Portland – Arrival and Exploration
We had an uneventful flight from National Airport to Portland, Maine — a small blessing, given that the airline had moved our departure up an hour, meaning a 4 AM wake-up instead of the more civilized start we’d planned for. I made good use of the extra time in the air, catching up on the sleep that we’d sacrificed. By around 9 AM we had dropped our luggage of at the Westin Harborview and set out on foot up Congress Street toward the Portland Observatory, taking our time and letting the city introduce itself along the way.
On trips, Clare and I always walk around cities to get to know them better. In this case, the walk doubled as a tour of Portland’s landmarks. We passed the Portland Museum of Art, just blocks from the working waterfront, with its notable collection of American, European, and Maine-specific art. Further along first stood the First Parrish Unitarian Church, followed by City Hall, a granite, U-shaped landmark built in the early 1910s in the Renaissance Revival and Beaux-Arts style — its 200-foot clock tower unmistakable, and its rear wing home to a 1,908-seat auditorium and one of the largest pipe organs in the world. We also passed Eastern Cemetery, Portland’s oldest historic site, dating to 1668, with thousands of marked graves and thousands more unmarked — and the Maine Jewish Museum, housed in a restored turn-of-the-century synagogue in the East End, home to a rotating exhibition space and a permanent photo collection of Holocaust survivors who settled in Maine.
By the time we reached the Observatory itself, I had a good sense of why this hill was worth the climb. The tower — built in 1807 by Captain Lemuel Moody as a commercial signal station to spot incoming ships up to 30 miles out — is the only surviving historic maritime signal tower in the country, restored using its original pine timbers. The staircase inside curves in step with the octagonal exterior, narrow and a little disorienting, five floors up to the top. Our guide Elisse walked us through the tower’s history as we climbed: nearly 120 years of continuous use signaling ship arrivals to merchants below, until two-way radio made the whole system obsolete in 1923. The view from the top, over Portland’s rooftops toward the harbor, a bit scary for me but made the climb worth it.
From there, we walked down to Commercial Street in search of lunch at Luke’s Lobster, at 60 Portland Pier. We saw an interesting sculpture along the way as well as a rather large propeller. We arrived around 11:30 and had no trouble finding a table with a harbor view. Our waitress was attentive and steered us well on beer and sandwich choices — Clare went with a classic lobster roll, while I opted for the sampler, a trio of lobster, crab, and shrimp rolls. Both were excellent. I mentioned to our waitress that we hail from the Maryland-Virginia area, home to some of the best crab anywhere, but had to admit that Maine’s crab held its own — every bit as good as what we get at home.
We continued down Commercial Street toward High Street, detouring briefly so Clare could see the Victoria Mansion at 109 Danforth Street. By then the morning’s early start had caught up with us, so we skipped the tour and headed back to the hotel to rest.
Later, we met up with Shannon Keller from Road Scholar for the Coastal Maine: Portland to Bar Harbor program, ahead of joining the full group of participants for dinner that evening. Shannon (617) 315-8851 also does tours in Boston so if you’re looking for a tour guide in Boston, she might be right for you. Before heading down, we made a stop at the 15th floor of the hotel for the view from Top of the East — a fitting close to a first day that had already shown us so much of the city.
History, Old Port, and the Coast
After breakfast, we settled in for a lecture from Linda Pomerleau, a great primer on Maine itself — forests, population trends, potatoes, lobsters — the broad strokes we’d need as we started digging into the state in earnest.
From there, we headed downtown for a walking tour of the Old Port, strolling past the shops and restaurants lining Congress Street and Exchange Street. Among the buildings we passed was the childhood home of the renowned poet Henry Wadsworth Longfellow. We learned that Portland has a sister city, Shinagawa, Japan. Our guide had no shortage of material — Portland, it turns out, has burned down more times than seems reasonable for one city — and the walk eventually brought us to the waterfront, where industry and tourism sit side by side in a way that seems to define how Portland works.
