Are you looking for the perfect escape from New York City or Boston for you and your partner? Look no further! In this guide, we’ve rounded up the best romantic getaways in CT to help you plan a memorable trip.
Connecticut may be small, but it’s full of charming small towns that are ideal for a romantic escape with your significant other. Whether you’re looking for a cozy bed and breakfast, a luxurious spa retreat, or an outdoor adventure with breathtaking scenery, Connecticut has something for every couple.
In this post, we’ll be sharing our top picks for the most romantic getaways in Connecticut, along with links to our complete travel guides to the destination. Each guide covers the best things to do, romantic restaurants, and our favorite accommodations. In addition, we’ve added a unique Historic Preservation Tour Company, and a link to one very romantic, Connecticut-oriented photography book.
So, if you’re looking to escape the hustle and bustle of everyday life and spend quality time with your loved one, in front of say, a roaring gas fireplace, keep reading and get ready to fall in love with Connecticut’s romantic charm.
Looking for more romantic getaways? Check out our Best Getaways in New England post or 110 Surprisingly Romantic Getaway In Northeast USA.
Romantic Connecticut Destinations
Connecticut River Towns – Chester CT to Haddam CT
Performing, fine and culinary artists have been drawn to this mesmerizing ribbon of water, the Connecticut River, for centuries. We have several faves here, including the charming B&B, Chatfield Hollow Inn in Killingworth, Connecticut. It offers cozy accommodations in a serene natural setting.
Read all about it in our travel guide: Charming Connecticut River Towns.
Portland CT – Brownstone Quarries and Wesleyan University
Located along the Connecticut River, Portland, CT, is home to the famed brownstone quarries that once supplied building materials nationwide, adding a unique historic touch to this romantic destination. Couples can explore the scenic quarries, stroll along the charming riverfront, and soak in the tranquil beauty of this picturesque town, making it an ideal spot for a love-filled getaway.
Read all about it in our Portland CT travel guide.
ESSEX CT – Connecticut’s Maritime History
The Connecticut River and Essex in particular was, if not the center of the maritime universe, a prominent player in United States history. The first battleship ever to be built in North America, the Connecticut Warship Oliver Cromwell, was designed and launched from Essex in 1776. The American Turtle, the world’s first submarine, created to blow up British ships at anchor during the Revolutionary War, was built on a now-washed-away island nearby. The Brits burned American Warships offshore during the War of 1812, and then retired to a local tavern – still open and more popular than ever. The Connecticut River is stunning, historic hotels cozy and lovely, and the ice-cream parlors are prime. Add lots of American Eagles flying about and you’ve got a recipe for the Great Romantic American History Getaway in Essex CT.
Beach Vacations In Madison CT
No fudge shops or glitz and glamour here. Just serpentine rivers, a quaint harbor, an anachronistic winery, the largest beach State Park in CT, and one of the most highly regarded, award-winning, indie bookstores in the country. Plus, find the best lobster roll on the East Coast (Lobster Landing/Clinton). Stay in a hotel with private balconies overlooking the water. Or, in a quirky-luxe inn where your in-room record player comes stocked with music of your choice.
Read all about it: Clinton and Madison CT: Best Lobster Roll in New England
Mystic River Idyls in Mystic and Stonington CT
You’ll find great dining, great bar/restaurants, beluga whales, historic bridges, and quaint inns in Mystic CT. Bordering towns are equally quaint, especially Stonington with a main street that juts into Long Island Sound, and the charming Inn at Stonington.
Read all about it: A Romantic Mystic CT Getaway
Connecticut’s Northeast Corner
Sweethearts who enjoy discovering the newest “hot spot” together will love this formerly industrial section of Connecticut. It’s got a growing art district with lots of antique shops, and, ironically, plenty of nightlife.
Read all about it: Northeast Connecticut: The Quiet Corner Growing Louder.
Connecticut’s Northwest Corner
There’s a reason some of our favorite celebs have homes up here. Far from the maddening Hampton’s Season, the pace in this farmland and lakes section of Connecticut is slow and quiet. Quiet, that is, except for Lime Rock Racetrack. (Preferred by Paul Newman until he couldn’t race anymore in his early 80’s).
