its builders could have anticipated: advances in warships and artillery had made its design outdated by the time it was completed. Despite its imposing appearance, Fort Gorges never saw battle or had troops stationed there. Today, it is a city park, accessible by water rather than a road or bridge. If you’re picturing lawns and picnic benches, think more along the lines of an old stone fortress to explore, surrounded by views of the bay! I would have loved a closer look, but visiting the island will have to wait for another trip. Even from across the water, it became one of my favorite sights in Portland—and one more reason to return to Maine.

Cape Elizabeth, Maine

After Portland, I continued to Cape Elizabeth to see Portland Head Light. And what a beautiful way to finish my time in Maine! The white lighthouse, the red-roofed keeper’s house, and the rocky coastline made this a stop I was very glad I had included. Such a serene place for a sunset view!

Cape Elizabeth was my final stop before driving back to Boston. From a gloomy arrival to a sunny late afternoon by the lighthouse, this New England trip had given me quite a range of memories.

I had finally taken the trip I’d spent so long planning and wishing for. Five states, plenty of time on the road, and a hundreds of pictures later, I was heading back with a much longer list of places I wanted to revisit. And yes, New Haven was on that list too. I’m still thinking about the pizza. Another trip that I really enjoyed after returning to Boston was one to Martha’s Vineyard. I talk about my time in the vineyard in one of my posts. If you haven’t read that one yet, please do!

Happy Wandering!