These towns have the best of everything–including incredible coastal living.
If you’re craving vacation vibes in your everyday life, these Connecticut suburbs deliver in a big way. We’re talking beachfront living, yacht clubs, summer concerts, and beach bonfires—all with great schools, charming town centers, and an easy ride into Manhattan.
If you’re ready to trade crowded city splash pads for sunset sails, here are four beachy Connecticut towns where summer never really ends.
1. Greenwich
Greenwich is spectacular year-round, but in the summer, it turns into something else entirely. Picture sandy toes, paddleboards at the ready, ferry rides to secluded beaches, and backyard clambakes that last all night. This is where city families go when they want all the amenities—with a lot more space and a serious waterfront upgrade.
A must-visit while house hunting? Greenwich Point Park, also known as Tod’s Point, in Old Greenwich. With over 1.5 miles of sandy beach, picnic areas, walking and biking trails, and views of the Manhattan skyline on clear days, it’s a true coastal playground. You’ll also find the Old Greenwich Yacht Club, where residents can rent kayaks, take sailing lessons, or just kick back and enjoy the breeze.
Looking for a little more adventure? Hop on the Island Beach Ferry from downtown Greenwich and head to Island Beach, a town-owned island two miles offshore. The ferry runs regularly in summer months and is only open to residents and their guests. Once there, you’ll find calm waters, picnic tables, lifeguards, and even a concession stand. Locals swear it feels like a private island—and it kind of is.
Pro tip: Want to make it a lifestyle? Greenwich residents can also join Greenwich Boat & Yacht Club, a nearly 100-year-old club offering year-round social events, from movie nights to seafood bake-offs to the annual St. Patrick’s Day bash.
2. Westport
Consistently ranked among the best beach towns in the tri-state area, Westport is the rare combination of laid-back and luxurious. Think breezy beach days and farmers markets by morning, upscale dining and art festivals by night. And during the summer? It’s a nonstop celebration of the outdoors.
Compo Beach is Westport’s crown jewel, a sprawling 29-acre park along Long Island Sound and the Saugatuck River. Yes, there’s a gorgeous beach and tidal pools for the little ones, but there’s also a skate park, basketball courts, sand volleyball, a massive playground (designed by kids!), and even BBQ areas and picnic tables for your whole crew. Lifeguards are on duty all summer long, and there’s plenty of parking with a seasonal pass.
One unique perk? South Beach, the quieter end of Compo, allows alcoholic beverages—so pack a picnic (and your favorite beverage) and enjoy the sunset over the Sound.
3. Fairfield
With five miles of coastline and five public beaches, Fairfield delivers the ultimate New England beach town experience—minus the ferry lines or the Cape traffic. Add in top-rated schools, a thriving downtown, and express trains to the city, and it’s no wonder so many families are making the leap.
Jennings Beach is the town’s biggest and most beloved sandy stretch. Families love the gentle waves, the Sand Castle Playground, and the regular Bonfire on the Beach nights, complete with live music, s’mores, and views for days.
Looking for a more laid-back vibe? Head to Penfield Beach for quieter days, shady picnic spots, and walking paths along the dunes. Or check out Sasco Beach in Southport, a hidden gem that feels almost private—with stunning views and just enough space to unwind.
Fairfield also goes beyond the beach. There are 31 public tennis and pickleball courts, bocce ball, and even community garden plots for summer tomatoes and late-August dahlias. You’ll also find hiking trails throughout town and Lake Mohegan, a freshwater alternative with a splash pad and forested trails just minutes from the sand.
4. Darien
Tucked between Stamford and Norwalk, Darien is a small town with serious summer appeal. Its two resident-only beaches offer very different vibes—and both are worth exploring if you’re house hunting nearby.
Weed Beach is the action-packed option. It’s got tennis courts, a concession stand, shaded picnic spots, a paddle sports launch area, and a ship-shaped playground that’s basically legendary. This is also home to the Darien Junior Sailing Team, where kids as young as 8 learn to navigate the Sound like pros.
For something quieter, Pear Tree Point Beach is a more intimate setting. Here, you can launch a kayak, moor your boat at the Darien Boat Club, or just chill on the sand while sailboats glide by in the distance. Bring a book, grab a lobster roll nearby, and you’ve got the perfect Sunday afternoon.
Bonus for golf lovers: the Country Club of Darien is one of the area’s most exclusive clubs, with a stunning course, newly renovated tennis and aquatics center, and top-tier kids programming all summer long.
Ready to dive in? Whether you’re craving beach days or just want to swap sidewalk chalk for seashells, these Connecticut towns offer year-round perks—with that unbeatable summer energy.
