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

Sunset over the beach on Sherwood Island

If you’re looking for charming New England towns, Westport, Connecticut is your spot. This town in Fairfield County is like stepping into a postcard, with its beautiful beaches, quiet streets, and the serene Saugatuck River.

Ready to explore the best things to do in Westport CT? Let’s get into it:

Quick Hits

  • Beaches: Relax on the sandy shores of Westport’s picturesque beaches.
  • Paddleboarding: Glide along the Saugatuck River and enjoy the peaceful scenery.
  • Downtown: Explore high-end shops, award-winning restaurants, and a vibrant arts scene.
  • Farmers’ Market: Visit the market started by actor Paul Newman in 2006 for fresh local produce.
  • Outdoor Concerts: Enjoy live music in the open air during the summer months.

 

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

Westport’s history is rich and fascinating. Archaeological evidence suggests that people have lived here for about 7,500 years. European settlers named the area Machamux, meaning “beautiful land,” after the Pequot tribe who lived there.

Revolutionary War in Westport

During the American Revolution, British forces led by Major General William Tryon landed on Compo Beach on April 25, 1777. They aimed to destroy the Continental Army’s supplies in Danbury, but local Minutemen attacked them from behind.

1800s Heyday in Westport

Westport was officially incorporated on May 28, 1835, thanks to Daniel Nash and 130 residents who petitioned for its recognition. The town blossomed into a shipping hub, especially known for transporting onions. Unfortunately, the onion industry collapsed due to blight, and mills and factories took over as the town’s economic engines.

The Modern Era in Westport

In the 20th century, Westport became a favorite for New Yorkers looking to escape the city. Its population boomed from the 1950s to the 1970s, and it became known for its vibrant artistic, musical, and literary community. By the turn of the century, the Westport community had evolved into a center for professional, scientific, and technical services, as well as finance and insurance.

The Best Things to do in Westport CT

If you’re looking for a mix of history, outdoor fun, tasty food, and artsy vibes, Westport, Connecticut, is the place to be. From beautiful beaches and scenic river views to a vibrant downtown and rich history, there’s plenty to do. Read on to see what makes this town so special.

Downtown Westport

A view of Downtown Westport with vibrant shops and restaurants

First stop: downtown Westport! This area is the heartbeat of the town, full of independent boutiques, upscale shops, and yummy eateries. Imagine classic New England charm mixed with a walkable design—perfect for a leisurely stroll.

  • Shopping: From quirky local shops to fancy international retailers, there’s something for every shopper.
  • Food: Plenty of spots to grab a bite, whether you’re in the mood for a quick snack or a sit-down meal.
  • Historic Buildings: Enjoy the timeless architecture as you wander around.

The downtown area sits along the Saugatuck River, offering stunning views and a rich cultural scene. Be sure to check out:

  • Westport Country Playhouse: A renowned spot for theater lovers.
  • Levitt Pavilion: A hub for performing arts and community events, perfect for a day trip or longer stay.

Outdoor Things to Do in Westport, CT

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

Westport is a playground for nature lovers with tons of fun activities. From beaches to water sports, there’s something for you. So, grab your sunscreen and sunglasses, and read on to dive into the top outdoor things to do in Westport!

Sherwood Island State Park

The beach at Sherwood Island State Park

Sherwood Island State Park is perfect for a day of fun. This 234-acre park has it all—beaches, picnic tables, a preserved salt marsh, and even a Nature Center.

  • Nature Strolls: Take a leisurely walk and enjoy the beautiful scenery.
  • Picnics: Pack a lunch and enjoy a meal with a view.
  • Bird-Watching: Spot some feathered friends during the New England summer.

It’s easy to get to via the Sherwood Island Connector from I-95.

Water Sports on the Saugatuck River

If you’re an adrenaline junkie, the Saugatuck River is calling your name. With crystal-clear waters and stunning scenery, it’s perfect for:

  • Stand-Up Paddleboarding
  • Surfing
  • Kayaking

So, grab your gear and make a splash!

Compo Beach

Man sitting at Southport beach

Compo Beach isn’t just any beach—it’s an activity hub for the whole family. You’ll find lifeguards, sports courts, a skate park, and off-leash areas for dogs (outside of summer).

  • Family Fun: Pack a picnic, bring sunscreen, and get ready for a fun-filled day.

Learn to Sail at Longshore

Ever wanted to sail? Longshore Sailing School in the picturesque Longshore Club Park offers courses for all ages and skill levels. Plus, you can enjoy other activities like:

  • Skating Rink
  • Tennis Courts
  • Seasonal Outdoor Swimming Pool
  • Golf Course

Why not unleash your inner sailor and create some 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 technology behind cultivating these delicious bivalves and enjoy a unique, immersive experience.

  • Fresh Oysters: Don’t miss tasting fresh oysters straight from the farm.

