Back in August 2021 I took a road trip with Jake to Maine, and we had a blast! I had never been to the state before – Maine’s a pretty long trek from Houston. The summer weather was outstanding, and our lobster roll per day ratio at one point was averaging over 1. We started in Portland, ME and concluded the drive north in Bar Harbor, ME, the town right by Acadia National Park.
Day 1 – Drive to Portland, ME (Saturday, August 21)
The trip started with bagels in Connecticut before getting on the road to drive to our first stop: Portland, ME. The weather started off pretty nice, but it started to get SUPER foggy and rainy the further we got north. Our trip was perfectly timed with Hurricane Henri’s descent on the east coast, but it made Portland all the more cozy. We ended up getting dinner at this place called Scales that a person in our Airbnb apartment hyped up to us. It was delicious!
Day 2 – Exploring Portland (Sunday, August 22)
We had booked tickets to go on a “Seafood Lovers” walking tour in Old Port. The weather ended up cooperating for the most part, and I would definitely recommend the tour. We got to try all sorts of different seafood, and our tour guide Glenn was very knowledgeable and funny.
Later that night, we went and ate dinner at Glenn’s favorite restaurant in Portland, which was called Street & Co. I’m pretty sure Jake is the one who asked Glenn what his fav restaurant was, and everyone on the tour listened very intently to Glenn’s response lol. One thing I hadn’t planned for this trip was any sort of food reservations. Jake and I had both been working a lot in the weeks leading up to the trip, and we had really only planned out hotel accommodations and high level ideas of what we wanted to do in each place. I did not realize Maine is such a vacation destination, and no restaurant had reservations available for weeks! So yes, we showed up to Street & Co. at 5 pm, when they opened, and sat at the bar. It was awesome. Jake and I still debate which meal from this trip was our favorite, but I still think this was the best one. I think maybe because we got to talk to the staff a lot behind the bar and watch them shuck oysters, which I thought was neat 🙂
Afterwards, we walked around Old Port and visited a speak easy Glenn had told us about. It was a really nice time!
Day 3 – Head to Boothbay Harbor (Monday, August 23)
Before we left Portland, we woke up before our Airbnb checkout time and walked in the misty rain to get donuts from Holy Donut. I had multiple people tell us to go there after I had told them about our planned trip to Maine. They made it sound like it was a non negotiable to skip. And I think you could say they were right. Apparently this place has a line always, and we were lucky that it was a Monday and rainy because we did not wait very long at all. The place is famous for its potato donuts. We got the chocolate sea salt and maple bacon donuts because that’s what Glenn said was best (he really influenced our culinary experience in Portland).
Side note: I have eaten so much food over the last few days during the holidays, and I’m cringing as I write about all this food I ate on the trip. I think I’m going to have to go on a shame run after I post this hahahaha
After we ate these donuts, we went to go see the Portland Head Lighthouse. It was so beautiful. The weather was foggy, but it just let us see the lighthouse in a different way.
Afterwards, we set off to drive to Boothbay Harbor, our next stop. I had read online about this lobster roll stand called Red’s Eats near Boothbay, in Wiscasset, ME. It had rave reviews and a gazillion awards from all sorts of reputable food associations. I had also read that it always has a line. We really had no plans for the rest of the day, so we decided to give it a shot. I cannot lie – this line was so long. We probably waited from start till we got our food for 2 hours. I can say it was the best lobster roll we had on the trip and was definitely the best bang for your buck for $ versus amount of lobster received. I have no regrets, and Jake and I had a lot of fun just waiting together. If you ever go to Red’s, just don’t show up hungry!
Afterwards, we drove to our bed and breakfast, Topside Inn, in Boothbay Harbor. I was really excited for this place. It was the fanciest place we had booked, as the other places we stayed at we had booked and got good deals through my employer’s rewards portal, but this one was the special one we didn’t do that for. It had great reviews, and I had read this person’s blog post that hyped up their breakfast. And I was super excited for our room. All my expectations were EXCEEDED. Jake and I both agree that it was our favorite place we stayed at. It was one of those bed and breakfasts that the best part of where you are at location wise is the bed and breakfast. Boothbay Harbor itself is a really cute small town too, don’t get me wrong!
For the rest of the day, we mostly just hung out, and Jake watched me take 5 million photos of the inn. I was super excited for the next day because 1) the forecast looked much more promising and 2) if you remember, the Topside Inn breakfast.
