From Greenwich to New Haven: The Best Places to Visit in Connecticut

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Gillette Castle
Gillette Castle, a striking historical home completed in 1919, is now open to the public in Gillette Castle State Park. Photo credit: Gillette Castle State Park

Connecticut is often treated as a way station rather than a destination, but this New England state has fantastic things to do, whether for a weekend getaway or longer trip. We started traveling here when our kids were little, since it was a (mostly) short trip from New York City, and the ideal destination for squirmy or car-sick prone kids. We uncovered a wealth of activities, from big city art museums to hiking trails in small towns. There are many sites on the National Register of Historic Places, along with major tourist attractions like Mystic Seaport.

Best Places to See: Where to Go in Connecticut

You can stay coastal, along I-95 and the Long Island Sound, or head up the scenic Merritt Parkway and the small towns along the Connecticut River. And many Connecticut attractions are easily accessible by trains, so you don’t have to drive.

Read More: J House Greenwich CT Review: Dreamy Grownup Getaway

Bruce Park in Greenwich, CT
Bruce Park, where kids can run around after visiting the Bruce Museum in Greenwich. Photo credit: Judy Antell

Weekend Getaway in Greenwich

Greenwich, just over the border from New York state, has tourist attractions for the young and more mature. When our kids were younger, we spent weekends at the Bruce Museum, a natural history museum currently undergoing a $60 million expansion. What particularly drew us to the Bruce Museum were the kid friendly exhibits, and the large playground right across the street where we could let the kids run wild after the short train ride or long drive here.

There is also a large park, Bruce Park, less than a mile from the Bruce Museum.

SheBuysTravel Tip: If you aren’t familiar with New York City traffic, ignore distance as a measure of time. A 20 mile trip can take 30 minutes or three hours, depending on what time of day you leave, what time of year you are traveling and how much your kids like to poke each other in the back seat.

The Greenwich Audubon Center is great whether you are into birdwatching or just using the hiking trails at the nature center. The Nature Play Trail is great for families with strollers. It is also wheelchair accessible.

Note: Because the Greenwich Audubon Center is a bird sanctuary, dogs are not permitted.

The Glass House in Connecticut
The Glass House is nestled in natural beauty. Photo credit: Judy Antell

More in Fairfield County: New Canaan and Norwalk

New Canaan

The Glass House, a National Trust Historic Site, offers tours April through December. This must-see attraction in New Canaan requires advance planning, as the tours sell out.

The Historic Site includes 13 structures along with the signature Glass House: an art museum, a sculpture gallery, a Pavilion in the Pond and a Ghost House. If you want to see the fantastic landscape, take either the extended tour or self-guided tour. We did a self-guided tour, and docents were able to fill in gaps that the leaders of guided tours would have provided.

Note: Tours leave from the Visitors Center, which has no public parking. You take a short shuttle ride to The Glass House from there. Children have to be at least 10 years old to come on tours.

Downtown New Canaan has lovely restaurants and boutiques, but for hotels, you have to go to Greenwich or Norwalk.

Kayaking in Norwalk Harbor
Kayaking in Norwalk Harbor. Photo credit: Norwalk Sailing School


The Mystic Aquarium may be better known, but the Maritime Aquarium at Norwalk is another great option for marine life lovers. There are seals, sharks, otters, penguins, jellyfish, a touch tank and a 4D theater.

For more on the water, at Norwalk Sailing School you can learn to sail, rent a kayak, or paddleboard, or take a kayaking guided tour of Norwalk Islands and the harbor.

Other cultural attractions in Norwalk include the interactive Stepping Stones Museum for Children and the Lockwood-Mathews Mansion Museum, a National Historic Landmark. The mansion, which is closed in winter, can only be seen by guided tour. If you don’t want to commit to a guided tour, or have squirmy kids, special mini tours allow you to see the first floor Period Rooms for a reduced fee.

Read More: Top 5 Man-Made Beaches in Connecticut

Apple picking in Deep River, CT
Apple picking in the Connecticut Valley, not just for kids. Photo credit: Judy Antell

Deep River

One of the best small towns in Connecticut is Deep River. When we had a wedding in Deep River, my husband and I, along with a few other couples, turned it into a New England weekend getaway. We stayed at an inn and went hiking and apple picking.

Hiking trails in Wadsworth Falls State Park may not provide the the waterfalls you expect in a state park with “falls” in its name, but the secluded hiking trails more than made up for that. The natural beauty of the area shines in fall, where you can see the leaves changing and go apple picking at Scotts’ Connecticut Valley Orchard.

But you can enjoy the bucolic New England setting year round. The hiking trails are great for snowshoeing in winter. Stonington Vineyards offers tastings all year. In nice weather, you can picnic at the winery, which has a Friday Night Summer Concert Series in July and August. Another winery, Chamard Vineyards, has a farm-to-table bistro.

Gillette Castle State Park, in East Haddam, CT, has wooded hiking trails open free year round. Even more important, the restrooms and visitor center are open as well. William Gillette built the 24 room castle in 1914. It is open for guided tours May to September. You have to pay for the guided tours, and reservations well out quickly, so be sure to reserve in advance. We didn’t think far enough ahead and were shut out since we had a large group.

