Blake Walsh

20 Best Things to Do in Westport, CT

  • Published 2022/10/22

Visit Westport in Fairfield County, Connecticut, to capture the charming essence of a New England town.

Covering an area of about 33 square miles, Westport is one of Fairfield’s eight communities along Connecticut’s Gold Coast off the estuary, Long Island Sound.

The places to see and things to do in Westport have been woven deftly around the town’s establishment dating back to 1648.

The town’s founders were five men called Bankside Farmers, who settled along Long Island Sound after following cattle to the area.

The founders’ legacy remains today in the Greens Farms, Westport’s oldest neighborhoods named after John Green, which is one of the Bankside Farmers.

Incorporated in 1835, Westport has grown a vibrant downtown and a bustling commercial space over the years.

While it offers modern conveniences, Westport has retained the vibe of a New England town.

Visitors and residents enjoy this rare mix because of the local community’s commitment to conserve the town’s natural resources and preserve its traditions.

Thus, the town can boast a wide range of opportunities for leisure and recreation as can be seen in these things to do in Westport.

Enjoy the Waters of Sherwood Island State Park

Waves crashing at the shore of Sherwood Island State Park

James Kirkikis /

On the record as the first state park of Connecticut, this charming destination remains one of Westport’s finest.

This park features a picnic grove, a salt marsh nature trail, and the sandy Sherwood Beach of Long Island Sound.

This beach is ideal for swimming, especially from Wednesday through Sunday, as there are beach lifeguards on duty on those days.

A foot path at sherwood island.

James Kirkikis /

You can also go surf or shore fishing anywhere on the park’s shoreline outside the designated swimming areas.

The Sherwood Island State Park features an observation platform where you can view nearby marsh and its resident wildlife.

The park likewise runs a nature center with a wide range of exhibits and displays the rich diversity of Sherwood Island’s animal and plant life.

A stone dedication at sherwood island.

James Kirkikis /

Tour the Westport Museum

Aptly enough, the Westport Museum for History & Culture headquarters is the circa 1795 Bradley-Wheeler House along the corridor of Avery Place.

This house on a half-acre parcel has been remodeled in the 19th-century Italianate style.

Both registries of the U.S. and Connecticut list it as a historic landmark.

The interactive Westport Museum flaunts extensive archives and artifacts, including textiles.

Walking tours, history happy hours, author talks, and film showings are among the activities supporting the museum’s exhibits.

The museum’s grounds also feature the 1865 Cobblestone Barn Built, unique with its eight-sided roof.

This historic structure formerly used as a dairy also fascinates visitors with its underground ice house.

In addition, the Westport Museum maintains the historic Adams Academy on Morningside Drive.

This historic gem at the northern part of the town is an authentic one-room schoolhouse that served Westport from 1837 to 1867.

Explore the Christmas Tree Farm

Trees and grass at christmas tree farm.

Jllm06, CC BY-SA 4.0, via Wikimedia Commons

Regardless of whether it’s Yule season or not, it would be a delight to visit the H. Smith Richardson Wildlife Preserve and Christmas Tree Farm.

The Connecticut Audubon Society manages this nature sanctuary on Sasco Creek Road comprised of three parcels.

One of these is a 24-acre Christmas tree farm, where you can pick and cut your centerpiece tree for the holidays during the pre-Yule season.

A bird on a tree at christmas tree farm.

Jllm06, CC BY-SA 4.0, via Wikimedia Commons

This preserve also takes pride in its newly restored 14-acre wildlife habitat and a 36-acre evergreen plantation likewise fully restored to accommodate native wildlife.

For public appreciation, there are informative signs in the preserve describing its restored habitats and the value of their native plantings.

This preserve is popular among birdwatchers, as it attracts a great variety of avian species year-round.

The birds that frequent this preserve include the American Woodcock, Song Sparrow, and Gray Catbird.

Welcoming sign at Smith Richardson Wildlife Preserve and Christmas Tree Farm.

