35 Entertaining Things to do in Connecticut in the Winter

The summer months are high tourist season in Connecticut, but if you want to experience some cozy New England charm, consider a trip to the Nutmeg State in the winter.

In this post, I have compiled 35 of the best things to do in Connecticut in the winter, categorized by indoor, outdoor, and kid-friendly activities, as well as some popular festivals.

I also provide a list of nice winter getaway destinations in Connecticut if you have a little more time to spare. Bundle up and have fun!

Indoor winter activities in Connecticut

Here are some fun ways to escape the winter cold in Connecticut:

1. Explore the bookshelves of Sterling Memorial Library

Sterling Memorial Library is Yale University’s largest library and built in the beautiful Gothic Revival style. You could spend an entire day browsing through the shelves housing more than 2.5 million volumes.

2. Check out Beinecke Rare Book and Manuscript Library

Not far from Sterling Memorial Library is the Beinecke Rare Book and Manuscript Library, one of the largest libraries in America dedicated to rare books and manuscripts.

When you enter, you’ll see a six-story, glass-enclosed chamber of bookshelves in the center of the room, with public exhibits surrounding it, including one of the 48 remaining Gutenberg Bibles.

Note that the glass chamber is not open to the public, but students, faculty, and researchers can make a request to view a certain book in the reading room.

3. Visit the Yale University Art Gallery

The Yale University Art Gallery is the oldest university art gallery in America, with more than 300,000 different items on display. It is free to the public, making it a great place to explore on a cold winter day and see art pieces from all around the world.

4. Learn about natural history at the Peabody Museum

Visit one of the largest and oldest university natural history museums in the world. The Peabody Museum of Natural History at Yale University was founded in 1866 and is best known for its “Great Hall of Dinosaurs” with its juvenile brontosaurus.

Note that the museum is currently undergoing major construction and is closed to the public until 2024.

5. Discover the Yale Center For British Art

See the largest collection of British art outside of the United Kingdom at the Yale Center for British Art. Here you will find more than 2,000 paintings, 250 sculptures, 20,000 drawings and watercolors, and 35,000 rare books and manuscripts dating all the way back to the fifteenth century. This place is also free to the public.

Note that the building will be undergoing construction from February 27, 2023 through the end of the year and will be closed to the public until 2024.

6. Go to an indoor ice skating rink

Ice skating is always a fun activity to do in the winter, and there are several nice public rinks in Connecticut, including the Veterans Memorial Ice Rink in West Hartford and Bolton Ice Palace in Bolton.

7. Hop from one coffee shop to the next

One of the best things to do on a cold winter day is enjoy a warm cup of coffee inside a cozy cafe. Both Hartford and New Haven have a great selection of cafes to choose from, or you could also visit one of Connecticut’s many quaint small towns to find a special brew.

8. Browse unique shops and boutiques

It’s fun to browse through the small stores in New England towns, but it’s an especially nice thing to do in the winter when you want to get out of the cold.

I love finding one-of-a-kind treasures in thrift and antique stores, boutiques, and gift shops. Even if you’re not interested in buying anything, it’s still interesting to check out what they have!

Some possible shops to explore:

• Vintanthro Modern & Vintage, New Haven
• EBM Vintage, New Haven
• Quality Thrift Shop, Kent
• The Black Dog General Store, Mystic
• Peppergrass & Tulip, Mystic
• Hartford Prints!, Hartford

9. Encounter sea life at Mystic Aquarium

Come see the only aquarium in the continental United States to care for Steller sea lions: Mystic Aquarium. You’ll find these marine animals and thousands of others here, and you can learn about the conservation and research efforts the aquarium has in place to keep ocean species thriving.

10. Learn about maritime history at Mystic Seaport Museum

The Mystic Seaport Museum is America’s leading maritime museum and a fascinating place to learn about the country’s seafaring past. You can see more than 500 historic watercraft here, including the 1841 Charles W. Morgan whaleship, America’s oldest commercial ship still in existence.

