Weekend in Portland Maine (August 2023)
After any good trip, you will hear both Jenn and I say, “We should travel more.” It to me is the sign of a good vacation and since COVID we have started to ramp up our travel both with work and on our own. After we arrived home from Seoul we were deep in planning mode for where we wanted to go next. We had toyed around with going somewhere after my July work trip, but our schedules didn’t align. We thought about going to Cancun to finish off our goal to see the 7 wonders of the world, but it was far more money than we wanted to spend to go to Cancun. What we landed on given our limited availability was taking a road trip to Portland, Maine.
Day 1 -
A Chance
of Pasta
August 4, 2023
We left New York on Friday, August 4th after Jenn wrapped up a 7-9 AM call and made our way out of the city. Our first stop was to Chatham where we dropped Frasier off at Far Fetched Acres for the weekend. The drive took us about 45 minutes outside the most direct route which would have been fine had the rain not started immediately after dropping him off. We stopped 30 miles later to get gas and grab a quick bite at McDonalds before finishing the drive to Portland in non-stop rain. Don’t worry Jenn thought it was fine, she fell asleep for over an hour only waking for the last few minutes of the drive.
We ended up missing our reservation at Scales at 4:30 PM (the only one they had indoors that evening) and made a late drive decision to go to Solo Italiano which had one reservation left that evening. We arrived in Portland a little after 5 PM at the Press Hotel one of (if not the) nicest hotels in the city. We were able to find the valet (who was hiding from the rain) and take our bags to the second floor where we’d be staying for the next three nights.
After quickly unpacking and getting settled we made the brief walk down to the waterfront to Solo Italiano for our first meal in Portland and outside of a hamburger and fries our only real meal of the day. The meal started off great with a friendly waitress and a great glass of white wine for Jenn and red for me. We ordered the tuna tartare which was by far the worst dish we had the entire meal. From there we had a flatbread with prosciutto and mozzarella that completely made up for the first dish and was divine. For our main entree, Jenn had a clam pasta and I had a truffle duck pasta. Not the best pasta dishes ever but good.
We decided that with the rain stopping we’d venture out for our dessert. We didn’t get far because a few doors down from Solo Italiano was Coastal Creamery. We split a small cup of cookies and cream and of course immediately after we walked outside with our ice cream it began to pour. We hid in a small enclave waiting out the worst of it munching on our ice cream. Fifteen minutes later it slowed down so we made a run back up the hill to our hotel and called it a night. Although we spent most of today driving we’re excited for sunny weather tomorrow here in Portland.
Day 2 -
Will Travel for Wine
August 5, 2023
We woke up relatively early for a Saturday after a good night's sleep at the Press Hotel. Jenn worked for a few hours in the morning while I grabbed her Starbucks, went for a run along the beach, and grabbed a coffee at Bard Coffee near the hotel. By the time I got back, Jenn was getting ready and we left our hotel a little after 10 AM to go out and explore.
Given our late start, we didn’t have a ton of time but made a quick stop at the long line of Holy Donut. These are potato donuts (didn’t know that was a thing) and incredibly popular. We got cinnamon and an old fashion and they were fine. I think we both preferred regular donuts but it was good to try them. From there we went across the street to Starbucks where Jenn got her Maine mug and we got a glass of water for the road.
We made our way back to our hotel to pick up our car for our morning excursion. We jumped in the car and made the nearly two-hour drive to Cellardoor Winery which from what we read is the best winery in Maine. Granted they do have a tasting room in Portland we thought it would be nice to drive north, take in more of Maine, and get some wine. The drive up was stunning and as we wound around a beautiful lake and into the hillside we made it to Cellardoor Winery right at our 12 PM reservation. We got a table on the beautiful patio overlooking the vineyard and had two tastings of their signature wines with cheese, meats, and crackers and later a glass of their sparkling wine. The wine wasn’t anything to write home about but the combination of the cheese boards, the wine, and the beautiful view and it made everything taste so much better.
