A Romantic Road Trip: Boston to Portland Along the New England Coast

From the moment we left Boston Logan Airport, we felt the thrill of escape—trading city skylines for winding coastal roads, sea breezes, and the kind of scenery that makes you roll the windows down just to breathe it all in. The drive itself was enchanting: stretches of sandy beaches opening beside us, old New England houses with clapboard siding and widow’s walks standing proudly by the roadside, and glimpses of luxury coastal homes perched on rocky cliffs with sweeping views of the Atlantic. It was more than a journey; it was a romantic seaside drive, with surprises waiting at every turn.

Credit to Anne Trout

Boston, Massachusetts: An elegant beginning

Before setting off up the coast, we spent our first night at The Newbury Boston, a landmark hotel overlooking the Public Garden. With elegant interiors, sweeping city views, and a timeless sense of sophistication, it offered the perfect blend of Boston history and modern luxury. Cocktails by the fireplace and dinner at the rooftop restaurant set the stage for the adventure ahead.

Credit to Anne Trout

Salem, Massachusetts: Legends, trials & fall charm

Our first stop on the road was Salem, a town where history and legend intertwine. Best known for the Salem Witch Trials of 1692, the city holds a deep and sometimes haunting legacy. At the Salem Witch Museum, we stepped back into that dark chapter of colonial history, learning the stories of those accused and the hysteria that defined the time. The solemn atmosphere of the memorial reminded us how this town’s past still echoes today.

Yet Salem is far more than its trials—it is a thriving downtown full of boutiques, quirky shops, and cafés. We wandered Essex Street, where cobblestones led us past bookstores, crystal shops, and antique stores, each brimming with character. The air was festive, filled with buskers, costumed performers, and laughter spilling from pubs and breweries.

In the fall, Salem transforms into a seasonal wonderland. Pumpkins line the streets, leaves crunch underfoot, and the town comes alive with Halloween spirit. From ghost tours and haunted houses to the Salem Haunted Happenings Festival, every corner of the city seemed wrapped in autumn magic. Even as we explored, the crisp air carried hints of apple cider and woodsmoke, making the town feel warm and inviting despite its haunting history.

At the harbor, schooners bobbed gently on the water, a reminder of Salem’s maritime heritage. Between its seafaring past, witch trial legacy, lively downtown, and fall festivities, Salem offered a tapestry of experiences that set the perfect tone for the journey north.

Credit to Anne Trout

Newburyport, Massachusetts: A harborfront gem

In Newburyport, brick-lined streets met a lively waterfront. At The Grog, we enjoyed lunch in a tavern where sailors once gathered. The harbor outside glittered with sailboats, and we strolled the boardwalk where the sea seemed to meet the town’s history.

Portsmouth, New Hampshire: Colonial streets & coastal charm

Crossing into New Hampshire, we arrived in Portsmouth, a small city brimming with character. Market Square was alive with cafés and shops, while cobblestone lanes led us to the Strawbery Banke Museum, where historic homes offered glimpses of life across the centuries. We stopped at Portsmouth Brewing Company, the state’s oldest craft brewery, for a refreshing pint before wandering the banks of the Piscataqua River. With its colonial architecture and harbor views, Portsmouth felt like a timeless chapter in our coastal journey.

Credit to Anne Trout

Kennebunkport, Maine: Waterfalls, mansions & Hidden Pond

As we crossed into Maine, the drive grew even more beautiful—pine trees hugging the shoreline, stretches of sandy beach, and grand summer estates gazing out to sea. We paused at First Falls, where the Mousam River tumbles gently into town, then continued into Kennebunkport.

Driving along Ocean Avenue, we slowed to take in the luxury homes perched above the water, each one framed by waves crashing on the rocks below. The Bush family compound stood quietly on the shore, a reminder of the town’s legacy as a beloved retreat.

Before heading to our resort, we stopped at Batson River Brewing & Distilling, where inventive cocktails and locally crafted beer paired perfectly with a playful, rustic atmosphere. Its design—equal parts hunting lodge and modern brewery—made it a fun, lively stop that captured Kennebunkport’s creative spirit.

