Top-Rated Things to Do in Westport, CT


By Omar Perez

If you’re looking for a picturesque New England town with a charming coastal vibe, look no further than Westport, Connecticut. Located just a short drive from New York City, this small town offers a variety of activities and attractions that are sure to delight visitors of all ages.

One of the top-rated things to do in Westport is exploring the beautiful beaches that line its shores. From Compo Beach to Sherwood Island State Park, these sandy stretches offer the perfect place to relax, soak up the sun, and take a refreshing dip in the Atlantic Ocean. Whether you’re a beach lover or just looking for a peaceful stroll along the shoreline, Westport has you covered.

In addition to its natural beauty, Westport also boasts a vibrant arts scene. The Westport Country Playhouse, a historic theater dating back to the 1930s, hosts a variety of performances throughout the year, from classic plays to contemporary productions. Art enthusiasts will also enjoy browsing the local galleries and visiting the Westport Museum for History and Culture, which showcases the town’s rich heritage.

If you’re a foodie, Westport won’t disappoint. The town is home to an array of top-rated restaurants and cafes that serve up a variety of cuisines, from fresh seafood to farm-to-table dishes. Whether you’re in the mood for a casual meal or a fine dining experience, Westport has plenty of options to satisfy your taste buds.

For outdoor enthusiasts, Westport offers ample opportunities for hiking, biking, and exploring nature. The Aspetuck Land Trust, a local conservation organization, maintains several scenic nature preserves that are perfect for outdoor adventures. From walking trails to birdwatching spots, these preserves provide a peaceful escape from the hustle and bustle of everyday life.

No matter what your interests may be, Westport, CT has something for everyone. From its beautiful beaches and vibrant arts scene to its delicious dining options and outdoor activities, this charming New England town is worth a visit.

Explore the Best Attractions in Westport, CT

Westport, Connecticut is a charming coastal town with plenty of attractions for visitors to explore. From beautiful beaches to historical sites, there is something for everyone to enjoy. Below are some of the top-rated attractions in Westport that you won’t want to miss:

  • Compo Beach: Located on the Long Island Sound, Compo Beach is a popular spot for swimming, picnicking, and enjoying the sun. The beach also offers beautiful views of the water and has a boardwalk for seaside strolls.
  • Earthplace: This nature discovery center is perfect for families and nature lovers. Earthplace features a variety of exhibits, including live animals, a bird sanctuary, and nature trails.
  • Westport Country Playhouse: Known as “The Playhouse”, this historic theater has been entertaining audiences since 1931. Catch a show and enjoy world-class performances in an intimate setting.
  • Sherwood Island State Park: Connecticut’s first state park, Sherwood Island is a great place for outdoor activities. The park has beaches, picnic areas, walking trails, and a nature center.
  • Museum of Contemporary Art: Experience the vibrant art scene in Westport at the Museum of Contemporary Art. The museum showcases modern and contemporary works by both established and emerging artists.

These are just a few of the many attractions that Westport, CT has to offer. Whether you’re looking for outdoor adventures or cultural experiences, you’ll find it all in this charming coastal town.

Visit the Westport Country Playhouse

If you are a lover of the performing arts, a visit to the Westport Country Playhouse is a must when you are in Westport, CT. Known as one of the top regional theaters in the country, the Playhouse has a rich history dating back to 1931.

The Westport Country Playhouse has been home to numerous world premieres, including works by renowned playwrights such as Tennessee Williams and Neil Simon. It has also hosted productions with notable actors such as Paul Newman. Today, it continues to showcase a wide range of performances, including classic plays, musicals, and contemporary works.

Aside from its exciting lineup of shows, the Playhouse also offers educational programs and workshops for aspiring performers. You can take part in acting classes, attend behind-the-scenes tours, or even join a talkback session with the cast and crew.

