Gilmore Girls Inspired Connecticut Getaway

Travel

August 16, 2022

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I'm Kristy May

When I first met my husband, Ryan, we bonded over our shared desire to live somewhere with seasons. We were living in south Louisiana at the time which basically has two: wet and cold and very hot and wet. It was ultimately Hurricane Katrina that sent us up to NYC, so weather was a big factor.  While we were dating, I made him watch Gilmore Girls with me. We both loved the small town quirky vibe, fast and funny dialogue and of course, the seasonal changes in the fictitious Connecticut town of Stars Hollow. 

During the pandemic someone went back and watched the first 5 seasons he’d missed and the rest of the series again. He won’t admit it, but he is probably a bigger fan of the show at the moment than I am. 

When an opportunity to go away for a 3 night trip recently arose, I decided it was time to visit “Stars Hollow” for real. Well, as real as visiting an imaginary place can be. The show’s creator took inspiration from several towns around Litchfield County, Connecticut.  With our daughter off to Girl Scout Camp in NJ, we headed north for a 2 hour drive to look for Stars Hollow. 

Even if you aren’t a Gilmore Girls fan, this area has so much to offer. It is a short drive from New York City and has some super romantic inns and a fantastic local dining scene. The landscape is dotted with well maintained classic white colonial style homes, shingled summer getaways and adorable red barns. While we visited in Summer, it is a year round destination though some of the below activities may not be open. (And even in the peak season, many places are closed on Monday or Tuesday, or both.)

Gilmore Girls Trip Map

Day One

We arrived at the Hopkins Vineyard on a Sunday evening in August. From 2-5pm on weekends seasonally there is live music and one can buy a flight or bottle to enjoy overlooking the vineyard. We bought a cheese box which included 2 cheeses, (one hard, one soft) crackers, bread, corn nuts, plates and a napkin. It was all good.

While the winery and the Hopkins Inn where I’d made a reservation bear the same name, they don’t have the same owners. However, they are across the street from another so there is no driving needed. Perfect!

The historic Inn dates back to 1847 and has an Austrian restaurant on the first floor and terrace. I booked room #17 because it overlooks Lake Waramaug. It was just perfect for a few nights and the view was great!

Dinner is another matter. Having lived in Germany and visited Austria, I was a bit disappointed by the food. It wasn’t bad, I’ve just had much better. However, the location was perfect after a day of driving and wine.

Eat & Stay: Hopkins Inn

To Do: Hopkins Vineyard

Day 2

Marty’s Cafe

Many businesses are closed on either Monday or Tuesday so I had to plan strategically. We first explored Washington, CT. A guide I’d read said Marty’s was like Luke’s diner so we started there. While it is not a diner (more like a tastefully appointed cafe), we did see scores of locals arriving for their morning coffee. 

While visiting the Hickory Book Shop, I spied a tiny light-up Stars Hollow sign. I secretly bought it for Ryan’s birthday which was just a few days away! It was one of the few Gilmore Girl souvenirs to be seen. The area is not touristy at all, or, obviously so.

After more looking around in New Milford (gazebo) and shopping in New Preston, we took naps to prepare for dinner at Community Table. The local farm to table restaurant did not disappoint. But do yourself a favor, order the cardamom rolls for dessert. They are so delicious but filling.

Eat

  • Marty’s Cafe in Washington, CT (aka, Luke’s)
  • The Smithy Cafe in New Preston
  • Community Table

Shop

  • Hickory Book Shop
  • Privet House
  • Plain Goods

To Do

  • New Milford – Gazebo
  • Village Center for the Arts – Barn Quilt Trail
  • Falls in New Preston

Day 3

While dinner at the Hopkins Inn didn’t impress me, I did enjoy my fruit pancakes overlooking the lake. To kick off the day, I used All Trails to find the Hayfield Loop to work off that tasty breakfast. It is beautiful and an easy walk. A local recommended we visit the Thorncrest Farm for chocolates. She was right, they are delicious and you can even visit with the cows making the milk. (tours only on weekends) Stumbled upon the Sister Parish offices in Litchfield. (I love following Eliza, and the designs of course!) After lunch in a former prison, we visited the Litchfield Distillery for a fascinating tour and tasting and got ice cream at the Arethusa Dairy. 

To celebrate Ryan’s birthday (the next day) we had dinner at the Mayflower Inn. This is the inn where the Gilmore Girls creator, Amy Sherman-Palladino, stayed and inspired the show. Not only that, it is a 5 star luxury resort with impeccably designed rooms, a spa and lush gardens. Weddings can be held under a sailcloth tent overlooking the formal Shakespeare Garden.

I have no idea if this is a coincidence or not, but we were seated next to each other. The table was quite large, so perhaps to increase romance they seat couples that way? Ryan remembers an episode where Rory goes on a date in college and gets seated in the same way. So naturally, she must call Lorelei for help! Dinner was excellent and we went back to the inn to watch that episode, laughing the whole time.

Eat

  • Market Tavern in Litchfield – The restaurant is in a former prison
  • Mayflower Inn 

Shop

To Do

Day 4

This was our last morning so we packed-up and headed to Kent State Falls for a hike. Out of state license plates must pay using a confusing system when no guard is present, so that was annoying. The hike up the waterfall was pretty easy and very scenic. The trip back down the other side was less scenic and more difficult. But still not hard. We rewarded ourselves with lobster rolls, which were totally out of the way but it was Ryan’s birthday, so he got to pick.

It was a fantastic quick getaway. I’d love to see the area in the fall. When we got back home, I presented Ryan with the little light-up Stars Hollow sign for his desk. A fun reminder of a place we can’t visit, but we can still dream about. 

Eat

  • General Store in Warren, CT
  • Westshore Seafood

To Do

  • Hike at Kent State Falls – (out of state parking fees)

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