How to Visit the “Real Life” Gilmore Girls Towns in Connecticut

May 19, 2020 Julia R

What small towns to visit in Connecticut if you’re looking for the real life “Stars Hollow” experience.

If you look closely, you might be able to tell that I’m wearing an “A Film By Kirk” shirt. Most people never understand this shirt.

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Years visited: 2019 & 2021

Time of year: October

For Gilmore Girls Fans

(or just fans of cute small towns!)

If you’ve spent countless hours visiting the TV world of Stars Hollow (I know I have), then chances are you’ve spent countless hours (or at least a few hours) wondering what small towns to visit to create your very own Stars Hollow experience.

And chances are, you may have heard that Washington Depot, CT is the inspiration for the TV show Gilmore Girls, and therefore the town to visit.

Well, I’m here to clear up that misconception. And to tell you exactly where to visit.

What’s in this Article:

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One of the downtown streets in New Milford, Connecticut.

Unfortunately for the world of make-believe lovers, there is no one town to visit that is quite exactly like Stars Hollow. Your best bet for the full Gilmore Girls town experience would be to actually visit 4 towns:

Fortunately, they are all close together!

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I don’t know why these 4 in particular are the ones to visit. I will say that almost the entire state of Connecticut is made up of cute small towns, all of which have something of a Stars Hollow vibe to them.

So you don’t have to limit yourself to these 4, but as they are the main accepted influences, I will focus on them.

And honestly, even of the four of them, although they all have things that make them like Stars Hollow, I don’t think they all necessarily “feel” like Stars Hollow.

So I’m going to give you my reviews of all four towns, and how ultimately “like Stars Hollow” each one is.

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Litchfield feels a lot like an old colonial town. It is adorable and charming, but in my opinion, the least like Stars Hollow.

While Litchfield does have some Stars Hollow-y aspects, the architecture and the vibe of it just lend it more to a Revolution era town. It’s definitely worthy of being explored for that aspect, but honestly, as a Gilmore Girls town, I would say you can skip this one.

I didn’t visit any of the local restaurants in Litchfield, but I did visit the Tapping-Reeve House & Law School. I was very excited to find a “Scarecrows in the Field” festival going on while I was there! That was definitely a Stars Hollow type festival.

The traffic in downtown Litchfield was crazy! It was a weekend, so it would probably be less busy on a weekday.

How is Litchfield like Stars Hollow?

Scarecrow Festival at the Tapping Reeve Law School.

Litchfield Town Green
White steeple church
Cute Downtown
Antique Stores
Tapping Reeve House & Law School

Check out my full review of how Litchfield is like Stars Hollow (it will open in a new window, so you won’t lose your place in this article).

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Washington Depot is the first town I heard of being touted as the inspiration for Gilmore Girls. That makes sense, considering this is where the Mayflower Inn is located.

However, when I first visited Washington in 2019, I was disappointed with its complete lack of “Stars Hollow vibe.”

I must admit that after further research and my second visit to Washington Depot in 2021, I will give it more Stars Hollow points than I originally thought.

Washington Depot is small, and does not have the amount of cute storefronts the other towns have. They do have a town green with a white steeple church, but it is actually 10 minutes down the road from the main town.

However, they do have a local grocery store, and most elements of town life right nearby. Washington does feel like the most isolated small town. You can’t drive 2 minutes down the road to the actual grocery store, thus you actually do your shopping at Washington Food Market.

The elementary school is also right downtown, so I feel like I can imagine Amy Sherman-Palladino sitting in one of the cafés, looking out the window at all the people grocery shopping and little kids going to school, and start dreaming up her sitcom.

Ultimately, I feel like Washington is the least tourist friendly of the four towns, and has the least amount of fun things to do.

But, life in Washington Depot does have a lot of similarities to life in Stars Hollow. And you can buy a copy of the Gilmore Girls cookbook or a Rory Reading list book at the local bookshop.

Check out my full review of how Washington Depot is like Stars Hollow (it will open in a new window, so you won’t lose your place in this article).

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The book sale was literally three times as large as the tiny library!

