15 Best Things to Do in Westport (CT)

By Long Island Sound, along the lower reaches of the Saugatuck River lies one of the richest towns of its size in the United States.

Westport has an artistic pedigree and the sort of sophisticated downtown that I would never expect from a town of just 27,000.

Actor Paul Newman moved to Westport in the early 1960s and would stay until he passed away in 2008.

Newman was active in the Westport community as a driving force behind the highly-regarded Westport Country Playhouse. He also gifted land to the town, and even opened the Farmers’ Market in 2006.

In summer Westport truly comes alive. You can hit the public beaches, go paddleboarding on the Saugatuck River, and play a round at one of the state’s best municipal courses.

After, I can think of no better way to spend an evening than at an outdoor concert at the famous Levitt Pavilion.

1. Downtown Westport

Westport has the sort of central business district that any town would aspire to. This blends the cuteness and charm of a New England coastal town with cosmopolitan shopping and dining.

In the walkable Saugatuck area you’ll discover independent boutiques, mom-and-pop stores, local chains, museums, historic buildings, galleries, and eateries of all descriptions. These are all complemented by a slew of upscale international retailers.

I’m talking Tiffany & Co, L’Occitane, Urban Outfitters, lululemon and J. Crew, to name a handful.

Nothing is more than a couple of minutes on foot, and there’s abundant parking, and views to behold across the Saugatuck River. From here you can admire the old wharves on the west bank, backed by woodland.

2. Sherwood Island State Park

Purchased in 1914, Sherwood Island is Connecticut’s first state park, and is still considered one of its best. In 238 acres there’s woodlands, wetlands and a gorgeous beachfront.

At East and West Beach you can relax by Long Island Sound and go for a swim, and the beaches are large enough to never get too crowded.

I’d recommend packing water shoes to protect your feet from the sharp stones and shells on the beaches.

Behind there are plenty of picnic tables, a picnic shelter and a couple of concession stands. A boardwalk trail will lead you into a preserved salt marsh environment. There’s a Nature Center open seasonally Wednesday through Sunday, with smart displays inside informing you about the park’s wildlife.

The center also organizes bird-watching, nature walks and more in summer.

3. Water Activities

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

First off, they offer a choice of tours in and around Westport. You could visit the harbor, or head off on a little expedition to offshore islands like Sprite Island or Cockenoe Island.

My pick is the tour coinciding with Westport’s Independence Day fireworks, for a once-in-a-lifetime experience.

If you want to go your own way there’s a wealth of paddlecraft available for rental, from paddleboards to double pedal kayaks.

For parents who want to keep their kids occupied in a constructive way Sea Kayak Connecticut also organizes summer camps. These are available for kids aged 9-12 and 12-14 respectively.

4. Compo Beach

This beach is a wide, gently curving bay, where the Saugatuck River flows into Long Island Sound.

There are lifeguards daily from Memorial Day weekend to Labor Day, and the beach is joined by a wealth of facilities.

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

There’s a concession stand with a deck right on the beach for when you get hungry. As is often the case in Connecticut, there are steep fees for non-residents at the parking lot in summer. If you don’t mind walking I’d park at the lot a mile away.

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

5. Earthplace

A natural history museum, nature center and sanctuary rolled into one, Earthplace is an edifying attraction set in more than 60 acres and dating back to 1958.

The museum portion is Natureplace, with hands-on exhibits and detailed dioramas showing the flora and fauna of Connecticut at different times of year.

There’s a large array of rescued animals that cannot be released back to the wild because of their injuries.

These include an eastern box turtle, a big brown bat, a bald eagle, a green frog, a turkey vulture and a red-tailed hawk. You’ll find them in outdoor enclosures and inside at the Animal Hall.

The grounds comprise the largest open space in Westport. Trails connect you with hardwood forest, meadows, streams, ponds, and wetlands.

Go quietly and you stand a chance of sighting wildlife like deer, chipmunks, wild turkeys and rabbits.

6. Westport Library

The town’s library has a perfect location, right on the Saugatuck River. When I wrote this article it had recently come through a spectacular transformation project.

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

If you’re looking for somewhere to work, read or just relax in Westport, this is the place to go. There are computer terminals, free Wi-Fi, cubicles for laptops, a silent reading room and a vibrant children’s section.

And, as with any great library, there’s a lively events schedule. This covers movie screenings, exhibitions from the Westport public art collection, children’s activities, talks, language conversation groups, and a great deal more.

7. Westport Country Playhouse

With a national reputation, this professional producing theater is run on a not-for-profit basis under the artistic direction of the esteemed Mark Lamos.

The Westport Country Playhouse’s season is from April to November during which you can watch productions of the highest quality at the 578-seat auditorium.

The venue has an interesting past. Dating back to 1830 it was originally a tannery, and was remodeled for Broadway shows in 1931 by the New York producer Lawrence Langner.

After moving to Westport in the 1960s Paul Newman championed the theater, earning it even more acclaim.

When I compiled this list some upcoming events included a conversation with Tony Kushner, and an evening with Fran Lebowitz.

8. Levitt Pavilion for the Performing Arts

On a scenic little peninsula in the Saugatuck River, the Levitt Pavilion for the Performing Arts hosts one of the biggest and oldest outdoor summer festivals in the United States.

From the end of June to the start of September there are just shy of 60 nights of entertainment.