11. Hunt for used books at the Book Barn

If you’re a bookworm, I highly recommend visiting the Book Barn in Niantic, not far from Mystic. There is both a Main Barn and Book Barn Downtown, with the Main Barn being the largest of the two locations.

Browse the selection of more than 500,000 used books, and if you have your own books to get rid of, the Book Barn will buy them from you. The store has the tagline “A Bibliophile’s Bliss” for a reason.

12. See a show at the Hartford Stage

The Hartford Stage has won Tony and Pulitzer Awards for past performances. Shows offered during the 2022-2023 season include The Art of Burning, The Winter’s Tale, and Trouble in Mind.

13. Tour the Mark Twain House And Museum

Visit the home of well-known American author Sam Clemens (who went by the pen name Mark Twain) and his wife Olivia, who lived in Hartford from 1874 to 1891. The 11,500-square foot home has 25 rooms spanning three floors, which you can walk through during a guided tour.

Note that since the home is only accessible via a guided tour, it’s recommended to book your ticket ahead of time to guarantee a spot.

14. Book tickets at the Bushnell Performing Arts Center

Watch a performance at The Bushnell, Connecticut’s largest arts organization. The Bushnell has been hosting world-class shows in Hartford for 90 years and is a cultural treasure for the state.

Shows in the 2023 line-up include Tootsie, The Tina Turner Musical, Hartford Symphony Orchestra’s Masterworks Series, and To Kill a Mockingbird.

15. Explore the New England Carousel Museum

For something a little unusual, check out more than 100 years of carousel history at the New England Carousel Museum in Bristol. You’ll learn more than you ever thought you would about carousels, which, as their website touts, were once “the pinnacle of amusement park joy.”

In the same building you will also find the Museum of Fire History, which takes you back to the early days of fire-fighting and gives you the chance to test out some early fire signaling devices.

16. Pamper yourself at the Mayflower Inn & Spa

If you’re a Gilmore Girls fan, you might appreciate that the Mayflower Inn & Spa in Washington, Connecticut is said to have inspired the writer of the show in her creation of the Independence Inn.

The Mayflower is a beautiful hotel set in the quiet, rolling hills of western Connecticut. You can choose to stay for a night or two or simply enjoy their luxurious spa for a day—cozy winter relaxation at its finest.

Outdoor winter activities in Connecticut

If you bundle up well, you can still enjoy Connecticut’s beautiful state parks and other outdoor spaces in the winter. Here are some of the best places to see:

17. Hike through Devil’s Hopyard State Park

The 1,000-acre Devil’s Hopyard State Park in East Haddam is most popular in warmer months for hiking and picnicking, but it’s worth visiting in the winter if you want to catch the icy beauty of the picturesque Chapman Falls.

Legend says that the name “Devil’s Hopyard” came about because of the “holes” in the falls, which people thought looked like footprints left by the devil while he was passing through.

18. Cross the tombolo at Silver Sands State Park

Head to Silver Sands State Park in Milford, Connecticut, a coastal park with a boardwalk giving scenic views of Long Island Sound. One of the most unique features of this park is the long sandbar, or tombolo, that connects the mainland with Charles Island.

Visitors are welcome to walk across the tombolo during low tide, but make sure to pay attention to when the water begins rising so you can make it back to shore. 🙂

19. Walk the trails at Hammonasset Beach State Park

A perk of visiting Connecticut’s state parks in the winter is you can avoid non-resident parking fees. Hammonasset is Connecticut’s largest shoreline park, where you can enjoy water views along the trails.

This park gets crowded in the summer but you can have the place almost all to yourself in the winter time — the scenery is still beautiful!

20. Climb to the summit at Sleeping Giant State Park

Sleeping Giant State Park, named for its two miles of mountaintop shaped like a sleeping giant, is another favorite hiking spot near New Haven.

There are several different trails of varying difficulty, and once you get to the top, you can catch beautiful views of New Haven and the Long Island Sound from the lookout tower.

