17 Things To Do In Westport CT Connecticut

Nestled along the scenic Connecticut shoreline, Westport is a picturesque town that effortlessly blends coastal beauty with cultural richness. From vibrant arts scenes to outdoor adventures and delectable dining, Westport offers a plethora of activities for locals and visitors alike. In this guide, we’ll take you on a journey through some of the must-visit places and things to do in Westport, ensuring your visit is filled with unforgettable moments.

  1. Saunter Through Downtown Westport:Kick off your Westport adventure by exploring the charming downtown area. Lined with boutique shops, art galleries, and cafes, Main Street radiates a welcoming ambiance. Spend some time strolling through the streets, discovering unique finds, and soaking in the town’s laid-back atmosphere.
  2. Westport Country Playhouse:Theater enthusiasts should not miss the iconic Westport Country Playhouse. Dating back to 1931, this historic venue has hosted renowned performances and Broadway-bound shows. Check the schedule for upcoming plays, and immerse yourself in the magic of live theater in this intimate and culturally rich setting.
  3. Compo Beach and Longshore Club Park:For a dose of sun, sand, and sea, head to Compo Beach. This pristine stretch of coastline is perfect for a leisurely beach day, complete with picnics, beach volleyball, and serene walks along the water. Adjacent to the beach is the Longshore Club Park, offering golf courses, tennis courts, and beautiful waterfront views.
  4. Westport Farmers’ Market:Embrace the local flavors of Westport by visiting the Westport Farmers’ Market. Held weekly, this market is a haven for fresh, organic produce, artisanal goods, and gourmet treats. Engage with local farmers and vendors while sampling the region’s culinary delights.
  5. Sherwood Island State Park:Nature lovers will find solace in the expansive Sherwood Island State Park. Whether you’re into birdwatching, hiking, or simply enjoying a picnic with an ocean backdrop, this park provides a serene escape. The Connecticut Audubon Society Coastal Center, located within the park, is a great spot for bird enthusiasts.
  6. Westport Arts Center:Immerse yourself in Westport’s thriving arts scene by visiting the Westport Arts Center. Hosting rotating exhibitions, workshops, and events, the center celebrates both local and international talent. Check their calendar for engaging programs that cater to a variety of artistic interests.
  7. Dining Delights:Westport boasts a diverse culinary scene. From seafood shacks offering fresh catches to upscale dining experiences, the town caters to every palate. Don’t miss out on the local favorites, and be sure to explore the variety of dining options that showcase the town’s culinary prowess.
  8. Historical Sites:Delve into Westport’s rich history by exploring its historical sites. The Bradley-Wheeler House and the Saugatuck Swing Bridge are just a few examples of the town’s well-preserved landmarks that offer a glimpse into its past.
  1. Burying Hill Beach:Another gem in Westport’s coastal offerings, Burying Hill Beach, offers a more secluded and serene atmosphere compared to Compo Beach. Enjoy a quiet day by the water, take a refreshing swim, or simply relax with a good book against the backdrop of the Long Island Sound.
  2. Westport Historical Society:Delve deeper into Westport’s history by visiting the Westport Historical Society. The society hosts exhibits, lectures, and walking tours, providing an immersive experience into the town’s evolution over the years. Gain insights into Westport’s past and its role in shaping the region.
  3. Earthplace – The Nature Discovery Center:Perfect for families and nature enthusiasts, Earthplace is a nature discovery center that offers educational exhibits, live animal displays, and hiking trails. Explore the interactive natural history museum and attend one of their nature programs for an engaging and informative experience.
  4. Sherwood Island Connector Trail:If you’re a fan of hiking and outdoor exploration, the Sherwood Island Connector Trail is a must-visit. This scenic trail takes you through woodlands and marsh areas, providing a peaceful escape from the hustle and bustle. Birdwatchers will particularly enjoy the diverse avian species along the way.
  5. Westport Library:Beyond its vast collection of books, the Westport Library is a community hub hosting a variety of events. Attend author talks, book clubs, and workshops. The library’s modern architecture and inviting spaces make it an ideal spot for both learning and relaxation.
  6. Playhouse Square:Playhouse Square is a vibrant area filled with shops, restaurants, and entertainment options. Explore the boutiques for unique finds, grab a cup of coffee at a local cafe, and enjoy the lively atmosphere. This bustling square is a hub of activity, especially during community events and festivals.
  7. Fine Arts Festival:If your visit aligns with the Westport Fine Arts Festival, consider yourself fortunate. Held annually, this juried arts show features a wide array of visual arts, crafts, and live performances. Stroll through the booths, meet artists, and perhaps bring home a one-of-a-kind piece of art as a souvenir.
  8. Tarry Lodge:Expand your culinary adventures by dining at Tarry Lodge, a renowned Italian restaurant in Westport. Indulge in authentic dishes crafted with fresh, high-quality ingredients. The inviting ambiance and diverse menu make it a favorite among locals and visitors alike.
  9. Westport Paddle Club:Embrace the coastal setting by trying stand-up paddleboarding at the Westport Paddle Club. Whether you’re a beginner or an experienced paddler, the club offers lessons and rentals, allowing you to enjoy the scenic waters of the Saugatuck River.


Westport, Connecticut, is a destination that seamlessly weaves together the beauty of its natural surroundings, a vibrant arts scene, and a rich cultural heritage. Whether you’re a history buff, an art enthusiast, or someone seeking a tranquil coastal retreat, Westport has something for everyone. Immerse yourself in the charm of this town, and create memories that will linger long after your visit.

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