Locations, Roadtrip stuff

Day 34: Old Lyme, Essex, New Milford, Kent and Washington Depot, CT (a.k.a. “The Gilmore Girls Day”)

Disclaimer: this post will not be interesting to you unless you are a huge nerdy Gilmore Girls fan like I am.

Connecticut is probably not on most people’s lists of top US travel destinations, but I had a special reason for going there – the TV show Gilmore Girls. I first saw an episode in 2008, and I have been obsessed ever since. I have the first three seasons on DVD (I know, old-school) and have seen every episode of all seven seasons in order. So obviously, I have dreamed of going to Connecticut to visit Stars Hollow and its quirky inhabitants ever since. I have to admit, I was a little upset when I found out Stars Hollow is actually a fictional town and the show is filmed on a set in LA, but I was not deterred – I discovered blogs with titles like ‘Finding the Real Stars Hollow’ where people have gone in search of small towns in Connecticut that are as close as possible to the real thing. It turns out I’m not the only one obsessive enough to travel to obscure places purely to go on a hunt for an ephemeral fictional town. I did my research and made a shortlist of five towns that seemed like the best fit: Old Lyme, Essex, New Milford, Kent, and Washington Depot.

1. Old Lyme

We arrived in Old Lyme at about 11 am and I got a bit excited when we saw a couple of New England houses that looked almost exactly like Rory and Lorelai’s house!

I got a bit squeaky and we got out of the car so I could jump around excitedly and take photos. The architecture was very reminiscent of Stars Hollow and we even saw an antique shop (sadly it was closed though so we couldn’t tell how reminiscent it was of Kim’s Antiques). There was a lovely family-run chocolate shop we went into called The Chocolate Shell where we bought some chocolate for Easter and had a nice chat with the friendly staff. Then we drove on to The Bee & Thistle Inn, which I had read on a Gilmore Girls fan blog looks very similar to the Dragonfly Inn.

Similarity to Stars Hollow: Old Lyme is very picturesque and quaint, but apart from the houses that looked strikingly similar to Lorelai and Rory’s house, I’d say it differs too much to be the real Stars Hollow. For a start, it doesn’t have a town square, which is the main identifying feature of Stars Hollow. Like many American towns, Old Lyme is more or less just a road that you drive down flanked with houses and shops on either side, which doesn’t make it feel like a town so much as a street. This lack of a ‘town centre’, as we would say in the UK, still feels quite strange to me, even after two months in the US, and definitely made it feel less Gilmore Girls-esque. The other thing was that, despite it being a Saturday, which I figured would be the most likely day of the week to discover lively small-town life, there seemed to be hardly anyone around – in contrast to Stars Hollow, which is always bustling with townsfolk any day of the week.

Overall verdict:

3/10 for similarity to Stars Hollow

7/10 for general pleasantness and New England quaintness

2. Essex

Our next stop was Essex, which I have to say as a Kent girl (the county in the UK neighbouring Essex) gave me severe doubts about how nice it could possibly be. Our first impressions were indeed not great. It turns out Essex is a conglomeration of three different villages: Centerbrook, Ivoryton, and Essex village. So we sort of drove through one of them (possibly Centerbrook, or maybe it was Ivoryton) and came out the other end a bit confused about whether we’d actually gone to Essex or not. Once again, it didn’t seem to have a clear centre or downtown at all; we just drove down a road with some houses on either side and left feeling a bit disappointed, underwhelmed, and vaguely confused. We decided that that couldn’t have been all there was to Essex, as a Gilmore Girls fan blog I read had clearly stated that Essex was magical, so we decided to try again. Undeterred, we went on to Essex Village, hoping that this was the magical Stars Hollow-esque town that the fan blogs had promised. It was definitely a lot closer. It had a street filled with cute little shops, and it even had a gazebo, which earns it loads of points!

It was also by a river, which while not a Stars Hollow landmark, was quite pretty. We went into a little café/coffee shop to try and use their toilets, but they didn’t have any, so we left.

Similarity to Stars Hollow: The cute shops were quite reminiscent of Stars Hollow, and it had the all-important gazebo, but once again, it didn’t seem to have that liveliness and life to it that Stars Hollow has. There didn’t seem to be many people milling around, which surprised me as it was a Saturday and I thought that might mean there would be people out and about, but it seemed pretty quiet. There were a few people around, but definitely not the hustle and bustle I was hoping for. Turns out real life small towns are decidedly sleepy.

