Field Trip: Litchfield County

As I’ve mentioned before, Adam and I have rented a series of houses—actually the same two houses over and over—in Litchfield County, Connecticut. If you haven’t made plans to get away this summer, you really should consider it. The only demerit is that it’s not even closer: The drive is about two hours, and if I’ve ever envied people who live on the Upper West Side, it’s been while sitting in traffic on the West Side Highway.

Litchfield is in the northwestern corner of the state, in the foothills of the Berkshires. I first heard of it when I was working at Travel + Leisure, and I got to visit Bill Blass at his house in New Preston for an article we were working on. (I also traveled to Boston and Kansas City with Mr. Blass; stories for another day.) Several years ago, when Adam vowed not to spend another summer in the city—he has heat-management issues—I said we might consider Litchfield. The editor of T+L also has a place up there, and if it’s good enough for her, I pointed out, it’s good enough for him.

On our first visit, we stayed at a B&B in New Preston, and I was all set to recommend it to you but it seems to have gone out of business—a shame, since the only other hotel we’ve stayed at is Winvian, a fancy cottage colony in Morris. Each cottage is designed by a different architect, many with kooky themes; it was ideal for us since we could take Howard and, unlike at hotels, he couldn’t hear other guests. I like Winvian even if it can’t quite live up to its own pretensions, but the cost makes me wary of recommending it. (I know a few other readers have places in the area—please suggest other lodging options!) Of course, the ideal solution is to rent a house, because you get more isolation. It’s a bit late to rent for the summer, but I bet you could still get July or August (we’ve only ever used Klemm Real Estate) or or even a week here or there (via Airbnb).

lilacsSome of the towns—Washington, Roxbury, Cornwall, Milton, Warren, West Cornwall—have little or no commercial aspect, but are incredibly picturesque. Other towns are more geared for visitors: Washington Depot, New Preston, Kent, Bantam, Sharon, Litchfield (a bigger town with an old Main Street strip and some amazing old houses), and New Milford (an even bigger town with a spacious town green), although even die-hard shoppers might find it hard to spend more than an hour in them, unless they stopped for a meal, too. I should point out that there’s a whole northern part of the county that we really don’t go to, for no good reason; from what I remember, Lakeville, Salisbury, and Norfolk are cute. Wherever you go, there’s not really much to do, and that’s the charm. My advice would be to just noodle around and stop whenever something—an antiques shop, a farmstand—catches your eye, but then that’s how I generally like to travel.

That said, there are some things you should consider going out of your way for:

1. Community Table (Washington). Chef Joel Viehland is cooking extraordinary food—it’s seasonal and local and amazing and a little frustrating because the menu changes every week so you can’t get too attached to a dish. This is probably our favorite restaurant anywhere, except Franny’s. And it’s not just because the food in the county is otherwise pretty unmemorable.

2. Arethusa Creamery (Bantam). Two Manolo Blahnik executives bought a dairy farm because they were concerned about losing their view, and then they caught the farming bug. Their ice cream shop makes the very best waffle cones—you’ll leave the place smelling like maple syrup. Do not order more than a single scoop! Portions are extreme.

3. Bantam Bread (Bantam). While you’re in Bantam, stop at Bantam Bread for a loaf or two of bread, a chocolate chip cookie (my favorite anywhere), a bag or two of granola. If the sign outside says, “Bread’s ready,” it’s open.

4. Shopping. Antiques shops of every stripe—from thrift stores to “galleries”—are everywhere. The best town for shopping of any kind is New Preston, even if I can’t recall* any of the shops’ names; it hardly matters, the town is one block long. There’s also a stylish home decor store in Warren New Preston [see comments] that feels like the Hamptons, and not in a bad way (except the prices). *One is J. Seitz & Co.

5. Elephant Trunk’s Flea Market (New Milford). I’m not really a flea market kind of guy, but the one in New Milford is huge. Go as early as you can possibly bear.

6. House of Books (Kent) and the Hickory Stick Bookshop (Washington Depot). The area is pretty fancy, and I happen to like that about it. One indication: Litchfield County has at least two great little independent bookstores.

7. Steep Rock Association (Washington). Part of the reason the area is so lovely is that a lot of residents have donated land into conservancy (for tax benefits), meaning it’s not at all dense with people. Around Washington, there are several patches organized under the Steep Rock Association umbrella; they have pleasant hiking and walking trails. Up by Kent, you can walk on parts of the Appalachian Trail.

8. Lake Waramaug (New Preston/Kent). Drive around the perimeter of Lake Waramaug, near New Preston—the housepeeking is fantastic. Even better, rent a kayak at the state park. You get a much better look at the houses from the water. (On weekends, the state park charges an exorbitant fee per car, totally screwing solo visitors.)

9. Clamp’s (New Milford). The ultimate roadside burger joint. I’ve found that it’s a good idea to choose “salt and pepper” as one of the toppings on your burger. And you must order the onion rings. (Outdoor seating only.)

10. I can’t even think of a tenth thing, and that’s why I love the place. Just go and watch the clouds and listen to the birds and admire the trees and relax.

This post was not sponsored by anyone.



  1. No tick issues with Howard?

  2. @Strollerless: Yeah, we have to put Frontline on him and occasionally (near the end of the monthlong cycle) one bites him. Hard to avoid in the northeast….