Jllm06, CC BY-SA 4.0, via Wikimedia Commons

Immerse in the Arts at MoCA Westport

Founded in 1934, MoCA is Westport’s first official arts organization and has grown its reach to over 20,000 people each year.

This town hub for the visual and performing arts occupies a refurbished circa 1920s building on Newtown Turnpike.

In this facility, visitors can access for free its contemporary art exhibits, including permanent and seasonal displays.

MoCA’s programs also include gallery talks, literature, film, jazz, singer and songwriters, and chamber music.

Visitors can also enjoy the full-service bar in this museum and its free drop-in studio for children.

Trace Westport’s Origins at Greens Farms

Look for Machamux Park, a small park on Greens Farms Road, to capture glimpses of Westport’s early settlement.

This pocket park is on a slice of land that once was part of the original West Parish of Fairfield, later Greens Farms, which started the Westport’s settlement.

The settlers’ first schoolhouse and meeting house were formerly located on the park’s site, featuring a commemorative bronze plaque on a granite boulder.

After viewing the Machamux Boulder, you can proceed to the quiet ambiance of the nearby Burying Hill Beach.

Located on Burying Hill Road and Beachside Avenue, this beach is a 2.39-acre park next to the Greens Farms Brook, a wildlife habitat.

This park has picnic tables, grills, a restroom, and changing area.

Have Fun at Compo Beach

The sea and the sand at compo beach.

James Christian /

This public facility off Compo Road is a 29-acre park flaunting off an extensive sandy beach.

Compo Beach provides two lighted basketball courts, two sand volleyball courts, a softball field, a large wooden playscape, and a boardwalk.

Groomed sand at compo beach.

James Christian /

In addition, a multi-purpose grass field, a skate park, and an open skate space have been integrated with this beach park.

Handicapped accessible, this Compo Beach also offers a pavilion, concession stand, bathroom facilities, and lockers.

The Ned Dimes Marina, located in Compo Beach, has boat slips, a boat launch ramp, and a clubhouse available for rentals.

Sand and the sea at compo beach.

WestportWiki, CC BY-SA 3.0, via Wikimedia Commons

Relish Life at Long Shore Club Park

This public park spreads over 169 acres of what was formerly the high-end Longshore Beach & Country Club.

As the private country club wasn’t making money, the town was able to buy this property in 1960.

The town of Westport, in turn, converted it into the Longshore Club Park and made its various facilities accessible to the public.

Visitors of the town can also stay at the park’s first-class Inn at Longshore with 12 guest rooms.

The perks of staying at this inn or just visiting Longshore Club Park include access to an 18-hole golf course touted as Fairfield County’s premier municipal links.

The park, virtually a town-owned country club, also provides a swimming pool, a marina, and a sailing school.

It also offers facilities for tennis, paddle tennis, and a skating rink during winter.

Check Out the Games at Westport’s Athletic Fields

There are a dozen sports arenas around Westport where you can watch either a pick-up game or an organized competition.

Wakeman Park on Cross Highway is one sports hub in the town where you’ll likely find some sports activities in progress.

This sports 27-acre park is the largest in Westport, featuring one fenced Babe Ruth baseball arena with hillside seating.

It also has a softball field, a quarter-mile track oval, three multi-purpose natural grass fields, and one multi-purpose synthetic turf field.

The 11-acre Doubleday Field Complex on Riverside Avenue provides similar facilities and four all-weather tennis courts.

Experience Broadway at the Westport Country Playhouse

Exterior and entrance of westport country playhouse.

M. Vinuesa /

This Westport stage was founded in 1931, behind the efforts of successful Broadway producers and husband-and-wife Lawrence Langer and Armina Marshall.

Westport Country Playhouse is on Powers Court, housed in an 1800s building that functioned from a tannery to a mill and a barn over the years.

Exterior of the westport country playhouse.

WestportWiki, CC BY-SA 3.0, via Wikimedia Commons

As a stage, the Westport Country Playhouse hosted more than 800 performances, some of which created the theater’s history.