The fires, as it happens, go back further than I expected. The first was no accident of fireworks or overcrowded harbors but an act of war: on October 18, 1775, British naval forces under Captain Henry Mowat bombarded and burned the town, then still called Falmouth, in retaliation for Patriot uprisings. Over 400 buildings were destroyed and more than a thousand residents left homeless just as winter was setting in. The city rebuilt in 1786, renamed itself Portland after the Isle of Portland in England, and carried on — only to burn again nearly a century later. On July 4, 1866, a firecracker tossed into a boatyard sparked what became the Great Fire of Portland, destroying roughly a third of the city and leaving some 10,000 people without homes. It was, at the time, the largest fire to hit an American city, and the rebuilding that followed reshaped both the skyline and the city’s approach to fire safety.
It’s a history that stretches back further still. The site was first settled in 1633 as a fishing and trading village called Casco, on land inhabited by the Abenaki before European arrival brought disease and conflict that reshaped the population. The village weathered Abenaki raids in 1676 and French attacks in 1690 before its 1786 renaming, and Portland briefly served as Maine’s first capital after the state split from Massachusetts in 1820 — a separation that came, fittingly for a country obsessed with balance, as part of the Missouri Compromise.
After a brief rest stop, we had lunch at the Old Sea Port Grill, where fish and chips seemed to be the dish of choice at our table, and then boarded the trolley for a tour with Steve — our driver and guide, and by far the funniest person we met all day. Steve took us out to the Eastern Promenade for a wide-open view of Portland’s grand old homes, then past the Portland Observatory (the same signal tower we’d climbed the day before, and, as Steve reminded us, the last of its kind still standing). We rounded out the day with a trip to Portland Head Light, commissioned under George Washington, with Steve peppering the whole tour with facts about Maine and Portland that kept us laughing as much as learning.
Rockland, and Camden
We began the day at the Maine Maritime Museum in Bath, where our guide Jeff led us around the grounds and talked us through what it took to build wooden ships at the old Percy & Small Shipyard. It’s a remarkable site — the only intact shipyard in the country where large wooden sailing vessels were once built — and it started, improbably, with seven Bath residents forming a small marine research society back in 1962. What began as a modest local effort has grown into a sprawling campus: the shipyard itself, the Victorian-era Donnell House where a shipyard owner once lived, and exhibits covering everything from lobstering to the wreck of the clipper ship Snow Squall.
Jeff clearly wanted us to leave knowing about the Wyoming — and it’s easy to see why. The largest wooden sailing vessel ever built in the United States was constructed and launched right on that site in 1909, and the museum has erected a full-scale evocation of its bow and stern in the exact spot where the original ship came together. Standing beneath it gives you a real sense of the scale these shipbuilders were working at, long before steel hulls took over. Clare and I spent some time in the museum and were delighted with many of the maritime exhibits. We wandered the grounds a bit more, had a lovely lunch, and then were back on the road.
Our next stop was the Farnsworth Art Museum where Clare and I, along with several others in the group, opted for a docent-led tour focused specifically on the Wyeths. The Farnsworth’s collection is enormous — nearly 16,000 works in all, including one of the largest holdings of sculptor Louise Nevelson’s work in the country — but it’s the three generations of Wyeths, N.C., Andrew, and Jamie, that the museum is perhaps best known for, thanks in part to a partnership with the Brandywine Museum that gives it access to thousands more Wyeth pieces. Clare and I would highly recommend going to this museum if you are in Rockland.
From there we made our way to the Lord Camden Inn in Camden, with just enough time for a short break before wandering over to 40 Paper for dinner. We also walked down to the Camden waterfront to see all the vessels in the harbor.
We closed the day with a lecture on “Strong Mainers” by Nicole Flores — a wonderful rundown of the women who shaped this state’s history. Abbie Burgess, Frances Perkins, the so-called Lobster Lady — there were so many stories packed into that hour, and it was a fitting way to end a day so steeped in Maine’s history.
Rockland, Camden, and Lobster Boats
After a delicious breakfast and an unhurried start, we traveled to the Sail, Power and Steam Museum in Rockland. Waiting for us was Captain Jim, who welcomed everyone with a lively ribald sea shanty before launching into what is obviously his life’s passion.
The museum is unlike any I have visited. Perched on Rockland Harbor, it is a fascinating collection of historic boats, engines, sails, maritime artifacts, and countless treasures that tell the story of Maine’s seafaring heritage. What began as Captain Jim and his wife Meg’s personal collection has grown into one of Rockland’s premier museums. Today it preserves New England’s maritime history through boat restoration, sailing programs, educational exhibits, and even concerts by local musicians.
