Last Updated on January 15, 2026 by Jacqualyn
Part I Of My New England Fall Travel Story — Through Boston, Maine & New Hampshire
At-A-Glance
Boston Fall Travel Guide: Where My New England Fall Travel Story of Healing Begins
Boston was the first stop in my New England fall travel story, and the city welcomed me with beauty, history, and unexpected moments of peace. Every morning in Boston’s Back Bay began the same way — with a slow walk to the little Starbucks inside the Hilton Boston Park Plaza, our hotel. I’d order my favorite chai tea — two shots of vanilla and cinnamon steamed in — and Michael would smile over the counter and ask for his caramel macchiato, extra whipped cream.
With warm cups in hand, we wandered to the Boston Public Garden — a perfectly manicured oasis designed by the same visionary who created Central Park in New York. The park was a masterpiece of fall, painted in shades of rust, gold, and pumpkin spice.
We’d find a quiet bench beneath the maples and just sit — watching squirrels chase each other, ducks gliding across the pond, and people walking their dogs along the cobblestone paths. That quiet bench felt like a prayer in motion — the kind of stillness that reminds you how important restful sleep and simple healing habits truly are.
After losing Miss Prada only weeks before, my heart had been aching for peace— a journey I’ve shared more deeply in my story of healing after 50. Somehow, sitting there among the leaves and laughter of strangers, I could finally breathe again. Boston whispered to me, “You’re going to be okay.”
🍁 Exploring Boston’s Charm
Exploring Boston’s charm felt like stepping deeper into my New England fall travel story, one filled with comfort, laughter, and little surprises.
In the afternoons, we wandered down to Cheers — the iconic little pub where “everybody knows your name.” Laughter spilled out the doors, and nostalgia wrapped around us like an old friend. Standing outside, I couldn’t help but smile at how surreal it felt to be at such a beloved piece of television history. People were snapping photos, swapping memories of the show, and joking with the staff, and for a moment it felt like we’d stepped right into an episode. We lingered there, soaking in the atmosphere, taking pictures, and just enjoying the simple joy of being in a place that had made millions of people feel connected through humor and heart.
From there, we strolled into Boston’s North End, the city’s beloved Italian neighborhood — brick-lined streets, balconies overflowing with flowers, and the sweet scent of espresso drifting through the air.
We stopped at Modern Pastry for homemade cannoli… the kind only crafted by hands that have rolled pastry for generations.
Later, we had lunch at Joe’s Waterfront, a perfect restaurant on the wharf overlooking the harbor. My heart smiled when I saw the name — my son’s name is Joey — and it felt like a little wink from heaven. The food was delicious, the laughter was easy, and the views across the harbor were even better.
A Funny Detour to St. James Catholic Church
One afternoon, we tried to attend the 4:00 Mass at St. James Catholic Church.
We walked six blocks in the wrong direction before Michael said I wasn’t following the breadcrumbs on the GPS — whatever that meant! We finally realized the church was the opposite way. Nothing like a little backtracking.
By the time we arrived, the sanctuary was dark.
“I promise Google said there was a 4:00 Mass!” I insisted.
Michael grinned:
“You stay here and say your prayers — I’ll be right back.”
Moments later, he waved from a staircase.
There was another sanctuary upstairs, glowing with light.
We made it after all… and smiled the entire time.
It was a beautiful Mass — full a cappella choir, drums, guitars, piano — and I truly enjoyed praying that day.
🦞 Boston Nights & Comfort Food
That evening, we had dinner at Legal Sea Foods, a restaurant that feels like Boston wrapped in a warm hug. The moment we walked in, the atmosphere was cozy and inviting — low lighting, the gentle clatter of dishes, and the smell of fresh seafood drifting through the air.
The service was warm and genuine, the kind where the staff makes you feel like an old friend rather than a visitor passing through. I ordered their famous clam chowder, and Lord have mercy… it was exactly what my soul needed. Creamy, comforting, and seasoned to perfection — like a bowl of pure New England love.
Michael and I lingered over our meal, laughing and replaying the highlights of the day. There was something magical about that dinner — maybe it was the cool fall air outside mixing with the warmth inside, or maybe it was simply the blessing of slowing down and savoring the moment.
