Stars Hollow vs. Real Life: An Analysis from a Local in Kent, Connecticut

By Sarah Pfeffer (Special Guest Blogger)

Does Gilmore Girls accurately depict small-town living in New England? Sarah Pfeffer, a local resident of Kent, Connecticut, compares her hometown (and the surrounding area) to Stars Hollow.

But, I’m a Gilmore (too)!

I’m pretty new to Gilmore Girls, and began my binge of the series alongside my husband. We live in a rural Connecticut town and we both work at boarding schools. Naturally, we were curious. And, you may not believe this, but my sister’s married name is Gilmore and she has a young daughter. I quite literally have Gilmore Girls in my own family.

As we fell in love with Stars Hollow, I began to research the real town it might be based on, and that’s when I discovered this blog, Finding Stars Hollow. Amy’s posts were fabulous, creative, and well thought-out, and I began to comment with my insights. I started up some fun conversations with her and other fans, and here we are! I’m honored to be posting a guest blog post!

Let’s get right into it. Today, I’m going to talk about some comparisons between my hometown of Kent and Stars Hollow, as well as some similarities and differences between Chilton and real boarding schools.

If Luke’s Diner and Al’s Pancake World Had A Baby…

The Villager Restaurant is the closest to Luke’s Diner in look and feel. Everything from the green and red motif, bar stools, and delicious breakfast options screams Luke’s. Interestingly, this is also a Mexican place so it has this unique juxtaposition of Mexican, New Englandian, and European decor. It’s one of my favorite spots. The food is on-point and the prices are great!

You’ll notice quickly that my husband is my willing subject for many of these photos.

Luke would probably NOT approve of the holiday decor.

(Sometimes) A Sleepy Town – No background actors here!

Amy was absolutely right that in the winter, the streets are pretty quiet! Unlike in the magical, fictional town of Stars Hollow, people tend to want to stay inside most of the time in the winter because it gets VERY cold; however, during the fall, spring, and summer, there are people (including international visitors as well as weekenders from New York City) all around! In fact, this past summer, I even saw…

A Troubadour on the Green!

Passersby enjoyed this guy’s tunes and even dropped him some tips (that’s more than the Stars Hollow troubadour got)! There is also a pop-up farmers market during the summer, quite like the one that was stationed right outside of Doose’s market (much to Taylor Doose’s chagrin)! The funny part is that the Kent farmers market is also pretty close to our small IGA grocery store.

Antique Shops – “You break, you buy!”

There are plenty of antique shops in Kent. My favorite is the one that has a sign that says:
“Fun to look at…easy to hold…but if you or your child break it…consider it sold.” I can just hear Mrs. Kim in my head saying irritably, “You break it, you buy it!”

Quintessential White Steeple

There are SO many of these in the area. The left photo is a picture of the First Congregational Church of Kent and the right photo is of St. Andrew’s Episcopal Church.

Small Town Events – Like An Outdoor Book Sale!

There are a lot of town events that bring locals together. Take the outdoor book sale, which goes from summer to early fall and benefits the library: it’s simple, but gets quite a bit of foot traffic from Kent residents and visitors. There are also annual events like the Pumpkin Run, Firemen’s Ball, and most importantly, ICE WATCH. When I first moved to Kent, I could barely believe Ice Watch was a real thing, and I knew then I was living in small-town America. Voting cards for Ice Watch are placed in establishments around town, and for $2, you can guess when the ice will freeze on the Housatonic River. If this is not a Stars Hollow type of activity, I don’t know what is. The New York Times even wrote about it in an article titled: Where Watching the River Freeze is Half the Fun.

Victorian Houses and Charming Historic Buildings

They’re everywhere. The houses in the photos below really remind me of Lorelai’s or Sookie’s house. I swear the house pictured below looks exactly like the porch where Kirk found termites (from Season 2, Episode 11: Secrets and Loans)!


Everything’s cute here; even the pharmacy (photo below). It’s one of my favorite places to go; I can find anything from tchotchkes to necessities. This building reminds me A LOT of Miss Patty’s Dance Studio and where Stars Hollow holds their infamous town meetings!

Foliage: Better in Real Life

Autumn here is absolutely unbeatable and quite similar to the colors displayed on the Gilmore Girls credit sequence.

Lorelai rides her bike down a similar road in Stars Hollow.

Babette, Miss Patty? Yes, Everyone Knows Everyone.

The everyone-knowing-you-thing is actually quite real. I have lived in several towns around the state, and Kent is the first place I’ve lived where this is really true. The girls in the coffee shop (Kent Coffee and Chocolate) learn your name and your favorite drink, and you become pals. Same thing with the market, the wine and spirit shoppe, and even the Post Office! These people are so friendly! It took me a little while to adjust to it, but I absolutely love it. It’s so personal. You always see someone you know and get a smile, a wave, and some friendly conversation.

