Litchfield is nice.
The inn was totally renovated about 15 years ago, I worked there when I was a kid. Crazily enough, I started the weekend after the old owner offed himself and they were having a memorial for him at the inn. That being said, It's not haunted no matter what anyone tells you, was only built in the 80s.
Great for hiking/walking - you've got the White Memorial Foundation property in Litchfield and Steep Rock Preserve down in Washington.
Town center is nice and has some nice restaurants. Locally you also got Materia and Arethusa al tavolo. If you want pizza before going down to New Haven area, Portnoy gave Sasso's in Torrington an 8.1. There is also an excellent Neapolitan pizza place in Torrington call Pizzeria Marzano.
You've also got several breweries - legitimus in New Hartford, clocktown in Thomaston, lasting brass in Watertown - and wineries/vineyards - Haight Brown and Sunset meadows are closest - in the area if that's your speed. And there is also the Litchfield distillery which gives tours.
The Litchfield Inn owner was a man wrapped in mystery, a lot of strange stories about how he made his money.
Haight Vineyard finally closed but there's several other vineyards up there now.
Materia and Arethusa are considered two of the best restaurants in the state but incredibly pricey for not a lot of food.
@NJHusky other restaurants-
@ The Corner in Litchfield- Carlos is a creative and skilled chef
Da Capo in Litchfield- good Italian food with a lot of options.
Tramonti in Thomaston- awesome Italian food. They bring out complimentary family style trays of bruchetta, antipast, and mussels in spicy red sauce even before you order your meals. Huge portions served in wood boats, deep wood bowls, and seafood in pots. It was in small storefront in a little strip mall and would get packed, I think they moved to a larger location nearby recently.
Geppeto's in Torrington- really good Italian food. Homemade pastas with a couple things like rabbit you won't see at most places.
GW Tavern in Washington Depot- country pub food with a pretty location.
Hopkins Inn on Lake Waramaug- Austrian food. They probably haven't changed the menu in 50 years or the decor inside but I like the place. Sitting outside on the deck for lunch gives you a beautiful view of the lake.
Zini's in Bantam which is a section of Litchfield- good Italian food. Doesn't look like much from the outside but it's a nice room inside with nice stonework and nice lighting.
Berkshire Cafe Torrington- local hangout for pizza, salads, sandwiches. Been there forever and it's a cool old building.
White Horse Pub in Marbledale- British pub food- solid with a big menu and really pretty location and cool building. One of the most popular restaurants in the state so call ahead for a reservation.
You're going to want to call ahead at all these places for dinner. Litchfield has become a destination town and a destination restaurant area. They're in the process of opening three boutique hotels in town.
