Connecticut
I skip the Hamptons and head to a coastal town in Connecticut instead. It's less crowded and wonderful year-round.
- For years, I spent countless hours stuck in traffic driving to the Hamptons from my home in NYC.
- I got fed up and started spending weekends in Madison, a coastal Connecticut town.
- Madison’s beautiful beaches and cute downtown offer lots to do without the crowds.
I vacationed in the Hamptons for decades but eventually got a bit tired of it.
I can’t count how much time I’ve spent sitting in traffic on the Montauk Highway, searching for parking spots at the beach, and waiting for tables at trendy restaurants.
Fortunately, “destination dupes” are all the rage right now with many turning to TikTok to find less-crowded, cheaper, and more under-the-radar alternatives to their dream vacation spots.
So, I found my own “dupe” of the Hamptons about 100 miles away in New England: Madison, Connecticut.
The town defines coastal calm, with just about everything the Hamptons has minus the crowds. It’s still upscale but less expensive — and my drive from New York City to Madison isn’t so bad.
Here’s why I love Madison so much.
The beautiful beaches get me every time
Allison Tibaldi
The local beaches attract me like a magnet. Fortunately, Madison has about a dozen.
My favorite is Hammonasset Beach State Park, with about 2 miles of Long Island Sound shoreline and trails that I can bike on. It’s felt clean and uncrowded each time I’ve visited.
Allison Tibaldi
I stay at a bed-and-breakfast that blends cozy with chic
There are several bed-and-breakfasts in Madison, plus a beachfront Hilton hotel.
I usually stay at The Homestead, an upscale B&B that hits the right balance between charming and modern. Its dozen or so rooms are individually decorated with high-end furnishings and posh perks like Japanese toilets, showerheads infused with vitamins, and record players with an eclectic selection of vinyl.
Each guest has access to complimentary bikes, towels, and beach chairs to borrow. Plus, its gardens and decks with firepits make it easy for me to spend time outdoors.
I also love its gourmet snacks and elegant breakfast buffet with things like quiche, cake, fresh fruit, and yogurt.
There’s plenty of retail therapy and artwork to be found in town
Allison Tibaldi
Madison’s downtown is low-key, laidback, and walkable, with excellent New England vibes.
I can get lost for hours at RJ Julia Booksellers, which I consider one of the best independent bookstores in the entire country.
I always stop at Savvy Tea Gourmet, which sells a variety of unique teas and has in-store tastings. When I’m not sure which tea leaves to buy, the owner steers me in the right direction.
The town also has a cluster of cute clothing boutiques. My favorite is The Dressing Room, where the staff is friendly and the sales are legit.
Allison Tibaldi
Along the way, I take in some of the local art. Madison has plenty thanks to the Sculpture Mile, a free outdoor public art installation of museum-quality sculptures scattered around town.
Madison Cinemas is perfect for rainy days
When it’s cold or rainy, you’ll find me at Madison Cinemas watching arthouse and international films.
The century-old theater has freshly-popped popcorn topped with real butter and local beer and wine.
There’s often something happening on the town green
Madison’s historic town green is its leafy centerpiece. I like to stroll the peaceful paths and listen to live music during the free concerts on Sunday evenings in the summer.
It hosts a great farmers market every Friday afternoon from May until Thanksgiving and the town often has seasonal festivals.
The culinary scene is great, too
Allison Tibaldi
Madison has a few eateries I try to stop at each time I visit.
French bistro Bar Bouchée transports me right to Europe with its ambiance and traditional Gallic fare. I can also never resist ordering the profiteroles drenched in warm chocolate sauce.
I book a table at The Wharf when I want to eat fresh seafood with a view of the water. My go-to order is the warm lobster roll served with a mountain of crisp shoestring fries.
When I crave pasta like my Nonna used to make, I head to Café Allegre. The Italian eatery serves classics like spaghetti with fresh clams and robust rigatoni with meatballs and sausage.
Madison is also lovely in the fall and winter
In the fall, the area’s numerous farms and farm stands overflow with fresh produce and pretty flowers. My favorite is Bishop’s Orchard in neighboring Guilford, where I go apple-picking each autumn.
