A few years ago, my daughter and I binge watched Gilmore Girls on Netflix. We have a very close relationship so naturally we immediately fell in love with the show, all of the characters and the fictional town of Stars Hollow.  As I like to say, she is the Rory to my Lorelai. Since we love to travel and Spring Break was approaching at the time, my daughter planned a Mother/Daughter Gilmore Girls road trip, visiting some of Connecticut’s most picturesque small towns (similar to our own Gilmore Girls Fan Fest).

We flew to Hartford and then ventured through Litchfield, Kent, New Milford, Washington Depot (which inspired the show’s creator Amy Sherman-Palladino to develop Gilmore Girls during her stay in town) and back to New Haven. My daughter put a lot of thought and planning into this trip and came up with the perfect itinerary.  The only thing I would suggest to do differently would be to maybe go in the fall, as in March the weather was cool and cloudy.  We had so much fun, here’s how our trip panned out.

Day 1, Hartford

We stayed at the Residence Inn Hartford Downtown and explored Hartford in search of “Emily & Richard’s house” and “Chilton”, where Rory went to school. We decided to also do a bit of sightseeing as this was our first time in Hartford. During our drive through town we stopped at Mozzicato DePasquale Bakery and Pastry Shop for a snack. This is a beautiful, genuine, Italian neighborhood bakery, which we loved and sadly do not have any of in Miami. We also visited the Mark Twain House & Museum, the Old State House and the Wadsworth Atheneum Museum of Art. In the evening we drove around West Hartford and had dinner at Barcelona Wine Bar.  Very yummy tapas.

Day 2, Litchfield

Litchfiled was definitely a quaint little town. We stayed at the very cozy Litchfield Inn and drove around searching for “Kim’s Antiques”. We found many charming shops in the center of town, in particular, Litchfield Candy Company.  We took some pictures of the First Congregational Church, visited the Shrine of Lourdes and finally stopped for a late lunch at the West Street Grill.

Day 3, Kent

The drive to Kent took us through some hilly roads so please have your GPS handy and definitely do not drive at night, unless you know the area. We stayed at The Inn at Kent Falls, a very beautiful B&B, which has sadly been permanently closed since our visit. We also strolled along Main Street, where most of the shops and eateries are located. We had some warm coffee and picked up some specialty chocolates at the Kent Coffee and Chocolate Co. and then stopped in at the House of Books. Very quaint little town, with many beautiful Victorian homes.

Day 4, New Milford & Washington Depot

New Milford was the least of my favorite towns, however, this is where we found the gazebo, similar to the one in Stars Hollow, on the New Milford Town Green.  We walked around and took in some of the shops and eateries on Main Street and Bank Street.  Before heading out, we drove up to the Canterbury School, which my daughter says appeared similar to Chilton, where Rory went to school.

We then headed to Washington Depot, the town that inspired the show. We stayed at the famous Mayflower Inn & Spa, which is absolutely gorgeous, I highly recommend a stay there.  While exploring the town, we had some coffee at Marty’s,  the “Luke’s” of the town and we also stopped in at the Washington Food Market, which resembled a small market like “Doose’s”. Washington Depot has many charming shops and restaurants, we also visited The Hickory Stick Bookshop  which is a beautiful, independent book store that also sells cards, gifts, plush and toys for kids.  Later in the evening, we had dinner at Community Table, which had amazingly fresh and delicious food.

Day 5, New Haven

A stop in New Haven was a must, as we had to visit Yale, where Rory went to college.  We stayed at the New Haven Hotel and explored the campus and its surroundings, including the shops on Broadway and of course the Yale Bookstore for t-shirts. We also had pizza at Pepe’s Pizzeria,  still considered one of the best pizzerias in the country.  I must say our pizzas were delicious. In the evening we stopped by Atticus Bookstore and Café for some coffee, scones and pretty postcards.

We truly enjoyed our Gilmore Girls adventure. Have you been to any of these Connecticut towns? I would love to know what you enjoyed most.