Smith Richardson Wildlife Preserve

If you’re into nature and wildlife, you’ve got to check out the Smith Richardson Wildlife Preserve. This 36-acre gem in Connecticut is a shining example of habitat restoration done right.

Until 2016, the preserve was overrun with pesky weeds and invasive plants like barberry and Asiatic bittersweet. But then the Connecticut Audubon Society stepped in with a big dream: to transform this space into a lush coastal forest and shrubland. With the help of dedicated volunteers and staff, they removed the invasives and planted over 3,000 native trees and shrubs.

Here’s what makes it special:

  • Pollinator Meadows: Two new two-acre meadows are buzzing with insects.
  • Diverse Habitats: Now, you’ll find meadows, shrubs, thickets, conifers, and open woods where once there was just a mess of weeds.

This place is now a haven for birds, butterflies, bees, and other wildlife. It’s nature’s version of an extreme makeover, and it’s incredible to see.

Indoor Things to Do in Westport, CT

Woman viewing art in a modern art gallery

Looking for some indoor fun in Westport? This town has got you covered with plenty of cool spots. Read on for the top indoor activities in Westport, CT!

Discover Earthplace Sanctuary & Museum

If you’re a nature lover, Earthplace Sanctuary and Museum is a must-see. This 62-acre wildlife sanctuary has fields, forests, ponds, and animal ambassadors. Inside, you’ll find a nature-based exhibit hall, outdoor amphitheater, picnic grove, and walking trails.

  • Swamp Loop Trail: Take a stroll and spot native wildlife.
  • Birds of Prey Exhibit: Check out the raptors in Animal Hall.

It’s perfect for nature enthusiasts of all ages!

Dive into History at the Westport Museum for History & Culture

Step back in time at the Westport Museum. Explore the town’s rich history through fascinating exhibits, walking tours, and engaging programs in history museums scattered around town:

  • Bradley-Wheeler Barn Museum: Discover stories from the past.
  • Archives: Dive into Westport’s colorful heritage.
  • Adams Academy: an authentic one room schoolhouse on Morningside Drive.

The Westport Museum is a must-visit for anyone curious about Connecticut’s history.

Relax & Learn at Westport Library

The Westport Library is not just for bookworms. It’s a community hub with vast resources, self-service check-out stations, and cutting-edge technology.

  • Events: Check out the library’s calendar for author talks, film screenings, and more.

Whether you’re reading, working, or just chilling, this library has it all.

Attend Events at MOCA Westport, AKA Westport Arts Center

For art lovers, MOCA Westport is the place to be. This museum offers a mix of visual arts, music performances, and comprehensive arts education.

  • Exhibits: Explore thought-provoking contemporary art.
  • Events: Enjoy jazz nights, chamber music, and engaging talks.

MOCA Westport is a must-visit for a dose of culture and creativity.

Things to Do in Westport, CT, at Night

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

When the sun sets, Westport’s nightlife kicks into gear with tons of fun options for everyone. From live theater to stargazing, there’s no shortage of things to do after dark in this charming New England town. Read on for the top nighttime activities in Westport, CT!

Enjoy Live Performances at Westport Country Playhouse

Get ready for a night of magic at the Westport Country Playhouse. This historic theater has been entertaining audiences since 1931 and has hosted big names like:

  • Paul Newman
  • Robert Redford
  • Liza Minnelli

They offer a mix of Broadway hits, local productions, free programming, and special events. Trust me, you won’t want to miss out on a night of unforgettable theater here.

Outdoor Entertainment at Levitt Pavilion

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

For a perfect evening under the stars, head to the Levitt Pavilion for the Performing Arts. This outdoor venue has it all—concerts, theater productions, movie screenings, and more.

  • Bring a Picnic Blanket: Relax on the lawn and enjoy live performances in genres ranging from folk to jazz and pop to rock.
  • Free Events: With many free events throughout the season, there’s always something happening.

Stargazing with Westport Astronomical Society

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

If you’re fascinated by the night sky, join the Westport Astronomical Society at the Rolnick Observatory. Open on Wednesday nights, the Westport observatory lets you observe celestial wonders like shooting stars, comets, and lunar eclipses through various telescopes.

Whether you’re an experienced stargazer or just curious, this is the perfect place to explore the cosmos.

Foodie Things to Do in Westport, CT

Calling all foodies! Ready for a culinary adventure in Westport? This charming town is packed with diverse dining options that will make your taste buds dance. Let’s explore some of the best spots!

Downtown Dining

Downtown Westport has everything from cozy cafes to upscale restaurants. Here are some must-try spots:

  • GG & Joe: Perfect for a laid-back coffee or a quick bite.
  • Rye Ridge Deli: Great for a classic deli experience.
  • OKO: Treat yourself to a 15-course Omakase featuring Edomae sushi and other exquisite dishes.

Many places source their ingredients from local farms and waters, so you can taste the freshness in every bite.

Quick Bites & Fine Dining

Westport is a culinary paradise with plenty of delicious experiences waiting for you. Whether you’re in the mood for local produce or handmade chocolates, this town has it all.

