Next to Long Island Sound, along the headwaters of the Saugatuck River lies one of the wealthiest cities in the United States. Westport has an artistic pedigree and the sort of sophisticated downtown you’d never expect from a city of just 25,000 inhabitants.
Actor Paul Newman moved to Westport in the early 1960s and would stay until he died in 2008. He was active in the Westport community as the driving force behind the much-regarded Westport Country Playhouse, but also awarded land to the city and even opened a Farmer’s Market in 1999. 2006. In summer you can visit Westport’s great public beaches, paddleboard on the Saugatuck River and sit down to an outdoor concert at the famous Levitt Pavilion.
1. Downtown Westport
The kind of central business district any city could aspire to, Downtown Westport combines the cuteness and charm of a New England coastal town with cosmopolitan shopping and dining.
In the walkable Saugatuck area you’ll find independent boutiques, mom-and-pop stores, local chains, museums, historic buildings, galleries, restaurants of all descriptions, and many high-end international retailers.
We’re talking Tiffany & Co, L’Occitane, Urban Outfitters, Banana Republic and South Moon Under, to name a few.
Nothing is more than a few minutes’ walk away, and there’s plenty of parking and views to behold across the Saugatuck River to the old pier on the west bank, backed by woods.
2. Sherwood Island National Park
Purchased in 1914, Sherwood Island was Connecticut’s first state park, and is still considered one of the best.
On 283 hectares there are forests, wetlands and beautiful beaches.
On the East and West Coasts you can relax in the Long Island Sound and swim, and the beach is wide enough that it’s never too crowded.
You may need to wear water shoes to protect your feet from sharp rocks and shells on the beach.
In the back there are plenty of picnic tables, picnic areas, and a few concession stands.
A wooden walkway takes you into a well-preserved salt marsh environment, and there’s a Nature Center open seasonally from Wednesday to Sunday.
Inside is a smart screen that notifies you about the park’s wildlife.
The center also hosts bird watching, nature walks, and more in the summer.
3. Water Activities
Among the shops and eateries on Riverside Avenue is Downunder Westport, a watersports shop that sells surfboards, paddleboards, kayaks and all the gear to bring.
The shop has three locations in the area, and here on Riverside Avenue, you can rent a paddle board by the hour to explore the Saugatuck River.
Paddleboarding is an easy activity to do, and the store has boards suitable for people of different weights.
For families, the Imagine Invader is a giant inflatable paddle board capable of accommodating eight paddlers.
If you visit the Darien Weed Beach location in Downunder, you can also rent a variety of kayaks by the hour.
4. Pantai Compo
Compo Beach is a wide, curved bay, just where the Saugatuck River flows into Long Island Sound.
There is a lifeguard every day from Memorial Day to Labor Day, and the beach has many amenities.
In addition to the enormous wooden playground, there are two basketball courts with floodlights, a volleyball court, a skate park, an outdoor skate area, a softball court and a multipurpose court.
There is a concession stand with a deck right on the beach when you are hungry.
As is often the case in Connecticut, there are hefty fees for non-residents in parking lots in the summer.
Dogs are allowed to untie in designated areas outside of the summer.
A natural history museum, nature center and nature reserve combined, Earthplace is an attraction that builds on more than 60 acres and dates back to 1958. The museum space is Natureplace, with hands-on exhibits and five detailed dioramas showing Connecticut’s flora and fauna at the time. different throughout the year.
There are a large number of rescued animals that cannot be released back into the wild because of their injuries.
These include eastern box turtles, large brown bats, bald eagles, green frogs, turkey vultures, and red-tailed eagles, and you’ll find them in the outdoor enclosures and inside the Animal Hall.
The grounds consist of the largest open space in Westport, with hardwood forests, meadows, rivers, ponds and wetlands.
Go quietly and you have a chance to see wildlife such as deer, squirrels, wild turkeys and rabbits.
6. Westport Library
The city library has the perfect location, right on the Saugatuck River and as we write this article in 2019 has just gone through a spectacular transformation project.
The Westport Library is a tremendous resource for a small town, and is one of the busiest in the entire area for book circulation per capita.
If you’re looking for a place to work, read or just relax in Westport, this is the place to go, with a computer terminal, free Wi-Fi, booths set up for laptops, a quiet reading room and a lively kids’ section.
And, as with any large library, there’s a lively schedule of events, for film screenings, exhibitions from Westport’s collection of pubic art, children’s activities, talks, language conversation groups, and more.
7. Westport Country Playhouse
With a national reputation, this professional production theater is run on a non-profit basis under the artistic direction of the esteemed Mark Lamos.
The Westport Country Playhouse season is from April to November where you can watch productions of the highest quality in the 578-seat auditorium.
The place has an interesting past, as a tannery dating back to 1830 and renovated for a Broadway show in 1931 by New York producer Lawrence Langner.
After moving to Westport in the 1960s, Paul Newman became a theater champion, earning him even more acclaim.
The Playhouse has long been a showcase for new talent, and currently the in-house playwright is David Wiltse, writing one play for each new season.
Some of the picks from the 2019 season are In the Heights, Skeleton Crew by Dominique Morisseau, Don Juan and Hershey Fielder as Irving Berlin.