Alternatively, the way Gilmore Girls handles small town gossip is no exaggeration. Word gets around very fast, both in town and on the boarding school campus. Everyone is living in this little bubble and it’s pretty much like a giant game of telephone. I try to avoid this aspect as much as I can, but it’s definitely there and it can even be comical at times. Even the students get involved. I was just watching the episode where Jess comes back to town and Babette is ranting to Lorelai and Rory about how horrible Jess is…hysterical. There are definitely characters here who closely resemble that personality. If you’re going to live here, though, you just have to accept it. It comes with the territory.

Here is the lovely Jess from Kent Coffee and Chocolate. Outside of being a fabulous barista, she is studying art at a local college.

Chilton vs. Boarding Schools in Connecticut

This is the administration building where I work, originally built as a French-inspired honeymoon chateau.

Just like at Chilton, boarding school students here are expected to dress in a neat, clean, and usually preppy way. For boys, this means coat, tie, and khakis, and for girls, this often equates to a white shirt, snap tie, and skirt. For formal days, there is a specific dress code, and other days, there is not an exact uniform, but there is a strict dress code. If a skirt is too short or footwear is not up to code, students will likely be written up and/or asked to change.

Check out the uniform I wore (below) when I attended a small private elementary school in eastern Connecticut. VERY Chilton-esque, but in an uglier color!

A Real Life Max Medina?

I think it’s fair to say that my husband may very well be a modern Max Medina. He teaches English (American Literature, to be exact) at a Connecticut boarding school, is a smart dresser, treats his students with kindness and respect, and most of all, he has the hair. Check him out on campus below!

The Puffs: Real or Not Real?

There are no secret societies like The Puffs at the schools I am involved in…that I know of…but I suppose the whole point of these clubs is that teachers/staff would not know about them. There are certainly cliques based on interests, whether in sports, arts, technology, or media.

Not Quite The Franklin, But We’ll Always Have Paris

It’s a digital world now, so some things are a bit different from Gilmore Girls times, while others remain. Student-created digital newspapers are still very much alive at boarding schools, and regularly report on goings-on at the school. The reporters do not receive the same esteem as those on the newspaper staff at Chilton, however, and are often simply students who are interested in journalism and want to get credit and experience in that area.

Sports in Gilmore Girls vs. Real Life

Hockey in prep school is huge, so watching the guys at our school duke it out with throngs of cheering fans is very reminiscent of Dean in his hockey days. I often think of the episode when Rory realized that Dean had a new girlfriend at his game.

Fencing is most definitely still taught at boarding schools, but at the one where I used to work, students took a swing (literally) at stage combat. They used real theater swords (they’re heavy and ornate, but blunt) and sometimes wore costumes.

Similarly, the tradition of golf is very much alive in boarding schools, for both boys and girls. One of my favorite episodes of Gilmore Girls is when Rory learns golf and gossips at the club with her grandpa. There are golf courses aplenty in this area of Connecticut, and when it gets cold, there are even indoor courses where students can practice in the off-season.

“George Washington rode past this place” and more obscure history

On Rory’s graduation day, she talked about how the marble floors in the halls of Chilton were once walked on by Harriet Beecher Stowe. Well, my ears perked up when I heard this because I knew that Amy Sherman-Palladino had done her homework on local history. One of the dorms at the school where I work is called Beecher – it was once the original Harriet Beecher Stowe house but that was taken down piece by piece in the 1990s to be rebuilt as a museum. The current dorm is built in the exact footprint as the original.

At Chilton, it was said that Robert Frost donated the staircase banisters and Thomas Edison once lit a sconce somewhere on campus. Although these exact references do not exist to my knowledge at the schools here, they are still steeped in history. There is a spot on campus with a sign that reads, “George Washington rode past this place.” No one acts like it’s a big deal, but when I first started working there, I freaked out. How cool is that? The people here must be so accustomed to having famous historical people connected to the school that they forget to be excited. Sounds very Chilton to me.

(Editor’s Note: Sarah’s “George Washington rode past this place” photo reminds me of the funny and obscure historic relics from the Stars Hollow History Museum as seen in Season 5, Episode 18 (“Live and Let Diorama”). Check out a couple of gems that Taylor Doose curated in the photos below.)

A “Civil War Era Cannonball” that fell through the floor

According to Luke, “It’s a possible circa 19th century portrait of what we think may have been the founder of a school that possibly educated Ben Franklin’s cousins.”

