"We're almost there and nowhere near it. All that matters is that we're going." (Lorelai Gilmore: Season 2, Episode 3, 'Red Light on the Wedding Night')
Day 1
New England is known for its antiques, small towns, cozy countryside, feel-good atmosphere, and the fictional town called Stars Hollow, Connecticut. Who could ever forget Lorelai, Rory and Emily, mother, daughter, and grandmother, the beloved characters of Gilmore Girls, each one stubbornly coming into their own, as we, their fans, laughed, cried and silently cheered them on. After Netflix aired "A Year in the Life," in 2016, my daughter, Tas, became equally hooked on the show, which led to the idea of our own Gilmore Girls road trip, after binge-watching the whole series several times. With a thermos full of coffee, a bag of junk food, and child-like anticipation, Tas and I embarked on a tour of the Connecticut setting that the show was based upon, including a trip to the Grace MayFlower Inn, Yale University, Cape Cod and Harvard University.
Upon arriving at our lodging, The Homestead Inn, New Milford, CT, we marvelled at the similarities to Lorelai and Rory’s house, the Independence Inn, and the Dragonfly, with the patterned red wallpaper, the antique furnishings, wooden trim staircase handrail, and familiar front porch. As we relaxed while sipping tea later that night, we reminisced front porch scenes, i.e. Lorelai and Rory painting their toenails, Rory and Dean’s first kiss, Luke fixing the rail, and the longing, lovelorn look from Jess in the last episode that no one will soon forget.
But before our front porch ruminating, we strolled into town and indulged ourselves by sitting on the steps of the gazebo that was such a central landmark in Stars Hollow, making it fitting that Lorelai and Rory sat on the steps in the first and last episodes of, “A Year in the Life”.
What struck me the most about the similarities to Stars Hollow’s gazebo was the location. It sat on the middle of the green, enclosed by town roads and bordered by side walks with a lazy, Saturday morning stroll to the Farmer’s Market feel. We dined on the patio at an Italian restaurant, situated directly across from the gazebo, where we continued gazing at the iconic landmark, while chowing down pizza in Gilmore Girls’ style. In amazement, as we were leaving, we stared, open-mouthed, as a large-chested man wearing an untucked plaid, flannel shirt with his hat on backwards crossed one of the empty town roads. Luke?
Day 2
One could easily visualize life of the Stars Hollow’s townsfolk unfolding here, and just as anticipated, the next day while wandering around town, we witnessed several friendly encounters from the regulars as they greeted one another in that familiar, small-town way. New Milford could easily have been Stars Hollow, with the dance studio that reminded us of Ms. Patties, a hardware store named Taylor and Sons, a movie theatre, a number of restaurants, and a cute ice-cream shop across from the gazebo.
It was my daughter who first spotted Theo’s Diner, a diner that screamed Luke’s, with its laid-back, welcoming feel. Opting to sit on the stools at the bar, we stole glances around the room, spotting the similarities to Luke’s: the miss-matched coffee mugs, the signs with the slogans, and most adored, the same style of curtains that hung in Luke's Diner's windows. Not knowing what to order, we looked up and saw the danish specials written on a whiteboard. Tas turned to me and said, "It's Danish Day: the happiest of all days" (Season 2: Episode 5, Rory Gilmore). We ate, lingering over the nostalgia, expecting Kirk to walk in any moment.
Later, we strolled around and discovered another piece of Gilmore Girls history. On the top of a hill sat the Canterbury preparatory school, which reminded us of Chilton, the expensive private school that Rory gained acceptance to in the pilot episode, and which she attended in the first three seasons.
Washington, Connecticut, the nearby town, gave us additional Gilmore Girl experiences. Our first stop was The Hickory Stick Bookstore, where the owner, Tom, indulged our obsession after we sheepishly confessed the purpose of our road trip. Tom led us to Lauren Graham's book and a compilation CD of Gilmore Girls songs, took photos of us, and then shared a list of notable places to visit, that resembled Stars Hollow. (Tip: Ask Tom for a copy of his Gilmore Girls Tour stops)
While strolling through one of the shops, we noticed the shop assistant had a Luke's sticker on her laptop. Thinking they were available in the store, we asked to purchase one, but the shop assistant informed us she bought it online.
Click the link if you want to buy a pack of 50 Gilmore Girls stickers, including the iconic Luke's yellow coffee cup sign.
