All travel, meals, and activities were self-funded.
Last summer, I crossed off a bucket list destination with a visit to Maine.
I’ve always been drawn to the Northeast and New England in particular, and though this trip happened nearly a year ago, I feel compelled to share the particulars. My parents and I visited my sister, who was doing a two-month research project at the University of Maine. What she was researching and its real-world implications remain a mystery to me. (Sorry, Madeline.)
Due to the research program schedule, my work schedule, and my parents’ work schedules, we could only visit Maine for a long weekend, which just so happened to be over the 4th of July last year.
Here’s how we spent the 4th of July in Portland, Maine:
📆 Trip Dates: July 3-7, 2024
✈️ Getting to Portland, Maine
If there is a long way and a short way to get to Portland, Maine, from Louisville, Kentucky, we took the long way, no doubt about it.
We flew on Delta Air Lines from Louisville to Boston, rented a car, and drove from Boston to Portland, where we checked into our hotel — more on that in a minute — and then drove another two hours to pick up my sister at the University of Maine’s main campus in Orono. All in all, it felt like about 9,549 hours of flying and driving, which is only a slight exaggeration. It was a lot of travel. We’ve learned our lesson: next time, just take the connecting flight into Portland.
On the plus side, though, it was an excellent way to see the state of Maine. The lack of billboards made for unspoiled views of the Maine coastline and the central region’s forested areas.
🛌 Where we stayed
We stayed at the Tru by Hilton Portland Airport Area using my banked Hilton Honors points. Despite an overzealous fire alarm system on the third night, it was a great hotel that provided exactly what we needed. Comfortable beds, some of the roomiest bathrooms I’ve seen in a hotel, and a well-appointed complimentary breakfast made this budget-friendly hotel a great, out-of-the-way place to stay. Similar hotels in the downtown area of Portland were going for $800–$1,200/night for the same time frame, whereas the Tru by the airport was less than a quarter of that per night.
One neat addition to the hotel that I don’t see everywhere was near the elevator bank. The staff had listed their recommendations for things to do, restaurants, and favorite local attractions, and we definitely took them up on their suggestions.
🏞️🌊🛍️ What we did
As this was a family vacation, emphasis on vacation, we went at a leisurely pace.
We arrived on July 3rd, and by the time we drove half the full length of the Pine Tree State, twice, we were exhausted.
Day 1: July 4, 2024
On the 4th of July, we were up and out of the hotel by 11 a.m. in search of our first destination: the Portland Head Light and Fort Williams Park. The Portland Head Light is perhaps one of Maine’s most iconic scenes, and the park was busy due to its notoriety and the holiday, but it never felt overcrowded.
I learned via a historical plaque—all of which I have to read—that poet Henry Wadsworth Longfellow often walked from Portland to the lighthouse and made friends with the keepers. It is believed that the Portland Head Light inspired his poem, The Lighthouse, which concludes with an ever-revelant call for human connection:
“Sail on!” it says, “sail on, ye stately ships!
And with your floating bridge the ocean span;
Be mine to guard this light from all eclipse,
Be yours to bring man nearer unto man!”
After exploring Fort Williams Park some more, we ventured into downtown Portland. Regrettably, I didn’t take many photos, but we enjoyed a delicious lunch at Cheese Louise, a grilled cheese shop in the “Old Town” section of Portland, and walked into many shops that were out of our budget range.
Post-grilled cheese, we drove south and ended up at Scarborough Beach State Park, one of the beaches near Portland. (In our naivete and due to a general lack of preparation, we didn’t realize there was an admission charge—Kentucky’s state parks do not charge an admission fee.) The beach was about to close for the day, and there were only a few families left when we arrived. The breeze made it a bit chilly, but we survived.
We finished the day with a seaside dinner—read more about that experience later—and a fireworks show we could see from the hotel.