There are so many things to remind you of Stars Hollow in Kent! The architecture of the store fronts and houses downtown are very similar to those in the show. There are also a lot of local restaurants and shops that feel like they could fit right in to Stars Hollow, and they have a gazebo.

The very best part of my visit to Kent was that the library was hosting a book sale, that literally looked just like the one at which Dean so patiently waits for Rory (plus I got some great books!).

I think Kent has a strong Stars Hollow vibe going for it. What I don’t like about Kent is how spread out everything is. It doesn’t exactly feel like a cohesive town center to me, the way that New Milford does. Everything is stretched out along Main Street, or hidden away in several plazas behind Main Street.

But they definitely do have a lot for tourists to see.

How is Kent like Stars Hollow?

Cute Downtown
Kent Green & Gazebo
House of Books
Kent Coffee & Chocolate
The Villager Restaurant
Antique Shops
Historical Museums

Check out my full review of how Kent is like Stars Hollow (it will open in a new window, so you won’t lose your place in this article).

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New Milford was my favorite of the four towns. I personally thought it felt the most like Stars Hollow. At least, as long as I stayed in the downtown area.

The downtown is cute and thriving, and is located right around the New Milford town green. While most of the restaurants and shops don’t really correspond to a specific one in the show, there are plenty to choose from!

And talk about a downtown with a view! Most importantly of all, New Milford has a centerpiece: the gazebo!

For me this really ties the town together and gives it that feeling of small town charm. So even though it doesn’t have as many specific Stars Hollow elements as some of the other towns, I think the layout and design of the downtown area feels the most akin to it.

But I do have to mention, the fact that you can drive two minutes down the road and suddenly be surrounded by shopping plazas and chain stores does destroy a bit of that Stars Hollow illusion.

How is New Milford like Stars Hollow?

Gazebo & Town Green

Cute Downtown
White Steeple Church
New Milford Historical Society & Museum
Bank Street Theater
Theo’s Downtown Diner

Check out my full review of how New Milford is like Stars Hollow (it will open in a new window, so you won’t lose your place in this article).

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The Mayflower Inn is where the idea of Gilmore Girls was first hatched! Amy Sherman-Palladino was staying here when she was inspired to create the show, and the Independence Inn that Lorelei runs is based on this one.

The inn is a beautiful country-side retreat, which features several dining rooms and a spa. The original building was a school for young boys until it was converted to an inn in 1920. It has gone through several owners and renovations since then.

See absolutely gorgeous photos of the inn (so you can visit without actually visiting!).

However, if you are traveling on a “Lorelei budget” (as opposed to an “Emily budget”), it may be a bit much to try to visit. Rooms run from about $800-$1000 a night.

You could visit The Garden Room (for $150 3-course meal), or The Tap Room (for an affordable meal), and pretend you’re eating some of Sookie’s creations.

Learn more about dining (or book a table)

I was planning on visiting The Tap Room for lunch, but in all my planning, I did not book my table far enough ahead of time (…and honestly, I wasn’t too sad about not paying $24 for a burger).

You can read a review of a Gilmore fan’s experience, although take note that this article is from 2014.

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One of the locals told me that Amy Sherman-Palladino used bits and pieces from all four towns to create the fictional metropolis we know and love. I can definitely see that. Here is my basic feeling of each town:

Litchfield:

Litchfield is a cute colonial town. It is nice to visit for American history, but low on my list of Gilmore Girls towns.

Washinton Depot

Washington Depot is credited as the influence for Stars Hollow. It has a lot of elements of Stars Hollow life, such as the local grocery store and the schools right downtown. It doesn’t have as much for tourists to do, and doesn’t have the charm or feeling of Stars Hollow.

Kent

The architecture of Kent really reminds me of Stars Hollow. You can find antique shops in beautiful old houses that look just like Mrs. Kim’s, wacky local restaurants, and a cute little book shop. But the downtown area is spread out all along Main Street, and not compact around any central area.

New Milford

New Milford doesn’t have a lot of specific Stars Hollow stores, but it definitely feels the most like Stars Hollow. It has a local diner, plus lots of other shops, a cute movie theater, and is centered around the gazebo and town green. But it also is surrounded by chain stores, and doesn’t neccesarily give you that small town feel.

