Litchfield County: Happening in the Hills

Day Trips

Day trips and afternoon drives, within a stone’s throw


Back in the Kitchen

Two words – Intelligentsia coffee. Back in the Kitchen is housed on the second floor of a darling, century old red brick building. Fresh baked goods, creative sandwiches such as BL roasted T, and a duo of soups are house made daily. Main Street’s back!


Tucked away in the hills just beyond the Wassaic station is this cozy, surprising hideaway. Helmed by Chef / Owner Serge Madikians, the exquisite Mediterranean cuisine at Serevan is imbued with the flavors of the Middle East, a celebration of the traditions of his Armenian background. Superb service from the time the breadbasket arrives to the final sip of a well-crafted drink. Request a seat by the fireplace when making your well-advised reservation.


Make like the 1920’s NYC literary set and make a date with this stately stone country inn. Set on over forty verdant acres, the Troutbeck resort features an English garden, babbling brook and an internationally recognized restaurant.

Wassaic Project

An art star comes to the Berkshire Mountain foothills in the nearby hamlet of Wassaic. Wassaic Project is a multi-disciplinary residency program and contemporary exhibition space within an exceptional old mill, their annual summer festival is not to be missed. An inspired example of community integration.


52 Main

It’s about time we got some tapas around here! This is a favorite stop after (or before) catching a first run at The Moviehouse a few doors down. And they made finding the place easy. Holed up there on a recent rainy night with sangria, plate of patatas bravas and live guitar music, we were temporarily transported to Spain – but glad to be so close to home.

Elizabeth’s Jewelry

Elizabeth’s Jewelry sure looks like a chain, but this is actually a good jewelry store with both fine and funky gems. Great for repairs and restyling.

Harlem Valley Rail Trail

We have bikes and will admit to letting them gather dust for a while until we found the Harlem Valley Rail Trail. Built from the remnants of the old train tracks currently connecting Wassaic to Millerton, but with plans for expansion all the way up to Chatham, the trail traverses creeks, winds through foliage and cuts through mossy rock formations. In other words, it’s a spectacular bike route – flat, free of cars so family and casual-rider friendly.

Harney & Sons Fine Teas

The reward for completing that bike ride – the most delectable PB&J ever. We don’t know if it’s the jam or excellent bread, but these things are tasty! There’s also something slightly mischievous about having a “kid’s” sandwich in the casually elegant surroundings of a tearoom. Speaking of…you know the name, but did you realize that the quality brand was based here? A food lover’s stop, the Harney & Sons Fine Tea boutique offers all manner of hostess and entertaining gifts, and the expansive tasting bar can answer all your burning leaf questions.

Her House

We wish it were ours, though guess that’s the point. With reasonable prices yet impeccably chosen merchandise, your home can benefit from a touch of Her House creativity.

Hunter Bee

A cross between an antiques store, a museum, and a flea market, Hunter Bee has a most unusual and quirky collection of objects and furniture. The merchandise is beautifully displayed, and the pieces scan a range of styles, from industrial to mid-century, to country. Cut yourself sometime to browse in this fun store.

Irving Farm Coffee House

Irving Farm Coffee House is a cozy spot to sit and chat, and has a cup of coffee that will keep you from pining for another. The beans are grown from estates around the world, but weekenders might recognize the aroma of the roasted beans from the java house’s multiple Manhattan locations. Locals love the original as a hub and for baked on premises grub. We’re talking cookies. Big ones.


Little shop of flora – stunning, artfully designed arrangements and hand selected gifts from the garden make Kamilla’s boutique an absolute visit for flower lovers. Her imaginative color combinations and displays are quite literally a breath of fresh, fragrant air.

Manna Dew Café

The largely organic offerings may taste like the big city but the laidback atmosphere at Manna Dew Café is decidedly small town, in the best of ways. No one will rush you out the door here. Linger over a glass of wine, take in some music if it’s the weekend or sit out back near the herb garden when the sun is shining. Good vibe, great down-to-earth food.

McEnroe Organic Farm Market

No surprise here, McEnroe Organic Farm Market has lots of fruits and veggies. But what we didn’t expect was the ample, fairly artisanal larder. Not to mention freezers full of naturally raised meat, regionally produced dairy and soups plus a kitchen turning out made from scratch sandwiches and wraps. In the summertime, snag a picnic table overlooking the distant hills and rows of multi-colored produce.

Millerton Antiques

Curios on consignment, on the corner. Like an estate sale gone wild, Millerton Antiques has a constantly changing panorama of intriguing items that warrants an unhurried poke around. The sprawling, two story, multi vendor store should be of particular interest to collectors of folk art, jewelry and ephemera.


EDITOR’S NOTE – If you’re looking for antique furniture, be sure to check out Johnson’s Antiques just around the bend.


Wonderful decorative items and home furnishings. Originally an antique collective, Nest has morphed into a stylish balance of antique and modern elements. The custom throw pillows are to die for. Hours are Friday to Monday 11 am – 5pm, or by appointment.

Oblong Books & Music

We do love a true blue bookstore and Oblong Books & Music just might take the cake. (Though the sister shop in Rhinebeck gets our props as well.) Find recent releases and obscure titles with the help of friendly and knowledgeable staff. The children’s section is especially delightful and we always check the windows for upcoming events. Long live indie!


An experience anchoring the village since 1946, Saperstein’s is a family owned and operated shop that sports practical, nostalgic necessities such as Carhartt coveralls and Dub-L-Knit work socks. Cross the street for another throwback, the Pendleton supplied, Terni’s. Back to the basics, stick with the classics.

The Moviehouse

Two for one entertainment, actually three: coffee bar, gallery and theater. The Moviehouse is home to FilmWorks Forum and projecting choice films with an independent bent, it’s easy to imagine the space as your own private screening room. First runs without a run on the box office, usually. It doesn’t hurt to get there early as you can always purchase tickets then stroll the strip.

The Oakhurst Diner

New and funky. We like the scene at The Oakhurst Diner, which is fun in the old diner. The food, while not always spot-on, is simple and reasonably priced. Open for breakfast, lunch and dinner.

Pine Plains


We’ve always thought this area of the country resembles the rolling terrain of Tuscany. So the concept behind this culinary retreat seems right at home. Featuring farm to table Italian fare by Chef Mark Strausman (Fred’s at Barneys), the man works magic with tomatoes. Spread the word, please, about Agriturismo, the Hudson Valley menu, and sustainable mission behind it.

Hammertown Barn

No one should go home from an excursion empty handed – who says all trinkets and keepsakes must come from abroad? Part of a locally owned (seek out the amazing Joan and her informative, fun blog) trio of stylish home décor stores, country living never looked so chic. Hammertown Barn regularly run remarkable red tag sales and we can’t get enough of their well curated, often quirky finds.

Pine Plains Fine Wines & Spirits

We’ve admired the minimalist beauty of their print ads for years, but the impressively stocked shelves of this specialty shop are the real attention grabbers. Stop in before your next picnic, dinner party or drive home for a thoughtfully selected bottle. Or case.

Stissing House

Don’t let the peeling exterior paint fool you. Behind the impressive balustrades is a fantastic wooden bar and gracious dining room. The rustic victuals served in this historic landmark beg to be enjoyed during a romantic evening for two or commemorating special occasions. Weeknights are also worthy.

  • Subscribe to our newsletter
  • salvatore anthony
    George Home
    Byrde + the b
    The Matthews Group HIH Ad
    KMR Arts
    farmington polo
    silo ridge
    Elyse Harney Real Estate
    Karen Raines Davis
    Westbury Realty
    Haver & Skolnick