Top 15 Must-See Attractions in Westport, CT

Situated along Long Island Sound, at the lower reaches of the Saugatuck River, lies one of the wealthiest small towns in the United States. 

Westport boasts an artistic heritage and a sophisticated downtown environment that is unexpected for a town with a population of merely 27,000.

Actor Paul Newman relocated to Westport in the early 1960s, remaining until his passing in 2008. 

Newman was actively involved in the Westport community, serving as a pivotal figure behind the highly esteemed Westport Country Playhouse. He generously donated land to the town and initiated the Farmers’ Market in 2006. 

During summer, Westport truly flourishes. You may enjoy the public beaches, engage in paddleboarding on the Saugatuck River, or play a round of golf at one of the state’s top municipal courses. 

Afterwards, I can think of no more enjoyable way to spend an evening than at an outdoor concert at the renowned Levitt Pavilion.

1. Downtown Westport

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Westport features a central business district that any community would aspire to attain. It combines the quaint charm of a New England coastal town with cosmopolitan shopping and dining.

In the pedestrian-friendly Saugatuck area, you will encounter independent boutiques, family-owned stores, local chains, museums, historic structures, galleries, and a wide variety of dining options, all complemented by a host of upscale international retailers.

These include Tiffany & Co, L’Occitane, Urban Outfitters, lululemon, and J. Crew, among others.

Everything is within a short walking distance, with ample parking and stunning views of the Saugatuck River. From this vantage point, you can admire the ancient wharfs on the west bank, framed by lush woodlands.

2. Sherwood Island State Park

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Established in 1914, Sherwood Island is Connecticut’s first state park and continues to be regarded as one of its finest. This 238-acre park features woodlands, wetlands, and a beautiful beachfront.

At East and West Beach, visitors can relax by Long Island Sound and swim, with the beaches spacious enough to avoid excessive crowding.

It is advisable to bring water shoes to safeguard your feet from the sharp stones and shells on the beaches.

Behind the beaches, there are numerous picnic tables, a shelter, and a couple of concession stands. A boardwalk trail leads into a preserved salt marsh environment. Additionally, a Nature Center is open seasonally from Wednesday to Sunday, featuring informative displays about the park’s wildlife.

The center also organizes bird-watching, nature walks, and additional activities during the summer months.

3. Water Activities

Among the shops and eateries on Riverside Avenue is Sea Kayak Connecticut, a watersports company that offers a variety of services.

They provide an array of tours in and around Westport. You might explore the harbor or embark on a small expedition to offshore islands like Sprite Island or Cockenoe Island. 

A standout is the tour that coincides with Westport’s Independence Day fireworks, presenting a memorable experience. 

For those desiring independence, a wide selection of paddlecraft is available for rental, ranging from paddleboards to double pedal kayaks.

Moreover, for parents looking for constructive ways to keep their children engaged, Sea Kayak Connecticut organizes summer camps for youth aged 9-12 and 12-14.

4. Compo Beach

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This beach features a wide, gently curving bay where the Saugatuck River meets Long Island Sound.

Lifeguards are present daily from Memorial Day weekend until Labor Day, and the beach is accompanied by a wealth of facilities.

Along with a large wooden playscape, there are two floodlit basketball courts, volleyball courts, a skate park, an open skate area, a softball field, and a multipurpose field.

A concession stand with a deck right on the beachfront is available for when you feel hungry. As is common in Connecticut, parking fees for non-residents can be steep during summer. If you’re willing to walk, parking is available about a mile away.

Finally, dogs are permitted off-leash in designated areas outside the summer season.

5. Earthplace

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Earthplace serves as a natural history museum, nature center, and sanctuary, providing an educational experience across more than 60 acres, with origins dating back to 1958. 

The museum section, Natureplace, features interactive exhibits and detailed dioramas illustrating the flora and fauna of Connecticut throughout various seasons.

A diverse range of rescued animals, unable to return to the wild due to injuries, are housed here.

This includes an eastern box turtle, a big brown bat, a bald eagle, a green frog, a turkey vulture, and a red-tailed hawk. Visitors can view these animals in outdoor enclosures as well as inside the Animal Hall.

The grounds encompass the largest open space in Westport, with trails leading through hardwood forests, meadows, streams, ponds, and wetlands.

Move quietly, and you may spot wildlife such as deer, chipmunks, wild turkeys, and rabbits.

6. Westport Library

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The Westport Library enjoys an ideal location along the Saugatuck River. As of the time of this writing, the library has recently undergone a remarkable transformation project.

Westport Library is an exceptional resource for a small town and is among the busiest in the region for book circulation per capita.

If you are in search of a place to work, read, or simply unwind in Westport, this library is the ideal destination. It offers computer terminals, free Wi-Fi, cubicles for laptop use, a silent reading room, and a vibrant children’s section.

Additionally, the library hosts an engaging calendar of events, including film screenings, exhibitions from the Westport public art collection, children’s programming, lectures, language conversation groups, and much more.

7. Westport Country Playhouse

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Renowned nationally, this professional theater operates on a non-profit basis under the artistic direction of the distinguished Mark Lamos.

The Westport Country Playhouse hosts a season from April through November, during which patrons can enjoy high-quality productions in a 578-seat auditorium.

The venue has an intriguing history. Originally established in 1830 as a tannery, it underwent renovation for Broadway productions in 1931 by the New York producer Lawrence Langner.

Paul Newman later championed the theater upon relocating to Westport in the 1960s, further enhancing its renown.

At the time of this writing, upcoming events included discussions with Tony Kushner and a night featuring Fran Lebowitz.

