Romantic things to do in CT: top guide to the best ideas

Are you searching for romantic things to do in CT in a hurry?


No worries, we’ve all been there.


Having been in your shoes before, this writer pulled everything we know about planning and enjoying romantic activities across our state into one helpful and as concise as possible place.


This guide to romantic things to do in Connecticut includes everything you need to know:

  • Date ideas
  • Romantic places for day trips
  • Where to confidently book romantic getaways
  • Top romantic places to eat across the state
  • Even what to do during different seasons, from winter to fall


Sounds good to you?


Then read on.

But first, a confession.


This entire guide developed during the largely inauspicious Covid-19 pandemic.


How so?


Well, when Connecticut shut down due to the statewide Covid quarantine lockdown, all the more typical romantic activities came off the list.

Romantic things to do in CT during the Covid pandemic

Romantic activities like dinner and a movie, museums and art galleries, even getting drinks at a local bar became risky, if not impossible.


But that meant that instead planning a weekend in Connecticut of romantic activities during Covid required more research.


And there was plenty of time to be had during the lockdown and afterwards.

Instead of the typical date night ideas, we found plenty of romantic activities to keep us busy.


A romantic weekend in Connecticut consisted of a lot of free attractions and activities, including:


All in all, it was a huge improvement over sitting isolated in your apartment all day.

Creative date ideas in Connecticut

Before the Covid pandemic, we were experts at planning romantic getaways in Greenwich, our hometown.

Date night ideas in Greenwich

Our town, the southernmost in Connecticut jutting into New York, has a little bit of everything for visitors looking for romantic things to do in Greenwich:

Add fantastic restaurants and nearby concert venues for ample date night ideas in Greenwich, and planning a romantic getaway here is easy.

Date night ideas in New Haven, Hartford, and more

But during the lockdown, when even entering nearby New York State was considered verboten for a time, this writer got the opportunity to explore more of Connecticut.


Read our favorite date ideas in Connecticut for the full list, but to whet your appetite:

  • Elizabeth Park is the oldest public rose garden in the country. It is not only one of the best free things to do in Connecticut, but walking through here when the roses are in bloom is one of the most romantic things to do in Hartford.
  • New Haven is an intellectual romantic’s playground, with art galleries, museums, and observatories hosted by Yale University. Plus, restaurants here regularly receive awards for having some of the best pizza and Italian cuisine in the USA.

11 of the most romantic places in CT for day trips

Speaking of which, exploring our charmingly quaint towns is one of the most romantic things to do in Connecticut.


While cities like Hartford and New Haven have their own appeal, many of the charming, cute towns in Connecticut are unlike anywhere else on the planet.


And if you plan well, they can be a very inexpensive way to enjoy your day. All you need to cover is gas and maybe a cup of coffee or a sandwich while you walk around a cute downtown or two.

Romantic places in Connecticut

Many of the towns that make this list are more than just a pretty face, though. They host unique shopping, hiking, museums, and more to keep you occupied once you’ve finished wandering around main street.


By region, some of the most romantic places in Connecticut include:

  • Greenwich & Westport in Fairfield County
  • Milford & Madison around the city of New Haven
  • Essex & Chester along the Connecticut River
  • Mystic & Stonington in Mystic Country
  • Cornwall, Kent, & New Milford in the hills of Litchfield County

Romantic restaurants in CT

couple enjoying a romantic evening at a cute restaurant in Connecticut, one of the most romantic things to do in CTFor such a small state, Connecticut offers a lot of variety.


Case in point: its restaurant scene.


Any meal can be an amorous one at the top romantic restaurants in Connecticut. It’s more a matter of choosing the right atmosphere:

  • Cozy, with a fireplace
  • Overlooking waves crashing on the shore
  • Above the heights of the surrounding cityscape


A good meal is guaranteed at any of these venues.


A few choice dining options scattered throughout the state include:

  • Le Penguin in Greenwich
  • Union League Cafe in New Haven
  • Bernard’s and Sarah’s Wine Bar in Ridgefield
  • Match in South Norwalk
  • Arethusa al Tavolo in Bantam

Romantic getaways in Connecticut

Enjoying that moment after filling-up on a good meal and winding-down before bed in privacy does require a bit of planning.


But fortunately, there are plenty of options for romantic getaways across Connecticut.