As interesting as the museum was, Captain Jim himself was the real attraction. His enthusiasm was infectious as he brought maritime history to life with one story after another. We watched a Foucault pendulum demonstrate the Earth’s rotation, learned about the great windjammers—including one Captain Jim built and sailed himself—and marveled at the clipper Red Jacket, which crossed the Atlantic in just over thirteen days, a remarkable achievement for its time.
One name that kept surfacing was Nathaniel Bowditch, the mathematical genius whose work revolutionized navigation and whose influence is still felt today. Captain Jim also delighted everyone with the dramatic story of the schooner Bowdoin escaping an Arctic harbor, earning enthusiastic applause from our group. By the end of the presentation, many of us were so captivated that we purchased his book before leaving. Spending time with someone who has devoted his life to preserving Maine’s maritime traditions felt like a privilege.
Back in Rockland, we enjoyed a simple but excellent lunch at the Atlantic Baking Company that Clare and I both enjoyed, followed by some free time to wander the harbor and browse the shops before returning to Camden for the highlight of the afternoon.
At 3:15 we boarded the Lively Lady for a lobster cruise with Camden Harbor Cruises. As we left the harbor, we passed Curtis Island Lighthouse and continued toward Rockland Breakwater Light, with magnificent views of the rugged Maine coastline and some impressive waterfront homes along the way. I enjoyed seeing some sailboats gliding along Penobscot Bay.
Of course, everyone was there for the lobsters. Our guide—who also happened to be a fellow Road Scholar participant—explained how Maine’s lobstermen divide and respect their fishing territories, relying as much on tradition and unwritten rules as on state regulations. Her presentation was both informative and entertaining. Those who wanted the full experience even had the chance to hold a live lobster, while several passengers left with brightly colored lobster buoys painted in shades of salmon, blue, and sea-green as souvenirs.
As we cruised back toward Camden, Mt. Battie rose above the harbor. Our guide pointed out that this very landscape inspired Edna St. Vincent Millay’s celebrated poem Renascence. Knowing that one of America’s finest poets found inspiration in the same view made the scene even more memorable.
By the end of the day, we had immersed ourselves in Maine’s rich maritime history, gained a new appreciation for the lives of its lobstermen, and enjoyed some of the most beautiful coastal scenery in New England. It was another wonderful day on the Maine coast.
Rockland Harbor, Fort Knox, and Bar Harbor
Our morning began aboard the Schooner Heron, which was built in nearby Camden by Nigel and Bonnie Bower. The schooner was designed specifically for day sailing along Maine’s spectacular coast. Bonnie, her daughter, and a crew member welcomed us aboard for a sail across Rockland Harbor. With a steady breeze filling the sails, we slipped quietly out into Penobscot Bay, enjoying one of those perfect Maine mornings when the wind, the water, and the coastline all seem to come together.
Bonnie proved to be much more than our captain—she was an exceptional storyteller. As we sailed, she shared the history of Rockland, explained the harbor’s ecology, and described how she and her family came to build and operate the schooner. Originally settled around 1769 by John Lermond, the community was once known simply as “The Shore” before becoming East Thomaston in 1848 and finally adopting the name Rockland two years later. The city’s fortunes were built on vast limestone deposits, whose lime was shipped throughout the East Coast from its deep, protected harbor. During the nineteenth century, Rockland proudly called itself the “Lime Capital of the World,” with smoking kilns dominating the skyline while shipbuilding, granite quarrying, and fishing fueled the local economy. When the lime industry eventually faded in the mid-twentieth century, Rockland reinvented itself, becoming known for the Maine Lobster Festival, the Farnsworth Art Museum, and a thriving downtown filled with galleries, restaurants, and shops.
One of her most entertaining stories was about Andre the Seal, an orphaned harbor seal adopted by Rockport harbormaster Harry Goodridge. Harry had hoped Andre would become his scuba-diving companion, but instead the seal became something of a local celebrity. Andre never truly returned to the wild and remained in Rockport until his death in 1986. Even today, the town remembers him with genuine affection, and it’s easy to understand why. Of course, there’s always some guy who can’t help himself but has to kiss Andre on the nose.