Overall verdict:

4/10 for similarity to Stars Hollow

5/10 for general pleasantness and New England quaintness

3. New Milford

As we drove from Essex to New Milford, I got a bit excited again because we were driving behind a car that looked (almost) exactly like Lorelai’s jeep for quite a while. You can just about make it out through Daisy (our car)’s beautifully smeared windscreen in the picture below.

New Milford was the biggest of the towns we visited. It was also the only town we visited that had something resembling a town square – a huge rectangle of massive proportions, not the cute little square of Stars Hollow, but still, it was the closest thing we saw. And it was not only a town square, but a town square WITH A GAZEBO!


New Milford gazebo
The gazebo in New Milford and a bit of the square


It also had a downtown cinema, which according to Bill Bryson are a dying breed. We went into a nice café and used their toilets. We thought about buying something but decided to wait until Kent because I had heard a rumour from a Gilmore Girls fan blog that there was a place there that had very similar vibes to Luke’s Diner.

Similarity to Stars Hollow: It had a town square and a gazebo, and it had a downtown cinema like in Stars Hollow (in Gilmore Girls it’s more or less just a screen and a projector in someone’s house though). It did seem to have a bit more life than the other two towns as well – there were children out playing in the gazebo and on the square, and the downtown cinema was also reminiscent of Stars Hollow, like some throwback to 1950’s small town life. But somehow the square and the town itself just didn’t have the same quaint vibe – the square was too long and rectangular, and there still wasn’t quite enough life and liveliness to really make it the ‘real Stars Hollow’. I began to think I was perhaps setting my standards too high and that I may never find the real Stars Hollow if I was expecting it to look almost exactly like it does on TV. But we still had two towns to visit so I tried to remain optimistic in the hope that one of those might be the winner.

Overall verdict:

6/10 for similarity to Stars Hollow

5/10 for general pleasantness and New England quaintness

4. Kent

It was getting kind of late by the time we got to Kent and most shops were closing, so we ended up just getting dinner and then going back to Kent the next morning. First impressions were that it was cute and New Englandy – it had those typical white churches and wooden buildings – but once again, not so much a square as a street.


Kent_general street life
Kent, CT


We had dinner at Gifford’s – it was more expensive than we were expecting from the menu we had looked up on Google, but the food was really good and we were glad to eat something nourishing and nutritious after all the junk food we had eaten recently.

When we tried to get back to Kent the following morning, we were half-guessing where to go a lot of the time and relying on a vague sense of direction and road signs (our first time trying to orient ourselves without GPS – woo!) because phone signal wasn’t very good. We somehow kept missing it and driving round in circles, but safe to say we got there eventually.

We went to the Villager Restaurant for breakfast, because I had read on a Gilmore Girls fan blog that it is very similar to Luke’s Diner. I had some delicious eggs Florentine, but I have to say that apart from the obvious fact of being a diner, it wasn’t particularly like Luke’s Diner – instead of a grumpy misanthrope running the place, the staff were mostly friendly Mexicans.


Kent_Villager Restaurant_breakfast
Eggs Florentine at the Villager Restaurant

Similarity to Stars Hollow: Like most of the towns we visited, it was lacking a square, but it did have a little gazebo. It was the only town we visited that had a diner, so that earns it Gilmore Girls points, and the general architecture was very quaint and New England. It also had a pharmacy in a barn-like building that reminded me of the building Miss Patty teaches her dance classes in.

Of all the towns we visited, it also seemed to have the most life and people on the streets.

Overall verdict:

7/10 for similarity to Stars Hollow

8/10 for general pleasantness and New England quaintness

5. Washington Depot

After our dinner in Kent we headed on to our Airbnb place in Washington Depot. Washington Depot is actually the town that Amy Sherman-Palladino, CREATOR OF GILMORE GIRLS, named in an interview as the inspiration for Stars Hollow. (I can confirm this because I have actually seen the interview – I watched all the extra bits on the DVD where they interview the cast and it’s on there.) She says that she was travelling around Connecticut and stayed at the Mayflower Grace Inn in Washington Depot, and the quirky small town feel and the way all the local people seemed to know each other struck her. So this was the town that we chose to spend the night in (and it also made sense to stay there in terms of our route to Boston the next day).

It was a fairly large house, very homey, and we had our own ‘annexe’ almost, with our own bedroom, bathroom and living room. It was just what we needed and we had a quiet, luxurious night in with baths and reading and relaxing (very important when you’re road tripping.)

