20+ Connecticut Bucket List Ideas for Every Season


Connecticut is a gorgeous New England state with stunning scenery all year long, plenty of things to do for the whole family, and a quaint charm that keeps visitors returning again and again. 

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Whether you’ve gone and want to return or you’re placing this state on your bucket list of places to see, you’ll be glad you took the time to visit. Here are the best things to do across the state for the whole family during all seasons of the year.

Connecticut Bucket List Destinations

Connecticut may be small, but it offers a ton of things to do. In addition to the season-specific items on this list, here are a few places you should visit no matter what time of year you go.

1. Yale University

If you wanted to go to Yale but never got there, now’s your chance. You may not be graduating with an MBA, but you’ll get to stroll around the same gorgeous campus, admire the architecture, and visit the Yale Peabody Museum of Natural History. This is a must-do any time you visit.

2. Bluff Point State Park

Looking for a location that provides ample opportunities to hike, bike, fish, walk, and camp? Head to Bluff Point State Park where 800 acres of pristine forest, hiking trails, and beach await your visit.

3. Devil’s Hopyard State Park

Explore this 860-acre wooded park with trails galore, wood bridges, stone underpasses, and gorgeous waterfalls. There’s something for everyone here.

4. Hidden Valley Preserve

Nature lovers will enjoy this hidden Connecticut gem. The 650 acres provide access to miles of hiking and walking trails, an abandoned quartz mine, rivers, stunning forest foliage, abundant flowers during spring, and plenty of wildlife.

Spring and Summer Connecticut Bucket List Ideas

Spring and summer provide opportunities for endless hiking, exploration, and viewing of some of the most stunning scenery anywhere around. We know you’ll love these must-visit places.

5. Wander through Gillette Castle State Park

A castle in Connecticut? Yep! The stone castle was designed in 1914 by William Gillette, the original American actor who became famous for playing Sherlock Holmes. 

6. Take a stroll through Harkness Memorial State Park

Walk around this estate-turned-state park with gorgeous buildings, lush botanical gardens, and ocean views. Hit it during the right time of year, and admission is free! That’s right—go after Labor Day and you’ll get your whole family in without paying a dime.

Pro tip: If you’re going to make a travel bucket list, be sure to add a state park or two, like this one.

7. Visit the Mark Twain House

The Mark Twain House and Museum is located in Hartford, where it was built in 1847 for $45,000 or around $1.5 million in today’s dollars. Twain, or Samuel Clemens, lived in the Hartford residence with his family for around 17 years, and it’s here that he wrote many of the novels he became famous for. 

You can tour the home inside and out and learn all about the life of the famous writer while there.

Pro tip: No time for a visit? Take the virtual tour, instead!

8. Visit Enders State Forest

Enders State Forest is well known for Enders Falls, a collection of six waterfalls that cascade into one another and collect into a natural pool at the bottom. Go in summer and dip your toes in to cool off after a long hike.

9. Explore Kent Falls State Park

Kent Falls is another stunning place to view, you guessed it, gorgeous waterfalls. Hiking trails are lined with stairs and observation decks, providing ease of access and stunning views from every angle.

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Fall and Winter Connecticut Bucket List Ideas

Fall and winter in Connecticut are beautiful times with stunning foliage, picturesque scenery, and something special for everyone. Here are the things we suggest for a fall or winter itinerary.

10. Drive along the Connecticut River

For a drive that provides plenty of gorgeous scenery and a trip through quaint New England towns, take a drive along the Connecticut River. 

Start out heading north on Rt. 154 from Old Saybrook toward Essex. Plan a stop in Essex to enjoy the quintessential New England-style homes and shops before heading back the way you came.

Pro tip: Go in fall for gorgeous, picture-perfect New England scenery with plenty of fall foliage. Choose winter if you’d rather a snowy landscape, instead.

11. Go on a train and riverboat excursion

Start your journey at the 1892 Essex Station and enjoy a 2.5-hour journey into the heart of the Connecticut River Valley and back again. Visitors have the option of booking a train ride, a riverboat excursion, or both. This activity is fun for the whole family.

12. Photograph stunning fall foliage

No matter where you go if you visit Connecticut during the fall, you’ll be awed by vibrant reds, brilliant oranges, and sunset yellows that adorn the trees. Connecticut is one of the best New England states for viewing fall foliage, and the stunning scenery will greet you at every turn.

Kid and Teen-Friendly Connecticut Bucket List Ideas

There are plenty of things to do with young and growing travelers. Here are just a few of the things that Connecticut has to offer.

13. Check out the Mystic Seaport Museum

The Mystic Seaport Museum is the largest maritime museum in the US, and it has so much to do that you might stay for a whole day. You can learn about the whaling industry, board the world’s last wooden whaling ship, explore historically restored buildings, and learn about life in 19th-century America.

14. View real dinosaur tracks

If you visit the Dinosaur State Park and Arboretum, you’ll get to see one of the largest dino track sites in North America. There’s plenty to see and do, so plan a good half-day at this stop. 

15. Visit the oldest amusement park in the US

The Lake Compounce Amusement Park has continuously operated since 1846 and is a Connecticut institution. There are plenty of things to do year-round, but if you want a light show, go during the winter where you’ll enjoy a holiday light spectacular.

16. Visit the PEZ Museum and Factory

No childhood would be complete without the introduction of PEZ. Now kids of all ages can see how PEZ is made and enjoy exhibits like the world’s largest PEZ dispenser and a motorcycle made entirely of PEZ.

Couples Bucket List Ideas in Connecticut

Cozy up to your special travel partner and enjoy these Connecticut bucket list items together.

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17. Go on a fondu date

If fondue, wine, and charcuterie sound like your thing, head over to Ballou’s Wine Bar in Gulliford. Started by a husband and wife team after their trip to Europe, you’ll enjoy a European café-like atmosphere, scrumptious offerings, and a beautiful outside or indoor setting. 

18. Cruise the Thimble Islands

Connecticut has its own archipelago of around 100 small islands right off the coast. Plenty of local tour companies offer cruises around the islands where you can bask in stunning scenery and spot abundant wildlife. 

While fun for the whole family, this quiet and enjoyable trip is a perfect couple’s activity if traveling with your significant other.

Pro tip: Ask your tour guide for stories behind the names of Potato Island and Mother-In-Law Island.

19. Overnight in a National Historic Inn

Enjoy staying in Captain Grant’s 1754, a historic B&B that first opened in 1754. Each room has a working fireplace and stunning decor. Guests are treated to a made-to-order breakfast on the deck during summer months or inside by a cozy fire during winter. Extras like dessert, wine, soda, and beer are available and complementary all day.

20. Traverse a swinging footbridge

Stroll along the Henry David Thoreau footbridge hand-in-hand and take in the lush scenery while you do. The bridge is 120 feet long and has quotes from Thoreau along the sides extolling the beauty of nature.

Bucket List Foods and Restaurants in Connecticut

You can’t have a travel bucket list without including a food bucket list, too! Here are some of the must-eats in the fair state of Connecticut.

21. Try a slice of New Haven-style pizza at Frank Pepe’s

You might have had pizza, but you probably haven’t enjoyed a New Haven-style pie. This pie is made on a coal fire instead of wood and turns out a super-thin, crisp, and perfectly chewy crust. 

Order yours from Frank Pepe Pizzeria Napoletana for a taste of the original New Haven-style pie first cooked up in 1925. Frank Pepe’s has locations all over Connecticut and is still run by the family.

22. Enjoy a lobster roll

If you’re a lobster lover, you’ll rejoice over this Connecticut creation. To create this dish, take hot lobster drizzled with butter and stuff it into a toasted roll. Voila! A hot melt-in-your-mouth lobster roll.

You can get these at any restaurant that offers seafood on its menu, and you won’t go wrong no matter where you decide to sample one.

23. Chow down on apple cider donuts at Lyman Orchards

Apple orchards are plentiful in Connecticut, and that means apple cider donuts! You’ll find this treat everywhere during fall apple season, but you’ll enjoy it the most at Lyman Orchards.

Lyman Orchards is the oldest apple orchard in Connecticut with a history dating back to 1741. It served as a stopping point in the Underground Railroad and is now in its ninth generation of family ownership.

Pro tip: This is a fall trip item, so be sure to visit from late August to mid-October for apple season.

24. Try a steamed cheeseburger

Steamed cheeseburgers? Yep, these burgers made to order are steamed, not grilled. You might think it sounds strange right now, but once you’ve had one, you’ll wonder where they’ve been your whole life. 

Pro tip: Try one at Ted’s or K LaMay’s in Meridian. Bonus points if you can get a seat at the counter and watch how they’re made!

Discover Connecticut

Whether you decide to explore this stunning state solo, with your entire family, or with your significant other, you won’t be disappointed. In fact, there are so many things to do, you might have to plan a second trip to see them all! 


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