A Very Gilmore Fall
Though I relate more to Rory Gilmore, I thought dressing more like Lorelai would be fun.
What do you think?
Since age 17, watching Gilmore Girls reruns has been my favorite fall activity.
Oh wait… drinking coffee. And eating blueberry pie. And hiking in cool weather. OK. Those are four other favorite fall things.
When we were last in New England, we stationed ourselves south of Boston in a town called Bellingham. It was the perfect spot to take all kinds of day trips around the region.
Of course, one of those had to include an October adventure to the iconic Connecticut towns that inspired the fictional but beloved Stars Hollow – and I’m here to share some of my must-see stops.
We explored Litchfield and Washington Depot, though New Milford is another spot that’s very GG fan friendly!
Hold that thought. I need to go check flights to Hartford so I can visit New Milford, stat.
OK, I’m back. Here’s how to enjoy a perfect fall day in small-town Connecticut:
West Stockbridge
OK, OK, so this first stop was in Massachusetts, not Connecticut. But it gave off some serious GG vibes. On our way to Litchfield, we decided to stop for a walk around the small downtown area (if you can call it that) and coffee at No. Six Depot Roastery & Cafe. It was a delightful place to hang out and enjoy the breezy fall morning. Nestled in the Berkshires, West Stockbridge is the kind of place you accidentally find and then never want to leave.
But we did leave. This blog is about Gilmore Girls and Connecticut, people!
Litchfield, Conn.
Litchfield was our first stop in Connecticut mid-morning, and it was super cute. Old brick buildings, white churches, and rustling red and gold trees welcomed us into town.
Before parking at city center, we swung by the Dutch Epicure Shop, home to European goodies like Belgian chocolates, teas, Dutch cheeses, fresh bread, and plenty of delicious German cold cuts like butterkäse and jagdwurst (yahk-voorst) – two childhood favorites thanks to my Oma. Luckily, we had our cooler with us, so we purchased several items before heading out.
Next we walked around the downtown area. Since we arrived before 11 a.m., a few businesses weren’t open, but we ran into Petraroia Deli for coffee, then checked out a couple of nearby shops – including a super cool Scottish-inspired outdoor store called BRĀEVAL!
Litchfield was a beautiful place to hang out, even though several stores weren’t yet open for the day.
The 60-degree fall weather was gorgeous, so we also strolled through some nearby neighborhoods. While walking, we happened upon a small charity event featuring a series of community-decorated scarecrows (very Gilmore-coded!)
Washington Depot, Conn.
Just 20 minutes southwest of Litchfield, accessible by tree-lined two-lane country roads, is Washington Depot. Seemingly enveloped by trees, this small town was probably my favorite spot of the day. It’s a bit more laid-back than Litchfield, yet there’s still plenty to do.
We first visited Five Janes, a boutique full of cute home goods, gifts, and local artwork, including fun Gilmore Girls pieces! With limited space in our RV, I made a mental note to come back for more goodies after we buy a home. Speaking of that… We also popped into a few local art galleries and makers’ spaces. Despite being a small town, there’s a vibrant arts scene here.
If you know me, you know I love to read, so I like to visit local bookshops on our travels. The Hickory Stick Book Shop was no exception. Situated in a beautiful brick building with charming paned windows, Hickory Stick offers a nice variety of new arrivals and beloved classics.
It was also fun to see Kelly Bishop’s book “The Third Gilmore Girl” and Lauren Graham’s books displayed prominently.
With just one day in the area and the pups with us, we needed a quick lunch. So, we ordered from The Pantry Restaurant & Bakery, and I’m so glad we did. I had tomato basil soup, which we ate outside under a big old maple tree.
And then it was time for some coffee.
I mean, “coffee coffee coffee”!
We headed to The Po Cafe (left), which serves up classic staples like sandwiches, bagels, breakfast tacos, eggs, and even homemade pop tarts.
Lorelai would be freaking out. Or maybe she’d just make fun of the idea.
I also involuntarily searched for Luke Danes in the back of the diner; sadly he didn’t show. Resigned, I purchased an iced coffee and we sat outside for a bit before driving to check out a few other sights just outside of town.
If you want to ooh and ahh, you can drive near the The Frederick Gunn School, which certainly resembles Chilton. Sadly, we didn’t get to visit the historic Mayflower Inn, the place where Amy Sherman-Palladino stayed during her vacation in Connecticut. They were closed for a private event, but typically, you can stroll the grounds and have tea. Next time!
Another recommendation is Spring Hill Vineyards, just outside of Washington in New Preston. You can enjoy wine, beer or other refreshments and sit out on the lawn. And it’s dog friendly!
Before we wrapped up our time in Washington Depot, we hiked the Little Pond Boardwalk Trail a few minutes away, located within the White Memorial Conservation Center. It was beautiful, and the dogs loved it!
If you check this place out, pleaaaase bring bug spray and check yourself and your pets or children for ticks before getting back in the car. It’s New England, after all.
One more stop in Litchfield
After being on the road for five years, you learn to pull over if something looks like it could be cool, even if you aren’t totally sure. As we were making our way back to Massachusetts, I found out that the Litchfield Distillery was just down the road. Ryan is a bourbon snob, so he was initially skeptical, but we checked it out anyway.
Alas, we were both pleasantly surprised. The distillery was truly an incredible experience! They even let us bring our pups inside and try a few sips of different batches. We had a great conversation with some of the staff and purchased a couple of bottles to take home.
I can’t believe I forgot to take a photo at this place! We were having too much fun!
If you’re looking for a very Gilmore fall, be sure to bookmark this post for inspiration!