Summer getaway: Explore these charming New York and Connecticut towns

It’s that time of year when, every Friday, laptops snap shut early and everyone starts taking off for the weekend to the usual suspects: The Hamptons, Catskills and Berkshires; the Jersey Shore and Connecticut coastline; Hudson Valley and Central PA.

For an under-the-radar destination, though, consider the New York-Connecticut border — where Dutchess and Litchfield counties meet, and the rolling green hills, plush forests, dairy farms and equestrian centers are plentiful. So, grab a rental car, head north and explore these charming small towns.



If bric-a-brac is your thing, you’ll want to poke around the antique stores and junk yards that flank Route 44, or head to the Millbrook Antiques Mall (3301 Franklin Ave.), which houses more than 30 individual shops selling everything from mahogany drop leaf tables to sterling serving trays to Bakelite bangles. Just leave time for other activities — like drinking wine. Millbrook Vineyards & Winery (26 Wing Rd.), a modern-rustic facility, offers tours and tastings of its celebrated chardonnay, pinot noir and other varietals.


Born in an abandoned mill, the Wassaic Project (37 Furnace Bank Rd.), a seven-floor exhibition space, is an emerging art lover’s dream. Take in an artist lecture, meet resident artists during open studios or just explore for free. And when you’ve worked up enough of an appetite, journey to the nearby Lantern (10 Main St.) for a Rattlesnake or Heart Throb pizza. They’re just two of the wood-fired pies topped with local ingredients at this celebrated casual and communal town eatery.


Many New Yorkers are familiar with Irving Farm’s coffee and cafes. The roaster is located in Millerton, and though visits aren’t permitted, there’s a lively café (44 Main St.) where you can enjoy breakfast, lunch or, of course, a cup of great coffee. Then stroll the sloped streets, where there are artsy shops like Gilmor Glass (2 Main St.) and Meta44 (5916 N. Elm Ave.). Top off the night with a pan-seared salmon or rib eye steak at locals’ favorite, Manna Dew (54 Main St.).



Think of this elegant town as the region’s Madison Avenue. There’s Rolling River Antiques (25 N. Main St.), Bella Jewelers (27 N. Main St.) and other hoity-toity shops and galleries. That’s not to say there aren’t other pleasures. The museum at the Connecticut Antique Machinery Association (31 Kent Cornwall Rd.) features tractors, steam engines and other mechanical relics, and Kent Falls State Park (462 Kent Cornwall Rd.) is a picturesque spot to hike or picnic.


Maybe you’ve been out paddling in a canoe or kayak on Lakeville Lake, or coming in off the Appalachian Trail, which cuts right through town. Either way, reward yourself with a great big lunch at the White Hart Inn (15 Under Mountain Rd.). It’s a friendly, welcoming spot to pass the time, whether at the café Provisions, cozy tap room or acclaimed dining room. Just be sure to save room for a treat — caramel pecan cheesecake, anyone? — at Sweet William’s Desserts and Scoop Shop (17 Main St.).