Casco Bay, Old Port, Portland, ME
4 September 2026
Our Jeff was early on the morning of August 20. I'd mostly loaded the car the night before. On the rack were Janice and Our Jeff's gravel bike. Crammed into the back, with one seat up, were: my suitcase; one of Our Jeff's duffels; several backpacks loaded with biking gear; a tote bag for my hiking boots and spare sneakers; another full of everything I'd need to make coffee in the hotel room for me, Heddy, and Ginger; a bag of snacks and my lunch; and a handful of Jeff's tote bags and a duffel containing I didn't know what. There was room left for Jack's giant suitcase and what I assumed would be one more bag from Jeff. A pair of wheels with gravel tires rested in trash bags on top of it all.
I was scurrying around. There was trash to be taken out, compost to be buried, and cats to be said goodbye to. I moved the car to the street so that Jeff could put his in our garage. I'd barely wolfed down my breakfast when Jeff pulled in and began unloading his trunk.
"That's not gonna fit" is hardly a proper greeting for a person one is about to spend ten days with, but that's what I said.
"I know," he replied, and began to rearrange his luggage. I opened the trunk as far as Janice's handlebar would allow and left him to it.
Somehow, we got it all in and I could still see out of the top back window. Jeff attempted to put his car in our garage, but his car is wider than mine and there was a wheelbarrow that made him nervous. He parked it in our driveway instead.
Heddy drove up with Ginger in the passenger seat. We convened on the sidewalk and chose our route towards Portland.
Jack wanted to sit in back, behind me, which meant he couldn't hear anything I was saying. I put Jeff on communications; it would be his job to text Ginger during the drive so that we could stay together.
I use Waze, an app Heddy didn't have, so I switched to Google Maps, which, for whatever reason, was not sending audio instructions through the car's speakers, or at all. We stayed together and took a quick break at the Vince Lombardi rest stop on the NJ Turnpike*.
After fighting our way over the GWB (I've seen worse), I got confused about an exit and, as I was about to make the turn, the map changed instructions. Heddy and Ginger, a few cars back, didn't make that mistake. We wound up on the same parkway eventually. It took a bit of doing to land at a rest stop with open parking for us to meet again for lunch. We were somewhere in CT, where road crews were blocking lanes to mow the medians. Jack and I have a contest that we never win: Can we make it all the way across Connecticut without coming to a complete stop? Not today either.
Somewhere north of that, I made another map-reading error, staying left when I should have gone right when the highway divided. We had to drive 13 miles to the next exit to turn around. Usually, Jack keeps an eye on the map, and Waze talks to me. Clearly I'm incompetent without these cues, and the guys were both asleep.
We were rewarded for our wrong turn, though, because, on our way back in the right direction, Jack spotted the Manac flying moose mudflap**.
Jack shouted, "Look ahead! Look!"
I said, "Jeff! Take a picture!" I drove strategically to get behind, then alongside, the trailer.
"This was worth the detour," I said. It was the only one we saw on the whole trip.
Our Portland reservations were at the same hotel we stayed at on the first night of the Canada trip in 2024, the Hilton Garden Inn (I misnamed it in the 2024 post). It was the only decent affordable option during high season. As soon as I stepped into the lobby, I remembered the place and the room I'd stayed in. This time, we were going to spend two nights and really see the city. Like last time, we unloaded the bikes into our rooms.
To do that, Jack summoned an Uber to drive us to the Old Port area, which is loaded with restaurants. We picked Brickyard Hollow, because Jack and I had eaten at their other location in Brunswick in the spring and knew it would satisfy everyone. They have creative pizzas. We ate some creative pizzas.
And, this being vacation, we had to get ice cream. Jack and I led the group up the hill to Beal's.
We turned in early. The plan was to meet for breakfast and take Heddy's car to the Portland Head Lighthouse while Jack would Uber into town to peruse the bookshops and drink wine samples at Grippy Tannins.
I had to take a picture of the waffle station and sent it to Martin.
