Gilmore Girls Weekend Itinerary

Looking for a weekend trip inspired by the Gilmore Girl’s show? Below is the itinerary Katie and I followed to knock out the Gilmore Girl’s iconic show inspirations, in one weekend!

Day 1 (Friday):

DTW>BDL (1.5hours) Arrived at 7pm

Modern Apizza (Top rated pizza joint, that has been around since 1934)

Checked in to Air B&B in New Haven, Ct $70/night

Watch Gilmore Girl’s episodes on Netflix, was in bed by 10pm to get good night rest to visit “Luke’s” in the AM.

Day 2 (Saturday):

Our day started at 7am

New Haven> New Milford (Estimated 1hr 15min)

Theo’s Downtown Diner (Luke’s)

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New Milford Town Gazebo (Gazebo)

Gazebo

Homestead Inn (Independence Inn)

Independence Inn.jpg

New Milford> Washington (20 mins)

Hickory Stick Bookshop (Stars Hollow Books)

Washington Food Market Inc (Doose’s Market)

Marty’s Cafe (Luke’s Diner)

Mayflower Grace Inn (Dragon Fly Inn)

Dragonfly

The Gunnery (Chilton Private School)

Pit stop to Averill, a apple orchard

Pit stop, happy hour at Haight-Brown Vine Yard

Washington>Litchfield (20 mins)

Went to visit Bradford House Antiques (Kim’s Antiques, but it’s gone now)

Litchfield> New Haven (55 mins)

Wander around Yale University Campus

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Night ended at 10pm

Day 3 (Sunday):

Our day started at 8am

Check out of Air B&B in New Haven

Breakfast at Choupette Crêperie & Cafè (French style crepes)

Katie did her personalized tour of Yale University

YaleUniversity1

Visited the Yale Newsroom (window was broken so snuck my camera in)

Newspaper.jpg

Visited a Connecticut beach

Village Chocolatier in Gilford (Taylor’s Old Fashion Soda Pop Shop)

Chocolate and Pop Shop.jpg

Gilford>BDL (Approximately 1hr)

 

 

 

 

A Gilmore Girls Weekend Q&A

Never did I think that in my 20’s I would visit the hometown inspirations of a show I used to watch as a kid. My show of choice throughout middle school & high schoool was Gilmore Girls. There was something witty and funny about watching the relationship between mother & daughter (Lorelei and Rory), while experiencing similar experience and life changes with my own mom. We could have definitely worked on our dictionary and historical references, but I will credit that to the writer of the show, which obviously my mom and I didn’t have the opportunity in hiring for our own chapters. 

About 4 months ago a former co-worker, Katie, and I, were discussing states we needed to check off of our bucket list and what better way to marry our favorite tv-show as a kid, and Connecticut. A Gilmore Girls inspired trip!

To start I will say I was somewhat disappointed in realizing the the show was filmed in a Hollywood Studio. I didn’t realize shows like this had sets built for years while the seasons unfolded. Quite remarkable when you think of it. 

Random questions people have been asking:

Q: Can you do this trip in one weekend 

A: Yes! Who would have thought the ritzy state of Connecticut could be driven in just a 3 hours from the two furthest points. This can definitely be done in a weekend, and with no rush! Katie and I even had time to visit an apple orchard, and the first half of the Michigan football game on Saturday (#GOBLUE).

Q: Did the places of inspiration truly look like the show? 

A: Some were a stretch. There was no doubt that the Independence Inn, Dragon Fly, and Gazebo were inspirations pulled from New Haven, New Milford, and Washington, Connecticut. But the others involved a little imagination and some re-watching of a few episodes.  Especially, the spot for the Kim’s Antiques, which the inspiration has been converted into a modern retail store. And with two girls with messy buns looking for Lane, did not feel welcomed; with a belt in the store costing nearly $300. 

Q: Was it easy to find affordable hotels to stay in Connecticut? 

A: I have mostly traveled alone, and so I have grown accustomed to rooming with strangers through Air B&B. On this trip Katie and I rented a room at an Air B&B in New Haven. I would recommend this location, as it is near Yale University and provides a serene unique setting. You could stay at the inspiration of the Independence Inn, or Dragon Fly, but the difference in price would be approximately $80 more a night.

Q: Were the cities bigger or smaller than you anticipated? 

The cities were quite small, with those living in them knowing our exact purpose for visiting. One store owner told us “our small town of Washington has many girls joining to find the Gilmore Girls inspiration. I don’t think some realize how small our town really is.” The towns inspiring the show of New Haven and Washington, were quite small- but quite refreshing. I mean Kirk had 30 jobs, so it’s not like Stars Hollow could have been that big. Just saying. 

If you have additional questions, please leave a comment and I will answer back!