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Fall Gilmore Girls Trip to CT
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items My sister and I wanted to explore the charm of small-town Connecticut with a fall travel itinerary inspired by Gilmore Girls. We visited the picturesque towns of Washington Depot, New Milford, Hartford, and Kent, which influenced the setting of Stars...
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Sections
4
The Stays
Night 1 - Kent
Day 2 - New Milford + Kent
Day 3 - Washington Depot + Hartford
The Stays
During our fall getaway, we stayed in a series of charming bnbs that perfectly captured the cozy, small-town vibe of Connecticut. From quaint country homes to historic inns, each spot offered a unique and welcoming experience, adding to the magic of ...
This cottage was the perfect place to sip a morning coffee and watch Gilmore Girls before starting your day! It was nestled perfectly between New Milford and Kent.
Cabin in New Milford · ★4.95 · 2 bedrooms · 5 beds · 1 bath
The owner of the inn, Laura, is the real life Loreli Gilmore! I highly recommend this stay near Hartford and you must ask her about her story yourself.
Charles Cheney Inn
Night 1 - Kent
The drive from the airport was stunning! The fall foliage was in full swing. I 100% recommend planning for your drive to happen during the day so you can see it all. After settling into our cozy cabin nestled between New Milford and Kent, we drove ou...
This was a wonderful dinner! It has the perfect cozy small-town vibe we were looking for. The black cherry margaritas are a MUST. I wish we had been there at the same time as the live piano player.
Fife 'n Drum Restaurant & Inn
Day 2 - New Milford + Kent
This was my favorite day of the trip! Both of these charming towns were a blast to explore. They are quite small, so it's easy to see both in one day. New Milford was my #1 place that I had visited on this trip. In each town, we visited an array of s...
This was the best coffe I had on the trip! The food was also fabulous. This is a MUST for breakfast.
River & Rail Cafe
This is a great dupe for Kim's Antiques. It's right across from the cafe and is very palatable for those who don't antique often as the store is very currated and smells great! There are many other roadside antique stores to and from the towns if you...
The Hunt
The gazebo in the town square look identical to the one in the show! This is a photo-op must. Once you park, New Milford is very walkable, so you should have no trouble accessing it.
The Real Life Stars Hollow: New Milford, CT - Planned Wanderings
There are so many adorable book stores in CT that replicate Stars Hollow Books, but this one was my favorite as it feature pre-love books for a more affordable price.
Honeybee Books & Tea
Not a soda shop like Taylor's Olde Fashioned Soda Shoppe, but they do serve some delicious ice cream as well!
Grassroots Ice Cream
This is a great little stop on the drive from New Milford to Kent! It's a dupe for the Old Muddy River Bridge and is surrounded by beautiful fall foliage and a few walking trails.
Bulls Bridge
Kent hosts the adorable used book sale, without Dean's bad vibes, lol. All proceeds go to the library.
2024 Annual Book Sale | Kent Memorial Library
This inn not only is a great place to stay, but they also serve a great dinner. The eclectic cozy vibes are perfect for fall and they have a wonderful cockatiels to try out.
Bull's Bridge Inn
Day 3 - Washington Depot + Hartford
I was shocked that Washington Depot was my least favorite town of the mix. I thought it would be my favorite. We did not spend much time there, but there are a few cool sights to see. After we drove toward Hartford (reffering to the general area, we ...
The place definetly has inspiration from Luke's, however the coffee and food was not very good. Very cute location though!
The Po Cafe
This was meant to be another Luke's dupe. We tried to get better food and coffee here… It was unsuccessful. We did not like this place at all.
Marty's Cafe
Such a cute shop! They have a Gilmore Girls section and guide to sights in the town that inspired the show.
Hickory Stick Book Shop
This was seriously adorable! It's the perfect Doose's look alike. Great place to grab a snack and take your picture with some corn starch!
Washington Food Market Inc
This is the inn the writer stayed in that inspired the show! It is expensive to stay here so we opted for visiting for photos. It is a lovely place!
Mayflower Inn & Spa | Boutique Hotel in Litchfield County, Connecticut
You MUST go to the cider mill for hot cider and apple fritters. They are so amazing and you can enjoy a petting zoo as well for $1. This was one of our favorite stops on our way to the inn in Machester!
Old Cider Mill
This charming town is easily walkable and lined with beautiful hostirc homes and small businesses. We had a great time exploring the area!
Old Wethersfield
So much more than pizza here. This was an amazing dinner! One of the best.
Mulberry Street Pizza
Nestled in a large park, this conservancy was so much fun to explore before heading home!
Elizabeth Park Conservancy |