Heddy and Ginger had already eaten. I met Jeff in the breakfast area and hunted around for something edible. I wasn't expecting much, and that's what I found. There was oatmeal and milk. Good enough. Jeff sat across from me and did his best with pork pucks and some sort of egg thing. When Jack was ready, he was thoroughly disgusted with everything on offer. Jack is a cat. He has his standards and his routine, and when things are off, he gets grumpy. He could find something in town later.
Jeff had snagged one of those tourist maps every city has, with ads framing a cartoon of the city center. I was in the passenger seat to help Heddy navigate. We had to drive through town to get to the road that would take us south, so they got to see some of the city.
Jeff was looking for souvenir shops. One of the ads caught his attention. "The Sexy Squirrel!" he called out.
I said, "Google that." Don't Google that!
Heddy and Ginger chimed in, "Don't Google that!"
"Incognito," he said, and Googled it. He read a review out loud, including something like "creative taxidermy."
I'm not about to Google it, not even incognito. But I will give you the link to the Maine Souvenir Shop, and you can watch what folks are carrying past the store on the homepage video. It's worth the click, trust me.
We arrived at Fort William Park early enough to find a good spot near the lighthouse.
There's a path along the cliff. We chose to go north. I'll shut up now and let the pictures speak for themselves.
We did pause to send our middle fingers to Tom, who had declined our invitation to join us on the trip.
A grass spider is hiding between the leaves of this milkweed.
We climbed down to a beach.
Ginger spotted what looked like another old fort on the other side of the beach, so we followed the trail up to the cliff. What we arrived at was the remains of the Goddard Mansion, which had gone from home to hotel to hazard. Rather than raze the structure, the flammable bits were burned away and the rest reinforced.
Sic transit gloria money.
We made our way back to the parking lot, stopping to look at the schooners in Casco Bay.
We ended back at the first fort.
The group did me a solid by agreeing to go to the Allagash Brewery for lunch. I wanted to get some more sour beer, and there was a fancy food truck there where Jeff could begin his crustacean crusade with some lobster roll.
I went to the bar area to get a flight pour of Coolship Red, the best sour beer ever (I don't like much); think Sour Patch Kids without the sugar. The woman serving me was chatty, and I found myself explaining something I hadn't planned to bring up.
"In the spring, I bought a case of Red and a case of Ruby," I said. "I tried the Ruby last week and the color was way off from what I remembered sampling. It was really bitter too."
"That's not right," she said. "I'm going to grab a bottle and we'll try it. I'll bring it to your table."
She arrived with three glasses and a bottle of Coolship Ruby. She opened and poured, frowning at the yellow color. We each took a sip. It was just like my bottles at home.
"Oh, yeah, no, this is off," she said. "Come into the store and we'll make this right."
"What are you going to do with all the bad bottles?" I asked. She said she'd talk to her manager, but they'd probably have to dump them. Such are the vagaries of small-batch craft brewing.
I'd already purchased another 6 bottles of Red. Now I was going to have to find space in the car for another six bottles (3 Coolship Red and 3 Little Sal). Jeff, too, had come out with 12 bottles as a gift. "We'll make it fit," I said, not entirely sure we could.
After lunch, I showed them the Eastern Promenade from Munjoy Hill. We parked at the top and walked down.
At the edge of the bay was an unfinished building that made us do a double-take. It's not a ship.
There's a small, sandy beach along the promenade.
In the distance, a group of small sailboats circled each other. We figured it was a sailing class.
Heddy had been searching for the best coffee shops in Portland. The one we were aiming for, the Speckled Ax, was now closed for the day.
"Princess needs her coffee," she said.
I remembered the shop I'd wandered into last spring on my way back from the top of Munjoy Hill. "Take Congress Street," I said, and Double Great Coffee was still open. Jeff and I had our first (and maybe best) blueberry lemonades of the trip.
We scooped Jack up at Grippy Tannins and went back to the hotel. A bit of restaurant roulette landed us at Luke's in Old Port, on the water. We took another Uber to the waterfront and walked there.
I had to stare at the boney things on the piling a while before I figured out they were whale baleens.
