Things To Do In Westport CT: Top 20 Most Unique Spots | Stanton House Inn

Sunset over the beach on Sherwood Island

Welcome to Westport, Connecticut! This charming New England town has a beautiful setting and many attractions. You can relax with bustling downtown shopping and tranquil Long Island Sound shores.


Westport has something for everyone. So come along with us as we explore the top 20 things to do in Westport, Connecticut.


map of attractions, activities, and things to do in Westport, CT
Map design by Stanton House Inn with elements from Flaticon

History of Westport, Connecticut

Archaeological evidence suggests that the first known residents of Westport arrived 7,500 years ago.


European settlers are said to have named this area Machamux, or beautiful land. This was chosen after the Pequot tribe who lived there.


The first colonists to settle in the area were the five Bankside Farmers. Their families grew and prospered into a community that reflected the same values.

Revolutionary War in Westport

During the American Revolution, Major General William Tryon led a British force of 1,850 soldiers. Tyron was the Royal Governor of the Province of New York. They landed on Compo Beach on April 25, 1777, to destroy the Continental Army’s military supplies in Danbury. The column was attacked from behind by local Minutemen.

1800s Heyday in Westport

The Town of Westport was formally incorporated on May 28, 1835. It was made using land from Fairfield, Weston, and Norwalk. Daniel Nash was joined by 130 Westport residents. They petitioned the Town of Fairfield for Westport’s incorporation. The petition to assist Westport was motivated by the need to support the seaport’s economic viability.


By the nineteenth century, Westport had grown into a shipping hub. This was thanks in part to the transportation of onions to markets. Westport’s economic engine was replaced by mills and factories rather than agriculture. This happened after the onion industry collapsed due to blight.

The Modern Era in Westport

Suburbanization occurred in the twentieth century. This resulted from industrialization, popularity among New Yorkers, and farmers selling off their land. Westport’s population grew rapidly from the 1950s to the 1970s.


New Yorkers moving from the city to the suburbs became aware of its artistic, musical, and literary community. By the turn of the century, Westport had become a center for professional, scientific, and technical services. It also became a hub for finance and insurance.

The Best Things to do in Westport CT

Explore Downtown Westport

A view of Downtown Westport with vibrant shops and restaurants

Step into the heart of Westport and immerse yourself in the vibrant downtown area. Stroll along the streets lined with independent boutiques. You’ll also want to check out upscale international retailers, eateries, and historic buildings. With its classic New England charm and walkable design, Westport Center is a must-see destination for any visitor.


This lively district is situated along the banks of the Saugatuck River. It offers a unique shopping experience and a rich cultural scene. It’s home to the renowned Westport Country Playhouse and the Levitt Pavilion. Downtown Westport is also a hub for performing arts and community events. This makes it a perfect destination for a day trip or an extended stay.

Westport, CT, Shopping

The bridge over the Saugatuck River in Wesport, CT

Discover the main shopping district of Westport. Nestled in the convenient Saugatuck area, it is easily explored on foot. Here, you’ll find everything from independent boutiques to mom-and-pop stores. There are also upscale international retailers, such as Tiffany & Co, L’Occitane, and Urban Outfitters.


Enjoy the stunning view of the Saugatuck River with its sparking water. Plus, you can park at Parker Harding Plaza or the library lot nearby.


At Downtown Westport, you can find trendy fashion, unique home décor, or artisanal gifts. Just take your time, meander the charming streets, and indulge a little.


Dining Options in Westport

In the mood for a culinary adventure? Downtown Westport boasts a diverse array of dining options. These foods range from cozy cafes like GG & Joe to Rye Ridge Deli. There are also upscale restaurants, such as OKO. Here, you can savor a 15-course Omakase (Chef’s Choice). It features Edomae sushi and other amazing dishes.


Many restaurants source their ingredients from local farms and waters. This allows you to taste the freshness in every bite.


You can find a quick bite at Bartaco, authentic Thai cuisine at Rainbow Thai, or a fine dining experience at La Plage at Longshore. So, go ahead and treat your taste buds to a gastronomic journey through the flavors of Westport.