8. Levitt’s Pavilion for the Performing Arts
On a picturesque little peninsula on 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 there are only 60 nights of entertainment.
This may be a concert for rock, pop, blues, jazz, folk, cabaret, world music, big band, or dance performances, theatrical productions, film screenings, circus performances or live comedy.
There is a special children’s series on Wednesdays, while before some concerts the program “RiverSwing” offers dance lessons given by professionals, with the style of music that will be performed.
The park opens about an hour before the curtains open, and you will be sitting on the lawn so you will need to bring a park bench or picnic blanket.
9. Westport Historical Society
Founded in 1889, the Westport Historical Society is headquartered in the refined Wheeler House, which dates from 1795 and was updated in 19th-century Italian style.
The public also cares about Adams Academy, a 19th-century one-room schoolhouse at 15 Morningside Drive.
The museum at Wheeler House goes above and beyond the typical local historical community, nestled in expertly curated and constantly changing interactive exhibits and free Wi-Fi.
To illustrate, in Fall 2019 “Taking the Cure” dealt with public health from 1880 to 1960, going behind the scenes at two Westport sanatoriums for the mentally ill since then.
Meanwhile, “Vision & Dignity” is a retrospective for the famous artist George Hand Wright, who moved to Westport in 1908.
10. Westport Arts Center
We’ve seen that Westport is passionate about culture, and this multidisciplinary venue was founded some 50 years ago to help keep local art vital.
The Westport Arts Center hosts important exhibitions in contemporary art, as well as jazz, folk, chamber and singer-songwriter performances, film screenings, readings, lectures, and more.
In September 2019 the center’s main exhibition featured Yayoi Kusama’s installations, Where the Lights in My Heart Go and Narcissus Garden.
The Westport Arts Center is also deeply involved in the community, running children’s educational programs for everything from toddler and parent art exploration, to sketching, photography, and clay modeling.
11. Westport Astronomical Society
Over the past half century, thousands of people have experienced the wonders of the night sky at this volunteer-run non-profit observatory.
The facility was set up on the former Nike BR-73 missile site and every Wednesday evening from 20:00 to 22:00 you are welcome to come and peek through the telescope.
The dome observatory is equipped with the Meade LX200 16″, and has the Explore Scientific 102mm f/7 ED Apochromatic Triplet Refractor on top.
On warmer nights, the massive 25” Obsession telescope is parked in the yard, and it is the largest publicly available stargazing apparatus in Connecticut.
The Society also hosts talks and discussions on cosmology, astronomy, and physics by academics in their fields, such as Yale, MIT, UConn, Columbia, and NYU.
12. Westport Farmers Market
Paul Newman himself opened the Westport Farmers Market in 2006. The market grew rapidly and soon moved to its current location at 50 Imperial Avenue.
Over the last ten years it has become an institution, liaising with local businesses and running all sorts of programs to eat healthy or to help local farmers who have fallen through hard times.
In 2019 there were more than 40 regular vendors at Westport Farmers Market, for fruit, vegetables, herbs, flowers, fresh fish, prairie-raised meats, pastries, cakes, pickles and exotic sauces.
Bring your appetite too, as there is a contingent of food trucks preparing wood-fired pizzas, empanadas, tamales, Thai soups and organic frozen desserts.
Neighboring Westport to the west is a short drive or just eight minutes by train, and there are plenty of reasons to make the trip.
First, there is the Maritime Aquarium, which is a stunning and creatively presented attraction with 75 exhibits comprising 2,700 marine animals from around the world.
You can admire sharks, jellyfish, rays, and loggerhead turtles and be mesmerized by movies at the IMAX Theatre, which has a six-story screen.
Elsewhere, don’t miss the opportunity to step inside the Lockwood–Mathews Mansion, built for railroad and banking magnate LeGrand Lockwood, and preserved as a shining example of a Second Empire-style country house.
You can also take a catamaran to sail to Sheffield Island, where there is an elegant lighthouse built in 1868 in the center of a nature reserve that supports waterfowl such as herons and herons.
14. Gallaher House and Cranbury Park
The park is barely ten minutes on Norwalk and comprises 227 acres of beautiful gardens and sculpture gardens around the Tudor Revival Gallaher Mansion.
This residence was built for industrialist Edward Beach Gallaher in 1931 during the Great Depression, and features bay windows, cross gable, hand-painted stained glass, and tempered window sills.
In front of the house was a large lawn, the carved garden, and a magnificent stone terrace.
The oak-paneled house is rented out for events, while the grounds are open to the public for hiking, tennis, dog walks, disc golf, picnics and taking the little ones to the playground.
15. Southport Beach
Not far to the east of Sherwood Island is another place to relax in the sun or take a walk in winter.
Southport Beach is small, only 2.5 acres, but comes with shower facilities and a concession stand that is open in the summer.
The good news is that the beach is open to the public, but the bad news is that only residents with a beach sticker are allowed to visit between Memorial Day and Labor Day.
Enjoy a sunny day outside this window and nothing will stop you from enjoying this beautiful part of Connecticut’s coastline.
Where to stay: Best Hotels in Westport, Connecticut (CT)
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