And yes… they even put on the LSU game for me.
When I heard that familiar roar of the Tigers come across the screen, my whole face lit up.
Geaux Tigers! 🐅💜
It was one of those small but unforgettable moments when you’re far from home, yet somehow something familiar finds you anyway. Boston really has a way of knowing just what you need.
A Quiet Morning at Trinity Church: Peace for the Soul
The next morning, we visited Trinity Church in Copley Square, a sanctuary so breathtaking it felt like stepping into a watercolor painting. The stained-glass windows caught the morning light and scattered it across the pews in soft blues and golds, wrapping the whole room in quiet serenity.
We sat for a moment just taking it in — the hush, the warmth, the stillness that settles deep into your spirit when God meets you exactly where you are. After days of travel, laughter, and bittersweet memories, this little pause felt like a blessing whispered straight to my heart.
Boston’s Spirit of Resilience: Fenway & The Marathon Line
I would be remiss if I did not mention our stop by Fenway Park and then walked to the Boston Marathon finish line. The memorial there was quiet and powerful — a reminder of resilience and unity that lives deep in this city’s heart.
A Step Into History: The USS Constitution (“Old Ironsides”)
Next we made our way to another unforgettable stop — the USS Constitution, America’s oldest commissioned warship still afloat. Walking up the gangplank felt like stepping straight into history.
The sailors onboard welcomed us with warm smiles and shared stories of battles, storms, and the ship’s legendary nickname, “Old Ironsides,” earned when cannon fire bounced off her oak hull during the War of 1812.
I ran my hand along the rail and felt a strange mix of pride and gratitude — a reminder of the strength, resilience, and courage woven into the fabric of our country, the breeze carried the scent of the harbor, and for a moment, everything felt still and sacred.
Old North Church: Faith, Courage & the Lantern That Shaped History
Before leaving Boston, we made one final unforgettable stop — the historic Old North Church — the very place where the famous lantern signal, “One if by land, and two if by sea,” sparked Paul Revere’s midnight ride.
The moment we stepped inside, the air felt still, almost reverent. Sunlight streamed through the tall windows, landing softly on the wooden pews that have held countless prayers across generations.
I walked slowly down the aisle, imagining families who once sat there during the Revolution, waiting, hoping, believing. It gave me goosebumps.
There was a quiet strength inside that church — a reminder that even in the darkest times, a single light can change the course of everything.
Standing there, I felt connected not just to history, but to my own journey of resilience and renewal on this New England fall travel story.
Staying Grounded: A Simple Routine That Helped Me Travel Well
All the walking, sightseeing, beautiful scenery, and emotions on this trip showed me just how important clarity and calm were for me. I’d started a simple cognitive fitness program before we left, and it helped keep my energy steady and my mind clear through long days of exploring.
Boston’s Gift: Peace, Gratitude & a Full Heart
Boston gave me what I didn’t know I needed — faith, laughter, peace, and gratitude.
The next morning, the skyline faded behind us as the motor coach carried us toward Maine.
Maine Coastal Getaway: My New England Fall Travel Story: Where The Sea Whispers and the Soul Listens
The road north was lined with fiery foliage — golden maples, crimson oaks, and sunlight that made everything shimmer and, more importantly, added so much to my New England fall travel story.
Our very first stop in Maine was the beautiful Spring Point Ledge Lighthouse in South Portland — a stunning white lighthouse perched at the end of a long stone breakwater. The sky was a soft blue, a sailboat drifted quietly beside us, and the ocean glimmered like polished glass. It was one of those peaceful moments that stay with you. Standing there with the salty breeze on my face and the sunlight dancing on the water, I felt the first deep sense of calm settle into my spirit on this New England scenic trip. It was the perfect beginning to our time in Maine — simple, serene, and absolutely breathtaking.
A Peaceful Morning at the Maine Maritime Museum
Bright and early the next morning, we headed to the Maine Maritime Museum in Bath, a place where wooden shipbuilding and salt-air history come alive. We walked through exhibits celebrating the mariners and craftspeople who shaped America’s coastal story—including the legendary Wyoming, the largest wooden schooner ever built. Standing where that massive seven-masted ship once towered over the shoreline felt like touching a piece of living history.
