6 Winter Wonderland Destinations in Connecticut Last Updated: July 2023
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 from January through February, you can golf at winter rates in November, December, and March as conditions allow. Then dine at the inn’s La Plage 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 Winter Farmers’ Market. It's held indoors on Thursdays all winter.
- MoCA Wesport has been offering for more than 50 years diverse and innovative exhibitions and features a concert series and family art days.
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. Currently, they are offering curbside pick-up and online offers.
- 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.
- Take a tour and tasting at 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.
- Looking for the perfect antique? Browse around the Housatonic Trading Company in Bantam for vintage items, antiques, art decor, and more.
- After a long day of exploring, check into the Mayflower Inn & Spa or Interlaken Inn for a relaxing country retreat.
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, in East Haddam, Allegra Farm provide a "Courrier and Ives" experience while bundled up, let the sleigh take you away to another place in time.
- 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 Wildlife 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.
- Historic downtown Norwich offers many dining opportunities including an authentic Irish pub, Harp & Dragaon Pub, or if your taste buds prefer local craft beer, try out These Guys Brewing Company.
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.
- Explore nearby Downtown Storrs and the celebrate the winter season with strolling carolers and musicians, ice sculpting, along with many dining and shopping options. A great way to spend a winter day.
- 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.
- Stop in at The Christmas Barn for holiday gifts and good cheer.
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.