Summer Isn't Over Yet: 9 Easy Getaways Close to Westport
One of my favorite things about living in Fairfield County is how much there is to do without getting on an airplane—or even spending half the day in the car.
As we head into the last few weeks of summer, there's still time to squeeze in another beach day, long lunch on the water, overnight escape or spontaneous weekend away.
Having lived in Connecticut for most of my life, I've had plenty of time to explore our little corner of New England. One of the things I love about living in Westport and Fairfield County is that within roughly two hours, you can be on an island, wandering through a historic seaside village, relaxing at a beautiful resort or enjoying some of the best beaches in the Northeast.
Here are nine of my favorite ideas for enjoying the final stretch of summer close to home—including some special places to stay if you want to turn your day trip into a mini vacation.
1. Greenwich, Connecticut: Shopping, Art & a Waterfront Stay
Approximately 30–40 minutes from Westport
Sometimes the best getaway is practically in your own backyard.
For a day that feels a little more like a mini vacation, head to Greenwich. Start with shopping and strolling along Greenwich Avenue, where you'll find a mix of designer boutiques, national brands, local shops, cafés and restaurants.
From there, spend an hour or two at the Bruce Museum, one of Fairfield County's cultural gems, with exhibitions spanning art, science and natural history.
Then make your way toward Greenwich Harbor for the perfect end to the day.
Where to stay: Check into the Delamar Greenwich Harbor, a beautiful waterfront hotel that feels worlds away despite being less than an hour from Westport. Its location directly on the harbor makes it especially lovely during the final weeks of summer.
Where to eat: Have cocktails followed by dinner at L'Escale, the Delamar's waterfront restaurant. The setting is one of the prettiest in Greenwich, particularly when you can sit outside overlooking the harbor on a warm summer evening.
My insider tip: Make a full day of it. Arrive late morning, shop Greenwich Avenue, visit the Bruce Museum in the afternoon and then head to the Delamar. Even if you don't stay overnight, drinks and dinner at L'Escale are a wonderful ending to the day.
2. The North Fork of Long Island, New York
The North Fork is one of my favorite nearby escapes because it feels like you've traveled much farther away than you actually have.
Think vineyards, farm stands, charming small towns, waterfront restaurants and beautiful views of Long Island Sound.
Spend the afternoon exploring Greenport, stop at a winery or two, browse the shops and finish with dinner overlooking the water.
Where to stay: For a stylish overnight, consider The Menhaden in downtown Greenport or Sound View Greenport, a waterfront hotel overlooking Long Island Sound.
My insider tip: Don't try to do everything. Choose a couple of places you really want to visit and leave time to simply enjoy Greenport. The North Fork is much better at a slower pace.
3. Sag Harbor & The Hamptons, New York
If you're looking for something a little more glamorous, head to Sag Harbor, Southampton or East Hampton.
Sag Harbor is particularly fun for a quick getaway. Walk around town, browse the boutiques, have lunch overlooking the harbor and enjoy that unmistakable summer-in-the-Hamptons atmosphere.
Where to stay: Baron's Cove is a great Sag Harbor choice if you want to be close to town and the water. For something more luxurious, Topping Rose House in Bridgehampton makes a beautiful home base for exploring the Hamptons.
My insider tip: Summer traffic can dramatically change drive times. Go early, consider traveling during the week and avoid peak Friday-afternoon traffic whenever possible.
4. Madison & the Connecticut Shoreline
Approximately 1 hour 15 minutes from Westport
Sometimes we forget just how beautiful our own Connecticut shoreline is.
Spend the day at Hammonasset Beach State Park, with its miles of shoreline for swimming, walking and enjoying one more full summer beach day.
Afterward, head into downtown Madison for shopping, lunch or dinner.
Where to stay: Make it a mini getaway with a night at Madison Beach Hotel, a waterfront property overlooking Long Island Sound. It's close enough to home to be incredibly easy, yet sitting by the water can make it feel like you've truly gone away.
This is one of those trips that's easy enough to decide on in the morning and still feels like a real escape.
5. Mystic & Stonington Borough, Connecticut
Approximately 1½–2 hours
Yes, Mystic is popular—but there's a reason.
Downtown Mystic has wonderful restaurants, shops, waterfront scenery and that quintessential New England summer feeling.
But don't stop there.
Continue over to Stonington Borough, which is smaller, quieter and absolutely charming, with historic homes, little shops and beautiful water views.
Where to stay: The Whaler's Inn puts you right in the heart of downtown Mystic. You can also look at one of the smaller inns around Stonington for a more intimate coastal experience.