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I scoured the web for places to stay in Connecticut that were affordable and cozy. And let me tell you, I found a lot that were super expensive. And some that were affordable, but not really cute.

And then I found the perfect AirBnB! It was absolutely perfectly decorated, had a cozy fireplace, little bowls of chocolate in almost every room… and the breakfast! It was SO good, I am 100% confident that Sookie could have made it.

Unfortunately, the people who owned the house sold it and moved (maybe I shouldn’t have bragged so much about it then…) so I can’t recommend it as a place to stay anymore.

In lieu of that, here are a few options to help you get started in your own search for the “Dragonfly Inn:”

The Litchfield Inn

(in Litchfield)

It’s not as cozy as our BnB was; it has more of an “Independence Inn” feel than a “Dragonfly” feel, but that’s still good! Their rooms are all uniquely decorated, and it looks really nice. It’s a bit on the pricey side, but, seeing as you can find a room under $200 here, it’s better than 90% of the other places I found.

Fife ‘n Drum Restaurant & Inn

(in Kent)

This cozy inn is right along the main street in Kent, so you can just step out your door and walk to the local coffee shop, antique store or book sale! The rooms look cozy, at around $200 a night, though check for cheaper rooms seasonally. They are pet friendly, so if you want to bring Paul Anka (dog Paul Anka) with you, this is the place to stay!

Homestead Inn

(in New Milford)

This is a lovely bed and breakfast to stay at, right in downtown New Milford. Again, the rooms run around $200, but you can find some for less. Plus it comes with breakfast! They even have a Gilmore Girls section on their website.

The Mayflower Inn

(in Washington)

This one is a bit (a lot!) of a splurge. The rooms range from around $800-$1000! But it is the inspiration for Gilmore Girls, so maybe it’s worth a bit of an extra splurge. Visit on a week day to get a better price.

Or check out AirBnB for lots of great (and affordable) places to stay in the area. Just make sure you account for the all the extra fees when you compare prices!

If you’ve visited the Gilmore Girls towns and stayed somewhere absolutely fabulous, be sure to share it with us in the comments below!

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Maybe you will visit during a festival, like this Scarecrow Festival in Litchfield, CT.

I personally think the best time of year to visit is October.

The leaves will (hopefully) be changing, plus fall feels the most “Gilmore-y” to me. But you might have great weather, or you might have a cold and cloudy day, so that will always be a bit of a gamble.

There are multiple festivals going on throughout the fall, so try to look out for those and plan to visit during a festival if you can.

Here are some festivals you might see:

Apple Festival in New Milford
Harvest Festival in Washington Depot
Pumpkin Run in Kent
Scarecrows in the Meadow in Litchfield

My second choice would be Christmastime.

Just imagine how cute these little towns will look decked out in holiday decorations! The weather will be colder, but it will be perfect to snuggle up in a cute coffee shop with a mug of candy cane hot chocolate (if they still have any!).

You might even hit a fun Christmas festival!

(Some of the back roads may not be fun to drive on in the winter though…)

How long do you need?

Because the towns are so close together, you could easily get to all four in a day. In fact, to start at New Milford and go around to all four in a circle, and then back to New Milford, would only take an hour and a half.

However, if you want to really experience each town, eat at some of the restaurants, explore the museums, and spend some time chilling in the gazebo, it may be a little hard to try to fit everything into one day (or at least into your stomach).

I would suggest two full days to spend time exploring and enjoying all four towns.

Plus there are lots of other cute towns and fun things to see around the area, like Bridgeport, New Haven, Hartford or Mystic. You could easily fill up a whole week exploring Connecticut.

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I expect to find tiny little one lane roads in England and New Zealand, but not really in the U.S. But so many of the roads in Connecticut just seemed so super tiny. Especially the roads around Washington Depot.

We also seemed to come across a lot of one-way bridges on our first trip to Connecticut, where you have to keep a look out and make sure no one is coming from the other direction. But I didn’t cross any on my second time through the state.

But you will definitely find some Instagram worthy scenic roads around here.