Read all about it: Connecticut Northwest Corner
Swanky Greenwich on A Budget (Kind Of)
This swanky Connecticut town is so much more than just the center of the Preppy Handbook universe. Known for its hedge fund billionaires, Captains of Industry and Hollywood types, Greenwich does not broadcast its considerable tourist assets. Ironically, many are inexpensive or free.
If you seek a funky, contemporary hotel, book a room at the The J-House (once a Howard Johnson’s!). It’s got a great full service spa and the fine-dining Tony’s. Stay in a lesser known, but splendid Stanton House Inn – on a residential street within walking distance of downtown.
Read all about it: Greenwich CT: A Cheap Getaway?
Hartford CT
Oh yes, literature lovers of all kinds will adore Connecticut’s capital city, Hartford. It’s got men and women of letters galore – most notably, Mark Twain, Noah Webster, and Harriet Beecher Stowe. Stay within the hulking commercial buildings downtown, at a recently opened boutique hotel. Or book a room at an artsy lodging in the upscale shopping and dining district of West Hartford.
Read all about it: Hartford CT: A Capitol Idea For A Getaway.
New Canaan’s Famous Glass House And More
What is it they say about Glass Houses? I’m guessing it’s not “you can tour the most famous Glass House in the world, designed by preeminent architect, Philip Johnson, now that he’s gone.” Mid-Century Modern fans can visit New Canaan to delve into the life of this world-renowned architect, walk the 80 natural acres of a new kind of environmentally sustainable Church, and stay in an antique inn with Revolution-era cred on this romantic, architectural Connecticut Getaway.
Read all about it: New Canaan CT: Mid-Century Modern Has Always Lived Here.
New Haven, Connecticut
Of course, Yale University takes center stage in New Haven, but foodies have been flocking to this college town for decades. It’s where America’s first hamburger was, and still is, served (Louis’ Lunch, 1895). It’s home to the classic “New Haven” wood-fired pizza (Frank Pepe’s, 1920; Modern Apizza, 1934, Sally’s, 1938).
And, thanks to Bridgeport-based Frisbie Pie Co. (1915, no longer in operation), Yale students took to skimming empty pie tins on the New Haven Green, thus creating that unique sport known to co-eds and dog owners the world over. Cool kids of all ages can stay in a variety of class-act boutique hotels. The Blake’s claim to fame is its uber-popular rooftop lounge, High George, and hip décor. You can’t go wrong, either, with The Study At Yale or Graduate New Haven.
Read all about it: New Haven CT: Arts, Food, Theater, and Yale University.
New London and Groton CT
As home to the United States Coast Guard Academy, maritime and Revolutionary War history, and Nuclear Submarines, New London seems an unlikely place for a Romantic Getaway. But the opening of a new glamorous boutique inn places it in that category.
Read all about it: New London and Groton CT Getaway.
Niantic and Waterford CT
With a shoreline boardwalk, quirky used book compound, idyllic kayaking, and a town straight out of a Colonial-time painting – plus a marina-set inn – this CT Getaway provides simple pleasures that add up to a lovely getaway.
Read all about it: Niantic – Waterford CT: Shoreline Getaway.
Old Lyme CT
Morning fog in Old Lyme CT transforms the landscape into the hazy tableau of an impressionist painting in the very place considered the Birthplace of American Impressionism. In the late 1890s, widow Florence Griswold opened her home to American artists fresh from studying in France, forming the country’s first European-style Art Colony – an “American Giverny.” Old Lyme is, on canvas time and time again, the very essence of romantic Connecticut.
Read all about it: Old Lyme CT: Birthplace of American Impressionism.
Old Saybrook, CT
Situated at the mouth of the Connecticut River where it meets Long Island Sound, Old Saybrook CT has drawn vacationers and celebrities for 150 years. Katharine Hepburn lived in the Fenwick neighborhood until her death in 2003.
Out on “the point,” The Saybrook Point Inn and Spa features two “Boutique Inns” – in addition to its already luxurious accommodations. Learn about Saybrook Point’s earlier incarnation as Terra Mar, frequented by Hollywood luminaries and gangsters. Discover, too, some surprising African American history on this down-to-earth but high-class Connecticut coastal Getaway.