Following Tom's advice, we drove to the Grace Mayflower Inn, reportedly where Amy Sherman Palladino stayed while first creating the Gilmore Girls script. Spectacular gardens surround the stately building, reminding us of The Independence Inn, where Lorelai and Sookie worked before starting their own inn.
Continuing our Gilmore Girls themed trip, we drove to New Haven to visit Yale University, where Rory earned her degree. Although New Haven didn't lend itself well to the Gilmore Girls vibe, Yale did. We could envision Rory buried in a book at the old, historic library or walking to classes through the freshman quarters.
From Yale, we ventured to Cape Cod, remembering the Valentine's Day episode where Luke and Lorelai accepted Logan's invitation to one of his parent's houses on Martha Vineyard (A Vineyard Valentine, Season 6, Episode 15), stopping along the way to eat at The Place, a unique outdoor seafood destination, where customers sit on logs and can bring their own drinks and snacks.
Day 3
Before arriving at our Cape Cod destination, we shopped at the Premium outlets at Clinton Crossing and then experienced our first lobster roll at Lobster Landing. This place is a must-see and the lobster roll a must-eat!
It was a long day and we had packed so much into our trip already, so when we arrived at the Lighthouse Inn, in West Dennis (Cape Cod), MA, USA, we felt like we had been gently kissed by God, as we melted into our seats and absorbed the sea salt breeze, relinquishing every thought and feeling.
Our evening ended with a stroll along the beach, after devouring the flavorful shrimp specials from the Lighthouse Inn.
The morning breakfast was just as fulfilling as our dinner. Afterwards we spent the day slowly walking along the beach, collecting rocks, and savoring each moment.
Following a local's suggestion, we drove to Schoolhouse Ice Cream & Yogurt.
Day 4
On our last day, we completed our Gilmore Girls tour at Harvard, the university Rory was determined to attend, and a destination of Lorelai and Rory's road trip in Season 2, Episode 4, 'Road Trip to Harvard'. Similar to the way Rory snuck into a lecture, Tas and I joined a group of prospective business students as they listened to a guide.
A prestigious Ivy league research university in Cambridge, Massachusetts, Harvard is world-renowned. Established in 1636, centuries of architects, styles and materials have shaped the iconic buildings that sets Harvard apart from any other university. We walked from the book store, where Tas bought a hoodie and we agreed she had to attend Harvard one day because her name was part of their motto, 'Veritas', meaning truth, to the historic and popular Harvard Square. With a Starbucks iced coffee in hand, we strolled along the pedestrian bridge over the picturesque Charles River and explored the Harvard Business school, before returning to our car and the road that led us back home.
Trip Route: https://goo.gl/maps/SvMBXw7rbqva94Ap9
Helpful Websites:
Connecticut Tourism: https://www.ctvisit.com/, https://www.visitconnecticut.com/state/
Visiting Yale University: https://www.yale.edu/about-yale/visiting
Cape Cod: https://www.capecodchamber.org/
Visiting Harvard University: https://www.harvard.edu/on-campus/visit-harvard
Gilmore Girls fan club: https://www.thefanfestsociety.com/
New Milford town: https://www.newmilford.org/content/3088/3136/5735.aspx
Tips:
1. Stay at The Homestead Inn. There was a bowl of candy in the room when we arrived - how Gilmore Girls can you get!
2. Ask Tom at The Hickory Stick Bookshop in Washington, CT for a copy of his Gilmore Girls Tour stops
3. Take the time to explore both New Milford and Washington - I wish we had planned to stay 2 nights instead of 1.
4. Don't skip the Grace Mayflower Inn, even if all you do is walk around the heavenly gardens, which you're allowed to do.
5. Bring your own snacks and drinks to dine at The Place.
6. Definitely stay longer on Cape Cod and include Martha's Vineyard and Nantucket.
7. Join one of the many visitor tours at Yale and Harvard
8. Do you remember the film, Mystic Pizza? It was partially filmed in Mystic, CT and you can add this to your tour, stopping along the way to Cape Cod.
Adding Manhattan, NYC to the trip:
Remember Season 2, Episode 21: Lorelai's Graduation Day, when Rory visits Jess in Manhattan? I thought it would be a welcome addition to add a trip to Manhattan to the itinerary. Depending on when you visit, check out my summer and winter blogs to Manhattan for ideas.
Update:
It brings me so much joy to learn that other mother/daughters are taking this trip as well. Please leave a comment and a photo so we can all relish in our Gilmore Girls nostalgia.