Why plan a Connecticut winter vacation?
Sure, the beaches are closed, and you may need to bundle up to go out, but winter travel has distinct benefits.
First, there are fewer tourists wherever you go, which is ideal for introverts or for those traveling during a pandemic.
Second, fewer winter travelers mean hotels and inns offer lower rates than during their peak season.
Often, the difference between planning CT fall getaways and Connecticut winter getaways just a few weeks later can be up to 50% off.
Cute places to Visit In Connecticut In the Winter
Start planning before you pack your parka!
Many of the cutest towns in Connecticut offer great reasons to visit in the winter.
Below are a few of our top picks, curated according to what Connecticut winter activities are available at each location.
Any of these places to visit in Connecticut in the winter make ideal winter getaways.
Map design by Stanton House Inn with elements from Flaticon
Greenwich
The closest town in Connecticut to New York City is our town: Greenwich, Connecticut.
Getting here is a breeze. Hop on a northbound train to New Haven or Stamford in Grand Central Terminal. If you’re driving, follow directions to Greenwich, CT, while driving north along the Hutchinson Parkway or Interstate 95.
Once you’re here, there’s more than enough to entertain you for a long romantic weekend winter getaway.
Top Indoor Winter Activities In Greenwich
Are you planning on spending as much time indoors as possible? Then there are plenty of options within walking distance of our downtown Greenwich inn, Stanton House Inn.
Here are some great winter activities to do in Connecticut for couples:
- Shopping in the downtown Greenwich Avenue district is always a unique Connecticut attraction. And that rule applies any time of the year.
- The rotating exhibits at museums in Greenwich are a perfect way to spend an afternoon.
- High afternoon tea service seems to make more sense in the winter months. And there are two options in Greenwich: Cady’s Tea Room in Stanton House Inn’s dining room or The Drawing Room in the nearby Cos Cob neighborhood.
- Finish the day or enjoy a mid-day meal by a fireplace at one of the top downtown Greenwich restaurants, such as The Ginger Man or L’Escale Restaurant.
- A short distance from Greenwich is the Maritime Aquarium in Norwalk to stay warm and learn more about the Long Island Sound sea life.
Best Places to Visit In Greenwich, CT, During the Winter Months
A biting wind should not deter you from enjoying the great outdoors on your Connecticut winter vacation!
Strap on your boots (in case it’s muddy or slippery, depending on the period of the winter) and hit up some of the best hiking trails near Greenwich, CT. A personal favorite in the winter is Mianus River State Park. Its varied terrain, views of the Mianus River, and cool farmstead ruins make for many a great winter picture opportunity. There’s a reason why this is one of the best state parks in all of Connecticut.
Another ideal place to get a great winter photo for Instagram is Greenwich Point Park. While this best of the beaches near Greenwich, Connecticut, is lovely to walk along in the winter, the best part is the southwestern corner. Visitors can catch a glimpse of the Manhattan skyline on the far horizon.
A little farther into the state but still close enough to be a Connecticut day trip from Greenwich are two major historical attractions. Both are emblematic of the artistic and architectural influence of famous Connecticut residents:
- Philip Johnson Glass House, in New Canaan
- Weir Farm in Ridgefield
Best Winter Festival to Attend In Greenwich
As winter festivals go, the biggest in Greenwich is the Reindeer Festival. On a typical (i.e., non-pandemic) year, this event stretches through December. The festivities start with a parade down Greenwich Avenue with Santa and his reindeer.
The reindeer will still be hanging-out at Sam Bridge’s Nursery this year, though much of the event has moved online.
Where to Stay For Your Greenwich, CT, Winter Getaway
Of the 4 Greenwich, CT, hotels, only one bed and breakfast remains in town: Stanton House Inn.
Start a quaint holiday tradition by booking one of our New England inn guest rooms with a fireplace in-room to enjoy the evenings of your romantic winter getaways. You could also reserve one of our king bedroom suites with a large bathtub to enjoy your own private spa day.
Be sure to check out our romance package to build your unique Connecticut Valentine’s day packages too. We also offer a couples in-room massage package, to add to a bit of luxury to your winter getaway.
You can also keep looking for more things to do in Greenwich, CT, in the winter to add to your itinerary when you read our guide!
Heading Further Into the State to Find More Places to Visit In CT During the Winter Months
While Greenwich is the first stop when traveling from NYC, there are plenty of other places to visit.
Directions for every other point on this list will be from Greenwich. That way, you can use it as a starting point to explore more day trips in CT for couples during your winter getaway.
Westport
With its cute downtown perched on the Saugatuck River and gorgeous waterfront, the town of Westport, CT is worth a day trip to explore.