Outdoor Things to Do in Westport, CT

A view of Sherwood Island State Park with picnic tables and beach

Take advantage of the beautiful outdoors that Westport has to offer with a variety of activities and attractions. Sherwood Island State Park’s beachfront and picnic areas are great for families. Plus, you can enjoy water sports on the Saugatuck River. Here, there’s no shortage of outdoor fun for the whole family.


Explore Compo Beach, learn to sail at Longshore Sailing School, or tour Hummock Island oyster farm. The choice is yours!


So, grab your sunscreen and sunglasses. Let’s dive into the top outdoor things to do in Westport, Connecticut!


Sherwood Island State Park

The beach at Sherwood Island State Park

Sherwood Island State Park offers diverse outdoor activities for visitors of all ages. This 234-acre park features a beachfront, picnic tables, a preserved salt marsh environment, and a Nature Center. There are also bird-watching activities in the New England summer.


You can enjoy a leisurely nature stroll, family picnic, or bird-watching day. Sherwood Island State Park is the perfect destination for outdoor enthusiasts. It’s an easy drive from I-95 and the rest of town via the Sherwood Island Connector.


Water Sports on the Saugatuck River

Get your adrenaline pumping with exhilarating water sports on the Saugatuck River. Crystal-clear waters and picturesque scenery make this place so special. The river offers the perfect setting for stand-up paddleboarding, surfing, and kayaking.


So, grab your gear, head to the river, and make a splash as you explore Westport’s natural beauty from a new perspective.


Compo Beach

Man sitting at Southport beach

Compo Beach is more than just a beach; it’s a hub of outdoor activities for the entire family. There are lifeguards, courts, a skate park, and designated off-leash areas for dogs outside of the summer season.


So, pack a picnic, bring sunscreen, and prepare for a fun-filled day at Compo Beach.


Learn to Sail at Longshore

Unleash your inner sailor at Longshore Sailing School. This spot is in Westport’s picturesque Longshore Club Park. It offers courses for all ages and skill levels. The sailing school also provides the perfect opportunity to learn a new skill while enjoying the scenic beauty of the Long Island Sound. Other activities here include a skating rink, tennis courts, seasonal outdoor swimming pool, and a golf course.


So, why not embark on a nautical adventure and create lasting memories on the water?


Tour Hummock Island Oyster Farm

Discover the fascinating world of oyster farming with a tour of Hummock Island Oyster Farm. Learn about the cutting-edge technology used in cultivating these delicious bivalves. Also, enjoy a unique, immersive experience that’s both educational and entertaining.


Don’t miss the chance to explore this thriving industry and savor the taste of fresh oysters straight from the farm.


Smith Richardson Wildlife Preserve

The 36-acre section of Smith Richardson is astounding. It’s one of the few places in Connecticut where you can see a significant habitat restoration project in progress.


Until 2016, the Smith Richardson Wildlife Preserve was overrun with weeds and invasive plants. The like included barberry and Asiatic bittersweet. Connecticut Audubon Society envisioned an ecological makeover. They wanted the space to become a lush, coastal forest and shrubland. Volunteers and staff removed invasives and planted over 3,000 native trees and shrubs. They provide seeds, fruit, and nectar all year for birds, butterflies, bees, and other wildlife with invasive species. Two new two-acre pollinator meadows teem with insects, and small patches of grasses that produce seeds ripen in the fall.


The result is a considerable improvement. It now has a diverse range of meadows, shrubs, thickets, conifers, and open woods, replacing the former tangle of weedy plants.


Indoor Things to Do in Westport, CT

Woman viewing art in a modern art gallery

If you’re looking for indoor attractions, Westport has plenty to offer. For instance, the Earthplace Sanctuary and Museum is in the Westport Historical Society. There’s no shortage of engaging and educational experiences for visitors of all ages.


Embrace your creative side at the Westport Arts Center or unwind with a good book at the Westport Library. And for those looking to immerse themselves in contemporary art, don’t miss the events at MOCA Westport.


Let’s explore the top indoor things to do in Westport, CT!


Discover Earthplace Sanctuary & Museum

Venture into the natural world at Earthplace Sanctuary and Museum. It’s a 62-acre wildlife sanctuary featuring fields, forests, ponds, and animal ambassadors. Here, there’s a nature-based exhibit hall, outdoor amphitheater, picnic grove, and walking trails. Earthplace offers a variety of activities for nature lovers of all ages.


