The last post ended with us leaving Boston, on the way to our next stop – Old Orchard Beach. Why Old Orchard Beach? Well, as I mentioned previously, where we ended up staying was picked mostly on a cost basis. Meaning the lower the cost, the more likely it would be that we would stay there.  (We’re millennials… You get it).

We knew nothing about Old Orchard Beach other than the name sounded nice, it was a good distance from where we were/needed to be and most importantly, we could afford to stay there. It had been very warm in Boston – I’m talking nearly 30 degrees, but by the time we reached Old Orchard Beach the weather had cooled a little. We had a nice, calm drive there – stopping off at a few antiques/thrift places along the way (where I really learned the difference between the two – the price tag). I can’t remember the names of any of these places I’m afraid but honest to god, you don’t need me to tell you – there were at least 5 on every stretch of road.

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Old Orchard Beach, MA 🌊

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Once we arrived, we were amazed by how empty is was; I think the holiday season had ended only about a week before we got there but it felt like it had been an eternity; it was like some kind of apocalypse had happened in that time. The theme park on the beach, the restaurants, the shops… Were mostly closed. I was on the hunt for a keyring for my boyfriend, who collects them, and it was a real struggle.

We walked around the beach area and only found one proper place to sit down for a meal. Thankfully, it was a great one. We were told this by a very enthusiastic gentleman leaving the place before we had even looked at the menu – so that was a good sign. It was called ‘JJ’s Eatery Too‘ and it was full of lovely staff, good food and a new one for us – local pumpkin spice beer with a sugar rim. Delightful.

The next day, we were headed to the enchantingly named ‘Killington’, with a few stop offs on the way; our first one, was Portland (Maine). I’ve seen it cited by a few people as the place to visit in that part of the world, so I had high expectations. In all honesty, high expectations with no knowledge of what was actually there.

I’ll admit, it took me by surprise to see that Portland is actually a small city. Apologies if I’m completely ignorant to common knowledge about how great Portland is but yeh, depending on what you want, it was very nice. There were definitely some cool spots, like the donut place we had breakfast in (Hifi donuts – an actual breakfast sandwich served between two donuts) and a paper shop I fell in love with (Gus and Ruby Letterpress). Unless we severely missed out on places, aside from that it felt quite touristy; I’m not saying that’s the worst thing in the world but a lot of shops were quite expensive. I liked that most places were independent and had local produce inside but unfortunately for me, a lot of stuff was out of my price range. I got the impression its a hot spot for middle aged people went there looking to spend a lot of money on pottery. Hell, maybe I’ll go back when I’m middle aged and spend a lot of money on pottery. Who knows?

As much as I enjoyed our visit, it was very expensive to stay there the night before and to be honest, I’m glad we stayed where we did – it only took us about 30 minutes to get into central Portland and find a parking spot, then we saw it in a few hours and went on with our day. I didn’t feel like I missed out on much.

Our next stop was Woodstock, via the Kancamagus Highway – it’s known as a scenic route and my god, it was breathtaking. The whole trip, Hamilton and I just kept saying how beautiful the scenery was and how much we were enjoying the drive. We avoided toll routes and kept to the back roads, and saw so much more of real America than we had seen before on other road trips. There were small towns with big houses, spectacular town halls, little pumpkin stalls and best of all, barely anyone else on the road (you don’t get any of that on the highway). As much as I loved the pumpkin stalls I’ll admit, I was a bit confused, seeing as we were there at the very start of October – in the UK, people pretty much just buy them for Halloween, I forget that they’re actually used for making pies etc in America.

Side note: I love a good pumpkin pie. But sadly, I didn’t have a single one the entire trip. Instead we saw and went to about three billion Dunkin Donuts, and felt supremely sick for a lot of the trip, after gorging on donuts and sugary chai drinks. I’m glad there aren’t any Dunkin’s near me in Toronto because good god, my body cannot function with it but if its an option for some reason I cannot help myself.

