A New England Road Trip

O hushed October morning mild,
Thy leaves have ripened to the fall

Robert Frost

A New England Road Trip. Written on October 25, 2025, by Anna Tang.

One weekend, in a moment of spontaneity, we decided to take our first New England road trip. Backing up a bit, my desire to see our country’s colonial states clothed in their renowned Autumn finery first kindled years ago on our son’s school trip to Washington, D.C., and that spark lingered for many years. And then last year, a fall business trip to Boston, against a graceful autumn backdrop, fanned that spark into flame. From that moment on, I began to talk about going back for a New England Road trip in earnest and exploring the countryside at leisure.

When the first day of Autumn arrived a few weeks ago, so did my longing to see the colorful leaves of New England. I asked my husband if we could, pretty please, take a real fall trip to New England that was just pure Autumn sightseeing- nothing else. My husband, being the great guy he is, knew how important this was to me, especially given that I am a big homebody who doesn’t care for road trips. So, within 48 hours, we plotted a course and booked our flight and hotels for the East Coast.

Our New England Road Trip Begins….

Our journey took us through four states selected based on recommendations for this kind of trip. We started our trip in Boston, and for seven days we drove winding country roads lined with thousands upon thousands of trees in glorious Autumnal shades of sunny gold, apple crimson, vermillion, marigold, and russet. The heavenly show of color was enchanting to people who live in the very green state of Oregon, and we greedily soaked it in. We drove through charming old towns filled with homes from the early years of America, ranging from simple wooden Puritan-style homes to jaw-dropping, ornate mansions. Old brick municipal buildings with their tall pillars added stateliness and elegance to towns, while the high steeples of their churches rose above the colorful forest canopy in the distance, guiding people to their doors.

Vermont was simply the best for Autumn leaves. Marigold trees glowed from the hillsides under the pure blue sky, and golden leafy arches hovered over many of the roads. Robert Frost’s poems came alive as we travelled through the countryside to the adorable town of Woodstock- well worth the stop for a couple of days. There was a sparkling river bordered with green velvet lawns that ran alongside the town with an old covered bridge. Incidentally, Vermont is the place to see those covered bridges. And because Woodstock is popular, we ended up staying a few miles outside of town at the stone mansion of a governor from the early 1900s. The mansion was beautifully decorated in period style, an experience all its own. And we also enjoyed an elegant dinner of Beef Wellington in their ornate dining room.

My heart belongs to Maine.

It took us three hours to cross New Hampshire from Vermont and into Maine, where I was unprepared for how much Maine’s beauty would move me. Yes, I wanted to go and see the place that inspired Frank Benson’s paintings of whimsical summer days that I love so much, but I didn’t think I would end up leaving my heart there. But when we walked into our hotel room and looked at the view that awaited us, I was gone. The lure of the cold blue waters of the Atlantic crashing on the rocky shore and the green velvet lawns with traditional Adirondack chairs under an azure sky painted a world of carefree summer days.

Small boats ventured out to fish along the shoreline. In town, people ambled in and out of little boutique shops. We dined on lobster at Mabel’s. And of course, we strolled the streets to look at the magnificent old homes. Nostalgia chased us everywhere we went. Even my husband wasn’t immune to its charm and fell under Maine’s spell. He thought it was more beautiful than his favorite place, Hawaii!

But we couldn’t leave Maine without seeing the iconic lighthouse at Cape Elizabeth, so we drove to Portland. The lighthouse stands against the Atlantic, where dark blue waters crash on the rocks, presenting a majestic yet formidable sight.

The rocky ledge runs far into the sea,
And on its outer point, some miles away, The Lighthouse lifts its massive masonry,
A pillar of fire by night, of cloud by day.

Henry wadsworth longfellow

Winding it up.

After Kennebunk, we left to head back down the coastline to Boston, but before arriving, we made a stop at Concord, Massachusetts, to see where the Revolutionary War began. We drove through the Currier and Ives-style town of Concord to the Minute Men Park, where the original battlefield was. The battlefield was a small field, with a nearby farm and a bridge. We walked across the Rude Bridge, where the first shot was fired that began the long fight to start our country. Standing on the battlefield, I was genuinely grateful to have made the stop and felt rather humbled by it.

Coming back home, my hubby and I are still in a bit of a daze from all the beauty and, admittedly, longing to go back again. We were genuinely moved by the graceful countryside, steeped in history, that we explored and from which we learned so much. And to say we enjoyed ourselves, well, that is an understatement. Undoubtedly, we will be going back for further autumnal adventures!

Have a beautiful day!