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Whenever we plan a trip to the US, it seems to follow the same pattern

  • Find one good reason to visit
  • Throw around a million ideas of other things to do while we’re there
  • Research those ideas forever without making a decision
  • Throw our hands up in the air and book something, anything, just so we don’t have to talk about it anymore
  • Totally luck out and have an amazing time
  • Congratulate ourselves on our excellent travel planning skills

And that’s how we found ourselves driving north of Boston in the pouring rain in late September, bouncing over roadworks on the highway while trying not to be side-swiped by bored truck drivers.

It wasn’t quite what I’d had in mind for my first time driving on the “wrong” side of the road in several years, but hey, Boston drivers are renowned for being polite and well-mannered and definitely not known as Mass-holes, so what could possibly go wrong?


We’d planned our trip around the Roger Waters shows in the city, since Lauren is kind of absolutely a Pink Floyd super-fan, and her buddy Drew had picked up tickets for them both. Since we were right there in New England anyway, and it was pretty much the perfect time to check out the famous fall colours that everyone raves about, while eating our body weight in lobster, we threw together a 10-day itinerary for doing exactly that.

Lobster roll

First stop: Maine. I’d only ever heard good things about the Pine Tree State, but had never quite managed to get there in the past. We’d barely arrived in Portland, our first stop, before I started questioning why the hell that was.

The crappy weather had cleared up by then, and the sun broke through as we started strolling along the downtown waterfront. With nowhere in particular to be, we just kept walking, following the old narrow gauge railway to East End beach. Yachts bobbed in the harbour, seagulls circled overhead, the sun fell into the ocean, and Maine quietly started to work its magic.

Portland, Maine boats

I’ve become a pain in the ass about what I eat these days, and since much of the US isn’t exactly renowned for small portion sizes and healthy options, I’d expected to struggle in New England. That was especially true for breakfast, which is why the Local Sprouts Co-op was a bit of a godsend.

As hipster as it was (and with homemade kombucha and a map on the wall showing where every single item on the menu was sourced from, it was definitely hipster), the food was tasty and made my stomach happy. So happy, in fact, we went there twice. +1 for Portland.

After a visit to the supremely-weird Cryptozoology Museum the next day (check out Lauren’s post for more about this home of imaginary weird creatures, and the equally weird people who believe in them), we took advantage of the gorgeous weather to explore Fort Williams Park and the famous Portland Head lighthouse just outside town.

Portland Head lighthouse

By exploring, I mean an hour of walking and taking photos, and two hours of lying on the grass in the sunshine and playing with friendly dogs as they bounded up to us. It was a good ratio.

Reluctantly dragging ourselves out of Portland the following morning, we had no idea what goodness lay in store. I’ll admit I don’t love driving on the Interstate highways in the US. They’re the most-efficient way to get from point to point… but on a road trip, I’m not looking for efficiency. I’m looking for scenic views, cute towns, winding roads, and a lot fewer trucks.

Why hi there, Maine Highway 1.

We were headed for Mt Desert Island and Acadia National Park, and with just 160 miles to our destination, naively believed we had more than enough time to explore the coastline along the way. We were wrong. Very wrong.

Next time, we’ll take a week to do the same thing. I’m not even kidding. This part of the country is seriously beautiful, and we only saw a fraction of it.

The section we were driving (the “Mid Coast”, if you’re a local) has turnoffs to dozens of gorgeous little towns and villages, sprawled out across some of the 3,000+ islands that dot the Maine coast. We left the highway just after Brunswick for no particular reason, slowly driving across three pretty little islands until we hit the appropriately-named Lands End. The road stopped abruptly at a gravel car park, a gift shop to the left, a hiking trail to the right, and calm blue ocean everywhere else.

Lands End, Maine

The sun beat down, making the water twinkle invitingly. Birds sang their hearts out, and it was only the occasional crunch of tires on gravel that reminded us we didn’t have this isolated spot entirely to ourselves. Most of the time, though, it felt like it. We didn’t do much, just idly exploring the rock pools, taking a hundred identical photos, and wondering aloud why we weren’t spending this entire trip firmly on the Maine coast.

It was past lunchtime by the time we finally rejoined the highway, and Bath, a little further down the road, looked like a good place to get a sandwich. Ok, so it was definitely a good place for a sandwich (thanks, Live Edge Deli), but the historic downtown area was seriously attractive as well. I was starting to sense a theme.

