We can’t remember exactly how it came about, this trip to Maine. We remember having the conversation, just not what it entailed or how it led us north. It could have been weather-related, prompted by our pre-summer selves already desperate for an escape from the heat that blankets Virginia. Or maybe it was just that it had been five full, COVID-ridden years since our last trip and it was time for a revival. Maybe I mentioned puffins, for reasons now forgotten, and their residence in Maine. Maybe it was a little bit of everything, all the things and none of them, too.

We checked our calendars and a few weather forecasts, did a touch of research on when whales and puffins grace the coast of Maine, and settled on six days in early June. After a quick initial planning session to firm up our dates and sort out a few key details, we added a third traveler to our ranks. Armed with a rough outline of where and when, I settled into planning mode to determine exactly what we’d be doing. What I came up with turned out to be an exceptional way to spend a few days exploring coastal Maine.

DAY 1: Eating + Drinking our way through Portland

Coming from Richmond, Virginia, a flight to Boston was cheap and direct, and we were on the road to Portland by 10 a.m. Two hours later, we arrived, parked our car at our waterfront hotel, and immediately set out to begin eating and drinking our way through the city, popping in and out of shops as we went.

Collectively, we were blown away by the food scene in Portland. The three of us have a deep appreciation for good food and drink, and fairly discerning palettes. We didn’t eat a single bad bite in Maine. A few standouts from our first day wanderings include the following:

1. Central Provisions: Our first bites in Portland were arguably our best bites. Arriving just in time for lunch, we split a few appetizers, including the bone marrow toast, eggs + crispy rice with Chinese sausage and a poached egg, and the seared white asparagus. Every bite was perfection.
2. Holy Donut: Scratch-made potato donuts with a seemingly legendary following. Get the chocolate sea salt.
3. the Thirsty Pig: The perfect spot to sit down for a drink on the patio and enjoy some live music before continuing.
4. Eventide Oyster Co.: Home to what I’m told is an epically good lobster roll, we split a few oysters, drank martinis, and fell in love with their red wine mignonette.
5. Fore Street Restaurant: Influenced by the cuteness of the building’s exterior, we wandered in, snagged three seats at the bar and feasted. The wood-grilled hanger steak was exceptional.
6. Portland Hunt + Alpine Club: Because it was still light out, we sat outside here for a cocktail. There’s popcorn on the menu too, and while we didn’t try it, we wish we had.

Full, a little tipsy, tired and giddy from first-day-of-vacation vibes, we were in bed by 9 p.m.

DAY 2: Lighthouses + Lobster Rolls

We started our day at Standard Baking Company. It opens at 8 a.m., and on my Maine-dwelling uncle’s recommendation, we were first in line at 7:45 a.m. Once inside, we gaped at the offerings and ordered a box full of delights, including a morning sticky bun with walnuts that we talked about for the rest of the week, a blueberry scone, a prosciutto and asiago scone, and a pain au chocolat. As a person who almost always travels alone, I found great joy in traveling with two like-minded eaters who weren’t opposed to sharing.

After breakfast, we headed out to visit a few lighthouses. I’d visited Maine, and the Portland area, back in 2019 for a cousin’s wedding, and relied on my lighthouse itinerary from that trip as our guide. We started at the Bug Light, officially the Portland Breakwater Light, the littlest and most ornate lighthouse we saw. From there, we checked out the Spring Point Ledge Lighthouse, one of 49 caisson lighthouses in the U.S., then visited the Portland Head Light, the oldest lighthouse in the state. The Ram Island Ledge Light is visible from there too, and after a quick jaunt around Fort Williams Park, we checked out the Cape Elizabeth Light. It’s on private property these days, but still active and, when it was built in 1828, was part of the first set of twin lighthouses to grace the coast of Maine.

My Portland-based cousin recommended The Lobster Shack at Two Lights for lunch. It’s allegedly not the absolute best lobster roll in Portland, but it is the best one with a view and, conveniently, it was located right next to our final lighthouse stop.