My insider tip: Stay overnight if you can. Mystic takes on a completely different feel in the evening after many of the day visitors have gone home.
6. Watch Hill, Rhode Island
Approximately 2 hours from Westport
If you want that I'm officially on vacation feeling without getting on a plane, Watch Hill is hard to beat.
Beautiful homes, beaches, a charming little village and classic Rhode Island coastal scenery make this one of my favorite end-of-summer escapes.
Walk through town, spend the afternoon at the beach and finish with cocktails or dinner overlooking the water.
Where to stay: This is the place to splurge on Ocean House. Perched above the Atlantic, it's one of New England's iconic seaside resorts and makes even a one-night getaway feel special.
Even if you don't stay overnight, consider stopping at Ocean House for lunch, cocktails or dinner as part of your Watch Hill experience.
7. The Litchfield Hills, Connecticut
Approximately 1½ hours from Westport
Not every summer getaway needs to involve the beach.
For something completely different, head north to the Litchfield Hills.
Towns like Washington, New Preston, Kent and Litchfield offer beautiful country roads, antique shops, restaurants, hiking, lakes and some of Connecticut's prettiest scenery.
Where to stay: For a special weekend, Mayflower Inn & Spa in Washington is one of Connecticut's best-known luxury country retreats. Another option is The Abner Hotel in the heart of historic Litchfield.
This is the perfect getaway when you want a little country air, a beautiful dinner and absolutely nowhere you need to be.
8. Shelter Island, New York
Located between Long Island's North and South Forks, Shelter Island feels wonderfully removed from the summer crowds.
It's quiet, scenic and laid-back—a great choice for biking, boating, beaches, long lunches and simply slowing down for a day or two.
Where to stay: The Pridwin Hotel & Cottages offers a classic Shelter Island summer experience with beautiful water views and a relaxed resort atmosphere. The Chequit is another charming choice near Shelter Island Heights.
My insider tip: I especially like Shelter Island as an overnight destination. Once the day-trippers leave, the island becomes even more peaceful.
9. Stay Right Here in Westport, Connecticut
And finally, sometimes we spend so much time planning where to go that we forget people travel here for exactly what we have in our own backyard.
Why not make your own Westport staycation?
Start with a morning at Compo Beach, walk or bike along the shore, have lunch in Saugatuck, shop downtown, take a boat out on Long Island Sound and finish the day with cocktails and dinner by the water.
Where to stay: The newly reopened Inn at Longshore gives us another reason to enjoy a staycation right here in Westport. The historic waterfront inn has been beautifully reimagined with redesigned guest rooms and its wonderful location overlooking Long Island Sound.
It's a great option for a romantic night away, a special occasion or for visiting friends and family who want the full Westport experience.
Where to eat: Enjoy dinner at La Plage, the waterfront restaurant at Longshore, and if the weather cooperates, sit outside and take in the views over the Sound.
There is something pretty wonderful about checking into a hotel minutes from home, having dinner by the water and waking up overlooking Long Island Sound—without dealing with traffic, packing for a big trip or going anywhere near an airport.
One of the Best Parts of Living in Fairfield County
When people ask me what it's like to live in Westport, Weston or elsewhere in Fairfield County, I always tell them that location is about so much more than the commute.
Yes, we have incredible access to New York City.
But we're also surrounded by beaches, boating, charming New England towns, countryside, restaurants, museums, vineyards and some fantastic weekend destinations.
Within a couple of hours, you can go from your morning coffee in Westport to a vineyard on the North Fork, shopping on Greenwich Avenue, a beach in Rhode Island or a beautiful country inn in the Litchfield Hills.
And sometimes, the best vacation is right here at home.
So before we start talking about pumpkins, fall foliage and everything autumn in Connecticut, I'm planning to enjoy every last bit of summer.
I hope you do too.
Thinking About Moving to Fairfield County, Connecticut?
If you're considering a move to Westport, Weston, Wilton, Fairfield, Southport, Norwalk, Rowayton, Darien, New Canaan, Greenwich, Stamford or the surrounding Fairfield County area, I'd love to help.
Having lived in Connecticut for most of my life, I don't just help my clients understand the real estate market. I love sharing the towns, neighborhoods, restaurants, beaches, hidden gems and lifestyle that make this area such a wonderful place to call home.
Whether you're buying, selling, relocating to Connecticut or simply wondering what your Fairfield County home may be worth, please reach out anytime.
Christine Finch Oleynick
Realtor | Keller Williams Prestige Properties
Fairfield County, Connecticut
Email: [email protected]
Website: christinefincholeynick.com
Instagram: @christine_finch_oleynick