After spending over an hour at the winery we closed out our tab and drove back to Portland. It was an uneventful drive back until the last twenty minutes when out of nowhere a storm came in for five minutes and got to the point where I had to put my emergency flashers on it was so hard to see. Luckily it left as quickly as it came and by the time we arrived back in Portland, it was wet but beautiful and sunny.
That evening we had dinner reservations at Twelve a beautiful restaurant on the waterfront. We arrived for our 5:30 PM reservations at the chef’s counter. We were seated directly in front of the meat and prep stations and were thoroughly entertained. The hardest working man in the kitchen was the one in charge of cooking the steak and chicken who I don’t think caught his breath once the entire two hours we were there. Of course, Jenn and I spent much of the evening trying to optimize the kitchen tasks which is half the fun of sitting at the chef’s counter. We began our meal with two cocktails and a beautiful and delicious charred cucumber dish. From there I had their Lobster Roll (had to have it while we were out) and Jenn had the Bluefin Tuna. For our main entree, I had the New York Strip and Jenn had the Sea Bass. To round out the delicious meal for dessert we had the ice cream sandwich and chocolate sundae. Although not a perfect meal we found it to be a very good, close to excellent and one that we had a great time at.
After dinner we walked around Portland for close to an hour before heading back to the hotel to watch Sleepless in Seattle (Jenn’s first time) and falling asleep after a beautiful first full day in Portland.
Day 3 -
The Light House
August 6, 2023
We had almost an identical start to Sunday as we did Saturday except we both slept in. Jenn continued to push out work this morning while I went back to Starbucks and had a beautiful run along the beach. I decided to try a new coffee shop Arabica which was even better than yesterday’s. Jenn was ready shortly after I came back with my coffee and we were off.
Our plan for today was to tour as much of Portland as possible. We started at the oldest bookstore in Maine (Sherman’s) where Jenn bought a few card games and I bought a first-edition signed copy of Tom Lake by Ann Patchett. From there we went to a pet store where we bought Frasier a small stuffed lobster which he played with today.
After a little more window shopping we made our way to Central Provisions for brunch where we once again sat at the chef’s counter. The brunch was set up more tapas style and so we ordered several dishes to go with my bloody mary and Jenn’s mimosa. We started off with their Korean fries which were outrageously good. From there we had their corn bread which was average and their fish sandwich slightly above average. We finished off our brunch with a delicious hash that only made us wish we had gotten one sweet item as well.
We left brunch full and made our way to Victoria Mansion. We weren’t initially sold on spending time there and when the gentleman that worked there said they only allow guided tours I made the executive decision that it wasn’t for us. Instead, we walked back and grabbed our car, and made our way to Portland Head Light a beautiful lighthouse a few miles from downtown Portland. After spending a bit of time looking for parking we were able to make our way to the beautiful lighthouse, take some photos and enjoy the beautiful afternoon. Given there wasn’t a lot else to do we didn’t spend a lot of time there instead driving back to Portland to drop off our car and do some more window shopping before dinner.
After visiting nearly every gallery that was within walking distance in Portland we made our way to our final dinner of the trip at Fore Street one of the most popular restaurants in Portland and one we were only able to get in after Jenn basically begged on the phone a few days before we arrived. We got there a little before 6 PM and had an incredible last meal in Portland. I started off with their take on a Gin Martini and Jenn had a beautiful summer cocktail that reminded her a bit of the honey deuce at the US Open. We started off with a half dozen fresh oysters and a seafood chowder both divine. Jenn had a steak and I had a white fish (forget the name). The entrees didn’t hit the same highs as the appetizers but were still great.
From dinner, we walked to Beal’s Ice Cream which had an even longer line than Holy Donuts from yesterday where I had the coffee Oreo ice cream and Jenn had cookies and cream. We did another walk around the beautiful Portland downtown before going back to our room to pack up our stuff and finish the last 30 minutes of Sleepless in Seattle which Jenn fell asleep on the night prior. Although the weekend flew by I a so glad we were able to be somewhere new and enjoy the stunning weekend in Portland.