The train from Greenwich to Westport is typically a 45-minute ride. Driving often takes about 30 minutes via the Merritt parkway or I-95.
Places to Visit In Westport, CT, In the Winter
Head to Westport on a Saturday morning to visit the Westport Farmers Market hosted indoors on Saturdays all winter. It’s an excellent way to start your visit, and your fresh produce won’t go bad sitting in a cold car on a winter day if you have other stops to make!
Have lunch at Terrain, a whimsically decorated restaurant and garden shop hybrid. Afterward, visit the MOCA Westport for their rotating art exhibition.
If the sun hasn’t yet set by the time you’ve finished at the MOCA, meander to Sherwood Island State Park to watch the sunset over Long Island Sound.
Drive right past Bridgeport, Connecticut to get to the next spot on our list.
New Haven
Most equate New Haven with two very different things: the elite and prestigious Yale University and severe urban poverty.
The city has been working to change its image, even offering cash payments to young urban professionals willing to move here.
Yet, this place of extremes offers plenty to curious visitors. In many ways, it’s a smaller and much more manageable version of New York City with a great food and arts scene.
How to Get to New Haven On a Connecticut Winter Vacation
New Haven is a straight shot from Greenwich—just drive an hour up the Connecticut shoreline on I-95. The Merritt Parkway is often a more pleasant drive, provided there are no accidents along the way, slowing traffic.
It’s also about an hour-and-a-half train ride from Greenwich. Take a train to Stamford, CT, then switch to an express train from there to New Haven if possible.
Ideal Places to Visit In Connecticut In the Winter: New Haven Edition
Many of my personal favorite things to do in New Haven are not unique to the season. That said, they’re still ideal for romantic weekend getaways.
Get to New Haven early enough in the morning to visit a museum before lunch. Yale University hosts several spectacular collections. A personal favorite is the Yale University Art Gallery, one of the oldest and broadest collections in North America.
Afterward, get ready for lunch. You could head to Louis’s Lunch, the restaurant that first developed the hamburger in 1895 and is still in operation, depending on the day.
Instead, head to Wooster Square, the old Italian neighborhood of New Haven, separated from downtown by I-91.
There, you can indulge in cold weather Italian-American comfort food: pizza. New Haven restaurants regularly receive awards for their creative or simply delicious pizza. Of them, Frank Pepe’s Pizzeria Napoletana has been setting a standard for its coal-fired pizzas since 1925. While they’ve opened franchises elsewhere, New Haven was the flagship restaurant.
Once you’ve filled up on cheesy goodness, the afternoon should have warmed-up a bit. It’s a perfect time to head out for a walk.
You can continue to explore Wooster Square or downtown New Haven. Or you can drive through the high-end East Rock neighborhood to East Rock Park for a sweeping view of New Haven. Alternatively, you can get another walk along the waterfront of New Haven’s harbor at Lighthouse Point Park.
Winter Festivals In New Haven
If our New Haven winter getaway itinerary isn’t enough, plan to head to New Haven on December 1 for the New Haven Holiday Tree Lighting in the Town Green.
Madison
Quaint, genteel Madison primly reclines on the Long Island Sound, only 20 miles from New Haven. It’s only another 25-minute drive downtown New Haven or a 30-minute train ride.
So that’s a 3-hour train ride from Greenwich, through New Haven or a 1-hour-and-15-minute drive.
Best Places to Visit In Connecticut In the Winter: Madison Edition
Head to Madison’s downtown shopping district as soon as you arrive on a winter’s day. Spend some time perusing the most interesting local shops, including R.J. Julia Booksellers and the Audubon Shop.
Then, walk the beach at the expansive Hammonasset Beach State Park in the afternoon. Afterward, have a drink and watch the sunset on the deck at the Madison Beach Hotel.
Where to Stay For Your Overnight Madison, CT, Winter Getaway
Does your itinerary sound like more than you can complete in just a day trip?
Stay over in Greenwich or Madison, or you can check out some of the other nearby towns like Guilford and Branford.
The local Guardiano family has been taking care of guests at their gracious 10-room bed and breakfast for over 30 years. The Homestead offers an intimate introduction to Madison and its stretch of the Connecticut shoreline.
Litchfield
Want to feel like you’ve wandered onto the set of It’s a Wonderful Life?
Then be sure to add Litchfield to your list of places to visit in Connecticut this winter.
Litchfield County is one of the quaintest corners of Connecticut, and Litchfield feels like the center of it all.
The drive from Greenwich to Litchfield is about an hour and a half. Along it, you’ll get the pleasure of some highways and backroads with gorgeous views of the surrounding winter scenery.
And once you’re there, there’s plenty to keep you busy during your Connecticut winter getaway.