Take a stroll down the Swamp Loop Trail and encounter native wildlife or explore the Birds of Prey Exhibit in Animal Hall. The choice is yours at Earthplace.


Dive into History at the Westport Museum for History & Culture

Step back in time at the Westport Museum. Here, you can explore the town’s rich history through fascinating exhibits and engaging programs. Discover the stories of the past at the Bradley-Wheeler Barn Museum. Or, delve into the archives to uncover Westport’s colorful heritage.


The Westport Museum for History & Culture is a must-visit on a journey through historic Connecticut with various events and educational programs. You won’t want to see what it offers as a unique glimpse into the town’s storied past.


Relax & Learn at Westport Library

The Westport Library is more than just a place to borrow books. It’s also a hub of learning and relaxation for the entire community. It has vast resources, self-service check-out stations, and cutting-edge technology. The library offers a welcoming environment for visitors to read, work, and unwind.


Don’t miss the library’s calendar of events featuring author talks, film screenings, and more to enrich your visit to Westport.


Attend Events at MOCA Westport

Experience the world of contemporary art at MOCA Westport. This museum offers diverse visual arts, music performances, and comprehensive arts education. Explore thought-provoking exhibits, attend engaging talks, or enjoy a jazz or chamber music night.


You won’t want to miss the dynamic programming and commitment to artistic excellence. MOCA Westport is a must-visit destination for art enthusiasts.


Things to Do in Westport, CT, at Night

A view of downtown Westport from the outdoor entertainment at Levitt Pavilion

Westport’s nightlife comes alive with various entertainment options for all tastes as the sun sets. There are live performances at the Westport Country Playhouse and outdoor events at the Levitt Pavilion. There’s no shortage of things to do after dark in this charming New England town.


For those with a passion for stargazing, join the Westport Astronomical Society. Here, you can discover the wonders of the night sky at the Rolnick Observatory. Let’s look at the top things to do at night in Westport, CT.


Enjoy Live Performances at Westport Country Playhouse

Experience the magic of live theater at the Westport Country Playhouse. This outdoor venue has been entertaining audiences since 1931. It has a rich history of hosting acclaimed actors, such as:

  • Paul Newman
  • Robert Redford
  • Liza Minnelli

The playhouse offers diverse new productions, free programming, and special events.


You won’t want to miss their Broadway hits or local productions. The Westport Country Playhouse is the perfect destination for a night of unforgettable theater.


Outdoor Entertainment at Levitt Pavilion

Church at night across the Saugatuck River from the Levitt Pavilion for the Performing Arts

For an evening under the stars, head to the Levitt Pavilion for the Performing Arts. This outdoor venue offers a range of entertainment options. These activities include concerts, theater productions, movie screenings, and more. Bring a picnic blanket and unwind on the lawn as you enjoy live performances in various genres, from folk to jazz and pop to rock.


With many free events throughout the season, there’s always something happening at Levitt Pavilion.


Stargazing with Westport Astronomical Society

A view of Westport Farmers' Market with local produce and cooking classes

Discover the beauty of the night sky with the Westport Astronomical Society at the Rolnick Observatory. Open on Wednesday nights, the Westport observatory offers a unique opportunity for visitors. They can observe celestial wonders such as shooting stars, comets, and lunar eclipses through a variety of telescopes.


You can be an experienced stargazer or a curious beginner. Still, the Westport Astronomical Society is the perfect place to explore the cosmos.


Foodie Things to Do in Westport, CT

Calling all foodies! Westport is a culinary paradise with many delicious experiences waiting for you. You can savor local produce at the Westport Farmers’ Market or indulge in handmade chocolates at Le Rouge. There’s no shortage of delectable delights to tempt your taste buds.


So, join us as we explore the top foodie things to do in Westport, CT, and discover the mouthwatering flavors this charming New England town offers.


Westport Farmers Market

A colorful display of locally grown fruits and vegetables at Westport Farmers' Market, one of the top things to do in Westport CT for foodies and health enthusiasts.

Experience the best of Westport’s local produce at the Westport Farmers’ Market. This spot offers a diverse selection of organic fruits, vegetables, herbs, flowers, and more. Founded by actor Paul Newman, this lively market features an array of vendors. Keep an eye out for Skinny Dip Farm, Movement Ground Farm, Scuttlebutt Coffee, and Old County Farm.


