Kent Falls State Park, CT
The three of us met at Grand Central at 2:45 and took Metro North up to Danbury. Grand Central is such an atmospheric place to catch a train; it was really a nice start to the trip. After calling a taxi to fetch us at the Danbury Station, we picked up our rental car from Hertz. We got a Hyundai Accent, which I'd driven before on my SoCal road trip. I was dorkily excited that the car was registered in Virginia, making the plates match my license.
We dropped our stuff off at the Courtyard Marriott before heading our for dinner. Our original plan had been to introduce Kate to the decadence of the Cheesecake Factory, but the wait time was ridiculous. We ended up at Friendly's instead - while it's still a chain, it was a much more New England-y experience. We got in our America-Eff-Yeah moment for the trip when Lis and I gleefully dragged Kate to the mall afterward. Living in New York is great, but it doesn't exactly give you a balanced picture of American life.
The next morning, we started out fairly early, heading north on Rt. 7. Our first stop was at Bull's Bridge, a covered bridge dating from 1842. It was Kate's first covered bridge! We walked across and wandered around some trails on the opposite side to get our nature fix.
Our next stop was the Belgique Patisserie in Kent. A small yellow building with red awning and a Belgian flag out front, the little shop charmed us even before entering. We each chose some treats from the glass counter - I got an assortment of truffles, which were honestly the best I've ever had, with fillings in flavors such as rum, violet, and raspberry. I also got hot chocolate and a madeleine to go, both of which were amazing. Sadly, the shop has since closed, making it a kind of Camelot or Shan-gri-la of chocolate. Seriously, don't believe me - read the Yelp reviews and cry over what you missed.
Sipping our hot chocolate, we wandered around Kent's main street. It was lined with little shops and restaurants and even had a typical New England church at one end. It was pretty busy and probably the most touristy spot we hit on our trip, but it was also one of our favorite stops. Lis and Kate were hungry, so we dropped by the Millstone Cafe for lunch - which is also now closed (really, Kent?). The Americans strongly encouraged Kate to try the lobster roll.
After lunch, we shopped a bit before getting into the car and heading for Kent Falls State Park. The state park was also fairly crowded, being a nice fall weekend, but the easy climb up to the falls was worth it.
Next we got off Rt. 7 and took a little detour to Ellsworth Hill Orchard and Berry Farm. The little road wound up some hills, past the adorable St. Bridget's Church in Sharon. We'd picked Ellsworth because it featured a corn maze, which we were a little disappointed in, but their hot apple cider and cider donuts were on-point.
We continued north through North Canaan, stopping less frequently now, just enjoying the scenery. West Cornwall was an exception, were we sidetracked to see a second covered bridge. The tiny town at the end of the bridge felt more "real" than Kent.
Our last stop of the day was at Hopkins Vineyard. They were having a festival next door, and the place was pretty packed. We managed to squeeze up to the tasting bar - for $6, we got to sample a flight and keep the glass. I walked away with two fairly inexpensive and tasty whites. The sun was near setting by the time we left and the colors over the lake and mountains were probably the prettiest we saw the entire trip. We got a little lost on the winding country roads, headed back to Danbury in the dark. It was a good preview for our slightly spooky itinerary on day two.