1. Iron Masters Motor Inn
City: Lakeville, CT
Category: Accommodations
Telephone: (860) 435-9844
Address: 229 Main St. (Routes 41 and 44)
Description: “Motor inn” no longer has the cachet it had in the 1920s, but this lodge with 28 large rooms that open out onto the parking lot is a classic of its kind, with Ethan Allen furniture instead of the usual cheap stuff. In the winter relax in the Hearth Room in front of a roaring fire, and in the summer splash in the outdoor pool. Iron Masters is sufficiently set back from the road so you won’t really hear the traffic, and the furniture and decor is certainly a step above a typical motel. They have 2 dog rooms, making this the perfect place to stop when traveling with your best friend. They even serve a continental breakfast, and in the winter offer a ski package deal. Named for the iron industry that dominated these hills in early America and made cannons for Washington’s army, this is a perfect spot from which to explore that amazing history.
2. Wake Robin Inn
City: Lakeville, CT
Category: Accommodations
Telephone: (860) 435-2000
Address: 106 Sharon Rd. (Route 41)
Description: This inn was once the Taconic School for Girls, and you’ll see little touches that remind you of that throughout the huge building on a hilltop well back from Route 41. Since 1914 Wake Robin has been welcoming guests, including the usual celebrities like Bette Davis and Douglas Fairbanks. The 23 rooms in the school building are all unique, with private baths, and were upgraded in 2002. There are also 15 less expensive rooms in a motel-like building nearby, which is only open May through Oct. On-site is Michael Bryan’s Irish Pub, where you can get a drink, and a dining room for a fine evening meal. Wake-robin is the common name for the white trillium flower, which blooms every spring and heralds the arrival of all the birds. It’s a great time to come to the Litchfield Hills.
3. Interlaken Inn, Resort, And Conference Center
City: Lakeville, CT
Category: Accommodations
Telephone: (800) 222-2909
Address: 74 Interlaken Rd.
Description: The original Interlaken Inn is in a Victorian bed-and-breakfast (with modern conveniences). But this popular destination has expanded, with duplex-style units with kitchens, 82 hotel rooms in a large building, and more. Set on 30 acres with 2 lakes, Interlaken features a restaurant, a pool, tennis, and more. Unlike most resorts in the state, dogs are allowed here. This is a popular conference site, but is always jumping with families and couples as well. Take a canoe out onto Lake Wononscopomuc or play a round of golf on their chip and putt course. If you’re in the mood to relax, they offer a full range of spa services, including facials, massages, and hot stone treatments. Or you might just sit in one of the ridiculously comfortable chairs by the lake and fall asleep.
4. Boathouse At Lakeville
City: Lakeville, CT
Category: Restaurants
Telephone: (860) 435-2111
Address: 349 Main St.
Description: With its rambling blue exterior and fireplaces and dark wood inside, the Boathouse is a difficult restaurant to categorize. The main menu is American and Italian modern cuisine, with dishes like four-cheese ravioli and beer-braised baby back ribs. The half roasted crispy duck with citrus soy glaze is crunchy fresh and rich all at once. But if you’re looking for Japanese sushi up here in the northwest corner, the Boathouse is also a great place, and, in fact, they have sushi rolls named for all the local private schools (it’s a popular place for families to bring their kids). The locals love this place, and along with the Woodlands, it is a destination for everyone wanting a comfortable meal in a place that will soon seem like home.
5. The Woodlands
City: Lakeville, CT
Category: Restaurants
Telephone: (860) 435-0578
Address: 192 Sharon Rd.
Description: This is the place people go for a fine meal after watching the races at Lime Rock Park. For years it was a local secret, off the Internet and off the culinary map, but recently the word got out, thanks to some tongues loosened by the wonderful wine selection. The menu is diverse but consistent, with lots of nice fish and steak dishes, a couple Mexican choices, and a sushi menu that is always impressive (get one of the special rolls). Many locals come here for drinks and appetizers, which are creative and delicious. Try the key lime pie for dessert. This place is so good that others in the area have tried to imitate the unusual menu, with less spectacular and consistent success.
6. Le Laurentis Brasserie
City: Lakeville, CT
Category: Restaurants
Telephone: (860) 596-4231
Address: 06039
Description: This new French bistro in the far northwest corner of the state has made waves immediately, earning rave reviews from diners and a nervous backwards glance from Lakeville’s other French restaurant. The owner, George Courgnaud, is from the Champagne region of France, where his family ran a restaurant for four generations. The hanger steak with red wine and shallot sauce is done perfectly, and the sautéed rainbow trout is full of lemony goodness. The menu changes, so look for specialties like calves liver or ratatouille. They are closed on Tues, and only open for lunch on Sun, but otherwise make a slightly less expensive alternative to the excellent Pastorale next door.
7. Pastorale
City: Lakeville, CT
Category: Restaurants
Telephone: (860) 435-1011
Address: 223 Main St.
Description: This charming French restaurant run by Karen Hamilton and Frederic Feveau (once the chef at the Birches) brought French cuisine to the far northwest of Connecticut. The colonial house it’s located in has been painted sunny Provençal tones, and the food you’ll get here will bring you straight to France itself. With positive reviews from the New York Times and Bon Appétit, Feveau did not get a swelled head, and maintains his steadfast devotion to great cooking, with classics like steamed mussels and steak and frites. You’ll also find a few southern French dishes here, edging into Italian territory and taking it over with joie de vivre.
8. Lime Rock Park
City: Lakeville, CT
Category: Tours & Attractions
Telephone: (860) 435-5000
Address: 60 White Hollow Rd.
Insider Pick:
Description: Racing fans need no introduction to this famous track hidden in the Litchfield Hills. The first road track designed using scientific principles (by Cornell Aeronautical Labs), Lime Rock is a 1.5-mile curving and up-and-down track that challenges drivers to increase their speed. The first event was in 1957, at which Walter Cronkite actually drove a car. Today you’ll find NASCAR stock cars here, as well as dozens of other types of racing. In 2008 2 additional complexes were added, which gave the track 4 different possible configurations, and this change has made it even more popular among drivers and fans alike. Paul Newman used to race here often, and did quite well. One of the world’s leading driver-training organizations, the Skip Barber Racing School, also practices on this track; to sign up for a class, call (860) 435-1300. Lime Rock is an exciting place to go, even if (or because) you’ve never watched a car race before.