When the chill of winter sets in, there’s no better way to embrace the season than with a cozy weekend getaway. Last winter, I did a getaway to the charming town of Kent, Connecticut and stayed at the lovely Kent Collection, which offers the perfect blend of warmth, luxury, and small-town charm. Whether you're looking to unwind, explore the beautiful winter landscape, or simply enjoy the town’s quaint shops and restaurants, Kent promises to be a memorable winter escape.

Arriving in Kent: A Picturesque New England Town

Kent, located in the scenic Litchfield Hills, is an idyllic New England town. Incorporated in 1739, Kent has a rich agricultural and iron ore industry history. Today, it is a rural community with about 3,000 residents and several small hamlets. Located 90 miles north of New York City, Kent serves as the gateway to Connecticut's rural Northwest Corner. The town's first center was located two miles north in the Flanders Historic District, now on the National Register of Historic Places, but was moved in the 1840s with the arrival of the railroad. As you drive through the town, you'll be greeted by quaint streets lined with local shops, historic buildings, and a peaceful quiet that can only be found in small towns. The Kent Collection, a collection of beautiful boutique-style accommodations, serves as the perfect base for your winter retreat.

The Kent Collection: Cozy and Elegant Lodging

The Kent Collection features a range of stylish, comfortable accommodations, from intimate rooms to spacious suites, each offering a mix of modern amenities and old-world charm. Whether you opt for the cozy atmosphere of a historic inn or the chic, contemporary style of a boutique hotel, the accommodations are designed to make you feel right at home.

During my trip, I stayed in The Little House, which is part of The Kent Collection's Garden Cottages. Located in an area once referred to as “the beehive” for its constant activity, the Kent Station area remains a lively hub today. The nearby restaurant features live music, Kent’s charming shops and eateries are just a short two-minute walk away, the town library is right across the street, and, true to its railway roots, a freight train occasionally passes by. Each of the three cottages is unique in size and design, yet they all share a cozy, casual, and eclectic vibe. These family- and pet-friendly cottages offer a perfect escape while keeping you connected to all that’s happening in the town.

The Little House is an open studio that features a spacious layout, with a king-size bed at one end and a sleeper sofa and fireplace at the other. Built in 2022, this charming space retains the same footprint as the original historic house that once stood here, preserving its original fireplace, chimney, floorboards, and beams. The studio also includes a fully equipped kitchen, gas fireplace, full bath with shower, private patio with a firepit and Adirondack chairs, Smart TV, WiFi, and is pet-friendly.

Winter Activities in Kent and the Surrounding Area

Kent is a perfect getaway for nature lovers, and winter is a great time to explore the outdoors (despite what some may think). Start your day with a morning walk at the nearby Kent Falls State Park, just a short drive from the town center. Kent Falls State Park, one of Connecticut's most treasured natural sites, offers stunning views and a refreshing experience year-round. You can explore the picturesque covered bridge, hike to the falls, and feel the mist as the water plunges 250 feet to the Housatonic River. The falls, fed by Falls Brook, are especially dramatic during spring snowmelt and summer storms, but the beauty of the cascade is captivating in every season.

Bulls Bridge is another gem in the area, one of the last remaining operational covered bridges in Connecticut. Built in 1842, it was originally constructed to improve access across the Housatonic River from New York, attracting more traffic to the area. The bridge was added to the National Register of Historic Places in 1972. In addition to the historic structure, the surrounding area features beautiful waterfalls, rapids, scenic overlooks, a small gorge, and several hiking trails. The bridge and falls are easily accessible from a free parking area, with a short walk to the sights. You can head straight to the bridge and then down to the rapids, which gives you the opportunity to admire the powerful waterfall from a former power station. A lesser-known path across the street from the parking lot leads to a peaceful overlook of the river below.

Kent Falls Brewing, a working farm brewery known for its focus on small-batch beers made with local ingredients is another great way to spend a day in Kent. Set in a picturesque location, the brewery offers a wide variety of styles, from hoppy IPAs to smooth stouts, all crafted with a commitment to quality and flavor.

If you’re looking for a slower pace, explore Kent’s charming Main Street, lined with unique boutiques, art galleries, and cozy cafés. There are several antique stores in the area along with bookshops and general stores. A few of my favorites are House of Books, Woodfords General Store

A Winter Evening in Kent: Dining and Relaxing

After a day of outdoor exploration, enjoy a relaxing dinner at one of Kent’s inviting restaurants. The town has an array of dining options, from fine dining to casual eateries, all serving delicious seasonal dishes. Whether you’re in the mood for a hearty meal or a light bite, the local culinary scene never disappoints.

Kingsley Tavern is a charming, rustic eatery that offers a warm and inviting atmosphere. Known for its delicious, locally sourced food and craft cocktails, the tavern combines classic American comfort with a contemporary twist. You can enjoy a hearty meal by the fireplace, and unwind after a day of exploring Kent's beautiful countryside.

Another favorite in the area is 109 Cheese Market, with some of the best grilled cheese sandwiches, artisanal cheeses, and specialty products. This is my favorite spot to come for lunch! We also love Wilson’s and Sophie’s Bakery for coffee and baked goods.

Wrapping Up Your Winter Getaway

As your winter weekend comes to an end, take a final walk through Kent’s charming streets, maybe spotting some snow falling over the town’s historic buildings. Whether you're unwinding at The Kent Collection, exploring the outdoors, or relaxing in a cozy café, Kent offers a tranquil setting for a winter getaway.