Back on shore, several of us enjoyed fresh lobster rolls while soaking up the sunshine before heading to one of Maine’s most impressive engineering landmarks—the Penobscot Narrows Bridge Observatory. An elevator carried us 447 feet to the observation deck, where panoramic views stretched across the Penobscot River, Penobscot Bay, and the distant mountains. Standing high above the river offered a remarkable view on the landscape we had been exploring all week.
Our next stop was nearby Fort Knox, one of the best-preserved nineteenth-century forts in New England. Construction began in 1844 to defend the Penobscot River Valley against the possibility of a British naval attack that, fortunately, never came. Named after Henry Knox, George Washington’s first Secretary of War, the fort eventually served as a training site for Union volunteers during the Civil War, including soldiers from the legendary 20th Maine Regiment.
Our guide, Dean Martin, serves as Executive Director of the Friends of Fort Knox, while his wife, Sherry, helps keep the fort’s operations running smoothly. Dean’s enthusiasm for the fort’s history brought the massive granite walls, underground passageways, and military architecture to life, making the visit far more engaging than simply wandering through the old fortifications on our own.
From Fort Knox we continued our journey to Bar Harbor. Along the drive, our Road Scholar leaders showed a short video about Andre the Seal, giving us a chance to revisit the story Bonnie had shared earlier that morning. After arriving, we had a little time to stroll through Bar Harbor before enjoying dinner at Testa’s Restaurant. It had been another full day—one that blended history, beautiful scenery, and memorable stories, all connected by Maine’s enduring relationship with the sea.
Acadia National Park
After a steep climb by bus up Cadillac Mountain, wandering among the wildflowers at the gardens of Sieur de Monts, and listening to the raucous calls of seabirds at Egg Rock, we experienced Acadia National Park in all its natural beauty. Before setting out for the day, I had awakened early to capture the first light of sunrise from the Atlantic Oceanside Hotel.
Our guide for the day was Gerry Berlin, with his capable assistant Mark. Gerry’s enthusiasm for Acadia was contagious as he introduced us not only to the park’s spectacular scenery but also to the people and history that have shaped it over thousands of years.
Long before Acadia became one of America’s most beloved national parks, Mount Desert Island was home to the Wabanaki—the Maliseet, Mi’kmaq, Passamaquoddy, and Penobscot peoples, collectively known as the “People of the Dawnland.” They traveled these waters in birchbark canoes, hunting, fishing, and gathering along the rugged coastline for countless generations. They called this place Pemetic, meaning “range of mountains,” a name later shared with the French explorer Samuel de Champlain when he arrived in 1604. Today, the Wabanaki continue to maintain a formal government-to-government relationship with the National Park Service.
Centuries later came the “Rusticators,” wealthy city dwellers who escaped the summer heat to experience Mount Desert Island’s fresh air and dramatic scenery. Their arrival helped transform the island into the vacation destination it remains today, while preserving much of the natural beauty that continues to attract visitors from around the world.
Our first stop was Cadillac Mountain, known to the Wabanaki as Wapuwoc, the “White Mountain of the First Light.” Rising nearly 1,530 feet above the Atlantic, it is the highest point on the eastern seaboard so close to the ocean, and for part of the year it is the first place in the continental United States to greet the sunrise. Although fog drifted across the summit briefly during our visit, the warm air made for a pleasant walk, and the shifting clouds gave the mountain an almost mystical quality. While I was a bit nervous about the height of the mountain, I was able to navigate the path.
From there we visited the beautiful gardens at Sieur de Monts, where native plants provide a living introduction to Acadia’s diverse ecosystems. Our next stop was Thunder Hole, where the Atlantic surges into a narrow granite inlet. At the right tide, the compressed waves produce a booming roar that gives the site its name. Even without a dramatic explosion of water, the relentless power of the surf crashing against the rocks was mesmerizing.
As we continued along the Park Loop Road, breathtaking ocean vistas alternated with dense evergreen forests. We crossed one of John D. Rockefeller Jr.’s graceful stone bridges, admired several quiet beaver ponds, and eventually arrived at the Jordan Pond House. Before enjoying a wonderful buffet lunch, we had time to stroll part of the famous carriage roads, another of Rockefeller’s enduring gifts to the park.