That evening, we retreated inland to Hidden Pond, one of Maine’s most exclusive luxury resorts. Tucked away in the forest just outside Kennebunkport, Hidden Pond felt like a secret world of its own. We stayed in a private cottage surrounded by birch trees and wildflowers, complete with an outdoor shower and a fireplace for cozy evenings. Dinner at Earth, the resort’s award-winning restaurant, highlighted local flavors in a setting that felt both rustic and refined. It was a stay that blended romance, privacy, and the beauty of nature in perfect harmony.

Credit to Anne Trout

Cape Elizabeth: Portland Head Light & Fort Williams Park

The next morning, our drive brought us to Cape Elizabeth, where the mighty Portland Head Light rose against the horizon. Built in 1791 under George Washington’s orders, it is Maine’s oldest lighthouse and one of the most photographed in the world. Its beam once guided sailors through the treacherous waters of Casco Bay, and today it still shines with the same quiet dignity.

Surrounding the lighthouse is Fort Williams Park, a sprawling oceanside park filled with history and beauty. We wandered past old military ruins, wide grassy fields, and cliffside trails with panoramic views of the Atlantic. Families picnicked on the lawns, couples strolled hand-in-hand along the water, and food trucks served lobster rolls under the shade of pines. Standing at the cliffs, watching waves explode against the rocks below, we felt a sense of timelessness—as though the sea, the light, and the land had been in conversation for centuries.

Credit to Anne Trout

Portland, Maine: A city by the sea

Just before reaching the city, we made a stop at the Dockside Grill in Falmouth, a beautiful waterfront restaurant with panoramic views of Casco Bay. Sitting on the deck, we watched sailboats glide past as we shared a leisurely lunch. The setting felt quintessentially Maine: relaxed, elegant, and defined by the ocean at its doorstep.

When we finally reached Portland, the presence of the sea was everywhere—the salty breeze drifting through the streets, the cry of gulls, and the sparkle of the harbor.

The piers of the Old Port were alive with energy. Wooden wharves stretched into the bay, lined with sailboats and working boats alike, their reflections dancing in the tide. Alongside them, waterfront decks bustled with people enjoying the sea views. It was a place where the city’s historic character and coastal spirit blended seamlessly.

At Luke’s Lobster on Portland Pier, we savored buttery lobster rolls with the water sparkling below us. To our surprise, a well-known celebrity sat just a few tables away, enjoying the same simple seaside meal—it was one of those delightful travel moments that felt both surreal and perfectly natural.

From there, we wandered past Union Wharf and Custom House Wharf, where old warehouses have been reborn as oyster bars and cafés. The sight of sailboats setting out into the bay, their white sails glowing in the sun, made the whole harbor feel alive.

That evening, dinner at Boone’s Fish House & Oyster Room was a feast of oysters and lobster, paired with the soft glow of twilight over the water. Later, we strolled the cobblestone streets of the Old Port before ending the night at The Press Hotel.

The Press Hotel, once home to Portland’s historic newspaper, is now a boutique hotel that celebrates both history and creativity. Each room feels like a writer’s retreat, with vintage-inspired desks, newsroom-style décor, and playful details that nod to its publishing past. The lobby buzzes with art exhibits and literary touches, while the on-site restaurant and bar feel chic yet welcoming. Its location, right at the edge of the Old Port, made it the perfect place to end our coastal adventure—with style, culture, and a true sense of place.

Credit to Anne Trout

Epilogue

Our journey from Boston to Portland was more than just miles along a map—it was a romantic coastal adventure, filled with beaches, ocean views, historic towns, and seaside surprises. From Boston’s elegant beginnings to Salem’s legends, from Newburyport’s harbor to Portsmouth’s colonial streets, from Kennebunkport’s creative flavors at Batson River and serene forest hideaway at Hidden Pond to Cape Elizabeth’s lighthouse cliffs, and finally Portland’s waterfront dining at Dockside Grill and its vibrant Old Port, the coast gave us endless reasons to pause, explore, and fall in love.

The drive itself was the greatest treasure: a ribbon of road winding along the sea, past old New England homes, sandy beaches, rocky shores, and grand coastal estates. Everywhere, the ocean whispered its stories, reminding us that sometimes the best journeys are those where the road is as beautiful as the destination.

Credit to Anne Trout

We visited in September—fewer crowds and absolutely gorgeous weather.

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