Years ago, someone—pretty sure it was my brother—said to me, “August is like one long Sunday night.” Every year around this time, I find myself thinking about that phrase. The sun starts setting earlier. The first day of school appears on the calendar. Fall sports practices and carpools creep into the schedule. As Labor Day draws near, the carefree feeling of summer begins to slip away.
As the mother of two teenagers, I’ve learned that summer doesn’t necessarily get less magical as children get older. It just gets shorter. Which is why I’m a big believer in squeezing in one last adventure before the school year begins.
The good news is that living in Fairfield County puts us within driving distance of some incredible destinations. Whether you have a free day, a spare night, or an open weekend, these easy getaways offer one final chance to make a summer memory before backpacks, lunchboxes, and alarm clocks return.
Block Island: The Island Escape
Even the journey to Block Island feels like an adventure. Ferries depart regularly from Point Judith, Rhode Island, and in less than an hour, the mainland begins to disappear.
The island is compact enough to explore on two wheels, so rent bikes at the ferry terminal—half the fun is discovering what lies around the next bend in the road. Spend the morning at Crescent Beach, then make your way to the dramatic Mohegan Bluffs, where a steep staircase leads down to one of the most spectacular stretches of shoreline in New England. Nearby, the Southeast Lighthouse sits atop the cliffs, offering sweeping views of the Atlantic.
Have a lobster roll lunch, overlooking the harbor. After, wander through Old Harbor's collection of shops and galleries, or find a quiet patch of beach and settle in.
The beauty of Block Island is that it doesn’t require a packed itinerary. A bike ride, a beach, an ice cream cone, and nowhere in particular to be is the itinerary.
Newport: A Weekend in the Gilded Age
Newport has beaches, harbor cruises and waterfront restaurants—and I do recommend sampling all of that!-—but the tonw’s enduring appeal lies in the way it blends history, glamour, and classic New England charm. For anyone who has recently become obsessed with HBO’s The Gilded Age, Newport offers the opportunity to step inside the world of the Vanderbilts, Astors, and more of America’s wealthiest families.
Start with The Breakers, the Vanderbilt family’s spectacular 70-room summer “cottage,” where marble staircases, gilded ceilings, and ocean views reveal the staggering wealth of the era. Nearby Marble House, built by William K. Vanderbilt as a birthday gift for his wife Alva, is equally fascinating and every bit as extravagant (this one is actually my personal favorite; the gardens in particular! Think: Hydrangea heaven).
After touring the mansions, head to the famed Cliff Walk, where crashing Atlantic waves sit on one side, and Newport’s grand estates rise on the other. Even a short stretch of the walk delivers some of the most iconic views in New England.
For lunch, grab a table at The Black Pearl on Bannister’s Wharf for its clam chowder and harbor views. Spend the afternoon browsing the shops along Thames Street and Bowen’s Wharf before ending the day aboard a sunset sail through Newport Harbor. Watching the sun dip below the horizon as sailboats glide across the water is one of those experiences that never gets old.
The Berkshires: Summer’s Last Deep Breath
The Berkshires’ rolling hills, charming towns, lakes, hiking trails, and outdoor concerts create an atmosphere that practically forces you to relax. Families can spend the morning paddleboarding on Stockbridge Bowl, hiking Monument Mountain, or exploring the grounds at The Mount, author Edith Wharton’s former estate.
In Great Barrington, independent bookstores, cafés, and boutiques invite leisurely browsing. Nearby farm stands overflow with late-summer produce. As evening approaches, many families spread out a blanket on the lawn at Tanglewood, home of the Boston Symphony Orchestra's summer season. Even reluctant teenagers tend to appreciate a picnic dinner as the sun sets behind the mountains and music fills the air.
By late August, the crowds thin and the evenings grow slightly cooler, making it an ideal place to savor summer’s final weeks.
Lake George: Classic Summer Nostalgia
There is an old-fashioned quality to a weekend in Lake George that feels refreshingly simple. Kids make friends at the beach. Families enjoy hours on the water, swimming, boating, and tubing. Rent a pontoon boat and spend an afternoon exploring the lake’s coves and islands. Take a cruise aboard one of the historic Lake George steamboats. Wander the village, challenge the kids to a round of mini golf, and finish the evening with an ice cream cone while strolling along the waterfront.
Surrounded by the Adirondack Mountains, Lake George offers just enough adventure while remaining wonderfully accessible. If your goal is to squeeze every last drop out of summer before school begins, Lake George is hard to beat.
The North Fork: A Getaway on the Water
Fairfield County families can board the Port Jefferson Ferry in Bridgeport and enjoy a scenic and traffic-free crossing of Long Island Sound. From Port Jeff, it’s about an hour's drive east to the North Fork, where a very different version of Long Island awaits, full of farm stands, fishing boats, and quiet beaches.
Spend an afternoon exploring Greenport, one of the region's most charming waterfront villages. Browse local shops, enjoy homemade ice cream from Aldo’s, or watch boats coming and going from the harbor. Families can spend the day at Orient Beach State Park, known for its calm waters, easy trails, and beautiful views.
Late August is prime farm-stand season, and roadside markets overflow with peaches, sweet corn, tomatoes, and fresh flowers. The North Fork lacks the see-and-be-seen atmosphere of the Hamptons, and that may be the best part.
One More Thing
Years from now, our children probably won’t remember whether the trip lasted one night or four. They won’t remember how much we spent or whether every detail went according to plan. What they’ll remember is racing down a hill on Block Island, standing inside a Vanderbilt mansion, jumping off a dock into a lake, watching sailboats on Newport Harbor, or eating ice cream on a ferry ride home as the sun sets over Long Island Sound.
August may feel like one long Sunday night, but remember: there’s still time before Monday morning arrives.
"As the mother of two teenagers, I’ve learned that summer doesn’t necessarily get less magical as children get older. It just gets shorter. Which is why I’m a big believer in squeezing in one last adventure before the school year begins."