Note that the trails can get quite icy if there’s snow on the ground, so unless you are an experienced snow hiker, it’s probably best to hike here when the ground is clear.

21. Enjoy city and water views from East Rock State Park

East Rock State Park isn’t that far from Sleeping Giant but is closer to New Haven, making it an easier place to get to if you’re staying in the city.

You can choose from natural hiking trails or a paved trail that winds around to the summit, where you’ll be rewarded with panoramic views of the city and Long Island Sound beyond.

22. Walk around the serene Lake Wintergreen

Connecticut has beautiful rolling hills and wooded areas, which become quiet and peaceful in the winter. One of my favorite places to walk when I lived in New Haven was Lake Wintergreen, which is part of West Rock Ridge State Park in Hamden.

There is free parking near the entrance of the 1.5-mile trail that loops around the lake.

23. Tour Yale University & Downtown New Haven

Since school is in session during the winter, Yale University campus is very much alive this time of year. Take a walk through the old campus and main campus and then stroll through the historic New Haven Green.

Stop for a bite to eat at Louis’ Lunch, one of the tiniest restaurants you will ever see. Fun fact: Louis’ is one of the places that claim to have invented the hamburger and is an iconic spot in New Haven.

Another great winter activity is restaurant hopping, and New Haven has a great food scene. Other great places to check out include Crepes Choupette, Sitar, and Pepe’s.

24. Go skiing or snow tubing

While Connecticut is not as known for skiing as its New England neighbors, the state still boasts four ski resorts with decently sized hills: Mohawk Mountain, Mount Southington, Powder Ridge Mountain, and Ski Sundown. These resorts are great places for beginner and intermediate skiers to practice their skills.

Mohawk Mountain and Powder Ridge Mountain also have snow tubing hills, a fun alternative to skiing.

25. Enjoy an outdoor ice skating rink

If you’d rather ski outside instead of indoors, there are several outdoor rinks in Connecticut as well. The Westport PAL Rink at Longshore in Westport and Mill River Park Rink in Stamford both offer public skating sessions and skate rentals.

To skate on a frozen pond, try Pickett’s Pond in Osborndale State Park in Derby or Owen Fish Park in Fairfield.

26. Grab dinner on the Essex Clipper Dinner Train

Enjoy a cozy meal on a vintage 1920s locomotive by reserving a spot on the Essex Clipper Dinner Train. The 2.5-hour ride will transport you back in time as you take in the winter scenery along the Connecticut River Valley and receive top-notch service on board.

Kid-friendly winter activities in Connecticut

Though many of the activities above would also be entertaining for children, here are a few additional activities specifically geared toward them:

27. Explore the Connecticut Science Center

The nine-story Connecticut Science Center in Hartford includes a number of fascinating exhibits to educate and entertain people of all ages. Visit the Engineering Lab, Butterfly Encounter, Invention Dimension, River of Life, and more.

28. Visit Stepping Stones Museum for Children

The hands-on Stepping Stones Museum for Children in Norwalk is geared toward children ages 10 and under and offers a variety of activities to keep them entertained and out of the cold.

29. Go wild at the Kidcity Children’s Museum

With a 4.8 out of 5-star rating on Google, Kidcity Children’s Museum is a wonderland for kids ages 1-7. There are three stories of interactive activities and exhibits, including a fishery and medieval village.

30. Challenge yourself at the It Adventure Ropes Course

Who knew that the world’s largest indoor ropes course is inside a furniture store? Located at Jordan’s Furniture in New Haven, It Adventure Ropes Course has more than 100 different challenges at varying difficulty levels: swinging beams, cargo nets, bridges, zip rails, and more!

Holiday/winter festivals in Connecticut

One of the most charming aspects of winter in New England is the array of festivals that take place, and in Connecticut that is no exception. Here are some of the most popular festivals to check out during the colder months.

Note that most of these festivals take place around Christmas and details for 2023 have yet to be released.

