Gilmore Girls Weekend Itinerary (Fall Road Trip)

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Are you a Gilmore Girls fan who wants to visit the real life Stars Hollow? Northwest Connecticut was the inspiration for the fictional TV town.

I absolutely love this part of CT, so I planned out a fall Gilmore Girls weekend itinerary that’s perfect for a girls getaway, sisters trip, or mother daughter road trip in Connecticut. (My best friend and I actually did this itinerary a few years ago, and it was amazing!)

Keep reading for my recommendations on what not to miss on a fall Gilmore Girls road trip in Connecticut.

✨ Highlights include: searching for Stars Hollow vibes in New Milford, Washington, and Litchfield (quirky town events included), drinking copious amounts of coffee, plus visiting Yale University for Rory’s college years.

Where is the real Gilmore Girls town? The town of Stars Hollow is fictional, but it was based on a trip that the show creator took to the town of Washington, CT. She had already pitched the idea for a show about a mother-daughter best friend duo, but the spark of inspiration to set their lives in small-town Connecticut happened while she visited what she later called a “fairy town.” Washington was the original inspiration, but there are numerous CT towns with a bit of Stars Hollow in them.

Road Trip Itinerary At a Glance

This weekend itinerary assumes you’ll arrive on Friday by mid to late afternoon and will leave on Sunday afternoon or evening. Here’s a very quick overview:

Friday: Depending on where you arrive, explore Hartford/West Hartford or New Milford. Have a Gilmore night in for the evening with takeout and some Gilmore Girls episodes! 

Saturday: Explore the Stars Hollow towns of New Milford, Washington, and Litchfield. 

Sunday: Head to Yale for the campus experience and search for the best New Haven pizza, or discover more Stars Hollow towns with no particular plans. 

Day 1: Lazy, Hazy, Crazy Arrival Day

Friday: A Gilmore Night In

Since Friday is a travel day, there’s not much planned on the itinerary, as it all depends on where you’re coming from. Below you’ll find options for getting to CT, along with a few bonus activities if you arrive early. 

My suggestion: Arrive in Connecticut in the afternoon, drive and get settled at your lodging, and kick things off with a Gilmore night in—complete with takeout and junk food. Turn on some favorite episodes of Gilmore Girls to get ready for the next couple of days!

Arrival Options

✈️ Bradley International Airport near Hartford (BDL): This is a small-medium airport and has rental cars. You can stay overnight in the beautiful town of West Hartford, or you can drive straight to New Milford on Friday if you don’t want an early morning the next day. (I suggest taking the northern route to New Milford for better scenery: to Winsted, down Route 8 towards Torrington, then through Litchfield and onto New Milford on Route 202.) Search rental cars at BDL here.

✈️ Tweed-New Haven Airport (HVN): This very small airport has two airlines with less frequent routes, Avelo and Breeze. There are some rental car providers at the airport, but I suggest checking their hours because this airport is extremely small (walk-on-the-tarmac small). Turo is another option. From here, drive to New Milford. (The route on 95 to Route 15 to 25 is more scenic than 91 to 84). Search rental cars at HVN here.

✈️ Other airports include Westchester County Airport (HPN), which is a smallish airport in New York. There are also JFK and LaGuardia (LGA) in New York City, both of which are huge and offer lots of flight options. However, these may add a lot of driving time due to unpredictable and potentially significant traffic, so I don’t recommend them for a weekend trip. If you are flying into one of these, I prefer LGA as it had major renovations done so it’s really nice.

🚗 From points south or west, I recommend heading directly to New Milford during daylight to enjoy the fall foliage. From points northeast, you could stay overnight in West Hartford, or head directly to New Milford if you don’t want an early morning start the next day.

Getting there early? (Friday bonus options)

If you arrive early in the Hartford area, take a drive down Prospect Street and Scarborough Street in Hartford for the Emily + Richard atmosphere. Other afternoon options for book nerds: embrace the Rory vibe and make a literary-themed stop at the Mark Twain House, Harriet Beecher Stowe Center, or Noah Webster House. Take a walk through Blue Back Square in West Hartford and read about Webster’s impact on American English spelling. 

If you arrive early but are planning to go directly to New Milford on Friday, you’ll have more time to just explore and see what you find on the way there and as you get to town. You can do some of tomorrow’s activities to give yourself more time for seeing the other towns on Saturday. Or check out one of these spots: antique stores (there are a few on the other side of the bridge), Village Center for the Arts (down-to-earth with a little Stars Hollow quirkiness), Grassroots Ice Cream (incredible unique flavors like Goat Cheese Blackberry), or River and Rail Cafe. 

Where to Stay (Night 1)

Depending on which option you choose for Friday night (decide that first based on the above!), here are some specific options for lodging. Unfortunately, I haven’t had the chance to stay at all of these yet, so this is just a starting point based on some research combined with my knowledge of the area. I hope to stay at more of these lodging options to provide my recommendations in the future!