The afternoon concluded with a nature cruise through Frenchman Bay. We saw the glacial erratic that is a prominent feature on the shore of Bar Harbor. Harbor seals basked on rocky ledges while gulls and cormorants wheeled overhead among the scattered islands, particularly on Egg Rock. Our naturalist’s enthusiasm was contagious, and by the end of the cruise the morning fog had given way to brighter skies, revealing yet another side of Acadia’s beauty.
That evening we gathered one last time for our farewell dinner. Naturally, lobster was the meal of choice for most of us, including several in our group who were trying it for the very first time. As the evening came to a close, it was hard to believe how much we had experienced in just one week. Acadia had offered us magnificent scenery, fascinating history, abundant wildlife, and warm hospitality—a fitting finale to an unforgettable journey along the coast of Maine.
Farewell in Bar Harbor
After breakfast, Clare and I said our goodbyes to our Road Scholar companions. Most were beginning the journey home or continuing on to other adventures, while we had one final day to enjoy Bar Harbor at our own pace.
Our first stop was St. Saviour’s Episcopal Church, renowned for its extraordinary collection of stained-glass windows. The church is home to ten windows created by Louis Comfort Tiffany, including several crafted from his patented Favrile glass, celebrated for its rich layers of color and shimmering iridescence. Together with more than forty memorial windows by British, German, French, and American artists, the church offers a remarkable survey of stained-glass artistry spanning more than a century.
Even for someone without a particular interest in stained glass, the church is worth visiting. The colorful light filtering through the windows creates a peaceful, contemplative atmosphere that invites visitors to slow down and simply take it all in which Clare and I took a few moments to appreciate.
From there we stopped for lunch at Lunch‘s (the clam chowder and sandwiches were quite good) before visiting the Abbe Museum, one of the places Clare and I had most wanted to see. Dedicated to the history and living cultures of the Wabanaki Nations, the museum tells the story of the Abenaki, Maliseet, Mi’kmaq, Passamaquoddy, and Penobscot peoples, whose connection to this land stretches back thousands of years.
What impressed us most was the museum’s emphasis on presenting history through Wabanaki voices. Rather than treating Native Americans as people of the distant past, the exhibits make it clear that these are vibrant, living communities whose culture and traditions continue today. The museum also addresses difficult chapters of Maine’s history, including disputes over land, water, and sacred sites, while highlighting ongoing partnerships with Wabanaki communities to tell their own stories.
It was a thoughtful and fitting way to conclude a trip that had introduced us to so much of Maine’s history—from its maritime traditions and coastal communities to the people who first called this environmentally spectacular place home.
We ended the afternoon exactly as we wanted: sitting outside at the Ivy Manor Inn, enjoying live music, sipping a cold beer, and reflecting on an unforgettable week along the Maine coast. There couldn’t have been a more relaxing way to bring our adventure to a close on this portion of the trip.
Day 8: Northeast Harbor, Southwest Harbor, and the Road South
Northeast Harbor, Southwest Harbor, and the Road South
Before leaving Mount Desert Island behind, I took one more morning stroll around Bar Harbor. I took a photo of the B&B we stayed in before walking down to the harbor where the sun was coming up over the glacial erratic. We spent one last morning exploring two of its harbors—Northeast Harbor and Southwest Harbor. Although only a few miles apart, each has developed its own distinct character, both shaped by a deep connection to the sea.
Our first stop was Northeast Harbor, long known as one of Maine’s most elegant summer communities. For generations it has attracted wealthy families seeking a quieter alternative to Bar Harbor, including members of the Rockefeller family. So many prominent Philadelphia banking families once summered here that the village earned the nickname “Philadelphia on the Rocks.”
The village still reflects that understated elegance. We admired the historic Asticou Hotel, the beautiful Asticou Azalea Garden and nearby Thuya Garden where we saw a couple having wedding photos taken, and watched activity in the marina, where hundreds of yachts spend the summer months. Despite its reputation, Northeast Harbor never felt pretentious—just peaceful and beautifully maintained.
A short drive brought us to Southwest Harbor, whose atmosphere could not have been more different. While Northeast Harbor caters to summer visitors, Southwest Harbor retains the feel of a true working waterfront. Lobster boats shared the harbor with pleasure yachts, and the sights and sounds of a community that still earns its living from the sea were everywhere.