Litchfield, Connecticut, Winter Vacation Activities
If you’re looking to stay inside, explore the area’s great antique shops like Housatonic Trading Company. Afterward, enjoy a favorite Connecticut winery by visiting Hopkins Vineyard near Lake Waramaug.
But outdoor activities are a major draw to Litchfield in the winter. Try snowshoeing or cross-country skiing through the 4,000 acres of the White Memorial Foundation. Downhill skiers or snowboarders can get their fill at either:
In Cornwall or New Hartford, respectively.
There are plenty more winter hiking trails to choose from at Macedonia Brook State Park. Or you can simply enjoy the winter scenery along Lake Waramaug with an 8-mile walk along the lakefront.
Winter Festivals Near Litchfield, Connecticut
There’s no question:
A trip to Bethlehem for the Christmas Town Festival is the most Christmas-y celebration imaginable in the state.
This holiday season festival is also one of the most family-friendly winter activities on this list. A typical year includes activities like:
- Face painting
- Hayrides
- A ride on the Christmas Town Train
- Live music
- And even craft and food vendors
The Christmas Town Festival runs the first weekend of December.
Middletown
As the name implies, Middletown is as central to the state of Connecticut as you can get.
It takes about an hour and a half to get from Greenwich to this Connecticut River town.
Places to Visit in Middletown, Connecticut, During Your Winter Vacation
From this town’s central location, you can explore a sizable chunk of the Connecticut River Valley.
Head to the nearby New Britain Museum of American Art or the Wadsworth Atheneum in Hartford if you’d like to soak-up some fine art during your visit.
Alternatively, explore our full list of attractions, activities, and things to do in Hartford during the winter.
Some of our favorite winter activities in Connecticut are just a short drive from Middletown. Powder Ridge Mountain is the place for:
- Skiing
- Snowboarding
- Snow biking
- Even night skiing
Head east from Middletown to Allegra Farm to schedule your very own horse-drawn sleigh ride through the winter fields.
And next, does getting a better view of the local winter wildlife sound appealing?
Then take a Winter Wildlife Eagle Cruise along the banks of the Connecticut River.
Don’t forget the wineries circling Middletown; a visit to a few of them are on our list of the most romantic things to do in Connecticut in the winter.
Check Out One of the Best Winter Festivals In All New England Near Middletown
Lyman Orchards in nearby Middlefield hosts the annual WinterFest. This top family winter activities fair features various winter activities. Some common features include snow carving demonstrations and horse-drawn sleigh rides. In previous years, Yankee Magazine declared this event one of the best winter festivals in New England.
Where to Stay On Middletown, CT, Winter Getaways
On the edge of Middletown’s business district on its main drag sits the Inn at Middletown. The hotel occupies the former CT National Guard Armory in a building dating from the 1800s. A stay with them may make planning your winter vacation just a little easier! Book their special winter package to receive passes for snow tubing at nearby Powder Ridge.
Essex
Regardless of the time of year, Essex is one of the cutest towns in Connecticut.
Winter months just amped up the cuteness with holiday decorations throughout this adorable town.
A holiday ride on the Essex steam train is one of the best things to do in December in Connecticut. That activity is closely followed by wandering the center of town to see those colonial decorations I mentioned earlier.
But mid-February is the time to visit Essex and nearby Chester, another cute town a little further up the Connecticut River. There, the annual Winter Carnivale draws huge crowds in a typical year. Watch a tractor parade and enjoy the Chilly Chili Cook-off. Or let an ice carving demonstration or two mesmerize you. And be sure to shop the local art galleries and shops for holiday specials.
Where to Stay For Quick Essex, Connecticut, Winter Vacations
Without question, the place to stay in Essex is the Griswold Inn. This is one of the oldest continuously operated inns in the United States. Its prime location in the middle of downtown Essex makes it easily accessible to all the winter activities and attractions in the area.
Old Saybrook
Downriver from Middletown, Essex, and Chester is Old Saybrook. This is one of the oldest towns in Connecticut, settled to defend the mouth of the Connecticut River.
Old Saybrook is an hour-and-20-minute drive from Greenwich or about a 2-and-a-half-hour train ride.
Things to Do On Old Saybrook, Connecticut, Winter Getaways
Needless to say, a town as historic as Old Saybrook is full of attractions to keep a history aficionado occupied.
And that includes the winter months.
Fort Saybrook Monument Park offers 17 acres to wander, with an introduction to the history of the town since its founding in 1635. The panoramic view of the Connecticut River’s mouth is also a major draw.
Revolutionary War fans will delight in touring the General William Hart House, run by the Old Saybrook Historic Society. The home of the political and military giant, built in 1767, and award-winning historical garden are on the National Register of Historic Places.