The theater itself is a charming and intimate space with a seating capacity of around 600. Its design reflects the classic New England style, with beautiful wooden architecture and a cozy atmosphere. From the moment you step inside, you will be swept away by the magic of live theater.

When planning your visit to the Westport Country Playhouse, be sure to check their website for the latest show schedules and ticket information. Whether you are a dedicated theater enthusiast or simply looking for a unique cultural experience, a trip to this iconic venue is sure to be a highlight of your time in Westport.

Delve into Art at the Westport Arts Center

When it comes to exploring the vibrant art scene in Westport, the Westport Arts Center is a must-visit destination. This renowned institution is dedicated to showcasing contemporary art and fostering a creative community in the area.

At the Westport Arts Center, you’ll find a variety of art exhibitions featuring works by local and international artists. From paintings and sculptures to photography and mixed media installations, there’s something for everyone to enjoy. The center’s rotating exhibits ensure that there’s always something new and exciting to discover.

Whether you’re a seasoned art connoisseur or just beginning to appreciate the world of art, the Westport Arts Center offers something for all levels of interest. The exhibitions are thought-provoking and are known to inspire meaningful conversations about art and its impact on society.

In addition to exhibitions, the Westport Arts Center also offers a range of educational programs and workshops. These programs are designed to engage visitors of all ages and provide a deeper understanding of art. From hands-on art classes to artist talks and panel discussions, there are plenty of opportunities to learn and engage with the art community.

If you’re looking to purchase art, the Westport Arts Center has a gift shop that features a carefully curated selection of artwork, books, and unique gifts. Whether you’re searching for a one-of-a-kind piece for your home or a thoughtful gift for a loved one, you’re sure to find something special.

Located in the heart of Westport, the Westport Arts Center is easily accessible and is surrounded by charming shops, restaurants, and cafes. Make a day of your visit and explore all that the town has to offer.

Whether you’re a local resident or just passing through, a visit to the Westport Arts Center is a must-do. Immerse yourself in the world of art and discover the creativity and talent that thrives in Westport.

Discover Nature at Sherwood Island State Park

Located in Westport, Connecticut, Sherwood Island State Park is a picturesque destination that offers visitors the opportunity to discover and explore the stunning natural beauty of the area. With its diverse ecosystems and abundant wildlife, this park is a haven for nature enthusiasts.

One of the highlights of Sherwood Island State Park is its beautiful beach, which stretches along the Long Island Sound. Visitors can relax on the sandy shores, take a refreshing dip in the water, or simply enjoy a leisurely stroll along the coastline. The beach also provides spectacular views of the surrounding landscape, making it the perfect spot for a picnic or to watch a breathtaking sunset.

In addition to its beach, Sherwood Island State Park boasts lush forests and scenic walking trails that showcase the region’s flora and fauna. Nature lovers can explore these trails, which wind through wooded areas and offer glimpses of native birds, small mammals, and wildflowers. It is a great opportunity to immerse oneself in the tranquility of nature and maybe even spot a deer or two along the way.

The park also features a salt marsh, which is a vital habitat for many species of birds and marine life. Visitors can observe these intriguing creatures in their natural habitat and learn about the importance of preserving such ecosystems. The salt marsh is teeming with life, and birdwatchers will be delighted with the opportunity to spot a variety of avian species, including herons, egrets, and ospreys.

For those who enjoy fishing, Sherwood Island State Park offers ample opportunities to cast a line and try their luck. The park has a fishing pier where anglers can engage in their favorite pastime and hope to catch a prized fish. Whether it’s reeling in a striped bass or catching bluefish, fishing enthusiasts will find plenty of action at this park.

Whether you’re looking to relax on the beach, explore the trails, observe wildlife, or go fishing, Sherwood Island State Park offers something for everyone. It’s a true gem in Westport, Connecticut, and a must-visit destination for nature lovers.

Indulge in Retail Therapy at the Compo Shopping Plaza

When it comes to shopping in Westport, CT, the Compo Shopping Plaza is a must-visit destination. This charming shopping center offers a wide range of retail options for visitors of all ages and interests.