31. Newtown Holiday Festival

While not technically in winter since it takes place in early December, the Newtown Holiday Festival is still full of winter vibes and Christmas spirit. There is a festival of trees, an outdoor holiday market, kids crafts, a gingerbread house display, and more.

The date for the 2023 festival has not yet been announced.

32. Festival of Trees and Traditions

Also in early to mid-December, the Festival of Trees and Traditions has become an annual celebration at the Wadsworth Atheneum Museum of Art in Hartford.

Local community members and artists decorate trees and wreaths to put on display in the museum, and each item is available to purchase to help fund the museum.

The date for the 2023 festival has not yet been announced.

33. Bethlehem Christmas Town Festival

Another Christmas festival takes place in — of all places — the little town of Bethlehem, Connecticut. This two-day festival features a Santa 5k run, hayrides, children’s crafts, tree lighting, fire truck Christmas light procession, and much more.

The 42nd annual festival is scheduled for December 1-2, 2023.

34. Winterfest and the Tunnel of Lights

The Connecticut Trolley Museum in East Windsor hosts an annual Winterfest and the Tunnel of Lights with more than 15,000 lights located both indoors and outdoors.

Outside, you can take a 20 to 30-minute trolley ride through the Tunnel of Lights while singing Christmas carols with the trolley operators.

The date for the 2023 festival has not yet been announced.

35. Fire & Ice Festival

The Fire & Ice Festival takes place in Putnam around Valentine’s Day and features an ice carving competition, ice bar, interactive ice sculptures, fire pits and torches, and fire demonstrations.

The 2023 festival is already past. Stay tuned for the 2024 date!

Winter day/weekend trips in Connecticut

While there are lots of lovely winter getaway destinations in Connecticut, below are a few of my favorite options:

Hartford: Connecticut’s capital city

The capital of Connecticut is filled with winter-friendly activities. See a show at the Hartford Stage or Bushnell Performing Arts Center. Visit the Mark Twain House and Museum or the Wadsworth Atheneum. Go ice skating at Veterans Memorial Ice Arena and then grab a warm cup of coffee at a cafe like Story and Soil or Semilla.

🛌 Where to stay in Hartford: The Goodwin

Washington: Small-town charm

The small town of Washington is quintessential New England with its white, steepled churches, historic homes, and narrow, curved roads. Nestled in the scenic Litchfield Hills of western Connecticut, this place is perfect for a quiet winter escape. Be sure to stop by The Po Cafe for a delicious breakfast or lunch.

🛌 Where to stay in Washington: The Mayflower Inn & Spa

Mystic: Coastal bliss

For a coastal New England winter getaway, consider visiting the historic seaport town of Mystic. Learn about Connecticut’s maritime history at the Mystic Seaport Museum or see an array of ocean life at the Mystic Aquarium.

Browse the shops and boutiques in downtown Mystic and taste fresh seafood at The Mariner restaurant.

If you’re a book lover, check out the Book Barn in nearby Niantic with its ginormous selection of used books.

🛌 Where to stay in Mystic: House of 1833 Bed and Breakfast

New Haven: University town and foodie paradise

New Haven is best known for Yale University, and it’s for good reason. Several of the city’s best winter activities are connected with the university: Sterling Memorial Library, Beinecke Rare Books & Manuscripts Library, Yale University Art Gallery, Yale Center for British Art, and the Peabody Museum of Natural History.

The historic New Haven Green is also worth walking through, which is in close proximity to Louis’ Lunch, BAR, Choupette Creperie & Cafe, G Cafe, Sitar, and a host of other great restaurants and cafes.

(New Haven has a great food scene and you could easily spend a trip hopping from one restaurant to the next!)

🛌 Where to stay in New Haven: Graduate New Haven

Wrap-up: Things to do in Connecticut in the winter

As you can see, there are plenty of things to do in Connecticut in the winter. Whether you live in or near Connecticut or are planning a visit from farther away, I hope this list has sparked some ideas of how to make the most of your time and chase away the winter blues!

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