Weekend Trips from Westport

Living in Westport, Connecticut, offers a wealth of luxuries in the heart of Connecticut’s Gold Coast—a vibrant community, gorgeous homes, and a majestic coastline overlooking Long Island Sound. However, one of Westport's most understated advantages is the access it offers to many of the region’s—and the East Coast’s—best weekend destinations.

Whether by land, air, sea, or rail, Westport is uniquely positioned less than three hours away from a wide variety of locales, from vibrant cities to coastal retreats to a standout collection of natural areas. That translates into more time at your getaway and less time getting away. Here’s your guide to the best weekend trips from Westport.

For those who love the freedom of the open road, Westport’s location puts you within easy reach of scenic parks, cultural hotspots, and historic towns—all without the need for flights or ferries.

Just a two-hour drive from Westport, Newport, RI, offers a perfect blend of seaside charm and historic grandeur. Known for its Gilded Age mansions, visitors can explore iconic landmarks such as The Breakers and Marble House, which provide a glimpse into America's opulent past. The Cliff Walk combines stunning ocean views with access to these architectural treasures. Sailing enthusiasts can enjoy Newport’s vibrant boating scene, while foodies savor fresh seafood at renowned spots like The Mooring or Clarke Cooke House. For accommodations, relax in style at The Chanler at Cliff Walk, a luxurious boutique hotel with unmatched coastal views.

Boston is the perfect mix of history, culture, and luxury. Wander through historic sites like the Freedom Trail, indulge in world-class dining at spots like No. 9 Park, or enjoy a relaxing afternoon in the Boston Public Garden. For a chic stay, book high-end accommodations at The Eliot Hotel or XV Beacon in Beacon Hill. For the ultimate in elegance and convenience, stay at The Newbury, a landmark hotel offering impeccable service and a prime location. Perfectly situated for shopping, dining, and exploring the city on foot, The Newbury ensures a sophisticated and memorable Boston experience.

Litchfield, nestled in the rolling hills of northwestern Connecticut, is a perfect blend of historic charm and natural beauty. Stroll through its quaint town center, dotted with antique shops, art galleries, and farm-to-table restaurants, or explore nearby nature reserves like White Memorial Conservation Center for hiking and birdwatching. For a truly luxurious escape, stay at Winvian Farm, a boutique resort set on 113 acres of countryside. With creatively themed cottages, a farm-to-table restaurant, and serene spa services, Winvian Farm offers a one-of-a-kind experience. Whether you’re seeking relaxation or outdoor adventure, Litchfield provides an idyllic weekend getaway, and it’s only an hour from Westport.

Vermont’s pristine landscapes make it an ideal destination for a peaceful weekend retreat. Explore charming small towns like Woodstock or Stowe, each offering quintessential New England charm with historic covered bridges, boutique shopping, and farm-to-table dining. Outdoor enthusiasts can hike scenic trails, bike through lush countryside, or visit picturesque lakes. In the winter months, enjoy top-tier skiing and snowboarding at resorts like Killington or Sugarbush. Stay at cozy inns such as Twin Farms, or The Woodstock Inn & Resort, two luxury properties offering personalized experiences, gourmet cuisine, and refined New England charm.

For those seeking a weekend of pure indulgence, these luxurious hotels offer unparalleled experiences. From serene countryside retreats to coastal elegance, these properties are destinations in themselves, each providing exceptional service, gourmet dining, and world-class amenities.

Nestled in the Hudson Valley, Wildflower Farms is a haven for relaxation and reconnection with nature. This upscale retreat features beautifully appointed accommodations surrounded by meadows, woodlands, and orchards. Guests can enjoy activities like hiking, cooking classes or unwinding at the on-site spa. With farm-to-table dining showcasing local ingredients, Wildflower Farms offers a rejuvenating escape just a short trip from Westport, CT.

Located in Watch Hill, Ocean House combines timeless coastal elegance with five-star luxury. This Relais & Châteaux property offers beautifully restored accommodations, a private beach, and gourmet dining experiences. Guests can indulge in spa treatments, relax in a cabana by the shore, or explore the charming town of Watch Hill. With breathtaking ocean views and impeccable service, Ocean House is a standout destination for a luxurious weekend.

Tucked away in the rolling hills of Washington, Connecticut, the Mayflower Inn & Spa is a sophisticated countryside retreat. This Auberge Resorts property offers spacious accommodations, a serene spa, and exquisite dining that celebrates New England’s culinary traditions. Guests can enjoy outdoor activities like hiking and cycling or relax in the beautifully landscaped gardens. The Mayflower Inn is the epitome of understated luxury and perfect for those seeking peace and tranquility.

