Does life imitate art, or art imitate life?
Not sure this guide can provide an in-depth answer to that question.
But in this case, you’re likely reading this because you’re hoping to imitate art.
At least, enough to make your dating life a little more glamorous.
But either way, there’s no question that dating is an art form. And why not steal an idea or two from the pros?
Hence, a guide to date ideas in CT that can recreate some of the most iconic dates from your favorite TV shows and movies.
23 of the best date ideas in CT
Sure, there are plenty of romantic things to do in Greenwich, CT. We’re an expert on planning romantic getaways in our hometown.
But what about the rest of the state?
There are so many romantic things to do in CT, it’s hard to choose. So we narrowed options down to date ideas in CT that recreate movies and TV shows.
And this writer is a millennial, so many of these references are a bit dated, admittedly.
We’ll cover the full lifecycle of dating, starting with fun first dates. Afterwards, Connecticut date ideas for:
- Outdoor dates
- Evening dates
- Even romantic road trip suggestions
Connecticut will be sure to rekindle (or ignite) the romantic flame in you both.
3 fun first dates in Connecticut
The goal of a first date is to keep it light without creating a platonic vibe.
The best rule of thumb is to pick an activity that you’re confident you’ll both enjoy. That way, you can talk without the risk of the conversation immediately going off the rails.
Better yet, pick something that fits with what you know about your date. That way, you’ll be able to show-off your attention to detail for those you care about early-on.
And for the love of all that is holy, don’t invite your friends, either in-person or via your phone, on your first date.
1. Gilmore Girls — a properly caffeinated date
Yes, coffee shops are the gold standard for the friend zone.
But avoid that pitfall by not spending all your time at the coffee shop!
Just spend your money there, preferably at a small, family- or locally-owned coffee shop, before wandering around one of your favorite cute Connecticut towns.
Considering the story of Gilmore Girls was based in Connecticut, this first date idea is a homerun if your date was a Gilmore Girls fan.
And several different towns claim to be the creative source for Stars Hollow, so you could probably pull-off claiming whichever one you’re in was the town’s raison d’etre.
A few of our favorite cute Connecticut coffee shops include:
- Coffee Lucca in downtown Greenwich, Connecticut
- Lorca Coffee in downtown Stamford
- Madison Coffee House in Madison
Coffee in hand, take your time strolling around while talking too fast and making witty references to obscure 90s cultural references.
2. Modern Love — Head to the Zoo
Modern Love, a collaboration between the New York Times and Amazon Prime, studies love in all its forms, and is well-worth watching.
Even the more painful episodes.
But one of the happier ones, When Cupid is a Prying Journalist, features a first date at a zoo. The show ends on a happily ever after note for the main character of the story, as the couple reunites at the zoo after drifting apart over the years.
Hopefully for your own happily ever after.
3. Hitch — Rent jet skis (or other water sports equipment)
Will Smith and his performance in the rom-com Hitch had to make an appearance on this list.
And why not the date which resulted in Will Smith kicking Eva Mendes into the water?
While renting jet skis and shooting around Long Island Sound sounds like a blast, it’s apparently an activity too easily litigated.
Case in point, someone could easily get kicked in the head, somehow.
But there are slower-moving ways to experience Long Island Sound. And they’re no less fun, especially on a first date.
SoundWaters in Stamford, Connecticut, rents paddle boards and kayaks for exploring the coastline.
Added benefits include:
- You’ll both get a little exercise to go with that sun
- You won’t drive wildlife away and people on the shore crazy with your noise level
Assuming you’re not a loud laugher.
7 of the best outdoor date ideas in CT
Little Connecticut offers a lot of diversity in a small package.
And that range of terrain from hills to shoreline, offers just as wide a variety of dating options.
Don’t get caught up in the same dating tropes, pick something a little more adventurous!
4. Parks & Recreation — Harvest Festivals
Taking your date on a fall activity will not be as dramatic an undertaking as Leslie Knope’s efforts to get a Harvest Festival off the ground.
But Connecticut fall festivals are sure to draw local celebrities as big as L’il Sebastian.
