Connecticut's Picturesque Playground Is A Small Artsy Town Oozing With New England Charm And Trails

Many of us are suckers for the allure of small towns — the quaint shops, the novel eateries — but sometimes that's not enough of a draw for just any type of traveler. The picturesque town of Kent, Connecticut, located about a mile from the northwest New York border, offers an additional trifecta of attractions that are sure to please every traveler. The requisite stores and restaurants are there in abundance, as are stunning hiking trails and even waterfalls, thanks to its perimeter along the Appalachian Trail; galleries for the arty connoisseurs; and history museums touting its heritage as a farming and ironworking community.

There's lots to do in Kent, but luckily, the town dotted with red barns, meandering pathways, and covered bridges is less than 50 square miles with a population of about 3,000, so it's easily manageable to squeeze in a busy itinerary no matter the time of year. Fall foliage is always a draw and can take your breath away, but spring and summer are great opportunities for outdoor adventures. Winter means fewer crowds, cozy fireside restaurant dining, and more leisurely walking (less intensive hiking) along scenic nature trails. Indeed, this charming town would make for a romantic winter getaway for the cold weather lovers.

If you're a nature-lover, you'll want to check out Kent Falls State Park, where a walk through a covered bridge leads you to one of Connecticut's largest waterfalls, which cascades down 250 feet to feed into the Housatonic River. The half-mile loop starts with a paved path to the base, ideal for those with wheelchairs or strollers, and then climbs up a series of stairs and platforms to reward trekkers with panoramic views.

Even bigger hikes and views await at Macedonia Brook State Park, including the rocky, steep 6.8-mile Blue Trail loop around the park, which leads to the top of Cobble Mountain, a perch with views of New York state and the Catskills. If you're planning to trek alone, keep in mind these safety tips to know before your solo hike.

For history buffs, a visit to the Connecticut Antique Machinery Association offers an illuminating window into Kent's past, reflecting the city's rich farming and mining history thanks to its rich geological resources. Tractors, internal combustion engines, and even access to oil wells are just one part of the displays. The museum's location gives visitors a visceral feel of the mining experience since it sits amid a former ironmaking operation near a marble quarry where iron ore would be smelted.

Hiking and museum visits may feed the soul and mind, but retail therapy never hurts either. Main Street or Route 7 is your destination for quaint, thoughtful stores that inspire lingering. Part of the appeal are their locations. The monumental, 7,000-square-foot showroom of RT Facts is housed in Kent Barns, a complex of six restored historic barns. You'll never know what you may discover at RT Facts with its mix of antiques and custom-made contemporary pieces, whether it's a neoclassical cast stone table with lion's paw legs or a pair of 18th-century carved limestone pineapple finials. Kent Station Pharmacy is housed in a former train station from the 19th century and is a one-stop shop for flu vaccines and thoughtful gifts. Located in a historic building, House of Books is a fixture and gathering place in town with more than 10,000 books and various community events.

The artistic vibe carries over to the vibrant galleries scattered throughout Kent. Morrison Gallery, which feels like a cathedral to art with its 24-foot ceilings in a newly completed 6,500 square feet space, features modern art such as pop and abstract expressionists, including Gene Davis' stripe paintings and Mike Hammer's colorful creations of pulsing circular blobs. Carol Corey Fine Art offers some high-profile artists such as Lisa Lebofsky, whose painting "Melting Iceberg 7" was on Apple TV's "Severance" show, and Roz Chast, a cartoonist for the New Yorker. If you're looking for a wall-less gallery, then stop by Sculpturedale, one of the best free museums in America. This 3-acre garden houses about 100 playful animals, dancers, and more, sculpted as if in mid-movement from steel and bronze by Denis Curtiss, whose work has attracted repeat buyers, including the 24 pieces bought by singer Andy Williams.

It's easy to see why a visit to Kent can be a great weekend getaway or part of a bigger trip, depending on where you start your adventure. Newburgh is the closest airport, about 36 miles away. You can also fly into New York's JFK Airport, which is over a two-hour drive away, and Kent is about an hour-and-a-half drive west from Hartford, Connecticut.

Lodging can be luxe or not. The Victorian is a high-end boutique hotel with five rooms that start at around $300 a night at the time of this writing. Amenities include gas fireplaces, claw tubs, and reading areas, along with morning teas and coffees, yogurts, and snacks. Family-run Cornwall Inn has more of a bed-and-breakfast vibe, with its Main Inn decorated with wrought-iron beds and its more casual Lodge that allows for pets. Prices start at $184 and include continental breakfast.

Post-hiking or post-shopping, you'll likely work up an appetite, and luckily, culinary options abound. The Villager offers comfort grub such as turkey clubs, chipotle BBQ pulled pork sandwiches, and beer-battered fish tacos. For a more formal evening, book a reservation for a prix fixe meal at Ore Hill, recently nominated as one of the best restaurants in America by the New York Times, with mostly locally sourced fare such as trout belly croustade and venison striploin with apple brandy. And, for a nightcap, find your way to Fife 'n Drum Restaurant & Inn, a family-owned piano bar where entertainers tickle those ivories four nights a week with live music.