Devil’s Hopyard State Park also in East Haddam, has hiking trails, along with bicycling paths, fishing and camp sites.

Essex Steam Train
One of the unique Connecticut attractions, the Essex Steam Train. Photo credit: Judy Antell

Old Saybrook

Close to Deep River and East Haddam is the waterfront small town of Old Saybrook. The Connecticut River flows into Long Island Sound here, in one of Connecticut’s oldest towns. Katharine Hepburn lived in Old Saybrook, and the Katharine Hepburn Cultural Arts Center, a theater also known as The Kate, has a free museum devoted to the actress.

In addition to its beaches, a Main Street filled with local restaurants and boutiques, and a marina where you can sail in and stay, Old Saybrook is a great place for bicycle riding. And if you are traveling with children, you are near the Essex Steam Train. See the natural beauty of Connecticut River Valley, by steam locomotive and riverboat.

For a bit of culture, the Florence Griswold Museum in Old Lyme is an art museum with beautiful historic gardens. The museum is on the National Register of Historic Places.

Camping hut at Lake Compounce
Deluxe hut camping about 40 minutes north of New Haven at Lake Compounce Campground. Photo credit: Lake Compounce

City Time in Connecticut: New Haven

New Haven is both a city and a university small town. Yale University has cultural attractions like free Yale University Art Gallery, a fine arts museum with programs for families and children. The Gallery, the oldest university art museum in America, has collections ranging from ancient to modern and contemporary art, with paintings, sculpture, drawings and photography. The Yale Peabody Museum, a Natural History museum, reopens soon after a three year closure for renovation. We visited it many times in its previous iteration.

We have traveled to New Haven by train from New York City. New Haven is equally convenient by train from Boston.

The Yale Bowl, a National Historic Landmark, is the premiere place to watch a college football game. Plan well in advance for tickets. You can play a really long game: take a tour of the Yale University campus with your kids. The Yale Visitor Center has a free Kids’ Architectural Treasure Hunt brochure and Yale students get a ticket to home games.

Whether or not you have a kid who might want to go to Yale University, the campus is a beautiful place for a stroll. It includes Connecticut Hall, on the National Register of Historic Places.

Lake Compounce, an amusement park in Bristol, is a simple drive from New Haven. The seasonal attraction includes a waterpark, roller coasters and a carousel built in 1898 and moved to Lake Compounce in 1911.

If you are traveling by RV or want a low cost overnight option, Lake Compounce has cabins, huts, camp sites and RV sites. And you get discounted tickets to the amusement park.

Mark Twain House in Hartford
The Mark Twain House & Museum is one of the top Connecticut attractions. Photo credit: Judy Antell


Connecticut’s capital city, Hartford, has tourist attractions like The Mark Twain House & Museum, Harriet Beecher Stowe House and Wadsworth Atheneum Museum of Art.

The Gothic Revival National Historic Landmark Mark Twain House, where the author lived and raised his family, is open by guided tour only. You can walk from The Mark Twain House & Museum to the Harriet Beecher Stowe House, another historic site. Again, the Stowe House is only open by guided tour. But you can explore the 11 gardens around the property for free. If you take both guided tours, you get a discount.

Keeping full employment for tour guides, the historic Hill-Stead Museum is only open by guided tour. It is surrounded by walking trails which you can explore for free. on your own. It is one of the most beautiful places in the state of Connecticut.

The Wadsworth Atheneum art museum in downtown Hartford is is the oldest continuously-operating public art museum in the US. Housed in five spectacular buildings in Gothic Revival, Beaux-Arts, International modern and Brutalist styles, the architecture alone is reason to visit. The art is equally inspiring, with antiquities, Surrealist paintings, Hudson River School landscapes and contemporary art.


Mystic Seaport, a recreated 19th century seaport village, uses historic buildings from around New England. It has a working shipyard, historic Greek Revival houses, a printing press and cooperage, among dozens of building you can explore. There are also a planetarium, a children’s museum and the world’s last authentic wooden whaling ship. The Mystic Seaport, run by Mystic Seaport Museum, also includes an art gallery at the historic Meeting House and a Research Center focused on maritime research.

If you are planning to visit Mystic Aquarium, be sure to buy a combination ticket so you save some money. Don’t go in one day – there is definitely too much to see.

Mystic Aquarium has penguins, a jellyfish gallery, a ray and shark touch pool and the only beluga whales in New England. You can see sea lions and seals, and learn about the differences between them. Don’t miss the Marsh Trek, where you can see ducks, herons, frogs and marsh plant life.

Explore more natural beauty around Mystic at Denison Pequotsepos Nature Center. The nature center has wildlife exhibits (there is a fee) and over 10 miles of trails, which you can roam for free.

Another way to sightsee is to rent a kayak from Blue Heaven Kayak & Paddle Board Rentals. You can kayak along the Mystic River and see another side of this tourist attraction.

Judy Antell is an empty-nester mother of 3 who spends a lot of time visiting her daughters. Why don’t they live in Brooklyn? Judy and her husband love to travel, by bike, car, or plane, whether to see their kids or have friend or couple adventures, mostly centered around vegetarian food.
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