The arts and culture scene of Old Saybrook is as big of a draw as its history. The Kate is named after the town’s most famous resident, Katharine Hepburn. It’s in a historic theater offering performing arts and cultural programs for all throughout the year.
Once you’ve finished, wander along the Main Street of Old Saybrook and explore their restaurants and local shops.
Where to Stay For Old Saybrook, Connecticut, Winter Getaways
Around the corner from Fort Saybrook Monument Park sits Saybrook Point Resort and Marina. This small resort inn hosts a restaurant, Fresh Salt, and spa. Book the couple’s massage at the Saybrook Point Spa to enjoy your own Connecticut couple’s retreat.
The annual Fire and Ice Festival hosted at Fresh Salt is worth the pilgrimage! With:
- Ice sculptures
- A fire bar
- Wood and ice carving demonstrations
- And entertainment, including a fire gypsy
This winter festival is sure to impress.
Niantic and Lyme
Connecticutians often equate Niantic and Lyme with summer. These waterfront destinations are ideal summertime beach getaway spots, but winter can be a lovely time to visit as well.
An hour-and-a-half drive up I-95, East Lyme and its neighborhood, Niantic, offer a tranquil weekend getaway in the winter.
Things to Do On a Niantic, Connecticut, Winter Weekend Trip
Wintry shopping can be as pleasant as summer shopping (with better sales), and the funky shops of Niantic will not disappoint.
Local hot spots include:
- A bookstore with 350,000 choices, including rare and out-of-print books
- The largest hobby kayak store on the entire East Coast
Rocky Neck State Park is a fantastic place for a winter walk along its marshes that feed into Long Island Sound or its small beach. Smaller McCook Point Park offers gorgeous views of the wintry Niantic Bay. It’s also close to access to the Niantic Boardwalk along the waterfront.
Where to Stay For Niantic, Connecticut, Winter Getaways
If you’d like to explore the area at your leisure, check out the Inn at Harbor Hill Marina. This small inn overlooking the water is the perfect place for a quiet winter getaway to Niantic.
Mystic
Connecticut’s premier tourist destination doesn’t disappoint, even in the colder months.
Mystic is only an hour and forty minutes away from downtown Greenwich along I-95. It’s also the center of an expansive area of attractions and activities, including during the winter.
Top Places to Visit In Mystic, Connecticut, In the Winter
The first attraction to come to Mystic existed before people were even thinking of ways to attract tourists to town.
Well, not exactly. But Mystic Seaport has been around a long time.
Mystic Seaport Museum hosts the nation’s leading maritime art gallery. It specializes in ship models and contemporary marine art. The museum is open through the winter and hosts holiday events and other winter special events, classes, and workshops.
Head outside to explore America’s foremost maritime museum’s National Historic Landmark vessels. Don’t miss the “Charles W Morgan,” the only surviving wooden whaling ship.
Nearby Olde Mistick Village is a great place for discovering unique winter shopping finds. The thirty boutiques sell everything from fudge to Himalayan crafts and Christmas ornaments.
If you really don’t want to see the winter sun for a while, head to either of the nearby casinos. There, you can enjoy some gambling, shopping, entertainment, or a mix of the three. Mohegan Sun and Foxwoods Resort and Casino are sure to keep you busy for most of the winter season if you’re so inclined.
Mystic Aquarium offers both indoor and outdoor attractions, including:
- African penguins
- Sea lions
- The only beluga whales in New England
In the final weeks of December, Mystic Aquarium celebrates Winterfest. The holiday event features different events scheduled every day:
- Ice carving
- Elves frolicking in the water with animals
- Winter arts and crafts
- Local entertainment
Where to Stay For Mystic, Connecticut, Winter Getaways
Sounds like a lot to do on a day trip?
No argument there.
Reserve a stay at the Whalers Inn in the center of Mystic for your next winter vacation getaway. There are few other hotels in Mystic with:
- Such a long history of being at the center of town
- Or that offer views of the town and the Mystic River from guest rooms
Still Deciding On Where to Go For Your Connecticut Winter Getaways?
Seriously?
Time to keep exploring, then.
Check-out our list of the best winter activities in Connecticut to find a spot central to what you want to do while you’re here.
Your trip may also be decided by when you’re planning on coming. Be sure to look at our guides for:
- Things to do in Connecticut in December for couples
- Top indoor activities in Connecticut, throughout the state
But let’s face it: There are tons of other cute towns across Connecticut. And each of them offers unique experiences during the winter months. Read our guide to the cutest towns in Connecticut if the above options don’t quite work for you.
Be sure to download a copy of our Winter in Connecticut guide before you make the trek!
Updated and republished: October 31, 2022