But there are plenty of other fall activities to take your date on, if crowds aren’t your thing:
And this doesn’t have to be a fall activity. Read our guide to summer festivals across Connecticut for even more options.
5.Pretty Woman — Be posh at a polo match
Where else can you enjoy the Sport of Kings and rub elbows with celebrities on this side of the continent?
Or even this side of the Atlantic, for that matter.
Regardless of whether your working hours are day or night, you’ll be welcome to enjoy a Sunday Greenwich Polo Club match.
It’s arguably one of the most unique things to do in southern Connecticut.
6. Notting Hill — Break into a private neighborhood garden
The next time you’re trying to impress one of the most famous American actors of the time, there’s no better way to do so than with a tour of a private garden.
Though we highly recommend against trespassing.
Instead, head to one of Connecticut’s more public gardens.
Stanton House Inn’s gardens
Enjoy free reign of the gardens surrounding Stanton House Inn when you plan a romantic getaway here. The ruins in the back, covered with scrambling vines, makes a terribly romantic spot for a picnic or idle conversation.
If you’re looking for romantic things to do in Hartford, Connecticut, look no further than the oldest public rose garden in America.
It’s easy to get lost in this garden featuring 15,000 rose bushes.
7. 10 Things I Hate About You — Go paintballing
Yes, paintballing hasn’t been popular since the 1990s, when 10 Things I Hate About You came out.
But that means that it will be an unexpected date! And it’s perfect if the two of you are a little competitive with each other.
This is not a first date kind of experience, though, as dressing to impress is not a strategic goal at a paintball field.
Some great paintball spots in Connecticut include:
- Yankee Paintball in Brookfield
- Hogan’s Alley Paintball is one of the best things to do in Meriden, CT
8. The Notebook — An afternoon rowing
This could also be a date modeled after The Little Mermaid.
Including the major hits of this date in movies, like wildlife singing to you, or an entire flock of white geese (not swans, as some fans claim happens in The Notebook), would be beyond this writer’s planning skills.
But finding an opportunity to have a relaxed row around the water is much more easily done.
That doesn’t mean it won’t be a bit of a drive, depending on where you want to go. In order of distance:
- Kayak Hudson offers kayak rentals (close enough) from nearby Rye Beach, one of the best Rye, NY, attractions
- Longshore Sailing School at Longshore Club Park in Westport, CT offers hourly rates for boat rentals, including canoes
- Drive up to Peekskill, New York, to rent a canoe from Hudson River Expeditions and take your date along the scenic Hudson River
- Or head to nearby Croton-on-Hudson, New York, to join a guided kayak tour or rent canoes, kayaks, and stand-up paddleboards from Hudson River Recreation
- Head to Lake Washining in Salisbury to rent a rowboat from O’Hara’s Landing Marina
9. Jane The Virgin — Camping
Mixed in with the crazy plot twists of a classic, romantic telenovela were a lot of great date night ideas.
Camping is not a trip to take lightly.
This is more of an opportunity to see how your date handles adversity. So, save this idea for after you’ve started to do some of the more embarrassing stuff around each other.
Not going into any further detail.
Some of this writer’s favorite camping locations in Connecticut include:
- Lake Waramaug State Park, for romantic lakeside camping
- Hammonasset Beach State Park, for even more romantic shoreline camping at one of the best state parks in CT
Check on Connecticut state park regulations regarding campfires before you light one to score some serious date night points.
10. Romeo + Juliet — Pooltime
We definitely do not recommend trespassing.
But a trip to the pool can be a very romantic outing. Layer on the romance if you have yet to see each other … in a bathing suit.
And while the seasonal outdoor pool at our Greenwich, CT, bed and breakfast can be quite romantic, we do ask that you be respectful of other guests.
And that your date has a happier ending.
Also in the interest of being respectful of other guests.
6 perfectly fun things to do at night in Connecticut
Remember when a nighttime date used to be a standard romantic ritual?
To the point where many of them were considered cliche date night ideas?
Well, after a pandemic and curfews imposed to limit spread, many of these date night ideas seem downright exotic.
Or even a little dangerous.
So live on the wildside (relatively speaking) and pick from our list of fun things to do at night for your next date.
11. Every TV show and movie, ever — Dinner and a movie
This is the penultimate in cliche dates.