Southwest Harbor is also home to The Hinckley Company, one of America’s premier yacht builders, whose craftsmen have been building exceptional boats here since 1928. We also learned about the Wendell Gilley Museum, dedicated to the region’s long tradition of bird carving, another reminder of the artistic heritage that has flourished along Maine’s coast.
As luck would have it, a local craft fair was taking place during our visit, giving us the perfect excuse to slow down and wander among the booths. We enjoyed talking with several of the artisans and picked up a few souvenirs to help us remember our time in Maine.
Leaving Mount Desert Island, we made our way back to Camden for lunch at Barren’s Distillery and Restaurant before continuing on to Rockland. There we checked into the Old Granite Inn and ended the day with dinner at Hill’s Seafood.
I should also mention our stay at the Old Granite Inn. The new owners and innkeepers, Greg and Kelly English, were warm, welcoming, and a pleasure to talk with. They generously shared the history of the inn and offered excellent recommendations for dining and things to do in Rockland, making us feel more like guests than customers. If you’re planning a visit to Rockland and enjoy the charm and personal attention of a bed-and-breakfast, I can highly recommend the Old Granite Inn.
A Slow Sunday Around Rockland
Sunday unfolded at an easy, unhurried pace—a day devoted less to major attractions than to discovering the small places that often become the most memorable. As usual, I started the morning with a walk, taking in the sunrise and looking for unexpected sights and experiences along the way. One of my discoveries was an osprey circling above its nest, a small but memorable moment that reminded me that sometimes the best travel experiences are the ones you don’t plan for.
Our morning began at Owls Head Lighthouse, perched high above Penobscot Bay. It isn’t one of Maine’s largest or most dramatic lighthouses, but its setting makes it well worth the visit. The views across the bay were beautiful, and the peaceful surroundings invited us to linger for a while before continuing on.
Just down the road we stopped at the Owls Head General Store, where we saw them making their renowned sandwiches. Right next door stood one of those quintessential small-town treasures—a tiny United States Post Office with a beautifully maintained flower garden tucked away behind it. It was the kind of unexpected discovery that reminds you to slow down and appreciate the simple pleasures of traveling.
Our next stop was Birch Point State Park, where a broad sandy beach stretched along the rocky Maine coastline. We spent some time walking the shoreline, enjoying the fresh ocean air and the constant sound of the surf. Later we visited nearby Crockett’s Beach, another pleasant stretch of sand, although for us it couldn’t quite match the natural beauty of Birch Point.
Back in Rockland, we happened upon the annual Lobster Day celebration. Local musicians provided the soundtrack while artists displayed their work and families wandered among the booths. It wasn’t a large festival, but it perfectly captured the friendly, unpretentious atmosphere we had come to appreciate throughout our stay on the Maine coast.
Before calling it a day, we made one final stop in nearby Rockport at Bleecker & Greer, a delightful specialty food shop offering fresh cheeses, cured meats, and excellent sandwiches. We enjoyed a quiet meal while reflecting on the past week’s adventures.
Sometimes the best days on a trip aren’t filled with famous landmarks or carefully planned itineraries. Instead, they’re made memorable by scenic overlooks, friendly conversations, small local businesses, and the unexpected discoveries that happen when you simply allow yourself to wander. Sunday was one of those days, and it was a fitting way to savor our last full day in coastal Maine.
A Wrong Turn to Port Clyde, and Boothbay Harbor
We left Rockland that morning with a carefully planned route. Unfortunately, the road—and our GPS—had other ideas.
Somewhere along the way, a lack of signs combined with a navigation system that seemed just as confused as we were sent us on an unexpected detour to Port Clyde, well beyond where we intended to be. When we finally stopped at the local post office to ask for directions, the postmaster smiled and told us we had reached “the end of the world” before pointing us back toward Boothbay Harbor.
It wasn’t exactly according to plan, but it reminded me of something travel writer Rick Steves often says: Getting lost while traveling can lead to unexpected adventures and opportunities to meet new people, enhancing your overall experience. It encourages exploration and can result in discovering hidden gems that you might not have found otherwise. While I wasn’t thrilled about losing time, our detour took us through quiet fishing villages and along scenic coastal roads we otherwise would have missed. Sometimes the unplanned moments become part of the adventure.