For a wellness-focused getaway, Miraval Berkshires in Lenox, Massachusetts, offers an immersive retreat centered on mindfulness and relaxation. With activities ranging from yoga and meditation to outdoor adventures and culinary workshops, this luxury resort caters to the mind, body, and spirit. Guests can rejuvenate at the Life in Balance Spa and savor healthy, gourmet cuisine in a serene setting. Miraval Berkshires provides a transformative experience designed to inspire balance and renewal.

For those seeking a weekend getaway beyond driving distance, several airports provide convenient access to the area. Approximately 30 minutes west of Westport, Westchester County Airport (HPN) in White Plains, NY, provides travelers with numerous seasonal and year-round destinations via non-stop flights under two hours. For even greater options, both LaGuardia (LGA) and John F. Kennedy (JFK) airports are less than 90 minutes away, offering destinations to suit any travel itinerary.

Nantucket is the quintessential New England island retreat, offering windswept beaches, historic charm, and high-end boutiques. Spend your weekend exploring cobblestone streets, visiting local museums, or indulging in seafood at The Galley Beach. With luxurious inns and resorts such as the adults-only Wauwinet or waterfront Harborview Nantucket, Nantucket delivers a flawless setting for relaxation and exploration, whether you’re staying for two days or four.

Washington, D.C., is an excellent option for a weekend filled with history and culture. Visit the monuments and museums along the National Mall, enjoy upscale dining in Georgetown, or relax with a picnic at Dumbarton Oaks Gardens. For accommodations, the Four Seasons Hotel in Georgetown or The Hay-Adams near the White House provides opulent stays with proximity to the city’s main attractions. It is also fun to travel here by train!

For a quick jaunt to paradise, Bermuda is less than a two-hour flight from the New York area and offers stunning pink sand beaches, turquoise waters, and warm hospitality. Explore the historic town of St. George, snorkel in crystal-clear waters, or relax at luxury resorts like Rosewood Bermuda or The Loren at Pink Beach. With its blend of British charm and island tranquility, Bermuda is an ideal escape for a long weekend.

Westport’s proximity to Long Island Sound and its access to local and regional rail lines offer residents the luxury of seamless travel to some of the East Coast’s best destinations. These trips earn bonus points as the journeys are often just as memorable as the destinations.

Among the country’s most celebrated retreats, your Hamptons getaway options are endless, including lounging on the pristine beaches of East Hampton, enjoying farm-to-table dining at Bridgehampton’s Topping Rose House, or shopping in the charming boutiques of Southampton. For accommodations, consider Baron’s Cove in Sag Harbor, The Reform Club in Amagansett, or a private oceanfront estate for the ultimate in luxury and relaxation. A ferry ride from Bridgeport to Port Jefferson, followed by a scenic drive into the heart of the Hamptons, takes three hours.

We’ll cheat just a bit for our next weekend getaway, considering the Block Island destination is worth an extra 30 minutes of travel time. Accessible by an hour-long ferry ride from Point Judith, RI—the overall journey takes just under three and a half hours—Block Island has infinite amounts of old-school coastal charm. Between its tranquil beaches and small-town vibe, you’ll find outstanding dining at Persephone's Kitchen and the seasonal Beachead. Accommodations here are intimate, with the 1661 Inn and Avonlea, Jewel of the Sea being among the highlights.

New York City is always an easy and exciting weekend destination. Whether exploring the latest exhibits at the Metropolitan Museum of Art, shopping on Fifth Avenue, or dining at Michelin-starred restaurants, the city offers endless activities. Stay at The Ritz-Carlton Central Park or The Plaza Hotel for a genuinely opulent weekend. Central Park strolls, Broadway shows, and high-end shopping complete the experience. Alternatively, head to the West Village to explore the Whitney Museum of American Art or take a scenic walk along the High Line for a unique perspective of the city.

One of the greatest luxuries of living in Westport, Connecticut, is the accessibility to such a wide variety of exceptional weekend destinations, including mountain escapes, relaxing beaches, vibrant cities, or immersive culture and history. Westport’s proximity to these destinations ensures that there’s always a new experience waiting just a short trip away.

There are plenty of unique luxuries to experience in Westport's luxury real estate scene, including stunning coastal homes and secluded multi-acre estates. If you're ready to discover more about luxury Westport homes, contact Cindy Raney & Team today for the best combination of experience and expertise.