Destinations North America

5 Unique Connecticut Winter Day Trips You’ll Love

Looking for interesting Connecticut winter day trips? These day trips will give you something to look forward to during the cold winter months ahead. I’ve broken down the locations by interest so you can experience a trip that is unique to you.

Art Enthusiast – Yale University Art Gallery, New Haven

The Yale University Art Gallery is the perfect spot for art enthusiasts of all ages. The gallery was founded in 1832. This makes it one of the oldest college art galleries in the whole United States.


The gallery’s collection includes works of art from Africa, Asia, Europe and Indo-pacific regions. Address: 1111 Chapel St, New Haven, CT 06510 Website: Yale University Art Gallery

Architect Major – Topsmead State Park, Litchfield

This beautiful tutor is a dream to look at. The cottage is open in the summer and fall. Don’t let that stop you from visiting in the winter.

The park is open year-round. Imagine exploring this place when its covered in snow. Check out my post, Topsmead State Forest Cottage, for a look inside the cottage. Address: 46 Chase Rd, Litchfield, CT 06759 Website: Topsmead State Forest (

Engineering Major – New England Air Museum, Windsor Locks

Any aviation engineer lover will love this museum. The New England Air Museum is the perfect Connecticut winter day trip for engineer lovers of all kinds.

Whether you love the U.S. space program, commercial aircraft or military planes, this is the place for you. This museum is the largest aviation museum in the Northeast. I talk more about the museum in my post, How to Visit the New England Air Museum. Address: 36 Perimeter Rd, Windsor Locks, CT 06096 Website: New England Air Museum – New England Air Museum (

Shopaholic – Downtown Westport

Downtown Westport is the perfect place to go shopping.  There are chain stores that you’ll recognize suggest The GAP, J. Crew and Anthropologie.  What sets this area apart are the unique one-of-a-kind small businesses. Fig Linens and Home sells luxury bed linens and home decor. The Westport Bookshop is a charming used bookstore. Then there is Tiffany & Co. Downtown Westport has something for every type of shopaholic.


This area is not indoors. Though I still suggest it as a great Connecticut winter day trip location.  Everything is close together and the stores located on Main Street have entrances facing both the street and the parking lot. This means not having to walk all the way around to get to your car in inclement weather.

Outdoors Lover – Sound Sailing Center, Norwalk

Have you ever heard of frostbite sailing? It’s the exhilarating feeling of sailing through the water in frigid temperatures.


Does it sound crazy to some? Maybe. Is it still an awesome experience? Yes. Sound Sailing Center offers frostbite sailing for sailors. Address: 54A Calf Pasture Beach Road, Norwalk, CT 06855

Is there a place that I missed? What are the places you love to head to during the colder months? What tops your list of Connecticut winter day trips? If you don’t live in Connecticut, what do you love doing in the winter where you live? Website: Sound Sailing Center | Instruction, Membership, Sales | Norwalk, CT

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