Truthfully, I’ve never been a big eater of sea creatures. Childhood trauma scared me away from it, mostly, but in all my years of scoffing at seafood, I’ve been told countless times that fresh is better and you’d be hard-pressed to find fresher lobster offerings than the ones in Maine. So, I got a lobster roll and, stranger yet, I liked it.

Sated, we headed to Portland’s East End and spent some time walking along the Eastern Promenade Trail. This multi-use, paved trail runs alongside the sea. It’s lined with beach roses, and along the way we encountered a groundhog and two birds who were definitely up to no good.

After our walk, we popped into Tandem Coffee for an afternoon pick-me-up, then headed to Oxbow Brewing, home to not only delicious beers, but also the Duckfat Frites Shack. We split poutine topped with duck confit, and a pile of fries paired perfectly with a flight of all five of their sauce offerings, with the curry mayo coming in as a top pick for all three of us.

After our fry feast, we dropped our car back at the hotel, freshened ourselves up, hit a few nearby stores and stopped by ViA VECCHiA, which we found to have good vibes and great cocktails. Then, it was off to dinner at Scales, the one and only place I’d made a reservation and where we enjoyed a full feast, incredible service and an exceptional Rhône Valley rosé. We capped off the night at Room for Improvement, a divey industry bar recommended to us by Bri, our server at Scales.

DAY 3: Northward Bound, Whale-Seeking + Puffin Peeping

After two solid days of glorious gluttony in Portland, we snagged coffee and an incredible selection of breakfast pastries from Tandem Coffee, declared we really should probably eat more vegetables, and headed north, popping into the massive L.L. Bean Flagship Store in Freeport on our way to Boothbay Habor, where we’d booked a Whale Watch & Puffin Combo Cruise with Cap’n Fish’s Cruises.

Determined to increase our intake of green vegetables, we ate lunch at McSeagull’s before the cruise. We all got salads, some topped with lobster, others topped with blackened chicken or salmon. It was a good reset and, excited for the day’s activity, we headed toward our boat.

I love the idea of a whale-watching cruise. It always seems like a great idea, like the perfect way to experience the ocean, but the reality is, the whales do what the whales want to do. There’s no guarantee, because whales are wild animals (same), and sometimes what they want is to avoid any and all sorts of human fuckery.

All this to say that no, we did not see whales. We did see puffins, though. They were happily doing puffin things around an island inhabited by a few scientists who camp out there for three months at a time researching all sorts of bird things, and we also saw a playful pod of white-sided Atlantic dolphins. We also learned that 4.5 hours on a boat is too much time on a boat, which is a lesson I will surely forget again in 4-7 years, just before I again board a boat in the hopes of seeing sea creatures.

After the boat, we hopped back in the car and headed an hour north, to Camden, where I’d booked us a room at the Lord Camden Inn. I parked the car while my companions dropped our bags and, when I made it back to the lobby, I returned to an assortment of delighted exclamations regarding the perfection of our room and its view. Knowing the room would be there later and because we’d snagged a last-minute reservation at Long Grain and were nearing a mutinous level of hunger, we headed out for what proved to be yet another delicious meal. We capped the night off with a whiskey drink at the rooftop bar at 16 Bay View, the sister hotel to ours, and tucked ourselves into bed just before 10 p.m.

DAY 4: Camden, Blueberry Pie + Cadillac Mountain

We spent our morning leisurely wandering around Camden, Maine, checking out the in-town waterfall, and shopping. A few of our most notable and beloved stops:

• Owl & Turtle Bookshop Cafe, where we ordered coffee, perused the stacks and all left with a tote featuring the store’s exceptionally cute logo, as well as 1-3 books each.
• Symmetree, which is filled with “Maine-inspired goods.” A true story: I walked in and exclaimed, wait, is this place made for me?!, the response to which was a firm yes from the shopkeeper. Also, fun fact, this is pretty much the only place you can get Good & Well‘s incredible Katahdin Woods & Waters candle, which is maybe the best candle of all time.
• Fatface, a U.K.-based outfitter, apparently, with the kindest and most helpful shopkeeper.

