Westport, Connecticut, is perfectly placed for weekend adventurers. Its prime location along the coast and easy access to major highways and rail lines make it an ideal launchpad for quick getaways. Whether you’re craving mountain air, seaside serenity, or a cultural city fix, these weekend escapes—ranging from 2 to 4 hours away—offer something refreshing and new. Pack your bag, hit the road Friday afternoon, and return Sunday feeling renewed. Here are nine of the best weekend getaways from Westport that strike the perfect balance between distance and reward.
Boston, MA
For those who crave culture, history, and city life, Boston is a rewarding escape just over three hours away. You can walk the historic Freedom Trail, explore Beacon Hill, or take in the art at the MFA and the Isabella Stewart Gardner Museum. Fenway Park, Harvard Square, and world-class seafood are all within reach. Boston blends old and new in a way that keeps you engaged from Friday night through Sunday afternoon.
Newport, RI
Less than three hours away, Newport offers a sophisticated coastal getaway with Gilded Age flair. Tour opulent mansions like The Breakers, stroll the scenic Cliff Walk, or enjoy a sunset sail in the harbor. The town’s historic downtown is filled with boutique shops, seafood restaurants, and charming inns, making it a perfect weekend blend of elegance and ocean breezes.
Catskills, NY
A weekend in the Catskills means mountain views, artist enclaves, and rejuvenating outdoor adventure. Just under three hours from Westport, this region offers hiking trails, waterfall walks, and cozy cabins. Spend your days antiquing in Woodstock, dining at farm-to-table restaurants, or relaxing at a stylish inn with a fireplace. The Catskills deliver a peaceful but invigorating break from coastal life.
Montauk, NY
At the eastern tip of Long Island, Montauk feels like a world away. The drive and ferry combo take about 3.5 hours, but you’re rewarded with dramatic shorelines, surfer culture, and iconic spots like Montauk Point Lighthouse. From seafood shacks to boutique hotels, Montauk blends laid-back charm with just the right touch of luxury. This is a summer favorite, but even the off-season brings windswept beauty.
Providence, RI
Just 2.5 hours from Westport, Providence is a creative and compact city with a vibrant arts scene. Explore the RISD Museum, stroll along the river, and dine in the city’s renowned Italian district, Federal Hill. If your trip coincides with WaterFire—an evening event where the river is lit with floating fires—it’ll be a weekend to remember. Providence is quirky, cultured, and unexpectedly romantic.
Tarrytown & Sleepy Hollow, NY
For a historic and literary-themed escape, head just two hours west to Tarrytown and Sleepy Hollow. Explore the grounds of the Lyndhurst Mansion, walk leafy paths along the Hudson, or dive into the lore of Washington Irving’s Legend of Sleepy Hollow. This area is especially magical in the fall, with vibrant foliage and spooky seasonal events, but its charm endures year-round.
Hudson Valley, NY
Stretching north from Westchester County to Albany, the Hudson Valley offers a rich mix of outdoor beauty and artistic culture. Spend a weekend in towns like Beacon, Cold Spring, or Hudson, where you’ll find galleries, indie boutiques, and riverside views. Dia:Beacon is a must-see for modern art lovers, while the surrounding area offers hiking, wineries, and farm markets. It's an effortlessly stylish retreat less than three hours away.
The Berkshires, MA
Rolling hills, cultural venues, and postcard-perfect villages await in the Berkshires, located about 2.5 hours from Westport. Visit the Norman Rockwell Museum, explore the trails at Mount Greylock, or catch a performance at a local theater. Quaint towns like Lenox and Stockbridge offer inns, bookstores, and fine dining. The Berkshires are ideal for a cozy and cultured countryside weekend.
Finger Lakes, NY
For an ambitious but deeply rewarding weekend, head four hours northwest to the Finger Lakes. This region is a dream for wine lovers, nature enthusiasts, and those who love scenic drives. Spend your time touring wineries along Seneca or Cayuga Lake, hiking through Watkins Glen State Park, or relaxing by the water. With its blend of rustic charm and natural grandeur, the Finger Lakes deliver a memorable escape worth every mile.
Where the Weekend Begins and Ends
Whether you're venturing north for mountain air or heading to the coast for salty breezes, Westport makes it easy to change your scenery without sacrificing convenience. These nine destinations offer everything from urban buzz to tranquil nature, ensuring that every weekend away feels like a true getaway. With the right plan and the right place to call home, the adventure always begins just beyond your doorstep.
Your Weekend Gateway Starts at Home
Finding the perfect home base for weekend escapes begins in Westport. With its unbeatable location, vibrant lifestyle, and scenic charm, this coastal town puts some of the Northeast’s most desirable destinations within easy reach. The Riverside Realty Group has the expertise to help buyers find a property that not only suits their daily needs but also enhances their lifestyle with travel, exploration, and convenience. Their team is ready to help you unlock the door to your next great adventure.
