A week after Hamilton and I moved to Toronto, we made the bold move to leave Toronto. Not because we didn’t love it here (we did/still do) but there were bigger plans afoot for the week, an entire season, in fact…

Autumn. AKA fall.

Ok yeh it was a bit random but it made sense at the time. We got a good deal on car hire and I had always heard about how New England is meant to be spectacular this time of year, so we made a somewhat rash decision and booked a trip to Boston. It felt very weird packing our cases and buying snacks (we got super healthy cinnamon buns, candy, chips and mini muffins for those wondering), from the local supermarket to go on a road trip to America; whenever these trips had happened before, it took months of planning, budgeting and discussion.

Hamilton and I very roughly plotted our route and booked hotels along it (based sheerly on price) but we didn’t spend that much time thinking about what we were going to do in each place. I wanted to go to Boston because it’s one of the big cities in America I haven’t been to and the drive was meant to be nice – simple as that.

Now, Boston was the point of interest on this trip but our general reasoning for it was really the fall colours. Now, if you’ve been outside in North America recently you may be aware of the fact that a couple of weeks ago, fall colours weren’t that prominent. The weather has actually been pretty hot. Nonetheless, I can confirm that we did manage to find autumn. It wasn’t easy but we did in fact find it, so don’t worry, the title ‘fall road trip’ is not clickbait. I mean, would I ever lie to you?


We got a streetcar along to the Toronto Eaton Centre and picked our car up from the roof of it (Thrifty is based there it wasn’t some shady deal but it was odd walking into a shopping centre with our bags I’m not gonna lie).

If you keep up with this blog, you will have seen my post about this very exciting rental car booking… Basically, we booked a ‘surprise car’ which meant we didn’t know what kind of car we were going to get. It was the second cheapest option (by about £3) and was maybe the most enthusiastic about getting a rental car I had ever been. It’s always fun picking up a car because you don’t know what you’re going to get – you know a rough category but this could have been anything (within reason). I full on expected a sports car/SUV/potentially a van.


I am sad to announce that we did not get any of those things…

We got a very simple Toyota Corolla. Not a Mustang, not a Jeep, not a Limousine.


But you know what? It was actually pretty great. It was really easy to drive, had space for everything, was comfortable… Ok I sound middle-aged but genuinely, it did what we needed. No, it wasn’t that exciting but we did make it there and back in one piece in the thing and it had a bit of pick-up, so I can’t complain.


Now the big announcement is over, let’s get back on the road. Our first stop was Lenox, Massachusetts – we had toyed with the idea of staying in Albany for the night but after a quite look on realised that Albany was, way too expensive for one night. So we looked elsewhere – Lenox had affordable but nice looking accommodation and it made our journey into Boston the next day a lot faster (okay yes this is because we had to drive further the day before but that was do-able). Hence, we ended up there.

The drive from Toronto to Lenox  (including the very dull, dragged out border crossing) took a long, long time. I’m talking 8 hours and counting kind of long. I didn’t necessarily help with this as I had read about toll roads being expensive because if they’re automatic, the rental company can charge you admin fees for them paying the toll charge and then getting the charge over to you, so I requested we take non-toll roads. This seemed a bit irritating at first as it added so much time onto our journey but actually, I really think it was the best way to go about it; we didn’t pay any toll charges and we saw some beautiful roads that we otherwise wouldn’t have seen.

It did mean we pulled up to Seven Hills Inn, Lenox in the dark but we knew we would get to see it in the day, so this wasn’t the end of the world. When we arrived, the staff had gone but they left an envelope on the desk for us with our key and a nice note about breakfast, which was appreciated. There were also copies of the New York Times, which I can never turn down. (Yes, we attempted to do the crossword and yes, it was too hard).

Our room was in the ‘Terrace Building’, next to the main house. I imagine some people think of it as a downgrade but we actually really liked it. It was very American; the building itself really reminded me of summer camp, plus it was quiet as everyone else had opted for the pricier, main house. The house itself was one of the oldest houses I had seen in America, which was cool. It was filled with antique furniture, fireplaces and antique people, who seem to love antique furniture and fireplaces. Plus, us.

We loved the whole place – it was cute, the staff that worked there were nice and the breakfast was fun. I mean, the breakfast was odd but we didn’t dislike it – the guy came out and said he was “thinking of making eggs and breakfast potatoes, did we want any?” It felt like we had gone into someone’s house and they offered to make us breakfast. Some other people in the dining room were less enthralled by his approach but we found it quite charming.

The only downsides to this place were in the room. A) There was no tea and coffee. B) The TV was from the past and constantly made a crazy high pitched noise. C) There was no Wi-Fi within the room. But I wouldn’t really complain about any of those things.


We left with full bellies and some looks of disdain from the older people, who definitely did not think we belonged there, and headed on our merry way to Boston for a very odd night in a hostel and a fair amount of tequila as a result, which I will discuss in the next post.

We didn’t stop anywhere on the way simply because we didn’t have time but I’m pleased to say that we managed it in every other drive, so if stories of a weird hostel don’t pull you in, maybe adventures in thrift shopping will (just saying).


Thanks for reading!







Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s