We got back on the road around 11, just before many of Camden’s stores opened, but every single place we went into was an absolute delight and filled with the nicest, most helpful people. Maine might be home to the kindest, most pleasant humans I’ve ever encountered, and I say that as a girl born and mostly-raised in Virginia.

Before heading north again, we popped briefly south to visit the Rockland Breakwater Lighthouse and get our steps in and then we were off, on toward Bar Harbor. We pit-stopped at The Chart Room for wine and some blueberry pie with a side of blueberry ice cream, and then, because I’d checked the weather for the following day, I was adamant that we head to Cadillac Mountain before even checking into our hotel.

In the summer, Cadillac Mountain is the first place on America’s East Coast to see the sun. It’s also the top of Acadia National Park. Rain was coming in the next day and I knew, from personal experience, that the mountain loves to get fogged in, which was why I’d demanded we head to the mountain while the sky was still blue. It did not disappoint.

After our foray to the top of Acadia, we wound our way back down the mountain, to Bar Harbor and our hotel, freshened ourselves up and popped in for a snack at Project Social, which we very much loved, and then ducked into an Irish pub just as a storm rolled in rain. After it cleared, we wandered around, taking in the town, watching as the sun set over the water and reveling in the rain-soaked lilac scent shaken free by the evening breeze.

DAY 5: Acadia National Park

We woke up to a misty, fog-filled morning, ready to spend a day elevating our heart rates. Eaters still, and knowing we’d need fuel for the day’s adventures, we started our day with breakfast at Mount Dessert Bakery in Bar Harbor before heading out to hike the Beehive Loop, one of the most popular hikes in the park. It’s a short loop, just about 1.5 miles in length, but rated hard because it requires hikers to scramble up a few cliffside ladders. One of the draws of this hike is, allegedly, the view, but I’ve never seen it. Much like when I hiked it the first time in 2019, the trail was fully entrenched in fog.

After our hike, we continued along Acadia’s Park Loop Road, stopping along the way to take in the views of Maine’s rocky coastline. We originally planned to stop for popovers at Jordan Pond House, but it was slammed when we got there, and after a handful of passes through the parking lot with no luck, we continued on, assuming that good food would come our way eventually and, after a few misses, we landed at Peter Trout’s Tavern & Inn. We ordered a few beers to refresh us from our arduous journey, made friends with the bartender and the woman sitting beside us, ordered lunch and left the place fully charmed (and exceptionally full).

Replenished from lunch, we continued on to do a bit more hiking and wandered down Ship Harbor Trail and the Wonderland Trail, both easy and about 1.5 miles. Then, for our final park experience, we visited the Bass Harbor Head Light Station, before heading back to Bar Harbor to clean ourselves up to meet my uncle, a Bar Harbor resident, for what proved to be an excellent dinner at McKay’s Public House.

DAY 6: Homeward Bound

Bags packed, we hit the road early, swinging back by Mount Dessert Bakery for a few more breakfast pastries to fuel us along our 4.5-hour drive back to Boston. The drive was not terrible, mostly because I’d never done it before, and after an uneventful flight, I was home by 6 p.m.

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Nice To Know

• The weather in Maine does what it wants. Pack a rain jacket, know that the weather forecast may change and if fog obscures your view, just think of it as being hugged by cloud.
• Acadia National Park is popular. I visited Acadia for the first time in June 2019, and it was quite busy then, but it was even busier this time around, and earlier in the season. Our National Parks have gotten more crowded since 2020, as more people flocked toward outdoor recreation hot spots in the wake of the pandemic. The good news is that Acadia has a free shuttle, the Island Explorer, that can help eliminate your need for a parking spot.
• I spent a rain-soaked few days in Acadia back in 2019, and truly, it’s a gem.