  3. I believe you are referring to Privet house when you mentioned a good shopping place in Warren. They have moved to New Preston making New Preston a great shopping destination. R Derwin is a good men’s store in Litchfield. Michael Trapp’s store in Cornwall bridge and Pergola in New Preston are home shopping essential destinations as well. We hike all the way to Litchfield county from Tribeca every weekend (well almost every weekend), because it is a great place to do nothing. For places to stay consider the Inn at Kent Falls in Kent or the Mayflower Inn ( not sure about the dog policy though). For meals,West Street Grill and The Pantry are excellent! Serevan and Woodland are a bit of a drive but worth it. Hope this helps. We have been weekenders there for the past few years and are still exploring and are still pleasantly surprised.

  4. @Joerel: Privet House has moved? Who knew? (New Preston makes much more sense for it.)

  5. @Erik: They did and their store is now the gem of New Preston. You have to come back and see it!. By the way Arethusa will hopefully open their wine bar next door soon.

  6. Waiting on the Bill Blass stories… We worked with him for 30+ years

  7. Erik: thanks so much for writing about Litchfield County. I was always curious about it and have wanted to visit for the past few years. I look forward to my next road trip. Many thanks!

  8. Try Norfolk, rspecially the student concerts at Yale’s summer music school/Norfolk Chamber Music festival. And there is, in, fact plenty to do.

  9. Speaking of Norfolk, Infinity Music Hall is one of the best places anywhere to hear music. It’s a toss-up whether we like Infinity better than City Winery. A beautiful intimate theater with a nice Bistro for a pre-concert dinner.
    We like Marty’s for breakfast or lunch in Washington Depot . And Adrienne’s in New Milford is lovely for dinner. The restaurant is in Adrienne’s historic house and there’s outdoor seating in the summer. Good News Cafe in Woodbury is also a very special place for dinner. Julio’s in Southbury has great pizza — better than anywhere in Tribeca for sure! (I know technically Southbury is just over the Litchfield County border, but it’s worth going there.)
    The Workshop in Litchfield has a great selection of women’s clothes and accessories, and the owner is very friendly and helpful.

  10. Great info, thanks again.

  11. We stayed at inns / b&b’s for several years before buying a weekend home last year. The area is special, kind of an anti-Hamptons for those who like pristine, pastoral country without all the hubbub and social scene

    Additions to the article and comments:

    Places to stay: on the higher end Rooster Tail Inn in Warren (large very comfortable and tasteful rooms), mid-end Starbuck Inn in Kent. Hear Longwood in Woodbury and Rock Hall in Colebrook are very nice but have not stayed. Can also find some interesting stays in guest houses and extra bedrooms on airbnb. Cool camping on a stream in Macedonia Brook State Park.

    Breakfast: Mamie’s in Roxbury, Wandering Moose in West Cornwall, Hidden Valley in Washington Depot, and Green Granary in New Milford exude country charm and have great food. American Pie Company in Sherman is also a great family place for breakfast or lunch.

    Lunch: Nine Main in New Preston makes a good sandwich, as do the general stores in Bridgewater and Cornwall Bridge. Primo’s Deli in New Milford has surprisingly good Latin/Cuban for what looks like a hole in the wall.

    Dinner: many top places already mentioned, Community Table and Serevan very worth the trips, Winvian’s restaurant also very good. Serevan is particularly unique as the menu fuses Armenian/Iranian and French cuisines in a charming farmhouse setting. Best pubs are GW Tavern in Washington Depot, White Horse, in Marbledale and Rooster Tail in Warren. Bulls Bridge Inn south of Kent is decent (one of few places left with a salad bar) and recently opened Kingsley Tavern in Kent is supposed to be good but haven’t tried yet. Piccoline in New Milford is the best Italian, Upper Crust in New Milford has solid pizza (probably the worst part about the restaurant scene up here is there are 3 Italian restaurants for every other kind of restaurant). Oliva in New Preston is charming and has a unique mediterranean menu. Cookhouse BBQ in New Milford is good but can get very busy and slow. RSVP in West Cornwall is supposed to be quite special but reservations are hard to come by and haven’t managed to get there yet.

    Drinks: Hopkins Inn on Lake Waramaug – the food is out of place and uneven (Austrian is ok but not a regular thing) and the inn decor seems pretty dated. But the view in summer from their outdoor patio overlooking Lake Waramaug from above, along with a very cool outdoor chandelier hanging from a 200 year old maple are well worth the visit.

    Grocery: Northville Market in New Milford and Bantam Market in Bantam manage to get some more sophisticated foods than the typical grocery stores. For local foods, The Smithy in an old blacksmith shop in New Preston is great if a little pricy. Nodine’s Smokehouse in Goshen has a huge variety of smoked meats. Great farm market on NY side on Rt 22 is McEnroe Farm Market

    Shopping: Woodbury is by far the most interesting with almost 50 antique dealers and many different styles from New England to Europe and French Canadian

    I’m not going to mention the best apple orchard because its the only we’ve ever found within 2 hours of the city that isn’t completely overrun with city dwellers making their once a year pilgrimage to the country. They can keep jamming up traffic at Outhouse Orchards in Westchester (yes, it’s as bad as it sounds) :-)

  12. Thanks to everyone for the recommendations! Been to some of them but certainly not all….