Day Trips In CT: Top 15 Most Unique Spots | Stanton House Inn

moped parked under a tree during one of the most romantic day trips in CT for couples

Connecticut is one of the most romantic destinations in the nation.


Do “Connecticut” and “romantic” not belong in the same sentence, in your eyes?


Then you’d better read on.


From the elegant scenery, historic charm, and variety of fun activities, it’s an ideal location for couples to escape their regular routine and fall in love all over again.


Greenwich, the home of our romantic Connecticut bed and breakfast, is a great place to start exploring the state. As this writer learned during a certain pandemic, there’s nothing more romantic than a short road trip to explore a new-to-you town together.


Just make sure you’re both well-fed, well rested, and well-hydrated before and during your excursions.


Ready to start planning your New England trip? Here are just a few of the best romantic day trips in CT that you absolutely must try!


Find all our favorite day trips in CT for couples in our free romantic guide to Connecticut.


Download your copy today to pick your favorite things to do near our romantic CT bed and breakfast and add them to your getaway itinerary.

Romantic day trips in CT for the two of you

So, what are the best New England towns to visit on your romantic day trip?


That depends on what you’re looking for, of course.


Watch our quick video on a few of our favorite day trips for couples, or scroll down for a map and the details. Or both!




A map of cute and charming towns in Connecticut, ideal for day trips
Map design by Stanton House Inn using resources from Flaticon


Starting in our neck of the woods, along Long Island Sound:

Greenwich, Connecticut

couple kissing under tree romantic day trips in ct for couples Day Trips in CT: Top 15 Most Unique SpotsEven before you venture out into other towns near NYC, there is plenty to do right here!

And at only about 33 miles from Midtown Manhattan, it’s at the top of the list for short day trips to Connecticut and New England.

Read our full guide to romantic things to do in Greenwich, CT, but a little primer includes:

A visit to one of the most unique places in Connecticut would of course lend itself to some of the most unique date ideas in CT.

Set Sail on a Private Cruise

If you’re in need of some much-needed alone time and an extraordinary experience, a private ride on a luxury yacht on Long Island Sound 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 a romantic evening.

More short day trips in Connecticut

Want to head a little farther afield?

Then check-out another charming town or two along Long Island Sound, such as:


  1. A diverse and sassy beach town feel of Norwalk, CT


  1. The avant-garde coastal town of Westport, Connecticut


  1. The home of both Impressionist and contemporary artists in Connecticut, Ridgefield, CT


But frankly, even Bridgeport, CT, can be a romantic destination. Just needs a little planning, a decent Bridgeport restaurant, and a trip that’s tailored to the two of you.


Even More Connecticut Day Trips for couples

Speaking of which, our romantic bed and breakfast near New York City is the perfect spot from which to plan even more romantic day trips in other parts of Connecticut! Some of our favorites hug the Connecticut coast, but there are plenty of charming towns in CT to explore on little day trips.

Day trips within 2 hours of CT 

Considering the size of Connecticut, it doesn’t take long to get from one side to the other.


Case in point, the drive from our Connecticut coast bed and breakfast in Greenwich to Stonington (and on to Rhode Island) is about two hours.


Some favorites of the most romantic places in Connecticut that are a little farther away include:

New Haven, Connecticut

new haven makes a great destination for romantic day trips in ct. yale university and wooster square are beautiful any time of yearThis is one of the largest cities in Connecticut. It hosts Yale University, which includes one of the best art galleries in the country, the Yale University Art Gallery. It’s without question one of the best free things to do in all Connecticut.



There are plenty of new restaurants to enjoy during your visit to the city.


In fact, just exploring the best things to do in New Haven, CT, would keep you busy for more than a day.


And one of the best state parks for beaches in the state, Hammonasset Beach State Park, is a short drive away.


New Haven is only an hour by train or car from Greenwich. It’s about 2 hours via car trip or train ride from NYC. Our romantic inn is within easy reach at the end of a busy day exploring some of the most unique attractions in CT.

Connecticut River Valley

According to National Geographic, the Connecticut River Valley is one of the world’s last great places for natural beauty. The Connecticut River is one of the world’s few rivers without a port at its mouth. So the New England marshes, forests, and hamlets are worth exploring.