Final Thoughts

There are almost endless connections between Kent and Stars Hollow. Every day, I find myself telling whoever is next to me: “That is totally a Stars Hollow type of person,” or, “This is such a Stars Hollow activity.” With all of its quirks, Kent is a beautiful place to live – nestled in the mountains yet still a train ride away from New York City – some might even say it is the perfect place to live.

Did I miss anything? Do you think your town is like Stars Hollow? Questions? I want to hear your thoughts in the comments section!

This is downtown New Milford. The town as a whole is dissimilar to Stars Hollow, but the center of town…it’s almost exact, gazebo and all!

16 comments

  1. Julie Dinsdale says:

    I have loved Gilmore Girls since it first aired. My girls and I have relationships like Rory and Lorali. We even had a Gilmore Girls Day. We made good from the show a binged watched the revival shows. I live in the California version on Stars Hollow, Benicia, California. Everyone knows everyone and their business. We celebrate very thing such as The opening of the straits. We are located on the Carqunez Straits. No far from San Francisco.

    • Sarah Pfeffer says:

      Hi Julie,
      That is so cool! I love how this how has connected to so many people in their lives and family relationships. My aunt lived in San Francisco for many years. Would love to go back and see the CA version of Stars Hollow.

    • Amanda says:

      Girl. Ask this blogger if u can submit an article of ur town, like this rockstar chickadee did above. Never thought of “star hallow” being in other places. But would love to view it from ur camera’s lense.😍

  2. Martha says:

    Love Gimore Girls and dreaming (actually planning) to retire on a place like Stars Hollow. Thank you for this article. Might want to visit your town one of these days👍.

  3. Stephenie Zito says:

    Absolutely love this! My mother and I watched GG when it was originally aired on tv as well as binging several times on Netflix. We’ve always wanted to visit a Stars Hollow town, and now I believe we’ve found a great place to start! Thank you for sharing your comparisons!

  4. Emeline says:

    Thank you for this fun article! I’m researching small New England towns to live. I’m eager to escape the hustle and bustle (and expenses) of living just outside NYC. I’m also a huge fan of Gilmore Girls and Kent does seem like a perfect comparison. I visited some family friends there and it is beautiful. Dinner at the Bull’s Bridge Inn, plus the lovely drive up through the foliage and covered bridges- quintessential New England!

    • Sarah Pfeffer says:

      Hi Emeline,
      You are not the only one! We get a lot of visitors from NYC, especially on weekends, who love the refreshing country vibe!

  5. Amy Hurst says:

    Love this article! My friend and I will be there for the fan fest in October and we can’t wait! First time to New England area, and at fall, even better! We’ll have to check these places out! What do you think of Washington Depot? Have you been there?

  6. Darcilyn Schriver says:

    Nice blog post! Before I read the caption for the last photo, I was gonna say hey that is New Milford! I agree NM is much larger than Stars Hollow but I think Theo’s on RR street has a kindof Luke’s vibe… live music on the green where we see many townspeople including the mayor….town hall meetings… are just a few similarities to Gilmore Girls and Stars Hollow ♡ Maybe I will see you around!

  7. Sandy says:

    I love the Gilmore girls n yes Kent n new Milford look a lot like stars hollow
    There extended series was disappointing I didn’t like the ending where Rory announces to her mother n says I’m pregnant and that was that

  8. Gracie Gomez says:

    My daughter & I will be taking a dream trip to your beautiful town for the Gilmore Girls Festival this fall. We can’t wait! ❤

  9. Bobbie Fitch says:

    What a great piece. Makes me want to visit Kent in three out of the four seasons. Thanks for helping the Gilmore way of life live on.

  10. Susan says:

    This is so awesome. I lived in a small town in New Hampshire for 23 years. Not quite Stars Hollow but close! Enjoy. I love Connecticut and Gilmore girls.

  11. Beth says:

    Very cool article! I live in Menomonee Falls, Wisconsin. We have a lot of similarities to Stars Hollow too!

    1) We have a gazebo (My daughter got married there!)
    2) Our mailman looks like Cliff
    3) we have a town meeting
    4) we have a diner and several coffee shops
    5) we don’t have an inn but we do have two hotels
    6) we have reenactors (they are for the Civil War, not the revolutionary war). It takes place at old Falls Village.
    7) we have a town Square, although we call it the four corners.
    8) we have a house that is a kin to the Twickham house.
    9) we have a bakery like Fran’s
    10) we have a small grocery store like Dosie’s
    11) we don’t have a Miss Patty’s, but we do have a Fred Astaire dance studio
    12) Although our town was not established in the 1700s, it was established in the 1800s. So as with Stars Hollow, it is an old town.
    13) We have an historical society
    14) We have four seasons
    15) We have a bike marathon “Wheeling for Healing”.

    I love living here! Come visit any time!

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