12 Day or Weekend Trips From Westport CT

12 Day or Weekend Trips From Westport CT


Westport, Conn., is known for its picturesque coastal views, vibrant arts scene, and charming New England ambiance. Living in Westport offers a serene yet engaging lifestyle with easy access to the hustle and bustle of nearby cities. For residents looking to explore beyond their hometown, there are numerous delightful day or weekend trips from Westport, CT, that promise adventure, culture, and relaxation.

Here are some of the best destinations you can visit.

1. New Haven - 45 minutes

A short drive from Westport, New Haven is a hub of culture and history. Home to Yale University, the city boasts impressive museums such as the Yale University Art Gallery and the Peabody Museum of Natural History. Stroll through the historic campus, enjoy a performance at the Shubert Theatre, or savor a slice of famous New Haven-style pizza.

Beyond the university, New Haven offers a vibrant arts and dining scene. Visit East Rock Park for stunning city views and surrounding areas. The city also hosts various festivals and events throughout the year, including the International Festival of Arts & Ideas, which features performances, lectures, and community events.

2. Mystic - 90 min

Mystic offers a quaint seaside escape with plenty to see and do. Visit Mystic Seaport, the largest maritime museum in the United States, and step aboard historic ships. The Mystic Aquarium is another must-see, featuring beluga whales and interactive exhibits. The charming downtown area is perfect for a leisurely day of shopping and dining.

In addition to its well-known attractions, Mystic also offers beautiful coastal views and outdoor activities. Take a boat tour along the Mystic River, explore the nearby beaches, or enjoy a meal at one of the waterfront restaurants. Mystic’s historic charm and scenic beauty make it an ideal destination for a relaxing day trip.

3. The Berkshires - 2 hrs

For those who love the outdoors, the Berkshires provide a perfect retreat with stunning natural beauty. Hike the scenic trails of Mount Greylock, the highest peak in Massachusetts, or visit the Norman Rockwell Museum in Stockbridge. The region is known for its vibrant arts scene, including the Tanglewood Music Festival. Visit the Berkshire Botanical Garden, drive along the Mohawk Trail, or explore the quaint towns filled with unique shops and local eateries.

4. New York City - 60 min

Just a train ride away, New York City offers endless possibilities for a day trip. Explore world-renowned museums like the Metropolitan Museum of Art and the Museum of Modern Art. Take in a Broadway show, enjoy a gourmet meal at one of the city’s top restaurants, or simply stroll through Central Park. Wander through the trendy streets of SoHo, visit the historic landmarks in Lower Manhattan, or enjoy the vibrant atmosphere of Times Square. With so much to see and do, a day trip to New York City promises an unforgettable experience.

5. The Hamptons  - 90 min ferry ride to Port Jefferson

The Hamptons are an ideal destination for a luxurious beach day. Take the ferry from Bridgeport and spend time lounging on the pristine sands of East Hampton or explore Southampton's charming shops and restaurants. The area’s vineyards and wineries are perfect for an afternoon of wine tasting. In addition to its beautiful beaches and upscale amenities, the Hamptons offer various outdoor activities. Take a bike ride through the scenic countryside, visit the historic Montauk Point Lighthouse, or enjoy a round of golf at one of the area’s prestigious courses.

6. Bear Mountain State Park - 90 min

Bear Mountain State Park offers a beautiful escape into nature with activities for all ages. Hike the trails for stunning views of the Hudson River, visit the Trailside Museums and Zoo, or enjoy a picnic by Hessian Lake. In the winter, the park offers ice skating and cross-country skiing.

The park also features a historic inn where you can enjoy a meal or stay overnight. During the warmer months, the park’s pool and playgrounds provide additional fun for families.

7. Hudson Valley - 2 hrs

The Hudson Valley is a picturesque region known for its historic estates, scenic views, and burgeoning wine country. Visit the Vanderbilt Mansion, enjoy a tasting at a local winery, or explore Beacon's art galleries and shops. The Valley is filled with hiking trails and outdoor activities and hosts numerous festivals and events like farmers markets or concerts at the Bardavon Opera House.

8. Boston - 2.5 hrs

A longer but worthwhile trip, Boston is rich in American history and culture. Walk the Freedom Trail to historic sites like the Boston Common and Paul Revere’s House. Visit the renowned Museum of Fine Arts, enjoy fresh seafood at a waterfront restaurant, or stroll along the Charles River. Boston also offers vibrant neighborhoods to explore, such as the historic North End, known for its Italian cuisine, and the trendy Seaport District, filled with restaurants and shops. The city’s mix of history, culture, and modern amenities makes it an excellent destination for a day trip.

9. Montauk - 3 hrs

Located at the eastern tip of Long Island, Montauk is known for its beautiful beaches, state parks, and historic lighthouse. Enjoy water sports, fishing, or simply relax by the ocean. Montauk Point State Park offers hiking trails and breathtaking views of the Atlantic. Montauk also features a variety of dining options, from casual seafood shacks to upscale restaurants. Explore the charming downtown area, visit local shops, or take a boat tour to see the area from a different perspective.

10. Newport - 2.5 hrs

Newport, Rhode Island, is famous for its stunning Gilded Age mansions, scenic coastal views, and rich maritime history. Tour the opulent Breakers Mansion, stroll along the Cliff Walk, or explore the bustling harbor area with its shops and restaurants. Newport also offers various outdoor activities, including sailing, kayaking, and beachcombing. Attend one of the city’s many festivals, such as the Newport Jazz Festival or the Newport Folk Festival, to experience the local culture and entertainment.

11. Block Island - 3.5 hrs with Ferry

Take a ferry to Block Island for relaxation and natural beauty. The island boasts pristine beaches, dramatic bluffs, and charming shops and restaurants. Rent a bike to explore the island’s scenic roads or visit the Block Island Southeast Lighthouse for panoramic views. Block Island offers various outdoor activities, including hiking, fishing, and bird-watching. The island’s tranquil environment and scenic beauty provide a perfect escape from the hustle and bustle of daily life.

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