Whether you’re in the mood for high-end fashion, home decor, or unique gifts, the Compo Shopping Plaza has you covered. With a mix of national chains and local boutiques, you’ll find everything you need to satisfy your retail cravings.

Start your shopping spree at one of the high-end fashion stores. Explore the racks of designer clothing, shoes, and accessories, and update your wardrobe with the latest trends. Whether you’re looking for a new suit, a glamorous evening gown, or everyday essentials, you’ll find it all at the Compo Shopping Plaza.

If you’re more interested in home decor, make sure to visit the stylish furniture stores and interior design boutiques. Discover unique pieces that will transform your living space into a haven of style and comfort. From modern minimalist designs to cozy country chic, there’s something for every taste and budget.

Don’t forget to browse the specialty shops and gift stores for one-of-a-kind treasures. From handmade jewelry and artisanal chocolates to handcrafted pottery and local artwork, you’ll find the perfect gift or souvenir to commemorate your trip to Westport.

After your retail therapy session, take a break and recharge at one of the many cafes or restaurants in the plaza. Enjoy a cup of coffee or indulge in a delicious meal while you soak in the charming atmosphere of this vibrant shopping destination.

So, if you’re in the mood for some retail therapy, make sure to visit the Compo Shopping Plaza in Westport, CT. With its diverse range of stores and charming atmosphere, it’s the perfect place to indulge in some shopping and discover unique finds.

Important Note: Please check the operational hours and any COVID-19 related guidelines before visiting the Compo Shopping Plaza.

Enjoy a Beach Day at Burying Hill Beach

When visiting Westport, CT, one of the top-rated things to do is to spend a relaxing day at Burying Hill Beach. This beautiful beach offers visitors a stunning sandy shoreline and breathtaking views of Long Island Sound.

Whether you’re looking to bask in the sun, take a leisurely swim, or simply enjoy a picnic by the water, Burying Hill Beach has something for everyone. The beach is equipped with lifeguards on duty during the summer months, ensuring the safety of all visitors.

In addition to the beach itself, there are also a variety of amenities available to enhance your beach day experience. The beach features ample parking, clean restrooms, and outdoor showers for rinsing off after a day in the sand and surf.

If you’re feeling more adventurous, Burying Hill Beach also offers opportunities for fishing and clamming. Cast your line into the water and try your luck at catching some local fish, or search for clams along the shoreline for a true New England experience.

For those who enjoy nature, Burying Hill Beach is located near several scenic hiking trails. Take a walk through the surrounding woods and soak in the beauty of the area’s flora and fauna.

Whether you’re a local resident or a visitor to Westport, CT, Burying Hill Beach is a must-visit destination. Its beautiful sandy beach, stunning views, and variety of amenities make it the perfect spot to enjoy a beach day with friends and family.

Explore Local History at the Westport Historical Society

Immerse yourself in the rich history of Westport by visiting the Westport Historical Society. This local organization is dedicated to preserving and showcasing the town’s unique heritage through various exhibits and programs.

At the Westport Historical Society, you can learn about the early settlers of the area, the development of the local economy, and the significant events that have shaped the town. The society’s collection includes artifacts, documents, photographs, and other historical items that provide a glimpse into the past.

One of the highlights of your visit to the Westport Historical Society is the opportunity to explore the museum’s exhibits. These exhibits delve into different aspects of Westport’s history, from its roots as a farming community to its transformation into a vibrant coastal town. Each display is carefully curated and provides a fascinating insight into the town’s past.

While at the Westport Historical Society, consider attending one of their educational programs or events. The society regularly hosts lectures, workshops, and tours that delve deeper into specific topics of local history. These events offer a unique opportunity to engage with experts and fellow history enthusiasts, further enriching your understanding of Westport’s heritage.

