6 Winter Wonderland Destinations in Connecticut Last Updated 11/16

By Kim Knox Beckius
Photo: Inn at Longshore, Westport

When Connecticut is covered in sparkling snow, some folks can’t wait to bundle up and head outdoors. But what if you’re the hibernating type? Here are six destinations sure to coax you out of your home—both frosty activities worth pulling on boots for as well as toasty comforts that will erase winter from your mind.

Warm Up to Westport

Westport is a great place to dip a toe into winter. It's near enough that you can spy Manhattan’s skyline from the shore, yet adequately distant to melt the city’s frenetic pace away.

  • Hike Earthplace, where you can search for animal tracks on an invigorating trek. Its wildlife sanctuary trails are open to the public year-round for free.
  • Stay at the Inn at Longshore, where rooms are bargain-priced off-season. You'll also find a historic golf course that celebrities once played. While it’s closed January through February, you can golf at winter rates in November, December and March as conditions allow. Then dine at the inn’s sophisticated Pearl at Longshore restaurant overlooking Long Island Sound sunsets.
  • For a breath of spring, dine at Westport’s Terrain Garden Café, a locavore gem hidden inside a picture-perfect garden shop.
  • Bring tastes of Westport home with a visit to the Westport Farmers’ Market. It's held indoors on Saturdays all winter.
  • On Monday nights, head over to the Westport Country Playhouse for one of its Script in Hand evenings. These readings of classic and contemporary plays—with no scenery or costumes, just actors engaging audiences—will sharpen your imagination. So you’ll be able to ditch winter any time you’d like. 

Breathe Deep in Madison

Soul-soothing experiences await in Madison: a coastal community that never shutters.

  • When summertime crowds disappear, so does the parking fee at Hammonasset Beach State Park. Dress for the weather, and you can hunt for seashells while the surf whispers reminders about what’s important in life. This is the only time of year your leashed dog can join you on Connecticut’s biggest beach.
  • In the heart of town, discover R.J. Julia Booksellers, an example of an endangered species: the independent bookstore. Interact with authors and book lovers at one of more than 300 events held here each year.
  • Stop into Madison Wine Exchange for advice on pairing a book with an equally enthralling red or white. On most winter Wednesdays, certified sommelier Joe Dolce leads themed tastings featuring entertaining commentary on six wines. Tip: reserve tickets online.
  • Dinner at Bar Bouchée is an opportunity to savor fine French cuisine without dressing up.
  • Retire to the Madison Beach Hotel and open that book or bottle you bought—or both—by the light of the fireplace in your king room. You’ll drift off with only one nagging to-do: waking in time for your appointment at the hotel’s Sounds of the Sea Spa.

Linger in Litchfield

Winter is a season of reinvention, and alluring Litchfield is the perfect place to stretch your limbs and your mind.

  • Fuel up on artisan baked goods at Bantam Bread (you have to try the Dirt Bombs), rent snowshoes at Sportsmen’s, and head to the 4,000-acre White Memorial Conservation Center for a calorie-burning crunch through the woods. Snowshoeing is as simple as walking, and cross-country skiing’s an option, too, if you bring your own gear. Live animals and exhibits inside the museum celebrate Litchfield’s natural diversity, and the gift shop showcases local artisans’ creations.
  • On weekends, tour Litchfield Distillery to expand your knowledge of spirits and sample Connecticut-made whiskey and gin.
  • Warming sips will awaken your appetite for a city-meets-country meal to remember at Arethusa al tavolo: the restaurant famously owned by Manolo Blahnik executives and Arethusa Farm proprietors George Malkemus and Anthony Yurgaitis. Portraits of their pampered dairy cows grace the eatery’s walls.
  • Haven’t seen a movie lately? Bantam Cinema, Connecticut’s oldest movie house, screens current and thought-provoking indie movies and serves real-buttered popcorn.
  • You may want to tuck in early, especially if you’ve reserved one of the Litchfield Inn’s fireplaced-themed rooms, like “cabin,” “wine cellar” or “bohemian.”

Take Flight in Middletown

Bald and golden eagles winter along the Connecticut River, and you’ll find this valley a welcoming place to land, too. As its name suggests, Middletown is smack in the middle of winter action in the state.

  • Family getaway packages at the Inn at Middletown—a former National Guard Armory turned 100-room hotel—include add-ons like Powder Ridge Mountain Park lift tickets. Even non-skiers love this mountain, where you can also try snow tubing or snowbiking.
  • If you’re dreaming of the wintry magic of a horse-drawn carriage ride, don’t miss the free New Year’s Day Open House at the Wadsworth Mansion. The historic property’s scenic trails are open free to visitors daily. You won’t find eagles nesting in Colonel Wadsworth’s specimen trees, though. They prefer the banks of the fish-filled river.
  • If you want to see eagles soar, drive south to Eagle Landing State Park in Haddam, or, better yet, reserve your spot aboard a RiverQuest Winter Wonderland/Eagle Cruise.
  • Middletown’s reputation as a foodie hangout is soaring, too. Treat yourself to Tschudin Chocolates’ artfully and meticulously crafted sweets, and don’t miss the wood-fired pizzas at Krust topped with locally grown, raised and made vegetables, meats and cheeses.

Find Bliss in Norwich

Located about halfway between Boston and New York, Norwich is “me time” central and an ideal meet-up spot, too.

  • Book a multi-day rejuvenating stay at the Spa at Norwich Inn. With 100 guest rooms, suites and villas, and an expansive spa with 37 treatment rooms, this historic haven is a premier destination and day spa, where every treatment is designed to pamper body, mind and spirit.
  • You don’t need to be an inn guest to dine fireside at Ascot’s: a cozy pub with a menu that transcends its casual vibe. 
  • Take a few spins on the ice during a public skating session at RoseGarden Ice Arena
  • Shoot photos of Indian Leap at Yantic Falls. The city’s storied waterfall is particularly mesmerizing when Mother Nature sculpts ice formations from its spray.
  • Need added incentive to gather a group of friends in Norwich? The Chestnut Street Playhouse stages White Christmas the Musical in December, and the annual Sun WineFest at nearby Mohegan Sun in January is a guaranteed cabin fever reliever.

Wind Down in Woodstock

When daylight hours are limited and you’re spending them all on must-dos, this rural hideaway in the Quiet Corner chases away seasonal blues. Gourmands know Woodstock is worth finding.

  • At the Inn at Woodstock Hill, sumptuous meals by firelight and rooms with working fireplaces combine to rekindle romance.
  • Woodstock is also home to Connecticut’s largest concentration of dairy operations. Schedule a free tour of family-owned Fairvue Farms to gain an appreciation for how milk reaches your table…and be thankful your job isn’t 365 days per year.
  • Need another reason to cheer? Check the schedule of UConn men’s and women’s basketball games at Gampel Pavilion, on the UConn Storrs campus. When the Huskies light up the scoreboard, you’ll understand why fans are happy to be blue.
  • A drive along country roads can be dazzling when fields and stone walls are glittered with snow. Trust your instincts and explore, or set your GPS for nearby Pomfret to visit the Connecticut Audubon Society, where guided nature walks and family programs are offered year-round.
  • Make reservations well in advance to sample award-winning wines before climbing the stairs for an exquisite dinner at Pomfret’s Sharpe Hill Vineyards’ Fireside Tavern. Glowing twin hearths give this 18th-century loft a dreamy glow.

 

From her home in Connecticut, Kim Knox Beckius is the voice of New England Travel for About.com, a Yankee Magazine contributing editor and the author of books such as New England’s Historic Homes & Gardens.