One of these was the 2002 Our Town revival with Paul Newman, which went to Broadway after a sold-out run at the Playhouse.

Schedules to watch out for in Westport Country Playhouse include its new productions and its free programming, activities for families, and cabaret-style benefit concerts.

Have Lunch at Hudson Malone

Describing itself as an Old World culinary saloon, this restaurant is also New York-bred and still maintains its original location on the Big Apple’s East 53rd Street.

At Westport, Hudson Malone set up shop on Main Street, building upon its successful foray into the New York City market.

Expect a spirited welcome once you enter this restaurant that has already built a great reputation among New Yorkers.

Hudson Malone swears to keep its promise of full delivery of rustic, comfort food and perfect classic cocktails.

For lunch entrees, even a few samplings of the choices come mouth-watering with the likes of whole grilled market fish and grilled free-range chicken breast on the restaurant’s menu list.

Try the Omakase at OKO

The OKO is a Japanese-inspired restaurant of Brian Lewis, a celebrated chef in the Northeast.

Brian blends in OKO his signature culinary style with Japanese cooking techniques and traditions.

He uses ingredients not only from local farms and waters but also sources other recipe items across the US and in Japan’s Tsukiji fish market.

OKO’s exclusive offering is its 15-course Omakase (Chef’s Choice) featuring Edomae sushi, and other masterful kitchen plays on a wide range of fish and shellfish.

Unwind at Sherwood Mill Pond Preserve

This 80-acre nature preserve is located at Hillspoint Road, occupying the former site of the circa 1940 Allen’s Clam House Restaurant.

The Sherwood Mill Pond Preserve provides a walking path for visitors to appreciate its natural wetland plant habitat by the water’s edge.

There are benches for nature observation and relaxation while viewing the park’s naturalized, vegetative buffer above the tidal zone.

Historic and wildlife information can be derived from the educational signage displays at this preserve that draws over 70 bird species.

The Sherwood Mill Pond Preserve likewise features a designated area for launching kayaks and canoes.

From the preserve, you can also easily access Old Mill Beach, a 1.8-acre park less than 400 meters toward the south.

Let the Kids Commune with Nature at Earthplace

A bear and its cubs statue at Earthplace.

WestportWiki, CC BY-SA 3.0, via Wikimedia Commons

Make your trip to Westport a learning experience for the kids by visiting Earthplace on Woodside Lane at the northwestern side of Westport,

Earthplace was formally founded as the Westport Nature Center in 1958, and it now runs a 62-acre nature and wildlife sanctuary.

Additionally, Earthplace offers a 22,000-square-foot learning center for educational programs connecting children to nature.

Earthplace also has a nature-based exhibit hall, an outdoor amphitheater, a picnic grove, and several miles of walking trails, with one accessible to wheelchairs.

Shop Organic at the Westport Farmers Market

Reserve a Thursday visit to Westport, as on this day, the town has a farmers market in the Imperial Avenue parking lot.

This market boasts the best in organic produce, in addition to artisanal meats, baked goods, and quick eats.

One must-try at the Westport Farmers Market is the Riverbank Farm Kitchen for its organic produce ranging from tomatoes to radishes and hummus.

Another local favorite, the Wave Hill Bread Station, offers the popular pastry monkey bread and focaccia baked using the best artisan flour.

This baker’s other tasty options include its classic multi-grain bread and a caramelized garlic loaf.

Go for an Italian Dinner at Arezzo

This Italian restaurant formerly operated in New York and found a new home on Riverside Avenue in downtown Westport.

Arezzo Ristorante & Bar boasts irresistible waterfront dining in its outdoor patio.

This restaurant offers Tuscan specialties in its rustic setting on the west bank of the Saugatuck River and overlooking the Saugatuck River.

Picks from this restaurant’s menu are top-billed by an array of fresh homemade pasta.