Inside the restaurant was an attempt to save a dying trade:
We were seated outside, under a canopy. While we were waiting for our food, Jeff saw the herring gull. It was perched on a roof between our table and the one behind us. I turned sideways to snap a picture.
Jeff taunted the gull. "Yeah, you think you're gonna come down here, don't you?"
Seconds later, the bird swooped down to the table behind us, grabbed a paper tray full of lobster roll, and proeeded to swallow the contents whole. From where I was sitting, I couldn't see it, but Heddy had a clear view and sent me the pictures.
"He did it again," the server groused, cleaing the mess left in the theft's wake.
Clouds were settling in over Portland's skyline as the sun went down.
The golden hour hit as we got up to leave.
We found ice cream and then walked around, arriving eventually at the Maine Souvenir Shop. We had to go in. The creative taxidermy did not disappoint.
I paused at the mouse, wondering if this was a pet or a lab animal. One of the shop workers approached.
"This is Sleazy CZ," he explained, turning the base around. "She has ambitions to be a paralegal."
I replied, "Any way you can make the money..."
We stood outside while Jeff took a look at the Sexy Squirrel sweatshirts, which were a muted pink. He wasn't sure about the sizes or the color, or the cost, and he left with nothing.
We walked around some more. There was a nightclub entrance with cassette tape blanks lining one wall.
I stopped for some unintentional street art. The group waited for me at the corner.
We'd gone in a circle and were now one short block away from the Maine Souvenir Shop again, the sign in full view. Jeff said, "I'm still thinking about the sweatshirt." I pushed him forward. He made a decision.
Having had their fill of pork pucks, Jeff, Heddy, and Ginger decided we should go out for breakfast. They picked the Sinful Kitchen, a few blocks away from the hotel. We loaded the cars, beer and all, and drove to the restaurant.
It was worth the trip, even though it was small and crowded and we had to sit at the counter. All their coffee mugs were thrift store finds. Mine was clearly from the mid-1970s. The walls were covered in crayon drawings made by customers, because each table was covered in construction paper. I asked for some. The server tore off a piece of paper and handed me a cup full of well-used crayons. I doodled. Whether or not these wind up on the wall, I'll never know.
Heddy, Ginger, and Jeff wanted to stop at the LL Bean flagship store in Freeport. The place was sprawling, with a ginormous parking lot and three buildings. The first was full of hunting gear. I found two moose.
The second building was a massive, temporary tent, fully fitted with HVAC, 2-story high supports, and a wooden floor. This was where the clothes were. I hadn't planned to buy anything, but I found a fleece sweatshirt sort of thing that was half price. I'm pretty sure it was the only colorful item in the store. It's lined and has pockets.
The others might have bought some clothes too. I don't remember.
We went into the home goods section next. I didn't figure anyone would actually buy anything here, but I was wrong. Jeff had disappeared, and when he emerged, he was carrying a giant bag. "I found a set of towels!"
"We cannot fit that in the car," I whined. Heddy graciously offered to stow it.
Down the road from LL Bean is Wilbur's of Maine's flagship chocolate shop, and you know I had to stop there. I'd planned for this and had left a space behind the passenger's seat, so when the others gave me grief, I was ready. It was a narrow enough bag to fit where I wanted it. I also introduced Jeff to chocolate-covered blueberries.
Now we were on our way. The highway narrowed to two lanes. We turned off onto Route 1. We were an hour out from Bar Harbor. I turned on my Pandora app and picked the funk station. We all agreed that Pandora doesn't know what funk is.
We reached Route 3 and, at the top of a hill, a mountain loomed in the distance. I see this every time, and, in the back of my mind, I wonder if it's Cadillac. This time, Jack asked. I said, "We're facing the right direction."
The mountain looked so big, so ominous. We'd be riding our bikes to the peak in a matter of days.
(*In grad school, I was at a party at the field station when somone challenged everyone to name all the NJ Turnpike rest stops. I couldn't do it then, and I can't do it now.)
(**This is another thing we do to keep ourselves entertained on long drives. If we're on I-95 on a weekday, we might find a flying moose mudflap. These days, they're a rare sight.)
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