This might be concerts for rock, pop, blues, jazz, folk, cabaret, world music, big band. But there’s also dance performances, theater productions, movie screenings, circus shows, and live comedy.

There’s a special children’s series on Wednesdays, and the quality never fails to impress me. When I went to press, Grammy-winner Pierce Freelon had just performed here.

The park opens around an hour before the curtain goes up, and you’ll be sitting on the lawn so will need to bring a lawn chair or picnic blanket.

9. Westport Museum for History and Culture

Set up way back in 1889, the Westport Historical Society is headquartered at the refined Wheeler House. This residence dates right back to 1795 and was updated in an Italianate style in the 19th century.

The society also cares for Adams Academy, a 19th-century one-room schoolhouse at 15 Morningside Drive.

The museum at Wheeler House goes above and beyond what I usually encounter at local historical societies. They lay on expertly-curated and constantly changing interactive exhibits and free Wi-Fi.

For a snapshot, the recent “Taking the Cure” covered public health from 1880 to 1960. I was fascinated to go behind the scenes at Westport’s two sanatoriums for the mentally ill from that time.

If you’re around in the holiday season, try to catch the charming Winter Market, with handmade crafts, seasonal treats, and a warming fire.

10. Longshore Club Park

The top municipal golf course in Fairfield County is on a lovely waterfront property in Westport. Also held as one of the ten best courses of any kind in the state, Longshore Golf Course dates back to 1920.

The course is just one of several first-rate facilities at Longshore Club Park. Additional facilities when I wrote this article were a driving range, tennis courts, a scenic picnic area, three pools, and a marina.

On the water is the Longshore Sailing School. In summer the school offers rentals for a range of sailboats, as well as paddlecraft like kayaks and paddleboards.

11. Westport Astronomical Society

Over the last half century thousands of people have experienced the wonders of the night sky at this volunteer-run, non-profit observatory.

This facility was established on a former BR-73 Nike missile site. Every Wednesday night from 8:00 PM to 10:00 PM you’re welcome to come and peer through the telescopes. I should point out that these sessions are weather-dependent.

The dome observatory is equipped with a 16″ Meade LX200, and has an Explore Scientific 102mm f/7 Essential Apochromatic ED Triplet Refractor above.

On warmer evenings the massive 25” Obsession telescope is parked on the lawn. This is the largest piece of stargazing equipment available to the public in Connecticut.

The society also arranges talks and discussions on a wealth of topics related to space science. These cover cosmology, astronomy and physics, and are given by academics at the top of their field, from the likes of Yale, MIT, UConn, Columbia and NYU.

12. Westport Farmers’ Market

Paul Newman himself opened the Westport Farmers’ Market in 2006. The market grew quickly and soon moved to its current location at 50 Imperial Avenue. In winter there’s also a weekly indoor market at Gilbertie’s Herb Garden .

Over the last 20 years it has become an institution, forging links with local businesses and running all sorts of programs. These cover anything from healthy eating to plastic collection to schemes for local farmers who have fallen on hard times.

When I paid a visit there was a big contingent of vendors at the Westport Farmers’ Market. On offer were fruit, vegetables, herbs, flowers, kombucha, perennials, freshly caught fish, pasture-raised meat, pastries, cakes, pickles, and exotic sauces.

Bring an appetite too, as there’s an assortment of food trucks. I saw wood-fired pizza, empanadas, tamales, Thai soups, and organic frozen desserts.

13. Norwalk

Westport’s neighbor to the west is a brief drive or just eight minutes by train, and I can think of plenty of reasons to make the journey.

First up is the Maritime Aquarium. This is an awe-inspiring, creatively presented attraction with 75 exhibits comprising 2,700 marine animals from around the world.

You can marvel at sharks, jellyfish, rays and loggerhead turtles, and be wowed by a movie at the IMAX Theater, which has a screen six stories tall.

Elsewhere, don’t miss the chance to step inside the opulent Lockwood–Mathews Mansion. It was built for the railroad and banking magnate LeGrand Lockwood, and is preserved as a shining example of a Second Empire-style country house.

You could also climb aboard a catamaran for a cruise out to Sheffield Island. Awaiting you there is an elegant lighthouse raised in 1868 amid a nature preserve supporting waterfowl like egrets and herons.

14. Gallaher Mansion and Cranbury Park

This park is barely ten minutes away in Norwalk and is composed of 227 acres of beautiful parkland and sculpture gardens around the Tudor Revival Gallaher Mansion.

The house was constructed for the industrialist Edward Beach Gallaher in 1931 during the Great Depression. It’s a stately residence, with mullioned windows, cross gables, hand-painted stained glass, and embattled window bays.

Fronting the house is an expansive lawn, those sculpture gardens and a stately stone terrace.

The oak-paneled house is usually rented out for functions, but was under renovation when I was in town.

As for the grounds, these are open to the public for hiking, tennis, dog walking, disc golf, picnicking, and to bring wee ones to the playground.

15. Southport Beach

Not far east of Sherwood Island is another place to unwind in the sun or take a bracing walk on a winter’s day.

Southport Beach is by no means large, at just 2.5 acres. But it comes with bathroom facilities and a concession stand that is open in the summer.

The good news is that the beach is free and open to the public. The bad news is that only residents with a beach sticker are allowed to use the parking lot between Memorial Day weekend and Labor Day.

Still, that doesn’t stop plenty of non-residents enjoying this pretty piece of the Connecticut shoreline.