2025 // Northeast on Film
Boston, Portland, Baltimore, Gettysburg, Washington D.C., Manassas
Massachusetts, Maine, Maryland, Pennsylvania, Virginia, October 2025
So the real story here is that Gina and I had been aiming for a 2025 sis trip. The back and forth we went through should be studied along with the potential destinations. I’m talking AUSTRALIA, NEW ZEALAND, THE COOK ISLANDS - nothing was off limits for us, probably to our detriment. August rolled around and we were scrambling to scrape something together since the year just flies when we enter the last third of the year.
We hadn’t been out to the East Coast in a minute and Lola was getting a full knee replacement, so we decided to crash Mom’s post-operative Pennsylvania visitation. Deciding where to go before visiting family proved to be another challenging decision-making process, but we opted for Portland, Maine as a fun, new destination to explore.
I was VERY excited by this prospect, mapping out a comprehensive itinerary and must-do’s to which Gina remarked “you know we’re only there for a weekend, right?”. Maine just has a lot to offer!
Boston to Maine
I hit a BIG snag at the start of my travel getting caught in the Alaska Airlines IT outage which grounded all Alaska flights. Ask me about it in person and I’ll drone on, but the short version is that it was a MESS. I made it to Boston the next day after an absolute rebooking headache. Mollie and Robert, my boyfriend’s sister and brother-in-law, were kind enough to host us in Boston (Gina for two nights!) and we had a fun evening catching up over dinner before taking the Amtrak Downeaster train to Portland the next morning.
The train to Maine was beautiful! The fall foliage was at peak color as was our yappiness, making the two hour ride feel like nothing. Gina really wanted to live life on the rails, so hopping on the train, armed with our pocket croissants was making her dreams come true.
Portland, Maine
With an ambitious itinerary and determination to cover as much ground as possible, we dropped our bags at the hotel, and immediately fueled up with a lobster roll which was 10/10. We bounced around restaurants and shops in Old Port, eventually making our way down to the Waterfront. There are all sorts of curated antique shops and hip stores selling Maine made products.
All this is to say, Portland is quaint and cute! Between the colonial brick architecture and seafaring spirit, coupled with the foodie energy, there’s so much to see and do.
We absolutely lucked out with the weather too as it was approaching the end of the tourist season. This was a crucial detail in our weekend activities as we were embarking on a Lobster Cruise with Lucky Catch. Out of all of my diligent research, this was an absolute must-do activity for me. Meeting at the docks on the Waterfront, we cruised out to Casco Bay to participate in the lobstering experience and gain some appreciation for fishing. Our captains were incredibly engaging, answering all of our questions and showing us the ropes of pulling, baiting and placing traps. Gina and I were endearingly referred to as “West Coast” since we were the only tourists from west of the Mississippi. As we finished up the tour, we caught a glimpse of the famous Portland Head Light, the most photographed lighthouse in the U.S. and oldest in Maine, in the distance.
The nice thing about traveling with your sister is that you have an understanding of what the other is game to do. We share a mutual understanding that we need to divide and conquer the food scene in order to try as many things as possible. Later that afternoon, Gina was a good sport and indulged in oysters with me as we discussed more potential plans. I will admit, the oysters were delicious (and so cheap!!!) but I do prefer west coast oysters!
Our conspiring over oysters led us to attend a Maine Mariners hockey game. We stumbled upon the office and they clued us in on the weekend games. The Maine Mariners are part of the ECHL and have a devoted following. Sadly, they lost 5-4 and I have now been let down by two different Mariners sports teams in the month of October. The consolation to the loss was that I became obsessed with the mascot, Beacon, an Atlantic puffin, who was roaming the arena and hyping up the crowd.
We couldn’t resist packing in one more adventure. To cure the post-game blues, we embarked on an excursion to the L.L. Bean Flagship in Freeport. It felt like a fever dream to squeeze that in before our final dinner at Street & Co., but that’s our travel style. L.L. Bean exceeded expectations despite being under construction. We spotted the famous Duck Boot and a Bootmobile! To add to the chaos, we spotted Eartha, the world's largest rotating and revolving globe, along the way. The dinner at Street & Co. satisfied our seafood cravings as we ordered delicious scallop and cod dishes. It was a fabulous dinner to cap off a jam-packed day.