Before the trip, I read a lot of blogs and articles about the prettiest towns in New England , and Woodstock stuck out as somewhere that was meant to be lovely but… Was also on  route, so do-able. I don’t know if it’s because we got there later on in the day but it was very chill – there were a few people out and about but they seemed like they lived there (walking their dogs, chatting to other people in the street). It was a nice atmosphere; there’s a small high street which is a mix between normal and gifty shops – it didn’t take us long to walk round it and it also didn’t take me long to find some gifts for my family from Clover Gift Shop. Hamilton also bought a beautiful shirt in Vermont Flannel (the shirts aren’t cheap but they are great quality – highly recommend a visit if you’re in the area).

It was getting a bit late by this point so we got back in the car and headed to our final destination of the day; Killington. Yes, my use of horror themed words was on purpose there. But no, it was not in any way scary. We stayed in a cute little place called the Butternut Inn; it’s a ski chalet, outside of ski season, so it wasn’t too busy but it was cosy. We had two large double beds and a TV that didn’t make high pitch noises, so we were content.

There were a few places to eat in Killington – the place right next door seemed a bit pricey for us (but it was very busy, so it probably would have been good), the next place down was a pretty basic pizza shop and the last place was a pub called JAX that looked a bit too local for us. We risked the last one, assuming we would walk in to glares from residents wondering who the hell these Brits were… Yeh, there was none of that. We had forgotten this was in fact a ski resort and therefore they were very used to tourists. They were very welcoming and the place had a nice atmosphere. Plus, the food was great and cheap as chips; I had a grilled cheese sandwich (WITH APPLE IN IT – absolute gamechanger, thank you Vermont) and a beer. It can’t have cost me more than a tenner.

We slept well and woke up to a pancake breakfast (ok we had to go to the dining room and get it but you know what I mean). Then we hit the road, to our last place – Gananoque, Thousand Islands. This was a long drive, that involved a border crossing (our last one took about an hour), so we only had time for one stop off on this journey – a little hike in upstate New York. Hamilton did an amazing job of finding it and it was a really nice stop off. It was basically one long uphill slog to the top, then a straight walk back down. It was in Adirondack State Park (a park I had never heard of before), which is massive. Lovely, unadulterated countryside, again with empty roads and lush countryside. I genuinely forget just how vast the American landscape can be.

Aside from this, the journey mostly consisted of Hamilton and I playing ‘Would You Rather’ and discussing what kind of bird we would be (I can’t even say this is because of a long drive, these are just the type of conversations we have day to day). After a very easy border crossing, we arrived at Riverview B&B (a place I cannot recommend enough) still quite late on, with very rumbly tummies. We met the host, who showed us to our room (which contained the BIGGEST BED I HAVE EVER SEEN) and then we pretty much headed straight back out again.

We randomly picked a place called ‘Riva’ for dinner, which turned out to be a very popular choice for a Saturday night. Somehow, we got lucky and they had a table for two immediately (we were made aware of just how lucky we were when we saw countless people turned away). The atmosphere was good, the food was even better and in general, we were pretty content. The bulk of the road trip was over but for once we weren’t too sad about it – we were aware that the next day, we would be driving back into Toronto, where our Canadian adventure would continue (for anyone not following the blog – we moved there a week before this trip).

Any US Road Trip we had taken before this took meticulous planning and budgeting, which inevitably ended up in a kind of high stakes road trip trying to see and do everything in time – this was a lot more relaxed and only made me love Toronto more. Yes, in the UK we are extremely lucky to be able to get out into Europe but honestly it still blows my mind that we could just get a bus or a train or drive into AMERICA or to MONTREAL OR QUEBEC OR OTTAWA from here, and it’s genuinely not that far. I understand that is simple geography but my mind is still pretty blown by it.

We’re still enjoying discovering things within our own city so I’m not sure what our next trip will be – if you have any recommendations of where we can go from Toronto (on a budget), please do let me know!





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