Living Well in Litchfield County, Connecticut

Day Trips

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


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.

6 Autumn Lane, Amenia

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.

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.


Enjoy the shops, galleries, restaurants, and other businesses in the more than dozen buildings. It is the ideal place in any season to spend time browsing shops, galleries, and restaurants.

Kent Barns
6 N Main St.


A 501(c)(4) organization, dedicated to protecting its forests and countryside, and offers countless trails and paths for visitors to explore. White Memorial offers over 40 miles of trails that cover various habitats and are open to non- motorized recreation, as well as a glimpse into the natural diversity found throughout the wildlife sanctuary.

White Memorial
80 Whitehall Rd, Litchfield


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

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.

1 John St, Millerton

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.

13 Main St, Millerton

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 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.


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.

54 Main St, Millerton

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.

5409 Route 22, Millerton

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.

25 Main St, Millerton

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.

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!

Oblong Books
26 Main St, Millerton

The Oakhurst Diner was established in 2010 by Paul Harney, Justin and John Panzer, Its name is in honor of the old Oakhurst Inn. It offers a retro vibe, local and speciality foods along with diner comfort classics.

19 Main St, Millerton

Pine Plains

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.

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.

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