Visit Gillette Castle State Park for great photo opportunities. This unique attraction offers a commanding view of the river. Follow Route 148 east to Devil’s Hopyard State Park, which has a beautiful waterfall. Follow Route 156 south through Lyme, stopping at the Florence Griswold Museum before crossing I-95 and back across the river. Head north and visit the delightful towns of Essex and Chester in Connecticut. In Essex, Connecticut, you can explore the Connecticut River Museum and take a ride on the Essex Steam Train.


Mystic and Stonington, Connecticut

mystic seaport in eastern connecticut is one of the best romantic day trips in ctOn the other side of the state are the quaint old towns of Mystic and Stonington. Both of these Connecticut shoreline towns are former whaling towns. Both were beautifully restored and welcome thousands of visitors each year.


Mystic Seaport Museum and its fabulous restaurants along the Mystic River help create a hefty list of romantic things to do in Mystic. There are plenty of things to do in Stonington, CT, as well.


As these are relatively small towns, a day trip from Greenwich can be enough to soak it all in with your significant other. That said, these are some of the most classic summer getaways in New England, which is hard to argue.


Hartford, Connecticut

Any interest in a romantic day trip to celebrate Victoriana?


About a hundred years ago, Connecticut’s capital city was the wealthiest in America. And much of the best things to do in Hartford, Connecticut reflect that period.


From public gardens to world-class museums, even Mark Twain’s favorite home; there’s much to keep you and your significant other busy. And Hartford is a short drive away from much of America’s Northeast.


Don’t miss these other nearby charming towns, if you’re feeling ambitious:


  • Lake Compounce, the oldest amusement park in America




Litchfield Hills

waterfall romantic day trips in ct for couples Day Trips in CT: Top 15 Most Unique SpotsThe cute, little towns of Northwest Connecticut are not to be missed.


Between the foliage and picturesque little villages with pretty, white, church steeples on greens; this area is ideal in the fall.


Visiting any of the following Litchfield Hills towns for a day makes for a perfect fall date idea:



  • Cornwall



  • New Preston


  • Washington


Discover Even More Romantic Things to Do in CT

In our opinion, anytime of year is a perfect time to plan a romantic getaway to Connecticut. If you’re looking for romantic winter activities in Connecticut, be sure to look at our itinerary of romantic things to do in CT in winter.

Below are a few more standard romantic activities throughout Connecticut, regardless of the time of year (seriously). And all of them are within an easy drive, and in some cases walking distance from, the most romantic inns in Connecticut.


Romantic inns in CT map Day Trips in CT: Top 15 Most Unique Spots
Map design by Stanton House Inn with elements from Flaticon


Romantic dining across the state

Because you’ll need to eat at some point, why not make it an event?


Be sure to read our guide to the most romantic restaurants across Connecticut. You’re sure to find a great pick near you.


Or plan a trip around the spot you want to check out!

Visiting the best Connecticut beaches

shoreline romantic day trips in ct for couples Day Trips in CT: Top 15 Most Unique SpotsThis most classic of date ideas in CT 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 in CT beaches!


Here are just some of Connecticut’s most beautiful beaches:

View Beautiful and Historic Mansions

Surprisingly, one of the most popular tourist activities in Greenwich is viewing the stunning mansions along the back roads of town. The Greenwich, Connecticut, real estate market offers some of the best in New England, and the homes are absolutely breathtaking!


Whether you are your sweetie are just dream building or looking for a new place to call home, you may want to consider this fun-filled bike trip to some of Greenwich’s most incredible mansions! 

Get a Taste of CT at Local Wineries

This activity among the most romantic things to do in CT! The Connecticut Wine Trail is abundant with stellar options for wine tastings, gorgeous vineyards, and out-of-this-world sunset views! While it’s impossible to pick our favorite Connecticut wineries, these are some that we consider as musts during your visit:

  • Sunset Meadow Vineyards
  • Jones Winery
  • Chamard Vineyards
  • Gouveia Vineyards

We hope you enjoy wherever the road takes you on your next couples’ day trip!

Updated and republished: June 28, 2022

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