Just like with dining, it’s more about knowing what sort of atmosphere and amenities you want to enjoy than necessarily what location.


Obvious exceptions being hotels, inns, and cabins overlooking the beach or water.


But many of the most romantic inns, hotels, even cabins feature the perfect combination of amenities for a romantic getaway:

  • Whirlpool or JACUZZI® tubs
  • Fireplaces
  • Seclusion
  • Scenic views
  • Attentive hosts


Read our full guide to favorite cabins, hotels, and inns to plan a perfect romantic vacation, but some favorites include:

Romantic things to do in CT throughout the year

Any time of year in Connecticut features its own style of romance:

Romantic things to do in CT in the summer

It’s a sad summer for a New Englander who doesn’t get on the water at some point in the season.

Visit the beaches in Greenwich and nearby

This classic date idea is a great way to spend a day in the sun with your partner! Whether you choose to simply soak in the sun’s rays, indulge in a romantic picnic, or take a boat ride, there are plenty of romantic things to do on CT beaches! Here are just some of the area’s most beautiful, coastal spots:

Set sail on a private cruise

If you’re in need of some alone time together, a private ride on a luxury yacht may be just what you need. Greenwich Boat Charters provides a variety of options including dinner and cocktail cruises, New York Harbor tours, leisure harbor cruises, and more! The lull of the waves and the stunning backdrop of a Greenwich sunset is the perfect setting for any romantic evening.


Another great option is the Thursday night cruise from South Norwalk to the Sheffield Island Lighthouse. The trip includes sunset views and a traditional clambake on the island!

Romantic things to do in Connecticut during the fall season

Traditionally, fall is all about harvesting and celebrating before the winter.


Today, it’s also about bonfires and observing the changing fall colors.


Hop in the car or on the train and visit a cute town anywhere in Connecticut during peak fall foliage season. There are some fantastic fall foliage driving routes to explore.


You could also plan your trip around farm visits, like apple picking in Connecticut orchards.


Or, the best afternoon of all could be had at one of the many Connecticut fall festivals throughout the state happening on almost every fall weekend in a typical year.

Romantic things to do in CT in winter

Romantic getaways in the spring, summer, and fall are easy in Connecticut. Many visitors often overlook the splendor of a romantic getaway here in the winter.


And yet there are plenty of romantic winter activities, both indoor and outdoor, to enjoy during a typical Connecticut winter.


It’s the ideal time to enjoy indoor activities such as:

  • Museums
  • Seeing an independent film
  • Shopping
  • Aquariums

Or just get cozy by a fire with a good book.


You could also try your hand at a new winter sport or hobby, some popular ones in Connecticut include:

  • Snowmobiling
  • Cross-country skiing
  • Winter hiking
  • Snowboarding
  • Ice fishing
  • Downhill skiing
  • Ice skating
  • Snowshoeing

A few more romantic things to do any time of the year in Connecticut

Regardless of the temperature outside, there are a few romantic activities that are delightful regardless of when you partake.

Get a taste of CT at local wineries

One of the most romantic things to do in CT involves indulging in some of the area’s finest wines! The wineries list of the Connecticut Wine Trail is packed with stellar options for wine tastings, gorgeous vineyards, and ethereal sunset views! It’s impossible for us to pick favorites, but here a few to try during your visit anywhere in the state:

Have a pint at a Connecticut brewery

Spoken from experience, winter day trips in Connecticut risk having an awkward period between when shops and attractions close around 5 or 6 and when you’re actually ready for dinner.


Stopping-in to a brewery is a perfect opportunity to pause, have a seat in a rustic industrial ambience, have a glass of local beer, and an appetizer.


An hour later and you’ll be ready to take-on the evening!


And there are so many local breweries here that the Connecticut breweries scene competes with some of the more famous beer lover destinations in America.

Looking for more romantic things to do in CT?

While certain activities are stereotypically romantic, anything can be romantic depending on the company.


Well, almost.


One of the best ways to be romantic is to plan a day or weekend that feels spontaneous yet somewhat organized.


So plan a quick romantic day trip around visiting some of the most unique things to do in southern Connecticut, from a polo match in Greenwich to enjoying a CT lobster roll in Stonington.


Or just head to our neck of the woods and enjoy the various romantic attractions and activities here in Greenwich, Connecticut.

Updated and republished December 3, 2021