But see above, spend a little time in the danger zone.
As far as restaurants and the dining scene goes, the world is your oyster in Connecticut.
If Italian’s not your preferred dining experience, there are plenty of other options for romantic restaurants in Connecticut.
If you’re in Greenwich or Stamford, take your pick from our list of restaurants in downtown Greenwich. Afterwards, head to the elegant and historic Avon Theatre to introduce your date to a more classic and unique movie-going experience.
Or explore any of our other travel guides for more ideas:
12. Hitch — Cooking Class
What’s more romantic than cooking the meal yourself?
Luckily, Yankee Magazine selected Fig Cooking School in nearby Milford, Connecticut, as one of the ten best cooking schools in New England.
Their cooking classes are a truly unique experience, with classes that take you around the culinary world in one evening.
Be sure to warn them in advance about any allergies.
13. La La Land — Head To A Planetarium
Discovering the wonders of the night sky can be a fun way to spend an evening with your significant other.
Especially if it includes a little mood music.
A few planetariums to visit throughout the state include:
- The Discovery Museum in Bridgeport
- Leitner Observatory in New Haven
- Treworgy Planetarium at Mystic Seaport in Mystic
Tap dancing and flying while on your date are optional.
Alternatively, you could also have a simpler (and less expensive) date at one of the local observatories:
- The Bowman Observatory is down the street from Stanton House Inn in downtown Greenwich, with free stargazing for the curious on Tuesdays
- The Westport Astronomical Society gazes at the stars at a former nuclear missile defense base. Not a romantic fact, yet interesting.
14. Grease — Drive-in movie
Going to a drive-in movie used to be the classic date night idea in America. Especially in a fancy car, watching a horror movie.
Shortly before the pandemic, they were wonderfully retro and exceedingly rare.
But the pandemic brought them back with a passion.
Just a few of the options for drive-in movie theatres in Connecticut include:
- Mansfield drive-in
- Southington drive-in movie theatre
- Pleasant Valley drive-in
Bonus points if you throw-in dinner at a retro diner, like Lucky’s Classic Burger & Malt Shop, in downtown Stamford. With details like booths and a checkered floor, this restaurant looks straight out of the 1950’s.
15. How I Met Your Mother — Enjoy a Rooftop View
You don’t need to propose to have a memorable evening on a rooftop.
In fact, there are few pleasures more highly sought after than relaxing on a rooftop, drink in hand, surveying the surrounding cityscape.
Preferably with nice weather, but you’ll sometimes take what you can get in New England.
There are some fantastic Portuguese dining options in nearby Westchester County, New York. But only one of them has a view of the Hudson River Valley, Long Island Sound, and even the New York City skyline from its floor-to-ceiling windows. Kanopi is at the top of the Opus in White Plains, New York, just over the state border from Greenwich.
Classic Mexican fare is on the menu at Evarito’s in downtown Norwalk. And yet one of the biggest draws to this popular South Norwalk restaurant is definitely the rooftop deck overlooking the surrounding city.
16. Dirty Dancing — Go dancing
Thanks to having older sisters, this writer cannot tell you how many times he’s seen the movie, Dirty Dancing, though never complete from start to finish.
But this movie is a cult classic for a romantic.
And while the Catskills resort on which the movie is based has long since closed, you can recreate your own version.
But first, you need to know how to move.
Luckily a dance class or two is a fantastic date night activity.
A few local options include:
- The Arthur Murray studio off of Greenwich Avenue offers group dance classes
- Metropolitan Dance Center offers both dance classes and dance practice parties if you and your date have found your new hobby
- Maria Fioras Dance Studio offers classes in Argentine tango, Club dance, Freestyle, Hustle, Latin, Salsa, Swing, and much more
Learning Argentine tango is nice, but what about learning something unique to Connecticut on your date?
Contra dance is a folk style of dance from New England.
Its creative sources include:
- English and Scottish country dances
- 17th century French dance styles
It involves long lines of dancing partners, not ideal for a pandemic.
But it’s a lot of fun, and definitely ranks high on the list of unique date ideas in Connecticut.
And you are sure to far surpass your daily step count with a night of this activity. Possibly your week’s goal.
A few places to quickly learn and practice contra nearby:
And may you and your dance partner have more off-screen chemistry than Patrick Swayze and Jennifer Grey.
16. Pretty Woman — An evening of the performing arts
This writer catalogues this date idea as a classier version of dinner and a movie.
While opera might be hard to come-by in Connecticut, there are plenty of other choices for the performing arts:
Perhaps you’ll be as compelled by the performance as Vivian and almost pee your pants.
4 of the most romantic road trips through Connecticut
Hopping on a motorcycle and exploring the countryside and whatever villages you find à la Roman Holiday can make for a splendidly romantic date.
But motorcycles are dangerous, and the only place this writer could find to rent motorcycles in Connecticut is a hike up to Bristol.
But weekend road trips in CT via car, bike, even on the train, can be pleasant, too.
And while you could plan your trip around fall foliage driving routes, why not pick a theme that works for you any time of the year?
Our list of top road trip ideas from NYC have plenty of suggestions for any direction any time of year.
17. Before Sunrise — Discover a new town
Skip the expensive plane ride to a European city and explore somewhere close to home.
The beauty of this date is the spontaneity.
Pick one of the most charming towns in Connecticut, head there, and spend an afternoon walking around it.
Sometimes you’ll hit a dud, but hopefully your conversation with your date will more than make-up for it.
18. Ferris Bueller’s Day Off – Explore town in style
You don’t need to head to Chicago to follow in Matthew Broderick’s footsteps.
Instead, write your own love story about your favorite town, and hopefully weave your own date in with it.
But to achieve this date idea, you need to ensure that you’re experiencing your chosen town in style.
Pick a day (or weekend), and borrow a fancy car to start. If you don’t happen to have a friend whose father owns an expensive car, you can rent an exotic luxury car for your trip from Veluxity.
Then, check-out a couple art installations:
- Greenwich Avenue art galleries will set you on the right track, or
- Head to Yale University’s various art galleries and museums for an even more in-depth day
Who knows? You may wind up in a parade for some reason.
19. Great British Baking Show — The Great Connecticut Baking Tournament
Why spend the day only visiting one town?
Instead, maybe you and your date would rather combine an activity that allows you to judge the greatest bakers in Connecticut.
And, if you’re feeling particularly competitive and paintballing wasn’t enough, you could turn this into some sort of competitive eating contest.
Hop in the car, on the bike, motorcycle, scooter, what have you, and hit some of the best bakeries in Connecticut.
Pick your favorite baked good and compare and contrast your unwitting contestants with your date.
You’re welcome to announce a winner, though telling the baker directly may result in some quizzical stares.
Some bakeries near us to start your day trip channeling your inner Mary Berry:
- By the Way Bakery in downtown Greenwich
- Black Forest Bakery, also in downtown Greenwich
- DiMare Pastry Shop, in the Riverside neighborhood of Greenwich and Stamford
- Kneaded Bread, in nearby Port Chester, New York
Like pizza, locals are always particular about their favorite bakery, so tread lightly with people’s feelings.
20. Community — Competitive Wine Tasting
Okay, so this episode admittedly wasn’t about competitive wine tasting.
But that doesn’t mean you can’t create your own reality.
Head to any of the best wineries on the Connecticut wine trail, or visit a bunch over the course of the day.
Some personal favorites for a romantic nice day are:
- Gouveia Vineyards, for the gorgeous view of their patio area
- Hopkins Vineyard, because how does having a glass of wine by Lake Waramaug not sound magical?
- Stonington Vineyard, a perfect addition to a visit to the charming borough of Stonington
The scenery is often amazing at wineries across the state, but no Herb Etlinger fruit wines to be found.
Follow the trail of the best breweries in Connecticut if beer is your preference.
Need any more date ideas in CT for your getaway?
There’s plenty more to do throughout the state, depending on your and your SO’s taste.
Keep exploring the state from the comfort of your screen with a few more of our guides:
- Fall in Connecticut
- Winter in Connecticut
- Activities, attractions, and things to do in the Greenwich, CT, Visitor’s Guide
We hope you and your date have a blast exploring our state!