Day 2: July 5, 2024
After an exciting day in the Portland area, we ventured north to Freeport for some shopping. Our only planned stop was the L.L. Bean Flagship store. There must have been something in the air, because we spent the entire day in Freeport shopping. I eventually lost count of how many hours we spent in the L.L. Bean store, and my credit card should have been glad that I only brought a carry-on size suitcase for the trip, otherwise I would have bought oh so many more things. I wanted one of everything in the pets section. Parker deserves it.
The highlight of our day in Freeport was discovering a Dooney & Bourke factory store. D&B is my mom’s absolute favorite purse brand — her collection is in the dozens — and it was a total surprise to see a Dooney & Bourke location in person. We arrived while the store was closed for lunch, but we were there promptly at 1:00 PM when they reopened. Already armed with a Dooney & Bourke purse and leather phone case, my mom inspected every bag in the store before making a decision.
After returning from Freeport, and likely several thousand dollars poorer, we all settled into our rooms for naps — shopping takes it out of you.
The night finished with a trip to Peaks Island, a small island of just 720 acres, just off the coast of Maine in Casco Bay. After taking the ferry over, we enjoyed a waterfront dinner at Jones Landing Oceanfront Bar & Restaurant and a leisurely walk around the island to admire the architecture and all the hydrangeas.
Day 3: July 6, 2024
My sister was called back to her research program at the University, which meant we spent the day traveling the two hours from Portland to Orono and exploring in between. Family road trip, part 3?
We had a full day, so we explored the area near the University, especially the city of Bangor — pronounced Bang-OR. One highlight was the former home of novelist Stephen King. The Victorian-era mansion was, well, spooky. I’m not a horror person, but I can appreciate a writer’s talent. The house, complete with bats and spiders in the wrought-iron fence, also had a spectacularly creepy wood statue in the side yard.
🦞 Where we ate
This may end up as a standalone post later on, but in short, we had So. Much. Lobster.
Maine versus Connecticut Style Lobster Rolls
I got a crash course in lobster roll styles while in Maine. Come to find out, there are two main styles: Connecticut and Maine. The main(e) difference? The temperature of the lobster. Mainers prefer the lobster in their rolls to be served cold, tossed in mayonnaise, and on a toasted hot dog bun. Nutmeggers, however, prefer their lobster rolls served warm and dressed with butter. I, of course, had to try both styles. My apologies to Connecticut, as I preferred the Maine style.
Our first lobster rolls came from a truck parked at Fort Williams Park, at the base of the Portland Head Light lighthouse. I didn’t get any photos — it didn’t last that long — but we did enjoy a quintessentially Maine scene as we ate our lobster rolls and Whoopie Pies under the watchful eye of seagulls who called the park home.
Oceanfront Lobster Rolls in Portland, ME
After our beach outing later in the day, we had dinner at The Lobster Shack at Two Lights, and it was, without question, my favorite meal of the whole trip. We ordered inside at a counter over tanks of live lobster. Your order number is called out over a loudspeaker, and you take your trays to a picnic table of your choice overlooking the Atlantic Ocean as waves crash against the coast below. (There is indoor seating available, but why would you?)
While in Freeport, we had lunch at another fast-casual restaurant within walking distance of the L.L. Bean store, the Lobster Cooker and Pub. The restaurant, housed in a refurbished barn, was very charming and busy. You order at a counter and wait until your order number is called, and you’re forgiven for sensing a theme as it too was delicious, though we skipped on the lobster this time. Luckily, there was plenty of fried haddock to go around.
Quick lunch spot in Old Port, Portland, ME
We had a no-frills lunch at Cheese Louise, a New England grilled cheese franchise in Portland’s Old Port district. I had the Vermonter, which consists of Cabot cheddar and Muenster cheeses on Sourdough bread, served with kettle chips. It was the perfect lunch spot after exploring the Old Port district and the surrounding areas of Portland.
Sweet Treat in Portland
While walking around the Old Port area, my sister and I enjoyed a very sweet maple flavored donut and iced coffee at The Holy Donut, which I’m just discovering was vegan. It was a perfect pick-me-up after lunch.
We had an excellent time in Maine and cannot wait to go back. The next time I’m in Maine, I plan to tackle Acadia National Park and get plenty of sunrise photos.
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