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Here are some other ideas of things to do on your trip to Connecticut:

Luke’s Donut Shop

There is literally a bakery/cafe called Luke’s. Donut. Shop. If that’s not a call for every Gilmore fan to come visit, I don’t know what is.

While not officially in one of the 4 “Stars Hollow” towns, Luke’s Donut Shop is only about a half hour drive from Litchfield.

Their donuts were a very unique texture. They definitely weren’t the greatest donuts ever, but still…it’s Luke’s.

So fill up your Luke’s travel mug from Etsy, and get yourself a Luke’s donut to go with it!

Psst: Want your own Gilmore Girls photo props? Check out my list of my favorite GG merch!

Dottie’s Diner

Dottie’s Diner may be the best (Luke’s-esque) diner around, despite the fact it is located in Stars Hollow’s rival town of Woodbury.

It wasn’t in what I would call a very Stars Hollowy location, but the diner atmosphere may make up for that. Plus, they have homemade pies with homemade cinnamon whipped cream!

You can sit down and order breakfast, or you can just order something to go from the counter, like a muffin, or one of their famous donuts. I read over and over again that they had some of the best donuts in Connecticut, so obviously I had to check them out. And yeah, they were pretty good (especially heated up in the microwave).

Woodbury is about 20 minutes from New Milford.

The Connecticut Pizza Trail

What could be more Gilmore-y than to literally road trip across the state (preferably in a very old jeep) in search of pizza?

If you have a hankering for the dish while you’re in Connecticut, be sure to check out a stop or two (or more!) along the Connecticut Pizza Trail!

Thorncrest Farm & Milkhouse Chocolates

I found this farm and chocolatier several years ago when I was researching things to do in Connecticut, and I’ve been looking forward to trying their chocolate ever since!

Thorncrest Farm & Milkhouse Chocolates is a dairy farm, and they make chocolate from their own cows’ milk. The chocolate is definitely more expensive than I realized, but it was delicious! You can also meet the cows, and, if you’re lucky, see a baby calf that’s only a couple weeks old.

I was worried it might be too far out in the middle of nowhere, but I don’t think it was really that bad (I’ve definitely been to places further in the middle of nowhere!). The road it’s on isn’t paved, but it’s still a pretty wide road, and you don’t have to go too far down it to get to the farm. All the roads leading up to theirs are paved, and it’s only about a 10 minute drive from Litchfield.

State Parks

Kent Falls State Park

Visiting a state park is a great way to work off some of those doughnuts you’ve (I’ve) been eating! And it’s a great way to see some fall foliage, if you’re there at that time of year. Note: Many CT state parks require you to pay a parking fee on your smart phone for out of state vehicles.

Here are some state parks in the area, if you do want to visit:

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Unionville, Ontario, where the pilot episode was filmed!

Canada

Connecticut doesn’t have a monopoly on charming small towns. In fact, there are several in, wait for it… Canada, that are rather reminiscent of Stars Hollow.

One, in fact, was actually the filming location for the pilot episode, before they moved to the studio lot!

Vermont

Basically all of New England has adorable small towns with white steeple churches and colorful fall foliage. But did you know that the town seen for just a moment at the very beginning of every Gilmore Girls show’s credits is actually South Royalton, VT?

This perfect little town has a bookshop, white steeple church, town green, and, surprisingly, a HUGE number of restaurants: Tacos, burgers, coffee, a local diner & more? Sound like Stars Hollow to anyone else??

The Warner Bros. Studio Lot

Stars Hollow is one of the many sets you can see on the Warner Bros. Studio tour in Burbank, California.

Usually during the holiday season they even have a special Gilmore Girls Holiday tour!

Chilton

Did you know you can visit the filming location of Chilton School? It’s actually a mansion in Beverly Hills (and it’s actually the filming location for SO many things!).

The park at Greystone Mansion is open to the public (for free), but the mansion itself is only open for special events (or you could rent it for a really expensive wedding…).

Other Show Settings

Stars Hollow, while the most charming, isn’t the only setting where the show takes place. Here is a list of several other real life places you can visit and pretend to be Lorelai & Rory: