Fun Things to Do in Connecticut: Ultimate Bucket List

A week into our northeast road trip, we cross over to the nutmeg state in search of inspiration for the perfect Connecticut bucket list. It’s the first New England state we enter since leaving Chicago. From the slow-rolling countryside and charming seaport villages to the historic city capitol and coastal drives, we discovered there are many amazing things to do in Connecticut! 

Connecticut bucket list of all the great things to see and do. Includes Yale University, the State Capitol, Mark Twain's House and Museum, Saville Dam with scenic drives and charming small towns.


Here are the must-see places and must-do attractions we think you should add to your CT bucket list trip.


1. The State Capitol

Although the city of Hartford is lackluster as a whole, there are a few things that make it worth a visit and the State Capitol is one of them.

Topped with a shiny gold dome, the marble Gothic building is easily one of our all-time favorites. The exterior is gorgeous; it is adorned with stained glass, sculptures, ornamental reliefs, and medallions.

Unique things to do in CT include a tour of the Hartford State Capitol Building
Are we in Europe? Nope, this beautiful building is in Hartford, Connecticut!

Typically, we find if a building is over-the-top on the outside the inside leaves something to be desired. Not at Connecticut’s capitol!

As we walk around, we discover an 18-foot impressive statue that once topped the dome, a model of the Civil War flagship Hartford and the wooden figurehead from the original ship, the statue of Nathan Hale, the Revolutionary War hero, the battle flags of Connecticut regiments from the Civil War, and a replica of the Liberty Bell.

Where: 210 Capitol Ave, Hartford, CT

Road tripping through the Gateway to New England? Here is the ultimate Connecticut Bucket List for your visit. All the cool and fun things to see and do.

One of the unique things to do in CT is a tour of the Connecticut State Capitol Building. Pictured is the large statue that once stood on top of the golden dome that can now be found inside.

2. Mark Twain’s House and Museum

If you’ve been following along on our adventures, you might remember when we took our nephews to Hannibal, Missouri to explore Samuel Clemens, aka Mark Twain’s, boyhood home or more recently his study and burial site in New York.

The man is a literary legend and I’m not only interested in his artistic genius but the man himself is quite intriguing.

Not only did he love to travel and considered himself a vagabond, but he was a literary celebrity.

He also dressed the part. Always wearing white from head to toe, even his untamed wild hair and eyebrows matched!

At the Mark Twain House and Museum, you get a glimpse into the lavish lifestyle that led him to financial ruin.

Built in 1847 for $45,000, the home has a medieval gothic feel with dark wood and rich colors. 

Road tripping through the Gateway to New England? Here is the ultimate Connecticut Bucket List for your visit. All the cool and fun things to see and do.
Touring the Mark Twain House – No pictures allowed inside

READ NEXT: 32 Best Things to Do in Hartford CT

No pictures are allowed inside, but on the tour, we learned Clemens and his family lived in the Hartford home for seventeen years and it is where he wrote many of his famous novels.

The house is filled with original furniture and even has silverware laid out on the dining room table etched with Olivia Langdon’s name, Twain’s wife.

If you are interested in American literature, Victorian architecture or history, the Mark Twain House and Museum is one of the best things to do in Hartford, Connecticut. 

Where: 351 Farmington Road, Hartford, CT

3. Picturesque Saville Dam

If you look for cool and unusual places on your travels, be sure to stop by Saville Dam and Reservoir.

Situated on the eastern section of the Farmington River surrounded by trees and blue water, the gatehouse is as Instagram-worthy as it gets.

It looks like a miniature castle with a stone turret and archways. 

Tip: The walk from the parking lot is on a 50 MPH road so stay within the walking area.

Where: 27 Saville Dam Road, Barkhamsted, CT

Road tripping through the Gateway to New England? Here is the ultimate Connecticut Bucket List for your visit. All the cool and fun things to see and do.
Saville Dam in Northwest Connecticut


4. Climb Mount Tom Tower

Take the short 1.30-mile loop trail to the summit of Mount Tom.

Climb to the top of the 34-foot stone tower for expansive views that extend to the Catskills in New York and Mount Everett in Massachusetts. 

Where: Mount Tom State Park, Washington Depot, CT

The stone tower at Mount Tom State Park in CT.
Mount Tom State Park is one of the oldest parks in Connecticut.

5. Hike to Kent Falls

Don’t miss this lovely little park situated in the quaint rolling countryside of the Litchfield Hills region. 

The stroll to the cascading waterfalls begins across a red-covered bridge and is only 1/4 of a mile long with three observation decks. 

Where: 462 Kent Cornwall Road, Kent

The red covered bridge at Kent Falls State Park.
Walk across the covered bridge to the waterfall trail at Kent Falls State Park.
A bridge and waterfalls of Kent Falls State Park
Kent Falls State Park is situated within the Litchfield Hills region known for antique stores, art shops, and historic homes.

6. Experience Gilmore Girls Small Town Charm

If there ever was a television show that exemplified the nuances of small-town living, it is Gilmore Girls.

The rural communities of northwest Connecticut provided the inspiration for the show.

And although I didn’t necessarily get the GG vibe in one town as a whole as I did later on in the trip (keep reading below) we did find a few Rory and Lorelei-worthy stops.

Connecticut Road Trip: Small Town of Washington
Town Hall in Washington, Connecticut

Washington: browse the aisles at the Washington Food Market (Doose’s Market), walk the grounds at Mayflower Grace like the show’s creator, Amy Sherman-Palladino (Independence Inn), try the coffee at Martys (Luke’s Diner), and pick up a book at Hickory Stick Bookshop (Stars Hollow Books).

Gilmore Girls Tour of Connecticut.
The Mayflower Grace Inn

Woodbury: Go shopping at Farmhouse Antiques (Mrs. Kims).

New Milford: Stop to see the green and white gazebo similar to the one in the Stars Hollow Town Square.

Road tripping through the Gateway to New England? Here is the ultimate Connecticut Bucket List for your visit. All the cool and fun things to see and do.
Discovering small-town charm in New Milford, Connecticut.

7. Walk Around Yale University Campus

Yale University is the third-oldest institution of higher education in the United States. Built in 1701, it is also one of nine Colonial Colleges built before the Revolutionary War.

The campus is enormous so put on your walking shoes and see what Ivy League is all about.

Do not miss the Old Campus surrounding Phelps Hall; it is the oldest part of the university and is where freshman students call home.

Make sure to see the Phelps Gate, College House, Congregational Church, and rub the toe of former Yale president Theodore Dwight Woolsey for good luck.

Connecticut Bucket List: Yale University tour, one of the oldest higher education institutions in America.
Looking for some good luck at Yale University!

Another must-see is the Beinecke Rare Book and Manuscript Library. It is a new addition to the university with a contemporary design, but you will not want to skip it.

It is home to Yale’s oldest books, including a copy of the Gutenberg Bible, and the interior is remarkable. You will certainly want to add this one to your Connecticut road trip.

Top Connecticut Things to Do: Beinecke Rare Book & Manuscript Library
How cool is the Beinecke Rare Book & Manuscript Library?

Where: Yale Visitor Center, 149 Elm Street, New Haven, CT

8. Try New Haven-Style Pizza

All that walking will make you hungry so head over to Little Italy on Wooster Street.

Stop in Frank Pepe Pizzeria Neapolitan for a coal-charred thin-crust pizza that has made this street famous.

Where: Frank Pepe, 157 Wooster St., New Haven, CT

Connecticut Bucket List: New Haven Pizza near Yale University.
New Haven-style pizza in Little Italy

9. Lighthouse Point Park

Just twenty minutes southeast of downtown New Haven is a pretty little park featuring an 80-foot lighthouse known as the Five Mile Point Light and an early 20th-century carousel. 

The current tower was constructed in 1847 and is listed on the National Register of Historic Places along with the light keeper’s house and the 1905 carousel. 

The coastal view from the Lighthouse Point Park in Connecticut.
The rocky shore of Lighthouse Point Park.
The Five Mile Point Lighthouse, one of the many lighthouses of Connecticut.
The Five Mile Point Light is in the Long Island Sound and was extinguished in 1877.


10. Visit the Real Stars Hollow Town of Guilford

Even though I enjoyed wandering around the small towns of northwest Connecticut, no one area seem to capture the all-encompassing Stars Hollow ambiance.

That was until we stopped in Guilford.

Road tripping through the Gateway to New England? Here is the ultimate Connecticut Bucket List for your visit. All the cool and fun things to see and do.
Gilmore Girls Magic in Guilford, Connecticut

The expansive town green is surrounded by buildings such as the Town Hall, a hardware store, a colorful chocolate shop, a small market, and a book store.

Top things to do on a Connecticut Road Trip.
Guilford, Connecticut: The Real Stars Hollow

We were immediately drawn into the quirky close-knit community.

A man asked us if we’d like a free barbecue grill he purchased at a garage sale that was barely used when he saw us browsing the selection at the hardware store, another stranger thought he photo-bombed a picture I was taking so he parked his car and got out to apologize, then we saw a cute older couple dressed to the nines on their daily walk around the square.

Can it get any more Stars Hollow than that?

11. Walk Along Connecticut’s Longest Stretch of Beach

With over 2 miles of shoreline, Hammonasset Beach State Park in Madison is one of the most popular attractions in the state. 

Take a stroll on the boardwalk, visit the nature center, swim, or relax in the sand on Connecticut’s longest stretch of beach. 

12. Drive a Loop around the Connecticut River

Flowing through four of the six New England states, the Connecticut River is the longest river in the region. From Old Saybrook head north on Route 154 to the historic town of Essex.

Stroll through the quintessential New England town with early Colonial homes, a waterfront harbor, and small boutique shops.

If you’re looking for things to do in Connecticut for couples, book a room at The Griswold Inn, the romantic Revolutionary War-era inn, and stay in the picture-perfect town overnight.

Here is the ultimate Connecticut Bucket List for your visit. All the cool and fun things to see and do. If you're looking for things to do in Connecticut for couples, take a road trip to the historic town of Essex.
The Maritime Community of Essex in Connecticut is loaded with small-town charm.

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At Haddam, detour to Eagle Landing State Park, for a view of the East Haddam Swing Bridge and Goodspeed Opera House, a unique theater where the musical, Annie, first premiered.


13. Visit Sherlock Holmes’ Whimsical Castle

Gillette Castle State Park is on the Connecticut River like the above stops but deserves its own special place on our list.

Even if you do not drive the loop around the river, the castle should make your itinerary as one of the most unique things to do in CT.

Connecticut Top Things to Do: Gillette Castle State Park
View of the Connecticut River from Gillette Castle, one of the most unique things to do in CT. 

Perched high above the river with beautiful views, the castle was built between 1914 and 1919 by William Gillette, the first Sherlock Holmes. The building looks more like a stone fortress from the Medieval era than an actual home.

Unfortunately, tours are only available from Memorial Day to Labor Day so we weren’t able to adventure inside. But the grounds are open year-round and the curtains pulled back so we were able to take a sneak peek.

Things to Do in CT: Gillette Castle State Park in East Haddam.
Connecticut Bucket List: The crazy cool Gillette Castle.

After reading the interior is just as extraordinary as the exterior with puzzle-like locks, trick mirrors, and secret passageways, we are definitely adding it back on our list of places to get back to.

Where: 67 River Road, East Haddam

14. Harkness Memorial State Park

After Labor Day, Connecticut state parks are free so we stumbled upon Harkness Memorial State Park on accident. We turned in one morning thinking it would probably have a trail or two to stretch our legs.

Connecticut Road Trip: Best Things to Do
Connecticut Bucket List: Botanical gardens at Harkness Memorial State Park

We were pleasantly surprised to find an estate with a flourishing garden and ocean views.

Where: 275 Great Neck Rd, Waterford

Connecticut State Parks
Loving the gardens at Harkness State Park

15. Try a Connecticut-style Lobster Roll

We are on the ocean! Do you know what that means? Lobster rolls are THE hot menu item, but there’s a catch. Pun intended.

The typical New England lobster roll is served cold and mixed with mayo and diced celery. Since I am not a fan of mayo, I am happy to find Connecticut style is served warm with melted butter.

Road tripping through the Gateway to New England? Here is the ultimate Connecticut Bucket List for your visit. All the cool and fun things to see and do.
Connecticut-style Lobster Roll is my favorite – just butter, please!

Stop in the tiny town of Noank at either Abbott’s Lobster in the Rough or Ford’s Lobster Restaurant, order a lobster roll, grab a picnic table, and enjoy the beautiful view.

Hot Tip: At both establishments, it’s BYOB, bring your own booze.

16. Find Giant Seashells at Bluff Point Beach

Bluff Point State Park is an 806-acre park that’s also designated a coastal reserve.

Tucked alongside the Pequonot River, it’s a beautiful place to hike, bike, bird watch, kayak, fish, or search for seashells and sea glass. 

Where: 55 Depot Road, Groton

The walking trail at Bluff Point State Park, Connecticut.
While you explore Connecticut, head over at Bluff Point State Park to discover an undeveloped coastline.
An entire beach of big shells at Bluff Point Beach.
Look at all these big beautiful shells at Bluff Point Beach!

17. Board the World’s Last Whaling Ship

What is the most visited place in Connecticut? Most of the above places make that list including this must-do attraction, the Mystic Seaport Museum.

Since our travels this year have taken us to a lot of museums, albeit fantastic experiences, we are feeling a little museumed out. We considered skipping the seaport museum, but we are thankful we did not.

Things to Do in CT: Mystic Seaport and Museum, a mus-do.
Connecticut Bucket List: Mystic, Home of Mystic Seaport

It’s not only the largest maritime museum in our nation, it also has the world’s last wooden whaling ship, the Charles W. Morgan.

If you are planning a family trip, it’s one of the top things to do in Connecticut with kids and adults alike. 

Spend the day among historically restored buildings and sailing ships learning about the whaling industry, preservation techniques, and what life was like in 19th century America.

Visit Mystic: Top Things to do in Connecticut in the fall

Mystic Seaport is a must-see museum on your road trip through Connecticut.
All Aboard! Charles W. Morgan, a restored whaling ship at Mystic Seaport.

18. Eat at Mystic Pizza

And finally, if you are a Julia Roberts fan like me, don’t forget to visit Mystic Pizza in town. Made famous by the 1980s coming-of-age movie, it’s a can’t-miss establishment. 

Inside bar at Mystic Pizza that has a neon sign saying, "A slice of Heaven"

If you are headed to Connecticut for a road trip, check out these cool places and fun things to do.

Have you been? What would you add to our Connecticut Bucket List? Share your favorite things to do in Connecticut below in the comments.

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Here is the ultimate Connecticut Bucket List for your road trip. All the cool and fun things to see and do in and around the state.


Follow Angela:

Angela E. is a travel writer from the Chicagoland area who has visited all 50 states in the US and has traveled extensively around the world. She is passionate about exploring the great outdoors and hiking in particular. Her love for nature has taken her to some of the most beautiful locations on the planet. She has written extensively about her travels on her own website, Dang Travelers, and has been published in collaboration with other travel websites and multiple visitor bureaus around the country.

22 Responses

  1. Lola La Paz

    You are doing an awesome road trip over there! That library does look amazing! And what about the size of that pizza? Looks like Connecticut has it all; nature, culture and good food!

  2. Carol Colborn

    Oh my! We only went to Yale and Mark Twain’s house. We missed so much. That State Capitol is very different from other states. And a visit to the last whaling ship would have been cool!

  3. Jane Frith

    Connecticut is one of the few US states we have not yet visited, but we hope to get there in the next couple of years. I shall definitely want to visit Mark Twain’s home and I doubt if I will be able keep Peter out of the Seaport Museum. And I shall definitely be sampling those delicious lobster rolls!

  4. Alison

    Connecticut looks amazing! You have really highlighted some fantastic places to visit. I would love to see Mark Twain’s home ( no idea he was extravagant), the Gilford girls town, the Yale library and that whaling ship! Thanks for all the great info. Love road trips.

  5. Jenn and Ed Coleman

    Connecticut looks just like I expected it to. I have a thing about visiting author’s homes since going to the Hemingway House. It’s fun to use it as a prompt to write a little memoir in the style of the author. Lots of Kerouac here in Central Florida (which is loads of literary fun if you give it a try). However, the top of my list was something Twainy. Seems like your bucket list is perfect for that. You could make it a twofer and write a little coming of age ditty a-la Mystic Pizza too.

    • P vinod Menon

      I have a book on hiking in connecticut maybe old but still can use it from the berkshires to the coast first published by sue and Gerry hardy lovely book since I like small hikes

  6. Michael Hodgson

    Love Connecticut! Much of my exploration there has been in the parks and trails with a little into the cities and historical sites. Mark Twain’s home is fantastic for sure. Now, about that Lobster Roll … a really good lobster roll, be it from Maine (the best) or elsewhere, should be so well done you never taste the mayo, even if you hate it. 😉

  7. Astrid Vinje

    We haven’t really spent much time in Connecticut, to be honest. It’s always usually just a stop over on our way to Massachusetts. We did stop in Mystic for pizza at the restaurant from the Julia Roberts movie, “Mystic Pizza.” I didn’t realize Mark Twain’s house is there. That’s a good reason for me to come back and actualy spend time exploring Connecticut.

  8. melody pittman

    Connecticut is on my bucket list for the spring so this is definitely getting filed away. Great things to see and do!! I can’t wait to explore Mystic, see the state capitol, and the Gilmore Girls stuff. That pizza…OMG that thing is enormous! Looks so tasty!

  9. Lara Dunning

    I would love to explore this area of the US and many of my ancestors came over early and settled in the New England area, one is one of the founders of Hartford. I really enjoyed your post and learning about the things to do there. I would definitely want to visit the castle and the dam!

  10. Ree

    There are some great choices here! I was born and raised in CT and there are things here I’ve never done. Thanks for the ideas!

  11. Alison

    Some added attractions, growing up here some other worthy places of interest are Greenwich for the upscale or window shoppers and Litchfield are are two of my most favorite destinations. To the north of our state is a beautiful New England race track made famous by Paul Newman, called Lime Rock Park. Even if you aren’t into automobiles, I enjoy it myself. Farmington Polo Club also has many events besides horses, charities host numerous reasons to visit there most of the year.

  12. Susan Lewis

    If you travel further west on the coast you will hit the town of Norwalk, Ct. I spent a great afternoon touring a civil war era mansion, the Lockwood Mathews Mansion, built in 1861 by Legrand Lockwood. The Precursor to the guided age mansions ofNewport, the woodwork and inlays alone are magnificent. Great docents that were very knowledgeable.

  13. George

    One location often overlooked is East Haddam, CT. Home to the Goodspeed Opera House and the Goodspeed Airport. One of the prettiest small generation aviation airports in the country.
    It also boasts the East Haddam Swing Bridge, one of the longest swing bridges ever built and still in daily operation in the US. Plenty of places to stop and eat while here.

  14. Kaarina

    There are so many good restaurants to stop at throughout Connecticut also to help keep you going! Nothing like a good out of the way local place to charge up and refuel.

  15. Ann

    Also visit the little-known Boothe Memorial Park and Museum in Stratford CT. Set at the turn of the century, this 30 acre park is the site of the Boothe brothers homestead, train museum, blacksmith shop, nature museum and 13 other small buildings. Only open Mid-May – Labor Day

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