After exploring the grounds, we boarded a small riverboat and began cruising along the Kennebec River. As we floated downstream, we passed the impressive Bath Iron Works, still one of the most active U.S. Navy shipyards in the country. Seeing the towering cranes and destroyers under construction from the quiet of the water was surreal—industrial strength on one side, gentle fall colors on the other.
The cruise carried us past small, historic riverside towns—those quiet little pockets of Maine where time seems to slow and stories cling to the trees.
The water mirrored shades of gold, crimson, and soft brown, moving like a watercolor painting under the morning sun.
It was peaceful.
It was healing.
It was exactly what my soul needed.
Freeport Surprises & Tuscan Brick Oven
We made a quick stop in Freeport — the Land’s End store was under construction, but that turned into one of the sweetest surprises.
Just a few blocks away, we found Tuscan Brick Oven Restaurant.
The seafood pasta was divine.
The “lobsta chowda,” as locals say, was unforgettable.
And the laughter made it even better.
An Afternoon of Lighthouses, Forts, and Island Charm
That afternoon, we boarded another harbor cruise — this time gliding past old coastal forts, tiny island communities tucked into the rocks, and quiet pockets of Maine life you’d never see from the road. The air felt cooler out on the bay, the kind of crisp ocean breeze that wakes you up in the best way.
As we rounded a bend, the captain pointed ahead with a grin.
“There she is… Portland Head Light.” The lighthouse rose from the cliffs like a storybook painting — bright white tower, red roof, endless blue sky. Just as everyone lifted their cameras, the captain leaned into the horn and absolutely laid on it.
“All the rich folks up there are gonna be real upset with me…” he shouted over the noise.
“…but don’t worry — they know I do it every day!”
The whole boat erupted in laughter.
And somehow, that one silly moment made the lighthouse feel even more magical.
That night we had dinner at DiMillo’s On the Water — a floating restaurant and Maine classic. We enjoyed a Lobsta Feast, complete with buckets overflowing with whole lobsters, corn, potatoes, and plenty of melted butter.
Watching people crack their first lobster was priceless — laughter, clinking glasses, steam rising into the cool night air. The whole room felt light and joyful, the kind of moment that makes strangers feel like old friends.
As we wrapped up our time along Maine’s rocky shores, every mile of this New England fall travel story felt like a new kind of grace — fiery foliage, golden light, and a peace my heart didn’t know it was missing.
Maine filled my heart with beauty, laughter, and grace… one tide at a time.
New Hampshire Autumn Adventure: My New England Fall Travel Story: Where The Mountains Touch The Sky
New Hampshire felt like another beautiful chapter in my New England fall travel story — full of mountain air, soft humor, and colors that didn’t seem real.
Leaving the rugged coast of Maine behind, our motor coach wound its way through winding roads and golden forests into New Hampshire, where the mountains seemed to rise straight out of a watercolor painting.
That morning, we boarded the North Conway Scenic Railroad Train for a ride through the White Mountains, winding along ridges painted in red and gold. The view from the windows was breathtaking — waterfalls tumbling through the forest, sunlight glinting off rivers, and the rhythmic hum of the rails beneath us.
On our way back, we stopped to watch the famous Cog Railway, the little engine that climbs Mount Washington. Its white smoke curled against the endless blue sky — a humble, moving symbol of perseverance.
From there, we visited the grand Omni Mount Washington Hotel, perched on a hill with sweeping mountain views. Its red roof glistened in the sun, the veranda stretched like a welcome mat to heaven, and the crisp mountain air wrapped around us like peace itself.
We explored covered bridges, meandering through time-worn wood and whispering waterfalls, then spent the next morning aboard the Mount Washington Cruise on Lake Winnipesaukee. The water mirrored the sunrise, painting the lake in hues of gold and rose.
I called my dear friends Tom and Diane, and though we didn’t get to meet, hearing their voices warmed my heart. The funny part? I hadn’t even told my Joey I was there — and right around the same time, Tom and Diane started blowing up his phone!