Bath waterfront park, Maine

Plans of a quick grab-and-go quickly shelved, we scouted out a picnic table at a waterfront park, the faint hum of traffic from the nearby Sagadahoc bridge doing little to lessen the ambiance. A family unpacked a hamper nearby, while we munched on our sourdough and continued the conversation about canceling the rest of our plans and just chilling out in Maine for the next week and a half/rest of our lives.

Twenty minutes further down the road, just for something different, we pulled over again. Wiscasset is often called the “prettiest village in Maine,” and while I’m not sure I’d agree, the old buildings, riverside setting, and free entertainment from the huge traffic jam sprawling across the bridge were totally worth the stop.

Red's Eats line, Maine

The cause of that gridlock? Red’s Eats, a little shack beside the bridge that apparently serves lobster rolls to die for. Given how long the line was, I suspect several prospective patrons did indeed bite the dust while waiting to order lunch. The decision to grab that sandwich in Bath was looking better by the minute, especially because we were already running out of time to get to Mount Desert before dark. Oops.

As a result we didn’t stop anywhere else along the way, and yet like an insecure younger sibling, Maine still kept trying hard to impress. Rockland was surprisingly attractive, as was Rockport, while gaping at Camden’s buildings seemed an almost surefire way for me to drive into oncoming traffic, even before I caught a glimpse of the town’s stunning harbour. And on it went. I could have happily spent days in pretty much any of the coastal towns we drove through in Maine. They really were something else.

When we finally got to our accommodation on the “quiet” side of Mount Desert island, the last rays of the sun barely penetrated the thick forest on all sides. We’d taken all day to drive Maine’s coastal route, yet felt like we’d seen hardly any of it. There was no question we’d have to return, and soon.

Still, with two nights in Acadia National Park, we were going to have time for plenty of hiking, and get a good feel for why it’s the second-most visited national park in the country. That, at least, was some consolation for what we’d missed on the drive up.

Sunset, Mount Desert Island

Lauren climbed out and headed over to the porch to greet the waving owners. I fussed around parking the car and grabbing our bags, arriving at the door to a conversation in full swing.

“Yeah, it’s funny,” said Steve, our Airbnb host. “Every single person who’s only booked for a couple of nights has left saying they really wished they’d stayed longer. You really need at least a week to get the most out of the park.”

Oh crap.

Remember those excellent travel planning skills I mentioned at the start of the post?

Apparently, sometimes, they’re just not that excellent at all.

We found our car, a generic, economical Nissan Versa ideal for a trip like this, through Alamo had the cheapest price on the day we looked, so that’s who we ended up using. Pickup in downtown Boston was straightforward, although I had to wait about half an hour to get to the front of the line. Dropoff at Logan Airport took about three minutes.

We decided to rent a toll pass device as well – the price was capped at $21, and tolls themselves cost another $12. It was worth it, since avoiding tolls would have added time and hassle to the trip, and I was never sure which toll gates accepted cash and which didn’t. Sailing through at fifty miles an hour seemed a much better option.

Houses in Somerville, MA

In Boston, we stayed in a delightful Airbnb room in Somerville, a pretty neighbourhood just outside the city centre. I’d only ever stayed downtown in the past, and had no idea this part of Boston even existed. With lovely owners, good restaurants and coffee shops within walking distance, and a Lyft into the city costing $10-15, it’s an easy place to recommend.

Our Airbnb in Portland was listed as room-only, but since the owner was away during our stay, we had the place to ourselves! The downstairs was a little gloomy, but our room was bright, with more than enough room. The back porch was ideal for sitting reading in the sun in the afternoon, and it was less than a five-minute walk to a kick-ass ramen place down the road (plus several other bars and restaurants, if you’re kinda-odd and don’t like ramen).

Steve and Joanna’s place on Mount Desert Island, though, was the highlight of the three. Steve’s wealth of knowledge about Acadia and the island was a godsend for people like us who clearly hadn’t done enough research, and he had impeccable recommendations for the best hiking trails, places to eat, driving routes, and more.

It’d be worth staying with them for that reason alone, but when you include that the room was immaculate, the shower hot and powerful, and the breakfast delicious, it’s a no-brainer. If you’re going to Acadia, stay here.

Note: if you haven’t used Airbnb before, use this link to get $35 off your first booking!


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Why you need to go to Maine right now


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