Located in the southwest corner of New England, Connecticut features stunning vistas, glimpses of history, and a rich sense of culture. Although small in geography, it is packed with attractions for couples and families alike. Connecticut not only varies in landscape from rolling hills to beaches; it also has communities on both ends of the spectrum. Whether you’re looking for a small rural town or a place that’s more high-end, Connecticut is a great destination to consider.

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The Destinations

The Escapes

Newtown, CT —
Nicer in Newtown

When I was seven, my family moved to Newtown, Connecticut which was one of those “small” quintessential New England towns. Back in the day, it was a sleepy town with two stop lights for the entire 60 square miles of the town. We spent our summers swimming at Dickinson Park where they had made a small lake into a swimming pool, climbing trees, hiking in the woods and playing cards. There were few eateries other than the Newtown Pizza Palace and the “Ice Cream Shop”. The sidewalks rolled up at 9pm because there was not much going on other than a neighborhood party or running around in the dark looking for fireflies. It was a hidden gem with close commuting to lower Fairfield County, New York City and Hartford, CT.

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Westport, CT —
Liveliest Neighborhood on the Long Island Sound

You might think a neighborhood with dozens of cool restaurants, a fantastic ice cream shop, a rowing club, kayak/paddleboard rental store, outdoor music and playground — all within a few steps of the train station — would be too much to ask for.
Throw in a Cape Cod clone — with a private island, two yacht clubs and a beach, just a short hop down the road — and you must think it’s really a figment of a realtor’s imagination.

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Roxbury, CT —
Roxbury is One of Those Places

There are a few spots in this state that make you slow down and sit a while. Roxbury is one of those places. Nothing fancy here. No big box stores, supermarkets, or shops. No stop lights. Yep, that’s right no stop lights. The only time traffic ever really backs up in Roxbury is during Pickin’ and Fiddlin’ when the Roxbury Volunteer Fire Department takes over Hurlbut Park for the day hosting picking and fiddling contests for all ages

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Darien, CT —
A Perfect Summer or Early Fall Weekend in Darien

Get up early Saturday morning and take a walk through Woodland Park with it’s many trails. You will feel like you are miles away from civilization. Alternatively, try the loop around Long Neck Point with beautiful vistas of Darien Harbor and Long Island Sound. On a clear day, you will be able to see New York City. You will likely see many other people out on this route jogging, pushing strollers or walking dogs. Then go out for breakfast at one of the many local spots for the perfect bacon, egg and cheese or a fresh bagel. Some favorite spots are Jake’s Place, Uncle’s Deli or UCBC for great bagels.

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Rowayton, CT —
The Oyster Town

Edging its way down the Five Mile River to Long Island Sound, the seaside village of Rowayton offers a unique blend of salty but traditional appeal. Once known primarily as an oyster town, Rowayton has developed into a combination of suburb and resort village.

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Fairfield, CT —
Fairfield’s Super Seven for Supper

Hands down, one of the most fabulous features of Fairfield is all the chic eateries downtown. So, I thought I would share with you seven of my favorite picks for dining and ambiance.

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New Fairfield, CT —
New York’s Best Kept Secret

New Fairfield, Connecticut is a fabulous suburban community located about one hour from Manhattan, just over the line from Brewster, New York. It’s a great location for commuting into Westchester County & NYC, as it is minutes from Metro North train line and holds itself as a true ‘vacation lifestyle’ town as one of five towns that surround beautiful Candlewood Lake.

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North Stonington, CT —
Own of North Stonington CT

North Stonington is nestled quietly on the border of Rhode Island, halfway between Boston and New York. While staying urban in areas of entertainment and transportation, it seems to be a step back in time; that is, until you see the Foxwoods Resort and Casino.
Originally part of the town of Stonington, North Stonington split off to be its own town in 1724. It is truly a quintessential New England enclave. Our bucolic town consists of 5,200 townsfolk with likely as many critters, cows, turkeys, alpacas, bison, and horses. North Stonington is also noted for its many working farms, providing Christmas Trees and fresh turkeys. It is home to the Beriah Lewis Farm which has been a cornerstone of the community and in their family for over 224 years! Over 300 cows are milked daily there at the farm.

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Middlefield, CT —
“Fielders” Have More Fun

Growing up, my Dad used to tell me that Middlefield was once a part of the city of nearby Middletown but a tax difference between the urban “Towners” and the rural “Fielders” caused tensions and so, the towns split apart. Although I haven’t found anything to back up his claim, Middlefield remains a sacred place to me and now, to my own family.

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Darien, CT —
Summer Nights in Darien

Baywater Properties and Grove Street Plaza are kicking off their annual Friday night concert series June 23rd from 6:00-8:30 and it’s one of my favorite event series in town. These free concerts are held at Grove Street Plaza and run through August 11th. The Darien Nights Concert Series was launched by Darien residents David Genovese and Penny Glassmeyer, who head up Baywater Properties and Grove Street Plaza, respectively. During the Winter of 2008-2009, the two decided it was time to do something positive for residents who would be staying around town because of the unsettled economic climate, and to encourage them to shop locally and support Darien’s merchants. The first series was such a great success this yearly tradition has continued ever since and every year attendance grows. “I love the opportunity to meet friends in town for dinner and then stroll over to Grove Street Plaza to hear some great bands and see community friends in a fun relaxed setting,” said Deirdre McGovern

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Stratford, CT —
Stratford’s best-kept secret!

Everyday when I drive home from work through the breathtaking views of the Long Island Sound and the marsh, I can imagine I’m going home to my little, private island. That’s the feel you get by living amongst the water in Lordship, CT. An intimate community with so much to offer, many longtime residents will tell you once you live in Lordship, you will never live anywhere else.

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Mystic, CT —
At the Mouth of the Mystic River

Located just downriver from Mystic sits the Village of Noank, part of the larger township of Groton and situated directly across from Stonington's Masons Island. Much of this quintessential shoreline village is elevated out of the floodplain and offers all the amenities and services you might wish for in a true coastal village. Every place here offers a unique family-owned approach to small business such as Carson's Store on Main Street, an ice cream shop with a classic lunch counter or Sherman's deli and convenience store on Pearl Street featuring delicious prepared daily specials, handmade granola, soups and sandwiches as well as various essential sundries.

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