The final day kicked off with the Mailboat Run, a ferry tour through the outer islands of Casco Bay to deliver mail. Again, we stocked up on pastries and coffee before we set sail. Somehow we ended up wearing the thinnest layered outfit of the whole trip. Luckily, Eli, my doting boyfriend, had implored me to pack my scarf because “it’s October on the east coast” and I swaddled myself up in that while we were out on the bow.
Another coffee to round out our double coffee days and we were off to the airport. Portland and Maine are places I’d love to visit again. We were struck by the hospitality of the city. Locals were genuinely curious to engage in small talk and excited that it was our first visit, often offering up recommendations for their favorite spots. Even with my flight fiasco at the start of the trip, camaraderie emerged between passengers; I have never spoken to so many people on a trip before. The locals are proud of their home and eager to share its magic.
Baltimore to PA — A Week on the Mason Dixon Line
No trip to the East Coast can be simple (for my family); there’s often multiple forms of transportation involved. Once we got to the Portland Airport, we flew to Baltimore, then drove two hours to Lola’s. It was a quiet week full of small town energy and quality time. We basically just watched the World Series. There were also visitations galore, a revolving door of people if you will. There was one day where 11 people just dropped by. The timing of the trip was quite fortunate as we were able to also visit Nana and celebrate her 93rd birthday. One of the most heartwarming things I get to witness is the community my grandmothers have made for themselves, especially since I don’t get the chance to visit them as often as I would like to.
A funny moment to cap off our time in Pennsylvania was when I somehow convinced Mom and Gina to make a detour to Gettysburg in order to stamp my National Park Passport. Mom rolled her eyes, Gina simply sighed in the back seat as I teemed with excitement of my first stamp. This was a sore spot because of the government shutdown and unreliable updates online about whether it would be open or closed. I would NEVER live down this excursion if the visitor’s center was closed and we made a 45 minute detour for nothing. Thank God (actually thank the Gettysburg Foundation and the workers and volunteers) it was open and I managed to get one of the stamps I was after. Sadly, I couldn’t convince them to do the cyclorama - next time!
D.C. to the West Coast
The week rolled by quickly which is always bittersweet. Gina and I dropped Mom off at Reagan Airport for her midday flight which left us with some time to kill before making our way to Dulles for our evening flights. The previous evening, post-Gettysburg stamp achievement, we were making our plan for D.C. and she asked “are there any spots there?”. Grave mistake. I looked up stamp sites and found that “George Washington Memorial Parkway is a passport stamp collector's treasure trove with 32 parkway-related stamps!” Gina’s LUCKY there was a government shutdown, because I would have had her go up and down the 25 mile parkway to collect all 32 stamps.
I bargained with her to go to Manassas National Battlefield Park and compromised by going into DC for brunch and coffee. Manassas, which I was pronouncing similar to molasses, is more commonly known as Bull Run, where the Confederates established themselves as an opponent, dashing the Union’s idea of a short war. The battlefield is now an expansive trail system with green spaces, parks, and dotted with historical landmarks like the Stone House.
To my dismay, the visitors center was closed, but we took some time to marvel at the hay bales, cannons, and monuments that signify the U.S. history. It’s such a Swiss Family kind of move to hit a literal battlefield before a flight.
Up and Down the Eastern Seaboard
Okay so it’s pretty clear we bounced around the East Coast: Boston, Massachusetts; traveling through New Hampshire; Portland, Maine; flying to Baltimore, Maryland; driving to Pennsylvania; venturing to DC. That’s the beauty of it all, traveling a mere few hours takes you through so many cities and states. I love the east coast and feel fortunate to be able to travel there for family. There is so much to see and do, so much history around every turn.
I am very grateful to have such a close relationship with my sister, one that allows us to both be excited about going on a sis trip together and getting up to whatever ridiculous things we can dream up! I can’t wait for the next trip back east!