So, grab a basket and indulge in Westport’s freshest flavors.


Indulge in Handmade Chocolates at Le Rouge

Satisfy your sweet tooth with a visit to Le Rouge Handmade Chocolates by Aarti. Here, you’ll find an array of hand-rolled chocolate truffles, toffee, and chocolate-covered fruits. There’s also fudge and frozen chocolate mousse bites.


Discover the craft of artisan chocolate making here. Don’t forget to sample the exquisite Heritage Truffle Collection. You’ll also want to try the delightful French Mendiants. With so many delectable treats, Le Rouge is a must-visit destination for chocolate lovers.



Arezzo Ristorante & Bar, an Italian restaurant on Riverside Avenue in Westport, provides waterfront dining. The restaurant, located on the west bank of the Saugatuck River, serves Tuscan specialties and fresh homemade pasta. Its prime-aged steaks and fresh seafood, as well as its rustic setting with an outdoor patio on the west bank of the Saugatuck River, have earned it high Zagat ratings.


Explore Nearby Norwalk Attractions

Gallaher mansion in Norwalk, CT

Looking to venture beyond Westport’s borders? The nearby city of Norwalk offers a wealth of attractions and activities to explore. There are historic sites like Gallaher Mansion and Cranbury Park. There’s also the beauty of Long Island Sound. There’s no shortage of things to see and do in Norwalk.


Join us as we uncover the top attractions in nearby Norwalk. Embark on an adventure just a stone’s throw away from Westport.


Maritime Aquarium

The Maritime Aquarium in Norwalk, Connecticut, attracts 500,000 annual visitors and is the only aquarium devoted to Long Island Sound. It features interactive exhibits, interactive exhibits, and a café. The aquarium is easily accessible from Westport and Manhattan via the Metro North Line to New Haven, CT.


Visit Gallaher Mansion & Cranbury Park

Gallaher mansion in Cranbury Park in nearby Norwalk, Connecticut

Step back in time and explore the historic Gallaher Mansion and Cranbury Park in Norwalk. This stunning 227-acre park features gorgeous parkland and sculpture gardens. There’s also the beautiful Tudor Revival Gallaher Mansion.


Enjoy a variety of outdoor activities. You can enjoy hiking, tennis, disc golf, and picnicking—all in the tranquil beauty of inland Norwalk.


Other attractions in Norwalk include South Norwalk restaurants, the Norwalk Historical Society, and the Lockwood-Mathews Mansion Museum.


Hotels and Inns in Westport, Connecticut

Ready to plan a CT weekend getaway in Westport?


Westport is about a half-hour drive from our Greenwich, CT, bed and breakfast. If you’re looking for something in-town, read on for a primer on hotels and inns in and nearby to Westport.

The Inn at Longshore

The Inn at Longshore, formerly an elegant private estate and exclusive country club, is now a popular small CT wedding venue, as well as a corporate event venue. It provides a relaxing and quaint setting for locals and visitors alike, with 12 guest rooms, award-winning cuisine, and stunning views of the Long Island Sound. Complimentary Wi-Fi, cable flat-screen TVs, premium bed linens, air conditioning, beach towels, and a mini-bar are among the amenities. The Inn is one of Fairfield County’s largest waterfront event venues.

Delamar Southport

The Delamar Southport is close to Westport in the Southport neighborhood in the town of Fairfield, CT. Guests can enjoy an on-site spa and Artisan, a French restaurant run by French chef Frederic Kieffer. It’s a seven-minute walk from the Metro North rail station and facing I-95. So its location makes it easy to explore Southport’s historic downtown or go gallery hopping.

Bed and breakfasts near Westport

There are no bed and breakfasts in Wesport, Connecticut. That said, nearby Connecticut bed and breakfast inns aside from Stanton House Inn include:


  • The Inn at GrayBarns on the Silvermine River, in Norwalk


Discover Even More Things to Do in CT, Near Westport

Park along the Saugatuck River, a major draw for the Westport community

Westport is a major destination within Fairfield County. And this charming town makes a fantastic day trip!


A few more unique attractions, and nearby cities and towns to explore include:


Be sure to read our full guide to attractions, activities, and unique things to do in the Fairfield County, CT Travel Guide.

Leave a Reply

Your email address will not be published. Required fields are marked *