7 Best Towns in Connecticut for a Winter Getaway
The state of Connecticut, positioned in southern New England, is one of the best places to partake in the outdoor joys of winter. Travelers should expect cold temperatures and plenty of snow, ideal for skiing trips, scenic walks along the Connecticut shoreline on the North Atlantic Ocean, and winter hikes spent admiring the forests, rivers, and waterfalls as they become dusted in snow. While Connecticut boasts plenty to do in the great outdoors, visitors may also revel in indoor winter activities, such as sipping cocoa by the fireplace, hopping between small towns, and keeping cozy in an inn. Whatever it may be, the small towns of Connecticut offer all the essential activities for a charmed winter getaway.
Litchfield
Litchfield, situated within the rolling Litchfield Hills, is one of the best small towns to visit in Connecticut. Colonial-era buildings line the charming village center, featuring nearby historic spots such as the Tapping Reeve House and Law School, the Litchfield History Museum, and the Litchfield County Jail.
For those looking to indulge in winter sports, visit Litchfield Hills and partake in options such as downhill or cross-country skiing, snow tubing, ice skating, sledding, and more. The White Memorial Conservation Center is another great skiing spot, with 35 miles of roads and trails open to the public. Topsmead State Forest is an ideal destination for families, with plenty of hills ideal for snow tubing or sledding. Visitors in search of a cozy place to shack up overnight may check out The Litchfield Inn or The Hopkins Inn and Restaurant.
Chester
Chester sits within the Connecticut River Valley, home to popular activities and things to do such as the Chester/Hadlyme ferry, which traverses along the Connecticut River, the historic Gillette Castle, and the Norma Terris Theater.
Travelers may enjoy snowshoeing, cross-country skiing, or snowmobiling through the Cockaponsett State Forest, which is the second-largest forest in Connecticut, in winter. Winter events include the Starry Night's Illumination Celebration, the Chester Holiday Market, and the Chester Winter Carnivale, featuring lovely scenes and celebrations that are ideal for the whole family. The best places to stay for a winter getaway include the Guest House Retreat & Conference Center and The Millhouse Downtown Chester.
Essex
Essex is one of the most adorable small towns in Connecticut, around two hours from Long Island Sound. The Essex Steam Train and Riverboat offer visitors and locals The North Pole Express experience, a nighttime ride with onboard performances, perfect for bringing the kids. Travelers may also enjoy wandering the waterfront of Safe Harbor Essex Island or a day at the Connecticut River Museum.
The Essex Winter Series brings fine music to the Connecticut River Valley, ideal for romantic getaways after a fun day outside, just under 10 minutes outside of town in the town of Deep River. Griswold Inn is one of the best spots for an overnight stay, having deep roots in history, dating back to 1776, as well as plenty of holiday cheer and sparkling decorations.
Cornwall
Cornwall is one of the most unforgettable small towns to visit in Connecticut, and it is around an hour and a half from the popular town of Old Saybrook. The Housatonic River flows to the west while the Berkshire Mountains backdrop the town, offering plenty of spots for outdoor adventure in the winter. Just outside the town's border, visitors may enjoy a trip to Housatonic Meadows State Park or the Pine Knob Loop via the Appalachian Trail. There are also several winter events, including the Annual Christmas Pageant, the Annual Christmas Fair, the Gingerbread House Competition, Tree Lighting, and Carol Singing. Travelers looking to extend their stay may cozy up in the Cornwall Inn or the Hopkins Inn and Restaurant.
Collinsville
Collinsville sits on the banks of the Farmington River, which runs near the Farmington River Greenway. Once railroad tracks, it is now a walking and biking trail where visitors may snowshoe or cross-country ski in the winter. The underrated town of Simsbury is just 15 minutes outside of Collinsville, where travelers can ice skate at Stratton Brook State Park. After a day spent outdoors adventuring, check out Antiques on the Farmington and other shops along the main street, which is chock full of Victorian industrial innovation and history, such as America the Beautiful Country Store. Enjoy the town's winter charm overnight at locations such as Avon Old Farms Hotel or Legends on the Farmington.
Branford
Branford is one of the coziest small towns in Connecticut, along the Long Island Sound shoreline, just a ferry ride away from the Thimble Islands. Whether visitors choose to explore the island or hop on the cruise, the 45-minute guided sightseeing cruise is not to be missed. There are a few beaches along the shore that visitors may enjoy a trip to during the winter season, such as Stony Creek Beach. For those inclined to enjoy a few local brews, be sure to visit Stony Creek Brewery, Thimble Island Brewery, and Duvig Beer Company. The Harrison House museum features artifacts and stories from the town, dating back to 1724 and transporting visitors through time. For a cozy place to stay, visit Baymont by Wyndham or Thimble Islands Bed and Breakfast.
Mystic
Once a significant seaport, Mystic is now one of the best small towns in Connecticut to chill out, especially during the winter season. The town sits on the banks of the Mystic River, the scenery which visitors may enjoy from the beaches or the Old Lighthouse Museum, built inside a lighthouse in 1840. During the winter, the town boasts several events and festivals, perfect for the whole family, including a Holiday Tree Lighting, the Mystic Aquarium’s Lights Extravaganza, the Downtown Holiday Stroll & Luminaria, and the Lantern Light Village at Mystic Seaport Museum. There are also offer a half million lights dazzling the Olde Mistick Village, as well as community caroling and live music throughout the town. Enjoy an overnight stay at historic and festive destinations such as Whaler’s Inn or Stonecroft Country Inn Bed and Breakfast.
Enjoy a Winter Getaway in Connecticut!
The small towns of Connecticut offer endless opportunities for outdoor adventure, with options ranging from winter waterfall viewing to ice skating and skiing. There is also plenty to enjoy indoors, as well, with plenty of museums, chalets, and local boutiques waiting to be explored. From the picturesque Mystic seaport to the White Memorial Conservation Area Forest in Litchfield, the winter season adds a sparkling dusting of snow around Connecticut that is not to be missed.
