Nestled on Connecticut’s Gold Coast, Westport is a charming town that offers a perfect blend of coastal beauty and cultural richness. You’ll find yourself captivated by its picturesque beaches, vibrant arts scene, and quaint downtown area.
Westport is worth visiting for its lovely beaches, golf course, and Sherwood Island State Park.
As you explore this coastal gem, you’ll discover a town steeped in artistic heritage. The Westport Country Playhouse stands as a testament to the town’s cultural significance, having attracted renowned actors and playwrights over the years.
You can stroll through the downtown area, lined with unique shops and eateries, or relax on Compo Beach with its stunning views of Long Island Sound.
Whether you’re seeking a peaceful getaway or an active vacation, Westport has something for everyone. You can enjoy outdoor activities, indulge in local cuisine, or immerse yourself in the town’s rich history.
This Westport, Connecticut travel guide will help you make the most of your visit to this captivating coastal town.
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How to Get to Westport
Westport is easy to reach by various modes of transportation.
You can drive to Westport from nearby cities and towns in Connecticut.
If you prefer public transit, buses are available. They offer an affordable option to reach Westport from other parts of Connecticut.
For those coming from further away, flying into nearby airports is a good choice. The closest major airport is Bradley International Airport in Hartford. From there, you can rent a car or take a shuttle to Westport.
Train travel is another great option. Westport has its own train station on the Metro-North Railroad’s New Haven Line. This connects you directly to New York City and other towns along the Connecticut coast.
Taxis and ride-sharing services are also available for local transportation within Westport and nearby areas.
When planning your trip, keep in mind that Westport’s weather varies by season. Summers are warm and humid, while winters can be very cold. Pack accordingly for your visit.
What to See in Westport
Westport offers a mix of cultural attractions and natural beauty.
You can start your visit at the Westport Country Playhouse, a historic theater known for top-notch performances.
For beach lovers, Compo Beach is a must-see. It’s perfect for swimming, sunbathing, and watching stunning sunsets over Long Island Sound.
Nature enthusiasts will enjoy Sherwood Island State Park. You can explore trails, visit the Nature Center, and observe local wildlife.
The Saugatuck River adds charm to the town. Take a stroll along its banks and enjoy the scenery.
For shopping and dining, head to downtown Westport. You’ll find unique boutiques and tasty eateries. The area has a variety of cuisines, including Italian restaurants.
If you’re interested in marine life, the Maritime Aquarium in nearby Norwalk is worth a visit. It showcases the creatures of Long Island Sound.
Westport also hosts various events throughout the year, including concerts and art shows. Check the local calendar for upcoming activities during your visit.
Where to Stay in Westport
If you know when you are planning to go but haven’t decided on accommodation, then use the map below to get an idea of which properties are available and to compare prices during the period you wish to travel.
Enter your proposed dates and use the ‘+’ to zoom in on a location and reveal more properties. Click on the price above a property to see more information.
(Please note that this selection will also include some vacation homes, AirBnBs, and VRBOs for those who are interested in that form of accommodation!)
History of Westport
Westport’s story begins in 1648 when the “Bankside Farmers” settled in the Greens Farms area. As a New England town in Fairfield County, it grew from colonial roots into a vibrant community.
In the early 1900s, Westport became a hotbed of creativity. Artists flocked to the town, turning it into a hub of cultural activity. The Famous Artists School and Famous Writers School were established here, drawing talent from across America.
Westport’s charm attracted many notable residents over the years. One of the most famous was actor Paul Newman, who lived in town until his passing in 2008. He co-owned a local restaurant, further cementing his connection to the community.
The town’s history is deeply tied to its coastal location. You can explore this heritage through the Head of Westport Walking Tour, which showcases the area’s architectural and industrial past.
Today, Westport beautifully blends its historical roots with modern amenities. As you stroll through downtown, you’ll find colonial-era buildings alongside contemporary shops and restaurants, offering a unique glimpse into the town’s evolution.
Towns Near Westport
Westport is surrounded by charming towns and cities that offer unique experiences.
Norwalk, just a few miles away, boasts a vibrant maritime scene and fascinating museums.
Stamford, a bustling city to the west, provides a mix of urban amenities and natural beauty.
You’ll find excellent dining options and parks to explore.
New Haven, home to Yale University, is about 30 miles northeast. This city offers world-class museums, theaters, and restaurants.
For a taste of big city life, New York is only an hour away by train. You can easily plan a day trip to enjoy its iconic attractions and diverse culture.
Closer to home, Fairfield County offers many quaint towns to discover.
Each has its own character and charm, from coastal villages to inland retreats.
These nearby locations make Westport an ideal base for exploring Connecticut and beyond.
You can enjoy small-town tranquility while having easy access to larger cities and their attractions.
Remember to check local events calendars. Many neighboring towns host festivals, concerts, and markets throughout the year, adding extra fun to your visit.
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Fairfield County Hotels, Apartments, B&Bs