Other culinary choices in Arezzo that helped it earn high Zagat ratings include prime-aged steaks and fresh seafood.

Grab a Good Read at The Westport Library

Front view of The Westport Library

WestportWiki, CC BY-SA 3.0, via Wikimedia Commons

The Westport Library is an architectural masterpiece and a technological wonder.

Located on a peninsula that jutted into the Saugatuck River and bordered by the verdant Jessup Green, this spot is hard to top.

While only locals with a library card can check out books, guests are allowed to use the library’s many computers and peruse the collection of magazines and newspapers.

Front view of The Westport Library

Jllm06, CC0, via Wikimedia Commons

You may play a board game or watch a movie in one of the many meeting rooms.

The library also hosts author talks (previous guests include James Patterson, RL Stein, Alan Alda, and Shonda Rhimes).

You’ll also see “Storywalk,” an outdoor piece using pages from a children’s book.

The inviting café is the perfect place to satisfy your hunger.

Enjoy delicious lattes and an unrivaled river view from the cafe’s patio.

Enjoy Open-Space Performances at Levitt Pavilion for the Performing Arts

Behind the Westport Library, on a little peninsula, is where you’ll find the Levitt Pavilion for the Performing Arts.

This popular venue draws crowds from around town for its free summer performances.

More than 1.5 million people have attended “50 Free Nights under the Stars” concerts at the Levitt, as locals know it.

It’s also the site of one of the country’s most celebrated free outdoor events.

Please bring a blanket or beach towel, a chair, and some food to share.

Then relax because you’re in for a lot of fun!

It also hosts concerts in every genre imaginable, including folk, jazz, pop, and rock.

Occasionally, performers will include actors and dancers.

Learn Sustainable Farming at Wakeman Town Farm

Wakeman Town Farm is one of the ideal locations in Westport to make lasting memories with your loved ones.

The sustainable farm aims to teach people the importance of eating well, taking care of the land, and giving back to the community.

Young people get an opportunity to learn both traditional and modern homesteading techniques at Wakeman Town Farm.

Learn animal husbandry and vegetable and fruit farming at the farm’s educational seminars.

Classes in the culinary arts, student internships, after-school environmental organizations, and summer camps are all available.

See Heavenly Bodies up Close at Westport Observatory

Front view of Westport Observatory

Pedro Xing, CC0, via Wikimedia Commons

Westport Observatory, formerly called Rolnick Observatory, is an astronomical observatory on top of the tallest hill in town, providing breathtaking night sky views.

This dome tower once served as a radar station during the Cold War.

Now, it’s a popular location to view celestial phenomena, including lunar eclipses, meteor showers, and even speeding comets.

The observatory houses a massive telescope for peering at faraway galaxies, informative exhibitions, friendly personnel, and a gift store stocked with celestial souvenirs.

The Rolnick Observatory is a fantastic place for families and amateur astronomers to learn about the universe above them.

Visit Le Rouge Handmade Chocolates by Aarti

For kids and kids at heart, check out Le Rouge Handmade Chocolates by Aarti.

It’s the perfect dessert store for those with a sweet tooth and an appreciation for fine chocolate.

In fact, this store has been awarded the finest chocolate shop in Westport for the last six years in a row, and it was just voted the best sweets business in town.

Lovely hand-decorated pastries, chocolate cakes, and attractive packaging that makes their chocolate ideal for gift-giving are what keep consumers coming back for more.

Get your sweet cravings satisfied with everything, including hand-rolled chocolate truffles toffee, chocolate-covered fruits, fudge, frozen chocolate mousse bites, and more.

Final Thoughts

Westport exudes an enduring New England town charm unspoiled by the din of its highly urbanized neighbors.

This town has preserved the natural environment that its early pioneers saw and enjoyed.

In addition, Westport has integrated many modern-day conveniences and cultural attractions that most visitors look for.

Keep this town in mind when planning to visit Connecticut, as so much delight awaits you in every minute spent on the things to do Westport.

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