The beaches are fun to visit throughout the year, too. The water usually stays warm well into October, so I can have a dip surrounded by fall foliage.
I even go in winter for chilly seaside strolls and snowshoeing on the maze of wooden boardwalks.
Connecticut
Marian Katz Obituary
Connecticut
CBIA BizCast: Snapshot of Connecticut’s Economy » CBIA
New data is shedding light on the state of Connecticut’s economy and labor force.
On this episode of the CBIA BizCast, CBIA Foundation director Dustin Nord joins host Amanda Marlow to talk about new Connecticut Department of Labor data that highlights the mismatch between increased job openings and a shrinking labor force.
Connecticut job openings jumped 2.6% in May to 87,356—however, since May 2025, 37,700 people have left Connecticut’s labor force.
Nord breaks down some of the reasons for this mismatch and what needs to be done to address Connecticut’s economic challenges.
He also shares insights into a U.S. Bureau of Economic Analysis report showing Connecticut’s economy expanded 1.8% in the first quarter of 2026.
Episode Highlights:
- Job Openings vs. Workforce Shortage
- Unemployment Trends
- GDP Growth Amid Labor Challenges
- Affordability and Long-Term Competitiveness
Headlines You May Have Missed:
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Connecticut
This Underrated Connecticut Town Is Getting National Recognition as One of the Best Places to Live
According to Islands.com, one Connecticut town is getting some well-deserved national attention, and it’s probably not the one you’d expect.
When people think about standout Connecticut destinations, places like Mystic, Greenwich, or New Haven usually dominate the conversation. But this time, the spotlight is on Cheshire, which was recently recognized as one of the best places to live in the state.
The national travel website points to Cheshire’s combination of small-town charm, outdoor recreation, local businesses, and great restaurants as some of the biggest reasons it’s become such a desirable place to call home. It’s also no stranger to high rankings. Cheshire was named the best place to live in New Haven County by Niche in 2025 and has also landed on Money Magazine’s list of the best places to live in America. Its public schools continue to receive high marks as well.
One of Cheshire’s biggest draws is its access to nature. The town is home to scenic orchards, beautiful greenhouses, and is known as Connecticut’s bedding plant capital. During the fall, local farms and orchards become popular destinations for apple picking, fresh cider, and seasonal treats. Outdoor lovers also have easy access to Roaring Brook Falls, Sleeping Giant State Park, and the Farmington Canal Heritage Trail.
Of course, no Connecticut town earns national praise without having some great food. Islands.com highlighted Cheshire’s pizza scene, including Fuoco Apizza and Pop’s Pizza, along with Viron Rondo Osteria for Italian cuisine. Beer lovers can also stop by Counter Weight Brewing, while Sweet Claude’s Ice Cream and Shef’s Bagels round out the town’s lineup of local favorites.
Cheshire may not get the same attention as some of Connecticut’s bigger destinations, but this latest recognition suggests it deserves a spot on your list. Whether you’re looking for a weekend road trip or thinking about putting down roots, this quiet New Haven County town is proving it has a lot more to offer than many people realize.
7 of the Most Beautiful Towns in the State of Connecticut
Connecticut is overflowing with both manmade and natural beauty. In some places, the two intersect to create a magical, almost fictional feel. Here are 7 Connecticut Towns that look like they came straight from a storybook.
Gallery Credit: Lou Milano
5 Historic Connecticut Towns That Feel Frozen in Time
Connecticut is full of towns people rush past on the highway without realizing what they’re missing. Everyone knows the big names, but some of the best places in the state are the ones that don’t always make the travel lists. These towns are quieter, full of character, and worth slowing down for at least an afternoon.
Gallery Credit: Lou Milano
Look Inside the Largest Indoor Collaborative Artwork in the World
I visited the American Mural Project in Winsted, Connecticut for the first time recently, and for those who haven’t seen it, here’s a quick peek at what to expect when you gaze upon the largest indoor collaborative piece of artwork in the world
Gallery Credit: Photos by Large Dave
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