• West Hartford: Delamar is in downtown West Hartford (this is a separate town from Hartford and is really clean and beautiful). We’ve splurged on a one-night stay here before, and it’s stunning. We’ve also seen pricing through the roof at times, so budget is definitely a factor.
• New Milford: Homestead Inn is popular for Gilmore Girls trips! They even have a Stars Hollow room. Another option is a home rental on Airbnb or VRBO. 

✨ Tip: Connecticut is the kind of place where you might stumble upon something unexpected, especially as you drive back roads in Litchfield County. As you make your way towards New Milford, be open to stopping if something catches your eye!

Day 2: Stars Hollow Extravaganza

Saturday is all about exploring several Stars Hollow towns! 

While there is no singular real life Stars Hollow, there are numerous Connecticut towns in Litchfield County that feel very Gilmore Girls—whether it’s the community spirit, the look of the town green, or unique town events. They each have a little something special and Stars Hollow!

(If you want to start a fight in a Connecticut Facebook group, just ask which CT town is the real Stars Hollow. 😂)

In reality, there is one town that sparked the idea for Stars Hollow for show creator Amy Sherman-Palladino, but there were reportedly a number of towns that were later scouted for inspiration by the show creators. 

Many shops in this area fully embrace that Stars Hollow fame, and they love having Gilmore Girls road trippers stop in! 

Breakfast (and Coffee, Obviously)

Start the day the only way the Gilmore girls would with coffee and breakfast at Theo’s Diner. This spot is mostly for the atmosphere—the coffee is not great (my friend and I pulled a Gilmore and only drank a few sips). I recommend heading up to River & Rail Cafe before or after for Lorelai-approved coffee (minus the GG vibe). 

Explore New Milford (Morning)

Check out THE Stars Hollow gazebo in the town green—sit on the steps, take a few photos, and then wander the green and nearby streets.

Sometimes when I visit New Milford, there’s nobody at the gazebo (locals may correct you to say it’s the bandstand ) and other times, there is a line of people waiting to take photos. You might make friends with fellow visiting Gilmore Girls fans!

My friend and I stumbled on a farmers market in the green, so we loved wandering around that and following our curiosity into Village Center for the Arts. Make sure to leave a little time to shop at the boutiques on Bank Street for some cute Stars Hollow merch!

Wander Washington (+ Lunch)

Around mid- to late morning, head to your next stop in Washington, Connecticut. This is the town where Amy Sherman-Palladino was staying when her idea for setting the show in small-town Connecticut was born!

Washington is a little different because it doesn’t have the classic Connecticut town layout with a central town green and historic congregational church. So to me, it doesn’t look as Stars Hollow as other towns. But it has a number of places that have a very Gilmore Girls feeling. 

For this part of the itinerary, you’ll drive around a few areas of Washington, and timing depends on when you want to get lunch or snacks and coffee, so this list is in no particular order. 

There are a few fun Gilmore Girls places to check out here:

• Hickory Stick Bookstore (Stars Hollow Books): They even have a little section for Gilmore Girls. 
• Washington Food Market (Doose’s): This is the town grocery store and feels very old school with some flowery wallpaper. If you go inside, please be cognizant of locals who are just doing their weekly shopping.
• Mayflower Inn (Independence Inn): We were not guests so I felt a little wary driving up to see the outside and hopefully step inside the lobby, as this is a pricey inn. The town’s website says the inn is only open to guests or those with a dining reservation. But I was very pleasantly surprised by how friendly they were when they saw we were on a Gilmore Girls trip (I guess they can spot us!) and we asked the valet if we could look around. This is a great spot to take photos outside. You can also opt for lunch reservations to get the full experience. And if you really want to pamper yourselves, and you can make room in the itinerary, you can also book a spa treatment. 
• Take a drive by The Frederick Gunn School (Chilton)

Food options in Washington:

• Get lunch at The Pantry (we went here and really enjoyed it!) or The Garden Room at Mayflower Inn. 
• Stop for a snack or coffee (and town gossip) at Marty’s.

Town Footbridge

As you head towards the next town of Litchfield, make a literary-themed stop at the Henry David Thoreau Footbridge on the way to Litchfield. It’s very close to the parking lot, so it’s a quick stop. 

My friend and I also took a short walk into the woods on the trail here to soak up some nature—not very Gilmore, but we had fun! 

Enjoy Litchfield

Next, make your way to Litchfield. The feeling here is a sort of down-to-earth community meets history meets wealthy vacationers. 

The layout isn’t as Stars Hollow-ish—though it does have a town green and church with a steeple—but it has plenty of unique town events and a few locations that feel like Stars Hollow. 

And it’s a place where history runs deep, including some very “girl power” history (as Leah, the owner of the former shop Hope and Honey, put it when we were chatting about her Gilmore Girls road trip recommendations). 

Places to check out in Litchfield: 

• Drive by Sparkle and Shine Dance (Miss Patti’s)
• Get ice cream at Arethusa Farm Dairy (Taylor’s Olde Fashioned Soda Shoppe)
• Head to downtown Litchfield to see the town green
• Stop into boutiques
• Vote in the annual town scarecrow contest at Tapping Reeve Meadow—a very Stars Hollow-ish town event.

