The Best Things to Do in Westport, CT

The Best Things to Do in Westport, CT


Westport, CT, beckons visitors with its blend of coastal charm, cultural vibrancy, and natural beauty. From its rich history to its thriving arts scene and culinary delights, this quaint New England town offers a plethora of experiences to indulge in. Whether you're a local resident or a visitor, here are some of the best things to do in Westport, CT, that promise to captivate your senses and leave you longing for more.

Embrace Nature at Sherwood Island State Park

Embark on a serene journey amidst the tranquil landscapes of Sherwood Island State Park, spanning over 234 acres. As Connecticut's first state park, Sherwood Island boasts stunning beaches, lush picnic areas, and scenic trails perfect for leisurely strolls or invigorating hikes. Breathe in the salty sea air as you soak up panoramic views of the Long Island Sound, or spend a leisurely day basking in the sun and building sandcastles along the pristine shoreline. Nature enthusiasts and outdoor lovers alike will find solace in this coastal haven.

Discover Artistic Treasures at the Westport Country Playhouse

Immerse yourself in the world of performing arts at the historic Westport Country Playhouse, a renowned theatrical institution dating back to 1931. Located in the heart of downtown Westport, this iconic venue hosts a diverse array of productions ranging from classic plays to contemporary performances to children's theater, showcasing top-tier talent from around the country. Take in a captivating show under the glittering lights of the stage and experience the magic of live theater in an intimate and inviting setting.

Indulge in Culinary Delights on Main Street

Tantalize your taste buds with a culinary adventure along Westport's vibrant Main Street, where a myriad of dining options await. From cozy cafes and gourmet bistros to upscale eateries and farm-to-table restaurants, there's something to satisfy every palate and craving. Sample freshly caught seafood at Nomade, top notch Japanese at OKO, or treat yourself to decadent desserts crafted by local culinary artisans at Chocolatieree. With its diverse culinary scene and welcoming ambiance, Main Street promises a delectable dining experience that will leave you craving more.

Explore Historical Landmarks at the Westport Historical Society

Journey back in time and uncover the rich history of Westport at the Westport Historical Society, which is dedicated to preserving and celebrating the town's heritage. Housed within a charming colonial-era building, the society's museum features fascinating exhibits, archival collections, and educational programs that offer insight into Westport's past. Delve into the lives of its early settlers, learn about its maritime legacy, and gain a deeper appreciation for the town's cultural roots through interactive displays and guided tours.

Soak Up the Sun at Compo Beach

Escape the hustle and bustle of everyday life and retreat to the sun-drenched shores of Compo Beach, a beloved local gem beloved for its pristine sands and panoramic vistas. Whether you're looking to swim, sunbathe, or engage in water sports, this idyllic beach offers endless opportunities for relaxation and recreation. Enjoy a leisurely picnic with family and friends, take a refreshing dip in the sparkling waters, or simply unwind as you watch the sailboats glide across the horizon. With its tranquil ambiance and natural beauty, Compo Beach is a must-visit destination for beach enthusiasts and nature lovers alike.

Shop 'til You Drop at Westport's Boutique Stores

Indulge in some retail therapy along the charming streets of downtown Westport, where an eclectic mix of boutique shops and upscale stores awaits. From chic fashion boutiques like Vince and art galleries (Clarendon Fine Art, Sorelle Gallery) to quaint specialty shops, there's no shortage of treasures to uncover. Browse unique gifts, discover one-of-a-kind finds, or simply wander at your leisure as you explore the town's vibrant shopping scene. 

Experience Outdoor Adventures at Earthplace

Embark on an outdoor adventure at Earthplace, a nature discovery center nestled amidst 62 acres of woodlands, wetlands, and meadows. Perfect for families, nature enthusiasts, and curious minds alike, Earthplace offers a variety of educational programs, interactive exhibits, and outdoor activities designed to foster a deeper connection with the natural world. Explore hiking trails, observe native wildlife, or participate in hands-on workshops and guided nature walks led by knowledgeable staff. Whether seeking solace in nature or expanding your ecological awareness, Earthplace provides an enriching experience for all ages.

Ready to Explore Westport?

As you explore the best things to do in Westport, CT, you may find yourself enchanted by the town's unique blend of charm, culture, and natural beauty. Whether you're strolling along its scenic beaches, immersing yourself in its rich history, or savoring its culinary delights, Westport offers a wealth of experiences to delight and inspire. 

If you find yourself falling in love with this idyllic coastal community, reach out to The Leslie Clarke Team today for expert guidance on Westport, CT, real estate. Search homes for sale in Westport here.



Work With Us

Our home is Westport. The Leslie Clarke team brings together a team of Fairfield County real estate experts with the passion, dedication, and resources to help their clients reach their buying and selling goals. With you every step of the way.

Follow Us on Instagram