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

Arezzo Ristorante & Bar, an Italian restaurant on Riverside Avenue in Westport, provides waterfront dining in CT. 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.

Westport, CT, Shopping

The bridge over the Saugatuck River in Wesport, CT

If you love discovering unique finds and trendy spots, you’ve got to check out the main shopping district in Westport. Nestled in the convenient Saugatuck area, it’s perfect for a leisurely stroll.

Shopping Highlights

Here’s what you can expect:

  • Independent Boutiques: Find one-of-a-kind items that you won’t see anywhere else.
  • Mom-and-Pop Stores: Support local businesses and discover hidden gems.
  • Upscale Retailers: Indulge at places like Tiffany & Co, L’Occitane, and Urban Outfitters.

Tips for Your Shopping Spree

  • Parking: You can park at Parker Harding Plaza or the library lot nearby.
  • Scenic Views: Enjoy the stunning view of the Saugatuck River as you shop. The sparkling water makes for a great backdrop.

What to Find

  • Fashion: Trendy outfits to keep you looking chic.
  • Home Décor: Unique pieces to spruce up your space.
  • Artisanal Gifts: Perfect for treating yourself or someone special.

So, take your time, wander the charming streets, and indulge a little. Happy shopping!

Explore Nearby Norwalk Attractions

Gallaher mansion in Norwalk, CT

If you’re ready to venture beyond Westport, Norwalk is just a hop, skip, and a jump away. This nearby city is packed with attractions and activities that’ll keep you entertained. From historic sites like Gallaher Mansion to the beauty of Long Island Sound, there’s no shortage of things to see and do in Norwalk.

Maritime Aquarium

First stop, the Maritime Aquarium in Norwalk, Connecticut. This place is a hit with 500,000 visitors every year and is the only aquarium dedicated to Long Island Sound. It features interactive exhibits and a café. Plus, it’s super easy to get to from Westport or 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 at the historic Gallaher Mansion and Cranbury Park. This stunning 227-acre park is home to beautiful parkland, sculpture gardens, and the charming Tudor Revival Gallaher Mansion.

  • Activities: Enjoy hiking, tennis, disc golf, and picnicking.

It’s a perfect spot to soak up the tranquil beauty of inland Norwalk.

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

Hotels and Inns in Westport, Connecticut

Ready for a weekend getaway in Westport? It’s just a half-hour drive from our cozy Greenwich, CT, bed and breakfast. Here are some great places to stay in and around Westport:

The Inn at Longshore

The Inn at Longshore, once an elegant private estate and exclusive country club, is now a popular event and small CT wedding venue. It offers a relaxing setting with 12 guest rooms, award-winning cuisine, and stunning views of Long Island Sound.

  • Amenities: Complimentary Wi-Fi, flat-screen TVs, premium bed linens, air conditioning, beach towels, and a mini-bar.

Delamar Southport

Close to Westport in Southport, the Delamar Southport is a fantastic choice. Guests can enjoy an on-site spa and Artisan, a French restaurant run by chef Frederic Kieffer. It’s just a seven-minute walk from the Metro North rail station and faces I-95, making it easy to explore Southport’s historic downtown or go gallery hopping.

Bed and breakfasts near Westport

While there aren’t any Connecticut bed and breakfasts right in Westport, there are some charming options nearby. Aside from our Stanton House Inn, check out:

Discover Even More Nearby Cities and Towns to Visit

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

If you love Westport, wait till you check out the surrounding areas. Fairfield County is packed with charming towns and unique attractions that make for fantastic day trips. Here are some must-visit spots:

Fairfield, CT

The list of things to do in Fairfield, CT, is long, so there’s plenty to keep you busy:

Whether you’re into history, art, shopping, or nature, Fairfield’s got you covered.

Bridgeport, Connecticut

Bridgeport, CT, is packed with fun activities and attractions:

  • The PT Barnum Museum: Learn about the famous showman.
  • Beardsley Zoo: Connecticut’s only zoo, home to exotic and endangered species.
  • Seaside Park: Enjoy waterfront views, picnic areas, and walking trails.
  • Discovery Museum and Planetarium: Interactive science exhibits and a journey through the universe.
  • Bridgeport Harbor: Ideal for a scenic stroll or boat tour.

Bridgeport has something for history buffs, nature lovers, and science enthusiasts alike.

Wilton, CT

Wilton, Connecticut, is a charming town with a ton of fun activities:

  • Weir Farm National Historic Site: Tour the only national park dedicated to American painting.
  • Norwalk River Valley Trail: Perfect for hiking and biking with beautiful views.
  • Woodcock Nature Center: Discover local wildlife through educational programs.
  • Wilton Historical Society: Dive into the town’s rich history with engaging exhibits.

Art, nature, and history lovers will all find something to enjoy in Wilton.

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

Updated and republished: June 23, 2024

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