Day 4 – Coastal Maine Botanical Gardens + Drive to Camden, ME (Tuesday, August 24)
I was not going to miss the breakfast. Jake and I set multiple alarms so we did not sleep through it. This day was so spectacular. The weather was perfect, and we ate this gourmet breakfast, enjoyed the views from our inn, and then went to go see the Coastal Maine Botanical Gardens. Cue the photo shoot of breakfast:
After breakfast, we enjoyed the views from our room and walked around town a bit.
Then we went to the Coastal Maine Botanical Gardens. These were gorgeous, and I highly recommend a visit if you’re ever in the area. We were lucky there was a special exhibit going on there. There were giant trolls made from wood by a Danish artist Thomas Dambo. They were so mystical!
Afterwards, we drove to Camden where we just spent the night before our drive to Bar Harbor the next day! We didn’t really do anything eventful in Camden (a lot of stuff was closed since it was a Tuesday), except Jake rocked his mustache after shaving his beard…
Day 5 – Drive to Bar Harbor (Wednesday, August 25)
The whole reason we had chosen Maine was we both really wanted to go to Acadia National Park. We woke up early in Camden and headed to Bar Harbor because we were supposed to go on a whale watching tour (one of the few things we had booked in advance) at 2 pm. We were really excited, but the tour ended up getting cancelled due to the seas being too rough from the hurricane I mentioned earlier. This ended up being in our favor because we got more time to explore Acadia and went on a really cool nature cruise on Saturday that was cheaper, shorter and we saw tons of wildlife on (spoiler alert for ahead)!
We used the extra time to just drive around Acadia and pop off at different spots to explore.
Later that night we walked around Bar Harbor and got drinks at The Barnacle, a cool little spot with kombucha cocktails, and ate dinner at Havana, a place Jenny’s parents had recommended to us. It was also delicious, and I think Jake says this was his favorite meal from the trip.
Day 6 – Hiking in Acadia (Thursday, August 26)
We were supposed to wake up early and go on this hike to Cadillac Summit, one of Acadia’s most popular destinations. You have to pay to drive up it, so we decided to hike up and down it instead. It turned out to be a 9 mile hike with how far we parked our car from the trail entrance. We ended up sleeping in and doing the hike later in the day, so this was the main activity of Thursday. Afterwards, we drove on Mount Desert Island out toward Seal Beach (it’s a lot less crowded the further away you get from Bar Harbor) and got lobster rolls for dinner from a little stand and watching the tail end of sunset. This was such an “exhausting” day haha.
Day 7 – More Hiking in Acadia (Friday, August 27)
On this day, we decided to do Beehive trail. I had nooo idea how treacherous this trail was – there are ladder rungs and rock climbing that you do throughout it. Apparently there were multiple warning signs I didn’t notice, but Jake did and was like well Claire seems fine with it so let’s do it lol. It was a blast though! It was a much shorter hike with quick elevation gain, and we got such pretty views so quickly. It was a nice contrast to the previous day’s longer hike.
Day 8 – Nature Cruise and Heading Back South (Saturday, August 28)
As I mentioned, our whale watching tour that was planned for Wednesday ended up getting cancelled. We booked this nature cruise instead with a different company on Saturday morning, and it was a great time. It’s hard to show in pictures, but we saw osprey, bald eagles (adult and juvenile), seals, and porpoises. The 2 hours really flew by in a minute!
After this, we got our last lobster roll of the trip and started the drive home. We live over an 8 hour drive from Acadia, so we split the drive and stopped in Providence on Saturday night. We just got dinner near our hotel downtown and explored a bit.
Day 9 – Final Leg of Driving Back to CT (Sunday, August 29)
The last day of the trip! Sigh. We got breakfast near Brown University in a cool area with lots of vintage thrift stores, where we bought a few things to decorate the apartment with. We then walked around the campus for a while before getting in the car and heading back to CT. We hit an incredible amount of traffic and got home in the evening and dealt with the fact that we had to go back to work the next day haha. It was a great trip, and I definitely want to go back to Maine soon, especially being driving distance from it.
I used some of the items we bought to decorate our bar cart area in the apartment, so I’ll show off that little corner below.
Thanks for revisiting the trip with me! If anyone has any fun nature places in the U.S. they recommend visiting, please fill me in!! Hope everyone is having a great holiday 🙂
Looks like such a fun trip. Love the mix of hiking and eating 🙂
Looks like a wonderful trip! Great pics!