We all laughed about it later. God surely has a way of keeping His sense of humor alive.
Before leaving Lake Winnipesaukee, we had a fantastic lunch & we made one last memorable stop — a little boutique in Wolfeboro where I spotted two cozy sweatshirts that I knew my sisters would love. They never ask for anything, but to my surprise, this time, when I was leaving, they specifically asked for sweatshirts from Lake Winnipesaukee! Go figure, because we had a bit of a problem. You see… we had absolutely no room left in our luggage. But Michael, with his calm confidence and that sly little grin, just said:
“We’ll make it work.” And somehow, he did.
By the time we left the next morning, those sweatshirts were tucked neatly into his suitcase like magic. I still don’t know how he managed it, but every time I think about it, I smile. It was one of those small special moments that becomes a warm memory — the kind that reminds you how love shows up in the simplest ways.
Unexpected Adventures & Sweet Surprises in New Hampshire
Our final morning in New Hampshire began with a stop at the New Hampshire State Capitol, a striking piece of American history standing proudly in the heart of Concord since 1819. It’s the oldest statehouse in the country where the legislature still meets in its original chambers — and you can feel that sense of legacy the moment you walk up those granite steps. The front courtyard was lined with rows of brilliant mums exploding in every shade of fall: gold, burgundy, pumpkin orange, deep wine, and soft buttery yellow. It was like the whole building was dressed for autumn. And this is where the saga of the sunglasses unfolded…
I’d lost my favorite pair before the cruise, bought a new pair in Wolfeboro, then somehow lost those before we even finished the Capitol tour. I laughed it off and bought another pair — but wouldn’t you know it? When we boarded the motor coach, my original sunglasses were sitting right there on the dashboard. Our driver found them when tidying up the bus!
Oh, I got teased plenty! But the moral of the story?
Sometimes you lose things only to find that what you started with was right where it was meant to be all along.
That evening, we drove south and arrived in Brookfield, Massachusetts, a town that truly feels like stepping into a colonial painting. We had a fabulous prime rib dinner in a warm, historic inn originally established in 1771, and the great-grandson of the current owners spoke of fond memories and long linage of history surrounding the place — wooden beams overhead, soft lighting, and that unmistakable New England charm that makes you feel instantly at home. To finish the evening we were served a delicious family tradition of cobbler ( I got the recipe). After a full day of sightseeing, laughter, hills, cobblestones, and little surprises, it was the perfect, comforting end to our first stretch of travel.
💼 A Heartfelt Thank You to Terry Rose & Vacations By Rail
I have to pause and give special appreciation to our guide, Terry Rose. From the moment our journey began, Terry set the tone — organized, warm, and wonderfully knowledgeable. She shared stories, history, and little details that made each stop feel like stepping into a living postcard. Her calm spirit and enthusiasm made the entire experience richer.
And to Vacations By Rail — thank you for crafting such a seamless and beautifully planned adventure. Every transfer, tour, and overnight stay felt smooth and thoughtfully arranged. It allowed us to truly relax and soak in every moment of New England in the fall.
🚌 Gratitude for Our Driver, Wayne Vasques
We were also blessed with an incredible driver, Wayne Vasques. His steady hands, friendly smile, and constant patience made every mile feel safe and easy. Wayne navigated busy cities, winding country roads, and crowded coastal towns with such skill that you almost forgot how much work it took. His kindness set the tone for our days on the road.
As this New England fall adventure carried us toward Connecticut, gratitude settled into every mile — the kind of gratitude I write about so often in my Stories & Inspirations and on My Favorite Health Depot itself.
And I’ll tell you this…
With all the walking, climbing, hills, stairs, cobblestones, and full days we packed in, I was extra thankful for the simple wellness routines and daily supplements that kept my energy steady and my body feeling good from sun-up to sundown.
They truly made the difference between just getting through the days… and actually enjoying every single moment of them.
Next Stop:
Connecticut — Castles, Eagles & A Sunset Dinner Train, and ending this wonderful trip at Martha’s Vineyard.