8. Levitt Pavilion for the Performing Arts

Source: Levitt Pavilion For The Performing Arts / facebook

Situated on a picturesque peninsula along the Saugatuck River, the Levitt Pavilion for the Performing Arts hosts one of the largest and oldest outdoor summer festivals in the United States.

From late June to early September, you can enjoy nearly 60 nights of entertainment.

This includes concerts encompassing rock, pop, blues, jazz, folk, cabaret, world music, and big band performances, along with dance showcases, theater productions, film screenings, circus acts, and live comedy.

A specially curated children’s series is featured on Wednesdays, consistently impressing audiences. At the time of this writing, Grammy-winner Pierce Freelon had recently performed here.

The park opens approximately one hour before the performance starts, and attendees will be seated on the lawn; thus, it is recommended to bring a lawn chair or picnic blanket.

9. Westport Museum for History and Culture

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Established in 1889, the Westport Historical Society operates from the elegant Wheeler House, a residence dating back to 1795, renovated in the Italianate style during the 19th century.

The society oversees Adams Academy, a 19th-century one-room schoolhouse located at 15 Morningside Drive.

The museum at Wheeler House surpasses what one typically encounters at local historical societies, featuring expertly curated and ever-evolving interactive exhibits along with free Wi-Fi access.

One notable exhibition, “Taking the Cure,” explored public health from 1880 to 1960. I was particularly intrigued by the behind-the-scenes look at Westport’s two sanatoriums for individuals with mental illness during that period.

If you are in town during the holiday season, be sure to experience the delightful Winter Market, showcasing handmade crafts, seasonal treats, and a cozy fire. 

10. Longshore Club Park

The premier municipal golf course in Fairfield County is situated on a charming waterfront property in Westport, recognized as one of the ten best courses statewide, with a history dating back to 1920.

The course is just one of many exceptional facilities at Longshore Club Park. Additional amenities include a driving range, tennis courts, a scenic picnic area, three swimming pools, and a marina. 

Along the waterfront, the Longshore Sailing School offers summer rentals for various sailboats, in addition to paddlecraft such as kayaks and paddleboards.

11. Westport Astronomical Society

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Over the past fifty years, thousands of individuals have engaged with the wonders of the night sky at this volunteer-run, non-profit observatory.

This facility, established on a former BR-73 Nike missile site, welcomes visitors each Wednesday night from 8:00 PM to 10:00 PM to gaze through the telescopes, weather permitting. 

The dome observatory is equipped with a 16” Meade LX200 telescope, and an Explore Scientific 102mm f/7 Essential Apochromatic ED Triplet Refractor is also available for use.

On warmer evenings, the impressive 25” Obsession telescope is situated on the lawn, representing the largest stargazing equipment accessible to the public in Connecticut.

The society organizes talks and discussions covering a broad range of topics related to space science, including cosmology, astronomy, and physics, led by experts from institutions such as Yale, MIT, UConn, Columbia, and NYU.

12. Westport Farmers’ Market

Source: Westport Farmers’ Market / facebook

Westport Farmers’ Market was inaugurated by Paul Newman in 2006. The market experienced rapid growth and soon relocated to its current site at 50 Imperial Avenue. In winter, there is also a weekly indoor market at Gilbertie’s Herb Garden. 

Over the past two decades, it has become a local institution, fostering connections with area businesses and running various initiatives ranging from promoting healthy eating to plastic collection efforts and support for local farmers facing hardships.

During my visit, I observed a considerable number of vendors at the Westport Farmers’ Market, offering an array of fresh fruits, vegetables, herbs, flowers, kombucha, perennials, freshly caught seafood, pasture-raised meat, pastries, cakes, pickles, and exotic sauces.

Be sure to arrive with an appetite, as a variety of food trucks are on site. Options included wood-fired pizza, empanadas, tamales, Thai soups, and organic frozen desserts.

13. Norwalk

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Westport’s neighbor to the west is a short drive or an eight-minute train ride away, and there are several compelling reasons to make this journey.

Prominent among these is the Maritime Aquarium, an impressive and creatively arranged destination showcasing 75 exhibits featuring 2,700 marine animals from around the globe.

Visitors can marvel at sharks, jellyfish, rays, and loggerhead turtles, while also enjoying a film at the IMAX Theater with its six-story screen.

Additionally, do not miss the opportunity to explore the exquisite Lockwood–Mathews Mansion, built for railroad and banking magnate LeGrand Lockwood, preserved as an exemplary Second Empire-style country house.

Another highlight is a catamaran cruise to Sheffield Island, where an elegant lighthouse from 1868 is nestled within a nature preserve populated by waterfowl such as egrets and herons.

14. Gallaher Mansion and Cranbury Park

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This park is located only ten minutes away in Norwalk and encompasses 227 acres of stunning parkland and sculpture gardens surrounding the Tudor Revival-style Gallaher Mansion.

Constructed for industrialist Edward Beach Gallaher in 1931 amidst the Great Depression, this stately residence boasts mullioned windows, cross gables, hand-painted stained glass, and embattled window bays.

The front of the house features an expansive lawn, sculpture gardens, and an elegant stone terrace.

Although typically rented for events, the house was undergoing renovations at the time of my visit. 

The grounds are accessible to the public for activities such as hiking, tennis, dog walking, disc golf, picnicking, and children’s playground use.

15. Southport Beach

Located not far east of Sherwood Island, Southport Beach offers another delightful option for sunbathing or taking a brisk walk on a winter’s day.

Although modest in size at just 2.5 acres, the beach is equipped with restroom facilities and a concession stand open during summer.

Importantly, the beach is free and open to the general public. However, only residents with a beach sticker are allowed to use the parking lot from Memorial Day weekend through Labor Day.

Nonetheless, this policy does not deter many non-residents from enjoying this charming segment of the Connecticut shoreline.