Maine Itinerary: Portland and Bar Harbor

This post is a hybrid itinerary and blog, due mostly to the fact that our trip up to Maine last fall had some …. complications early on. I’m going to include what we intended to do as well as what we actually ended up doing. This just goes to show that even the best laid (travel) plans have to be adaptable, and we ended up having an awesome trip despite a couple of snafus. Let’s get to it!

Day 1 – Portland 

Intended itinerary:

Real Life:

I had such great intentions for our first day in Portland. We were going to see so many sights and drink so much craft beer. But then the universe intervened. First, I got either food poisoning or a stomach bug about a week before our trip. There is literally nothing more nightmarish to me than a stomach bug. Fortunately, I don’t get them often, but when I do, they linger, so I was very worried it would impact all the food I wanted to eat. But I soldiered through and made sure I had enough Pepto with me to settle an elephant’s stomach.

The next curveball was waking up the morning of departure to a canceled flight and nearly no alternative options. We were scheduled to fly from BWI to Manchester, NH in mid-October, and it happened to be right when Southwest lost their damn minds and cancelled thousands of flights. After some (very quick) research, I was able to rebook us on a flight from Baltimore to Albany, and I was able to find us another rental car (albeit for about $400 more than the one we had booked). However, that doubled the length of our drive from the airport to our AirBnb in Portland. Effectively, our entire first day was shot. Between the long drive and my wonky tummy, we canceled our dinner plans and ordered takeout to our little apartment. But we made it to Maine!

Day 2 – Portland

Intended itinerary:

Real Life:

The next morning, which was now our only full day in Portland, began with a trip to The Holy Donut. We went to the location closer to the minor league baseball park as opposed to the downtown shop in an effort to avoid some waiting in lines, but we still ended up waiting probably 15 minutes. We ordered a half dozen donuts and taste tested each of them. The Chocolate Sea Salt was my favorite, but I would recommend getting there earlier in the morning than the 9ish am that we did for the freshest treats.

We then headed downtown to do some souvenir shopping and browsing, but there weren’t a ton of shops open that early, so we opted for plan B — adventuring to all the local lighthouses. Maine is known as the land of 1000 lighthouses, and Portland is home to several. Quite honestly, I had an idea of what a lighthouse looked like in my head and only one of the Portland locations even remotely resembled that. The variation in design and function was fascinating. It didn’t hurt that it was a gorgeous day in the upper 60s, so everything was picture perfect.

Post-lighthouse hopping, we grabbed some takeout from Duckfat and headed back to our apartment. You can read a million articles online about Duckfat, so I’m not going to reinvent the wheel with that, but my favorite feature of the Duckfat experience was the sampler of sauces. For all you sauce and dip aficionados, Duckfat is your mecca.

Day 3 – Portland to Bar Harbor 

Intended AND Actual Itinerary:

  • Stop in Freeport at the LL Bean Flagship store en route up the coast
  • Stop at the Coastal Maine Botanical Gardens and hunt for giant trolls!
  • Drive the rest of the way to Bar Harbor and check into our cottage at the Bay Meadow Cottages
  • Dinner at Abel’s Lobster Pound, a cottage turned restaurant in a spruce grove on a fjord where there are picnic tables and tiki torches

Visiting the LL Bean flagship store in Freeport is essentially a rite of passage for all visitors to Maine. This sprawling complex features a huge retail store, a separate home decor and furniture store, a Ben and Jerry’s ice cream shop, an outdoor movie screen, and more. It can be a little overwhelming if you don’t go in with a plan, but it’s definitely worth a stop. Plus, they can ship home any purchases that you don’t want to lug around with you or wait to have monogrammed.

Next we had tickets to visit the Coastal Maine Botanical Gardens, which was featuring an installation entitled “The Guardians of the Seeds.” This installation included 6 giant wooden troll sculptures in various locations throughout the grounds. If you found all six and solved the puzzle in the brochure, you then had directions to the seeds that the trolls were guarding. It was another gorgeous, fall day, so we took our time finding each troll, eating some lunch at the cafe, and finally making our way to the seed depository. I highly recommend stopping by regardless of whether the trolls are still there because it’s a lovely garden and a great way to break up the trip from Portland to Bar Harbor.

After a few hours of very scenic driving, we made it to our accommodations at the Bay Meadow Cottages just outside Bar Harbor. I highly recommend booking a cottage here because, first and foremost, the cottages are adorable and the bed was probably the most comfortable one we slept in the whole trip. Secondly, they have a view of the water and a bunch of firepits to enjoy on chilly nights. Third, it’s convenient to Bar Harbor without being priced like Bar Harbor proper.

The view from Abel’s Lobster Pound

For dinner that night we got lucky and made it to Abel’s Lobster Pound for the last night of the season. Be prepared to wait for a table at Abel’s. We got there probably around 5pm and had to wait at least an hour, but the scenery is excellent and beverages are available while you wait. Neither myself nor my fiancé are huge lobster people, but when in Maine, right? So we ordered a lobster to split along with several sides and some fresh blueberry pie for dessert. Make sure you check opening and closing dates for the lobster pounds because they are not open year round.

Day 4 – Bar Harbor/Acadia

Intended AND Actual Itinerary:

Acadia is obviously one of the highlights of visiting the Bar Harbor area, and that is especially true during foliage season. This day on our trip happened to be my birthday, so what better way to celebrate than with an early morning hike?? (I know, who am I and what have I done with Kate?) We ventured over to Jordan Pond and hiked the loop around the lake, which is a relatively easy 3-ish mile loop with some light rock scrambling around the back side. The weather was absolutely perfect and the colors in the trees were breathtaking. As with my other National Park hike suggestions, get here early. By the time we finished our hike, there was nowhere left in the parking lot and the trail was getting inundated with people.

We had wanted to get entry tickets for sunrise on Cadillac Mountain, which is allegedly the first place to see the sunrise in the continental United States, but tickets are VERY limited. They are released on line a few weeks prior to the date of your visit, and you have to move fast to snatch them up. If you’d like to park t the base of the mountain and climb up, you don’t need an entry ticket as those are mostly to regulate parking, but it’s going to be a long hike completely in the dark.

For dinner we went into Bar Harbor and had reservations at Geddy’s, which is a seafood mecca located right on the main drag. Reservations for restaurants in Bar Harbor are definitely recommended, even when it is off-peak season. It was a bit later in the evening, so a lot of the surrounding shops were closed, but I earmarked plenty I wanted to visit the next morning.

Day 5 – Bar Harbor

Intended AND Actual Itinerary:

  • Breakfast at Cafe This Way
  • Peruse the shops in Bar Harbor
  • Drive up to the summit of Cadillac Mountain

For our last day in the Bar Harbor area, we headed into town for some breakfast at Cafe This Way. It’s a super cute little breakfast only spot with indoor, outdoor, and tented seating (at least when we went in October 2021). The food is good and the service is quick, and it’s location is perfect for perusing the shops.

Our final activity was a midday drive up to the summit of Cadillac Mountain to take in the views. The weather was absolutely perfect, and the leaves were really starting to put on a show. I would love to get back to Acadia someday to do even more exploring, especially in a different season just to see how much the terrain changes. Do you have any favorite Acadia hikes you would recommend?

I hope this itinerary/blog is helpful in planning your own trip to the land of 1000 lighthouses. I can’t believe it’s taken me so long to get up to Maine, but it certainly won’t be my last visit. Leave a comment down below with any of your favorite sights, lighthouses, restaurant recommendations, or additional giant troll sculptures!

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