Don’t forget to visit the museum shop before you leave. It offers a wide selection of books, souvenirs, and locally crafted items that make for great takeaways and gifts.

Embrace the opportunity to explore the local history of Westport at the Westport Historical Society, gaining a deeper appreciation for the town’s past and its significance today.

Take a Scenic Stroll along the Saugatuck River

A visit to Westport, CT would not be complete without taking a scenic stroll along the beautiful Saugatuck River. This iconic river runs through the heart of town, offering a picturesque setting for a leisurely stroll.

As you walk along the river, you’ll be treated to stunning views of the water, lush greenery, and charming riverside homes. The peaceful sound of the flowing river and the gentle breeze create a tranquil atmosphere, perfect for unwinding and enjoying the natural beauty around you.

There are several walking trails and pathways that run alongside the Saugatuck River, allowing you to explore different sections of this scenic waterway. Take your time to discover hidden spots, charming footbridges, and quiet spots to sit and take in the surroundings.

During your stroll, keep an eye out for wildlife that calls the Saugatuck River home. You may spot ducks, geese, and other birds swimming lazily in the water, or turtles sunning themselves on rocks. There’s always something new to see and appreciate along the river.

If you’re feeling adventurous, you can also rent a kayak or paddleboard and explore the river from a different perspective. Gliding along the calm waters and navigating through the twists and turns of the river is a unique and exciting experience.

Whether you’re looking for a peaceful escape, a chance to connect with nature, or simply a pleasant way to spend an afternoon, a scenic stroll along the Saugatuck River is a must-do activity in Westport, CT. So put on your walking shoes, take a deep breath of fresh air, and immerse yourself in the natural beauty of this charming New England town.

Experience Live Music at Levitt Pavilion

One of the top-rated things to do in Westport, CT is to experience live music at the Levitt Pavilion. Located in the heart of downtown Westport, the Levitt Pavilion is an outdoor amphitheater that hosts free concerts throughout the summer months.

With a beautiful riverside setting and a state-of-the-art sound system, the Levitt Pavilion offers an unforgettable music experience. Whether you’re a fan of jazz, rock, pop, or classical music, you’re sure to find a concert that suits your taste.

Not only does the Levitt Pavilion provide a platform for talented musicians, but it also fosters a sense of community. Families and friends gather on the lawn, bringing picnic blankets and chairs to enjoy the music together. It’s a great way to relax and spend quality time with loved ones.

What sets the Levitt Pavilion apart from other music venues is its commitment to diversity and inclusion. The concert lineup features a wide range of musical genres, showcasing local bands as well as internationally renowned artists. The Levitt Pavilion is proud to offer a platform for artists from all backgrounds and cultures to share their talent with the community.

If you’re planning a visit to Westport, CT, be sure to check out the schedule of concerts at the Levitt Pavilion. Whether you’re a music lover or simply looking for a fun way to spend an evening, the Levitt Pavilion is a must-visit destination. Don’t miss the opportunity to experience live music under the stars in this vibrant and welcoming community.

Sample Delicious Wines at the Stew Leonard’s Wine Shop

When visiting Westport, CT, one of the must-visit destinations for wine enthusiasts is the Stew Leonard’s Wine Shop. This popular shop offers a wide selection of delicious wines from all around the world.

At the Stew Leonard’s Wine Shop, you can browse through their extensive collection of red, white, and sparkling wines. From bold and robust reds to crisp and refreshing whites, there is something for every taste preference.

Whether you’re a connoisseur or just beginning to explore the world of wine, the knowledgeable staff at Stew Leonard’s Wine Shop is always ready to assist you. They can guide you in selecting the perfect wine for a special occasion, recommend food pairings, or simply answer any questions you might have.

One of the unique features of Stew Leonard’s Wine Shop is their wine tasting events. They regularly host wine tastings where you can sample a variety of wines and learn about their characteristics. It’s a great opportunity to discover new wines and expand your wine knowledge.

