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 you would never expect from a town of just 25,000.
Actor Paul Newman moved to Westport in the early 1960s and would stay until he passed away in 2008. He was active in the Westport community as a driving force behind the highly-regarded Westport Country Playhouse, but also gifted land to the town and even opened the Farmers’ Market in 2006. In summer you can hit Westport’s excellent public beaches, go paddleboarding on the Saugatuck River and sit down to an outdoor concert at the famous Levitt Pavilion.
1. Downtown Westport
The sort of central business district that any town would aspire to, Downtown Westport 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, eateries of all descriptions and a slew of upscale international retailers.
We’re talking Tiffany & Co, L’Occitane, Urban Outfitters, Banana Republic and South Moon Under, 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 to 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 283 hectares there’s woodland, wetland 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 gets too crowded.
You may need to wear watershoes 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, and there’s a Nature Center open seasonally from Wednesday to Sunday.
Inside are smart displays informing you about the park’s wildlife.
The center also organises bird-watching, nature walks and more in summer.
3. Water Activities
Among the shops and eateries on Riverside Avenue is Downunder Westport, a watersports shop selling surf boards, paddleboards, kayaks and all the gear to go with them.
The shop has three locations in the area, and here on Riverside Avenue you can rent paddleboards by the hour to explore the Saugatuck River.
Paddleboarding is an easy activity to pick up, and the store has boards to suit people of different weights.
For families, Imagine Invader is a giant inflatable paddleboard able to accommodate eight paddlers.
If you visit Downunder’s Darien Weed Beach location you’ll also be able to rent a range of kayaks by the hour.
4. Compo Beach
Compo Beach is a wide, gently curving bay, just where the Saugatuck River flows into Long Island Sound.
There are lifeguards daily from Memorial Day 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 peckish.
As is often the case in Connecticut, there are hefty fees for non-residents at the car park in summer.
Dogs are permitted off-leash in designated areas outside the summer season.
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 space is Natureplace, with hands-one exhibits and five 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, and you’ll find them in outdoor enclosures and inside at the Animal Hall.
The grounds comprise the largest open space in Westport, 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 and when we wrote this article in 2019 had just 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, with computer terminals, free Wi-Fi, cubicles set up for laptops, a silent reading room and a vibrant children’s section.
And, as with any great library, there’s a lively events schedule, for movie screenings, exhibitions from the Westport pubic 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 theatre 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, as a tannery dating back to 1830 and remodelled for Broadway shows in 1931 by the New York producer Lawrence Langner.
After moving to Westport in the 1960s Paul Newman championed the theatre, earning it even more acclaim.
The Playhouse has long been a showcase for new talent, and at present the current playwright in residence is David Wiltse, writing one play for each new season.
Some of the picks from the 2019 season were In the Heights, Skeleton Crew by Dominique Morisseau, Don Juan and Hershey Fielder as Irving Berlin.
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, or dance performances, theatre productions, movie screenings, circus shows or live comedy.
There’s a special children’s series on Wednesdays, while before several concerts the “RiverSwing” program offers dance lessons given by pros, in the style of music about to be performed.
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 Historical Society
Set up way back in 1889, the Westport Historical Society is headquartered at the refined Wheeler House, which dates from 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 a typical local historical society, laying on expertly-curated and constantly changing interactive exhibits and free Wi-Fi.
For a snapshot, in Autumn 2019 “Taking the Cure” dealt with public health from 1880 to 1960, going behind the scenes at Westport’s two sanatoriums for the mentally ill from that time.
“Vision & Dignity” meanwhile was a retrospective for the celebrated artist George Hand Wright, who relocated to Westport in 1908.
10. Westport Arts Center
We’ve seen that Westport has a real love for culture, and this multidisciplinary venue was founded some 50 years ago to help keep the local arts scene vital.
The Westport Arts Center hosts important exhibitions in contemporary art, as well as jazz, folk, chamber music and singer-songwriter performances, film screenings, readings, talks and a lot more.
In September 2019 the centre’s headline exhibition showcased Yayoi Kusama’s installations, Where the Lights in My Heart Go and Narcissus Garden.
The Westport Arts Center is also heavily engaged in the community, putting on children’s education programs for anything from toddler and parent art exploration, to sketching, photography and clay modeling.
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 and every Wednesday night from 20:00 to 22:00 you’re welcome to come and peer through the telescopes.
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, and this is the largest piece of stargazing equipment available to the public in Connecticut.
The society also arranged talks and discussions on cosmology, astronomy and physics 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.
Over the last ten years it has become an institution, forging links with local businesses and running all sorts of programs for healthy eating or to help local farmers who have fallen on hard times.
As of 2019 there are more than 40 regular vendors at the Westport Farmers’ Market, for fruit, vegetables, herbs, flowers, freshly caught fish, pasture-raised meat, pastries, cakes, pickles and exotic sauces.
Bring an appetite too, as there’s a contingent of food trucks preparing wood-fired pizza, empanadas, tamales, Thai soups and organic frozen desserts.
Westport’s neighbour to the west is a brief drive or just eight minutes in the train, and there are a lot reasons to make the journey.
First up, there’s the Maritime Aquarium, which 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 Lockwood–Mathews Mansion, built for the railroad and banking magnate LeGrand Lockwood, and 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, where there’s 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 residence was constructed for the industrialist Edward Beach Gallaher in 1931 during the Great Depression, and has 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-panelled house is rented out for functions, while the grounds 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 small, at just 2.5 acres, but comes with bathroom facilities and a concession stand that is open in the summer.
The good news is that the beach is public, but the bad news is that only residents with a beach sticker are allowed to visit between Memorial Day and Labor Day.
Catch a nice sunny day outside this window and there’s nothing to stop you enjoying this pretty piece of the Connecticut coastline.