Our host was an older lady who was very lovely and made us an Easter breakfast in the

Washington Depot_Airbnb_Easter breakfast_1
Some of the lovely Easter breakfast

morning with brioche, painted eggs and melon balls, which was a lovely surprise. She admitted to us in a kind of half-embarrassed way that she had voted for Trump in the recent election and we ended up getting into an edifying political discussion, but it was nice to talk to somebody with a different point of view and escape the echo chamber for once.

She also had two dogs, who were very friendly, including this adorable dog who looked like he was always smiling:

Washington Depot_dogs_2

We drove a little bit through Washington Depot on our way back to Kent, but I have to admit I really didn’t see what Amy Sherman-Palladino was talking about with the cute small town life and everyone knowing each other. I had a similar feeling to Essex where I couldn’t tell where the town ended and began, and it didn’t have a square or any discernible centre at all, it was just a random conglomeration of houses and businesses.

We didn’t stop anywhere, partly because we couldn’t tell where was a good place to stop, and we just sort of drove around going, ‘Is this Washington Depot? Is this it?’ I don’t know if there was some big part of the town we missed, but what we saw wasn’t very impressive, either in quaintness, quirkiness, or similarity to Stars Hollow. I didn’t see anyone on the streets at all and it didn’t even look like it was very well-equipped for pedestrians, a salient feature of life in Stars Hollow. I will admit that driving through a town isn’t really the best way to see it so maybe we didn’t really give Washington Depot a fair chance, but I am not the only person to have wondered if Amy Sherman-Palladino got her wires crossed when she named Washington Depot as the inspiration for Stars Hollow – other fan blogs have said the same thing, and that the town is more just a holiday destination for rich New Yorkers rather than a bustling town with a life of its own, so that could perhaps explain the lack of people out on the streets when we were there in mid-April (it was also Easter Sunday so that could have been an additional factor.)

After our breakfast in Kent we returned to Washington Depot because I desperately wanted to see the Mayflower Grace Inn which Amy Sherman-Palladino had named as the inspiration for the Independence Inn. It was definitely a detour and we didn’t have phone signal which made navigation more difficult, but I felt I owed it to myself, since I was here, to make my Gilmore Girls pilgrimage truly complete. It was a bit difficult to find because the road that Google Maps directed us down didn’t lead us to the entrance, but with a bit of guesswork we eventually found it and drove down the extremely long driveway up a hill. We started to feel very out of place and like we were trespassing because the inn was a lot fancier than I was expecting and I felt like our Texas number plate betrayed us as riff-raff and that everyone was looking at us suspiciously. We ended up parking the car about halfway up the hill and I walked the rest of the way up and took some pictures, feeling like I shouldn’t be there and that somebody was going to come up to me at any moment and ask me to leave. Everyone there was very well-dressed and driving a Mercedes. After taking some photos I slunk away and we left satisfied that we had done our duty to Gilmore Girls.

Similarity to Stars Hollow: From what I saw, almost none at all, although we didn’t actually stop and walk around so I will concede that I may not be an authority on this. But from what we saw: no town square, (no town at all really), no gazebo, no diner, no bustling town life and friendly local folk who are all up in each other’s business. It does have the Mayflower Grace Inn, but it seemed far too posh and stuck-up to be the Independence Inn in my opinion. 

Overall verdict:

1/10 for similarity to Stars Hollow

2/10 for general pleasantness and New England quaintness

And the winner is…


Kent_welcome sign

And no, I’m not just saying that because it shares a name with the place I’m from. Well, perhaps I was a little biased… but I would say in terms of overall feel and vibes, it was definitely the closest to Stars Hollow. It was the right size, there seemed to be some semblance of life on the streets, and there was a gazebo AND a diner! Congratulations Kent, I formally award you the title of the ‘real Stars Hollow’ – or the closest I’m going to get in this life anyway.


3 thoughts on “Day 34: Old Lyme, Essex, New Milford, Kent and Washington Depot, CT (a.k.a. “The Gilmore Girls Day”)”

  1. this was a very good review of all the places and their similarity to stars hollow, and although i am nowhere near as much of a fan as you are, i appreciated it greatly 🙂 (i’m also biased though. towards both you and kent. despite having just complained about the unoriginality of the names given by the british settlers, in a photo of essex on your facebook album haha)


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