Westport: Neighborhood Guide

Welcome to Westport, Connecticut – the town with the most expansive ocean views in Connecticut. In this neighborhood guide, we’ll uncover the unique charm and dynamic energy that defines life in Westport. This Gold Coast gem possesses an irresistible blend of sophistication and small-town charm.


Location and accessibility

Situated in the heart of Lower Fairfield County, Westport enjoys a central location within commuting distance to major cities such as Stamford and Norwalk, as well as easy access to New York City. Its proximity to Interstate 95 and the Merritt Parkway ensures convenient travel by car to neighboring towns and beyond. Westport’s location is truly an ideal setting for commuters.

Saugatuck River, downtown Westport Connecticut
Saugatuck River – Downtown

Public transportation options

  • Metro-North Railroad: Westport is served by the Westport Metro-North Railroad station, providing commuter rail service along the New Haven Line. Commuters can travel to Grand Central Terminal in New York City, making it an ideal option for those working in the city or exploring its attractions. Residents can take the Saugatuck Station or Greens Farms.
  • Wheels2U Westport: A shuttle service that goes to and from locations in the designated service area and the Saugatuck or Greens Farms train stations. This shared ride service picks you up at your door and takes you to the train platform – it will also take you from the train platform to your destination!
  • Coastal Link Bus: Whether you’re venturing for business or pleasure, the Coastal Link Bus offers a convenient and cost-effective transportation option. The bus travels along the Route 1 corridor through Norwalk, Westport, Fairfield, Bridgeport, Stratford, and Milford — seven days a week.
  • Westport Door-to-Door: Daytime Door-to-Door transportation for Westport seniors and citizens with disabilities. Whether it’s a medical appointment, social outing, or simply running errands, Door-to-Door service provides peace of mind and independence.

Commute times

  • Grand Central 75m. by train, 1hr. 10m. by car
  • Westchester County Airport 35m. by car
  • LGA 60m. by car
  • JFK 75m. by car

Community and attractions

With a population of 28,000 residents, Westport thrives on a tight-knit community spirit. Through a variety of local events, neighborhood gatherings, and volunteer opportunities, residents actively cultivate connections and forge meaningful relationships that enhance their daily lives.

Immerse yourself in Westport’s cultural scene, where an abundance of attractions await to captivate and inspire residents and visitors alike! Take a stroll through downtown Westport and explore its charming boutiques, art galleries, and antique shops, where you’ll discover unique treasures and one-of-a-kind finds. Visit the Levitt Pavilion for the Performing Arts, an outdoor amphitheater that hosts free concerts and performances throughout the summer. Explore the Westport Country Playhouse, an iconic theater that showcases world-class productions and hosts engaging performances year-round. Take a trip to the Westport Library, a hub of learning and creativity that offers a wide range of programs, events, and resources for residents of all ages – don’t miss the park benches along the Saugatuck River for relaxing and picnics!

Main street in Westport Connecticut
Main Street

Take a scenic drive along the Sherwood Island State Park and enjoy panoramic views of Long Island Sound and the scenic coastline, offering a picturesque backdrop for outdoor adventures and leisurely drives. This state park has beaches, picnic tables and grills, nature trails, and the ability to go boating/kayaking!

Sherwood Island State Park in Westport Connecticut
Sherwood Island State Park

Westport offers a spectrum of culinary delights ranging from quaint cafes to upscale dining establishments. With its proximity to the coast, seafood is a standout feature, complemented by farm-to-table options and international cuisines, making it a haven for food enthusiasts seeking quality and variety. Book a reservation here!

This coastal town is is a paradise for families, with a wealth of attractions and activities that entertain kids of all ages. Spend a day at the Earthplace Nature Discovery Center, where children can explore interactive exhibits, hike nature trails, and get close to animals in their natural habitats. Head on down to Compo Beach, where you can soak up the sun, enjoy views of Long Island Sound, and engage in a variety of recreational activities amidst its sandy shores.

Compo beach in Westport Connecticut
Cotton candy skies at Compo Beach

Helpful resources

Below are some invaluable resources to guide you in exploring everything Westport has to offer:

Annual events

Some highlights of the year! For events within the current month click here.

  • Westport Fine Arts Festival: Held annually in May, the Westport Fine Arts Festival showcases the work of talented artists from around the country. Visitors can browse and purchase original paintings, sculptures, jewelry, and more, while enjoying live music, food vendors, and children’s activities.
  • Westport Library Book Sale: This iconic event, held in May, draws book lovers from near and far to browse through thousands of donated books across all genres. Proceeds from the sale support the Westport Library’s programs and services, making it a beloved community tradition.
  • Westport Downtown Merchants Association’s Halloween Parade: Families and children gather in downtown Westport each Halloween for a festive parade featuring costumes, music, and trick-or-treating at local businesses. It’s a fun-filled event that brings the community together to celebrate the spooky season.
  • Westport Dog Festival: Held in May, the Westport Dog Festival celebrates our furry friends with a day of dog-friendly activities, competitions, and demonstrations. It’s a paw-some event for dog lovers and their canine companions to enjoy together!
  • Levitt Pavilion Summer Concert Series: Throughout the summer months, the Levitt Pavilion for the Performing Arts hosts free outdoor concerts featuring a diverse lineup of musical acts, including rock, jazz, blues, and more. It’s a fantastic way to enjoy live music under the stars with friends and family.

Schools

Westport’s public school system is highly regarded for its excellence in education, innovative programs, and commitment to student success. Managed by The Westport Public Schools District, the system consists of five elementary schools, two middle schools, and one high school, serving a diverse population of students from kindergarten through twelfth grade. As of 2023, Westport’s public school system was ranked 7th nationally in a study of public schools conducted by TeachSimple.

Westport’s schools consistently rank among the top in the state and nation for academic achievement. The district places a strong emphasis on rigorous curriculum standards, innovative teaching methods, and personalized learning approaches to ensure that all students reach their full potential. Westport offers a wide range of Advanced Placement (AP) and honors courses at the high school level, allowing students to pursue challenging coursework and earn college credit while still in high school. These programs provide opportunities for academic enrichment and college readiness, helping students excel in their future pursuits.

In addition to its core academic offerings, Westport provides specialized programs and services to meet the diverse needs of its student population. This includes support services for students with special needs, English language learners, ensuring that every student receives a high-quality education tailored to their individual strengths and abilities.

Downtown Westport Connecticut
Holidays Downtown

Safety

Westport has a reputation as one of the safest communities in the state, with crime rates consistently below national and state averages. The town’s proactive approach to law enforcement, community policing initiatives, and neighborhood watch programs contribute to its overall sense of safety and security.

The Westport Police Department plays a pivotal role in maintaining this sense of security, ensuring the protection and well-being of the community through its vigilant law enforcement efforts and community outreach initiatives.

The Westport Police Department prioritizes the prompt dissemination of crucial information to residents. To achieve this, the department utilizes multiple emergency notification systems across the town. Click here to sign up for alerts to your device.

The State of Connecticut has implemented a state-of-the-art emergency notification system to alert residents anywhere in the state about life-threatening emergency conditions. Click here to sign up for alerts to your device.

Your Perfect Blend of Style and Serenity

In conclusion, Westport stands as a quintessential destination for those seeking a serene lifestyle. It’s clear that this coastal town offers a unique and enticing environment to call home. From its scenic landscapes to its stunning downtown scene, there’s no shortage of excitement and opportunity awaiting residents.