In addition to their vast selection of wines, Stew Leonard’s also offers a range of wine accessories. From wine glasses and decanters to corkscrews and wine stoppers, you can find everything you need to enhance your wine drinking experience.

So, if you’re a wine lover or simply want to experience something new during your visit to Westport, CT, make sure to stop by the Stew Leonard’s Wine Shop. Sample delicious wines, expand your wine knowledge, and find the perfect bottle to take home with you.

Unwind with Outdoor Recreation at Earthplace Nature Discovery Center

Escape the hustle and bustle of the city and immerse yourself in the natural beauty of Westport at the Earthplace Nature Discovery Center. This serene sanctuary offers a variety of outdoor recreational activities that allow you to unwind and connect with nature.

Explore the winding trails that meander through lush forests and open meadows, providing the perfect backdrop for a leisurely hike or refreshing jog. Keep an eye out for native wildlife, such as deer, turtles, and a variety of birds, as you wander along the trails.

If you prefer a more immersive experience, be sure to visit the center’s bird-feeding station. Here, you can observe a myriad of colorful birds up close as they flutter about and enjoy a meal. Capture the moment with your camera or simply take a moment to appreciate the beauty of these feathered creatures.

For those seeking a more hands-on approach, Earthplace offers a variety of educational and recreational programs for visitors of all ages. Join a guided nature walk led by an expert naturalist, or participate in a wildlife rehabilitation workshop to learn about the center’s efforts to preserve and protect local animal populations.

For families with young children, Earthplace also features an interactive outdoor playground where little ones can climb, swing, and explore in a safe and natural environment. This engaging space allows children to learn and play while surrounded by the sights and sounds of nature.

Whether you’re looking for a peaceful retreat or a fun-filled day of exploration, the Earthplace Nature Discovery Center offers something for everyone. Take a moment to unwind, reconnect with nature, and create lasting memories in the beautiful outdoor spaces of Westport, CT.


What are the top-rated things to do in Westport, CT?

Some of the top-rated things to do in Westport, CT include visiting Compo Beach, exploring Sherwood Island State Park, browsing the Westport Farmers Market, visiting the Westport Country Playhouse, and taking a tour of the Westport Historical Society.

Is Compo Beach worth a visit in Westport, CT?

Yes, Compo Beach is definitely worth a visit in Westport, CT. It is a beautiful sandy beach with scenic views of Long Island Sound, and it offers various recreational activities such as swimming, fishing, and picnicking.

What is there to do at Sherwood Island State Park in Westport, CT?

At Sherwood Island State Park in Westport, CT, you can enjoy hiking and walking trails, have a picnic, go bird-watching, or simply relax and soak up the sun on the sandy beaches. The park also has a nature center and offers educational programs for visitors.

What can I expect at the Westport Farmers Market?

At the Westport Farmers Market, you can expect to find a wide variety of fresh local produce, artisanal foods, baked goods, and specialty products. There are also often live music performances, cooking demonstrations, and other special events happening at the market.

Why should I visit the Westport Country Playhouse?

You should visit the Westport Country Playhouse because it is a renowned theater that offers high-quality productions of plays and musicals. It has a rich history and has hosted many famous actors and productions over the years. Watching a show at the Westport Country Playhouse is a great way to enjoy live theater in a charming and intimate setting.

Is there a beach in Westport?

Yes, there are several beaches in Westport, including Compo Beach, Burying Hill Beach, and Sherwood Island State Park.


Best Restaurants in Westport CT!!!

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Omar Perez

Omar Perez, a Caribbean correspondent at TravelAsker, is a skilled writer with a degree from Florida International University. He has published in prestigious outlets like The Miami Herald, Orlando Weekly, Miami Daily Business Review, and various New Times editions. He has also worked as a stringer for The New York Times in Miami, combining his love for travel and storytelling to vividly depict the Caribbean's charm.

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