Read all about it: Old Saybrook CT: Kate Hepburn’s Home on CT Shore.
Ridgefield CT
Are you and your main squeeze into the arts, in all of its forms? Then, consider a trip to Ridgefield CT – home to one of only two National Parks in the USA devoted to an artist. This “Fife and Drum” town also has several live theaters, a movie theater run by special needs adults with “sparkle,” and a Main Street right out of central casting.
Read all about it: Ridgefield CT: Art in the Connecticut Woods.
Fairfield and Southport CT
Historically, Fairfield and neighboring Southport CT have much in common with many Coastal Connecticut towns. Like so many other burgs within commuting distance to New York City, when automobiles and a train system allowed for easy access to work, they grew into upscale suburbs, collectively nicknamed “The Gold Coast.”
Stay in the charming Delamar Southport, a boutique hotel that early on became a refuge for New Yorkers escaping the pandemic-dense city. Beach it, learn American History, and just chill out with your loved one.
Read all about it: Fairfield CT: Art and History on the Connecticut Coast.
Washington CT and the Litchfield Hills
This hilly, lake-studded area of the state is so sweet, it could be the poster “child” for Romantic Connecticut. The Litchfield Hills are home to the glitterati who prefer to eschew the Hamptons scene for a much more subdued (and private) summer break.
This getaway brings you through some rustic-posh towns where the former executives of shoe crafter, Manolo Blahnik, set up shop. Although not the kind of shop you might expect. Spend a romantic weekend getaway in a helicopter. Or in a treehouse, or in a “Greenhouse.” All of these “lodgings” make up the very swanky Winvian Farm in Morris.
Read all about it: Washington CT and the Litchfield Hills.
Yes, Washington Slept In Wethersfield
If you and your honey love to curl up with the latest Revolutionary War history book, get all gooey-eyed over George Washington’s sleeping quarters, or even fantasize about growing Heirloom vegetables from seeds, you’ll love meandering around this very Historic District.
Just a few miles from Hartford, Wethersfield is home to two charming B&Bs, great restaurants, authentically restored pre-and-post Colonial homes, and two of the oldest packaged seed companies in the USA. Still in operation.
Read all about it: Wethersfield CT: Connecticut Started Here
Romantic Connecticut Books And Tours
Histoury Tours, Connecticut
Although not a destination, this tour company runs excursions that are perfect for couples passionate about architecture. The Historic Preservation focused Histoury.org runs immersive bus tours of the architectural heritage “found in communities throughout New England and New York.” Where do your interests lie? Pre-Revolutionary War Colonial? Mid-Century Modern? On the Historic Register? There’s a tour for that. (Check online calendar for upcoming tours.
Each of these extremely popular 3-4 hour coach bus tours are spiced up with narration from an expert in the field, and offer several stops to see building interiors. Each excursion is wrapped up with a wine and light bites – representing local cuisine. Founder/owner of HisToury, Georgette Blau, knows a thing or two about creating bus tours with buzz. She’s also the founder/owner of On Location Tours, which conduct movie and tv location tours in New York, Boston, and Chicago.
Connecticut Gardens, Photo Book by Caryn Davis
Again, not a destination, but for couples with a horticulturist bent, what can be more spine-tingling romantic than a garden in bloom? Photographer, Caryn Davis, tackled the monumental task of photographing an exhaustive number of Connecticut Gardens, refined to wild, public to private, in her beautiful book, Connecticut Gardens. Her dedication to these sumptuous plots of land pays off. Connecticut Gardens is a must-have for anyone who loves flowers, gardens, or Connecticut in general.
BONUS: More Romantic Getaways In Connecticut
- 10 Things To Do In Woodbury CT; Small Town Charm Near NYC
- A Hidden Gem: Exploring The Best Things To Do In Killingworth CT
- Stonington CT: Authentic New England Shoreline Town With Panache
- 13 Strange and Romantic Sites in Guilford CT: On The Connecticut Shore
- 15 Non-Gaming Things to Do At Mohegan Sun Casino and Resort: Uncasville CT
Additional Connecticut Travel Inspiration
- Best Under the Radar Things to Do in Connecticut
- 19 Most Romantic Hotels in Connecticut
- Rural Connecticut Fall Foliage Road Trip
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