Eventually we arrived in Boothbay Harbor, although later than expected, leaving us less time than we had hoped for exploring the area. Boothbay Harbor is a quintessential New England coastal town renowned as the “Boating Capital of New England”.
Our first stop was the Coastal Maine Botanical Gardens, one of New England’s true horticultural treasures. What impressed me most wasn’t just the beauty of the gardens but the story behind them. In 1991, a handful of local residents envisioned creating a world-class botanical garden on a stretch of rugged coastal forest. Their dream required sixteen years of planning before finally opening in 2007, and at one point several founders even put up their own homes as collateral to keep the project alive.
Today that vision has become the largest botanical garden in New England. More than 300 acres encompass beautifully designed gardens featuring native Maine plants, woodland trails, sculptures, and nearly a mile of tidal shoreline. Knowing how much determination it took to transform an ambitious dream into such a remarkable destination made the visit even more meaningful.
Although time was short, we still managed to spend an hour exploring the harbor itself. Boothbay Harbor may have only a few thousand year-round residents, but during the summer it comes alive with visitors, pleasure boats, and the activity of a community that still maintains its shipbuilding heritage. Five shipyards continue to operate here, including the well-known Washburn & Doughty yard, a reminder that this is more than simply a tourist destination.
Our favorite stop, however, was much simpler. We found an ice cream shop serving outstanding homemade ice cream. Unable to resist, I chose an indulgently rich chocolate flavor while Clare selected blueberry, a perfect taste of Maine. We carried our cups down to the waterfront, found a bench overlooking the harbor, and simply watched the boats come and go until it was time to leave.
Looking back, the day never unfolded the way we expected. We got lost, arrived late, and had less time than we planned. Yet we still discovered beautiful gardens, enjoyed one of Maine’s most picturesque harbors, and ended the afternoon sharing ice cream by the water. Perhaps Rick Steves is right—sometimes getting lost really is part of finding a place.
From there we drove down to Freeport to our hotel. Not much in the mood to go back out, we ordered a pizza from a local restaurant and enjoyed a quiet evening in the room.
An Unplanned Extra Day
After a leisurely breakfast, Clare and I packed our bags for what we expected would be our final day in Maine. As it turned out, Maine wasn’t quite finished with us yet.
Our first stop was south of Portland, where we hoped to find the Trudy Point Steel Observation Tower, a remnant of the coastal defenses built during World War II. The tower, constructed as part of the expansion of the area’s observation system, once supported the nearby Battery Cravens and Battery Ferguson installations. After the war, the towers were decommissioned and eventually acquired by the town of Cape Elizabeth.
We soon learned, however, that finding a historic structure and actually reaching it are two different things. A local resident we met before setting out warned us that the tower had become heavily overgrown and was difficult to access. Taking his advice, we changed plans and instead followed a nearby shoreline path he recommended. It turned out to be a pleasant alternative, offering beautiful coastal views and a chance to admire the impressive homes tucked along this stretch of Maine’s shoreline.
Since we were nearby, we decided to make one more visit to Portland Head Light, one of Maine’s most iconic landmarks. We walked the paths around the lighthouse, explored the remains of the old Fort Williams fortifications, and enjoyed one last look at the dramatic coastline before continuing toward Two Lights State Park.
That was when our plans changed.
While driving, I received a text message from American Airlines informing us that our afternoon flight home had been cancelled because of weather affecting the Washington, DC area. After considering our options, we abandoned our remaining sightseeing plans and headed directly to Portland International Jetport to figure out what came next.
After several attempts, we managed to secure a new flight for the following afternoon. With the extra night now added to our trip, we returned the rental car, checked into the Hilton, and accepted that our final day in Maine would look very different from what we had imagined.
We ended up having lunch at the Sea Dog Brewing Company, and although Two Lights State Park would have to wait for another visit, there was something fitting about the way the trip ended. After a week filled with history, scenery, unexpected discoveries, and wonderful people, our final Maine adventure was simply learning to adjust when circumstances changed.
Travel rarely follows the exact path we plan. Sometimes the best journeys are the ones that leave a little room for the unexpected.