Dinner & Evening

For dinner, there are several options in Litchfield. My friend and I ate at Market Place Tavern, which is located in the former Litchfield County Jail right on the town green. The food and experience were okay—there was an event going on and I think our waitress forgot about us for awhile. For me, the uniqueness of this spot is enough to give it another try (and mention it here), but I can also recommend @ the Corner as a nice spot for food and drinks. 

After dinner, you can chill for the rest of the evening with more Gilmore Girls episodes and snacks at your lodging.

Where to Stay (Night 2)

Litchfield is only about 30 minutes from New Milford, so you can stay back there for a second night if you want. However, these back roads are small and windy, so you may not want to drive them at night. 

I suggest staying in Litchfield Saturday night, as this is where the day’s adventures are winding down. 

We stayed in a little Airbnb—which felt a bit like one of Kirk’s business ventures with its very random location behind a pizza shop—but there are several inns in Litchfield as well. Check out The Litchfield Inn or Abner Hotel, which is located downtown in the old courthouse. Again, home rentals are an option here so check out Airbnb or VRBO. 

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Day 3: Choose Your Own Gilmore Adventure

On the final day of your weekend, there are two directions you can go. My recommendation is to switch things up and head to New Haven for Rory’s college years, but if you’re really loving the rural Connecticut scene, there is certainly more to explore. 

Breakfast

Before heading out for Sunday’s adventures, kick things off with breakfast and coffee. There are several spots in downtown Litchfield, as well as Arethusa a mano in the village of Bantam. 

My recommendation for a hometown feel is Love Hearts Bakery & Cafe. It doesn’t really look like Luke’s, but it has that small-town vibe (there are clearly regulars who come here to read the paper and you might even overhear some town gossip). The decor is not very Luke, but we had fun imagining that maybe he added a few signs, got tired, and then asked Miss Patti to take over decorating. 

I really enjoyed this spot for the slightly eccentric atmosphere and delicious breakfast sandwiches (including gluten-free friendly for my friend who has celiac). 

Option 1: Rory’s College Years

After breakfast, head towards New Haven! It’s about an hour away from Litchfield.

There’s a bit of wiggle room in the morning itinerary if you wanted to fit anything else in Litchfield County or you see something interesting on your drive.

In New Haven, spend a couple hours wandering around Yale’s beautiful Old Campus. (Yes, you are allowed to walk around. There is signage and it’s quite clear what is open to the public versus students only.)

I always feel like people are underwhelmed hearing the recommendation to wander around Yale, and then they actually go. Everyone I’ve taken here has really loved it.

A few places we enjoyed on our Gilmore Girls weekend:

• The gates to Old Campus Courtyard are often open, and it’s really fun to wander the pathways and see how old all the buildings are. 
• Peek into the little chapel at the corner of the courtyard. Admittedly, we stopped in here looking for a bathroom (which we found), but we stayed for a few minutes to listen to the beautiful music of the Sunday service. (We made sure to be very quiet and respectful.)
• Marvel at the beauty of Sterling Memorial Library (open to the public certain hours), and imagine all the places Rory would probably be found studying.
• The Beinecke Rare Book Library is an interesting stop for book nerds, and its architecture stands out on the Yale campus. While it is used for research, it’s more of a museum for visitors with its huge several story floor-to-ceiling display of books behind a glass case, along with exhibits around the exterior. As museums go, it’s small and can be a quick stop. 

For lunch, you have to try New Haven style pizza. Spelled apizza (and pronounced ah-BEETS, but most people still just say pizza).

This thin crust pizza is one of my top things to do in Connecticut. And, it’s totally Gilmore. (You could totally test the top three places to see which one you like best if you have the appetite!) 

You can try Sally’s, Frank Pepe’s, or Modern. My favorite is Sally’s but you can’t go wrong with any of the three. Be prepared to wait in line for quite awhile for a table, but it’s worth it. 

If you’re not feeling pizza, another great option is the Sunday brunch at Home in Branford. This place is phenomenal (and has gluten-free options). 

Option 2: Stars Hollow Era

Explore more small towns in Litchfield County and the region with no particular plans and see what you find! Autumn festivals? Antique shops? Unusual town events? 

Here are a couple ideas to get you started, but be sure to ask some locals and follow your curiosity:

• Kent
• Collinsville (check out LaSalle’s for a very Luke’s Diner ambience)
• Hogan’s Cider Mill in Burlington for sweet or hard cider

Gilmore Girls Road Trip Map

Feel free to open up this Google My Map and make a copy into your own Google account. Access it on the web to edit your copy or simply view it on the Google Maps app on Android or iPhone.

Frequently Asked Questions

Gilmore Girls Weekend Getaway Photos

Curious to see even more from this girls weekend trip in CT? Here are a few more photos for inspiration to plan your own!

Have you been on a Gilmore Girls road trip in CT? What else would you add to this itinerary? Let me know in the comments!